sci-form 0.15.0

//! CSD torsion preference data (837 patterns).
//! Format: (SMARTS, [s1, V1, s2, V2, s3, V3, s4, V4, s5, V5, s6, V6])
//! Energy: V = sum_k V_k * (1 + s_k * cos(k * phi))

/// Non-ring torsion preferences (365 patterns)
pub const TORSION_PREFS_V2: &[(&str, [f32; 12])] = &[
    (
        "[O:1]=[C:2]!@;-[O:3]~[CH0:4]",
        [-1.0, 78.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([N])!@;-[O:3]~[C:4]",
        [-1.0, 79.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]!@;-[O:3]~[C:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[O:1]=[C:2]!@;-[O:3]~[!#1:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[$(C=O):1][O:2]!@;-[c:3]~[*:4]",
        [1.0, 0.0, 1.0, 0.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][O:2]!@;-[CX3:3]~[*:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][O:2]!@;-[CH1:3][H:4]",
        [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][O:2]!@;-[CH2:3]~[C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[H:1][CX4H1:2]!@;-[O:3][CX4:4]",
        [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CH2:2]!@;-[O:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][CX4:2]!@;-[O:3][$([CX3](=[!O])):4]",
        [1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1][CX4:2]!@;-[O:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 8.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][CX4:2]!@;-[O:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[O:3][S:4]",
        [1.0, 0.0, 1.0, 3.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH0])!@;-[O:3][S:4]",
        [1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[O:3][S:4]",
        [1.0, 0.0, 1.0, 11.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[O:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH0])!@;-[O:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[O:3][c:4]",
        [1.0, 0.0, 1.0, 2.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[O:3][P:4]",
        [1.0, 0.0, 1.0, 2.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[O:3][p:4]",
        [1.0, 0.0, 1.0, 11.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH:1][c:2]([cH])!@;-[O:3][$(C([F])([F])[F]):4]",
        [1.0, 0.0, 1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[O:3][CX4H0:4]",
        [1.0, 0.0, 1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]([a])!@;-[O:3][CX4H0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1,n:1][c:2]!@;-[O:3][CRH1:4]",
        [1.0, 0.0, -1.0, 5.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1,n:1][c:2]!@;-[O:3][CH1:4]",
        [1.0, 0.0, -1.0, 7.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c:2]([cH0])!@;-[O:3][CX4H0:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[cH0:1][c:2]([nX2])!@;-[O:3][C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2:1][c:2]([nX2])!@;-[O:3][C:4]",
        [1.0, 0.0, -1.0, 44.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2:1][c:2]([nX3])!@;-[O:3][C:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[cH1:1][c:2]([nX3])!@;-[O:3][C:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[cH1:1][c:2]([nX2])!@;-[O:3][C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]([CX3])):1][c:2]([cH1])!@;-[O:3][C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2](cO)!@;-[O:3][C:4]",
        [-1.0, 61.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(cO):1][c:2](cO)!@;-[O:3][C:4]",
        [1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[O:3][C:4]",
        [1.0, 0.0, 1.0, 6.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH1])!@;-[O:3][C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[O:3][C:4]",
        [1.0, 0.0, -1.0, 19.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[O:3][CX3H0:4]",
        [1.0, 0.0, 1.0, 1.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH0:1][c:2]!@;-[OX2:3][!#1:4]",
        [1.0, 0.0, -1.0, 7.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H0:2]!@;-[OX2:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[H:1][CX4H1:2]!@;-[OX2:3][!#1:4]",
        [-1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4H2:2]!@;-[OX2:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4H2:2]!@;-[OX2:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4H2:2]!@;-[OX2:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4H2:2]!@;-[OX2:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2:2]!@;-[OX2:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2:2]!@;-[OX2:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4H2:2]!@;-[OX2:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4H2:2]!@;-[OX2:3][!#1:4]",
        [1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2:2]!@;-[OX2:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4:2]!@;-[OX2:3][!#1:4]",
        [1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]=O):1][NX3H0:2](C)!@;-[CX4H2:3][C:4]",
        [1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]=O):1][NX3H1:2]!@;-[CX4H2:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NX3H0:2]!@;-[CX4H2:3][!#1:4]",
        [1.0, 0.0, 1.0, 1.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NX3H1:2]!@;-[CX4H2:3][!#1:4]",
        [
            1.0, 17.9, -1.0, -13.3, 1.0, 9.2, 1.0, 4.7, -1.0, -2.3, -1.0, -0.9,
        ],
    ),
    (
        "[$(S(=O)(=O)):1][NX3H0:2]!@;-[CX4H1:3][H:4]",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NX3H1:2]!@;-[CX4H1:3][H:4]",
        [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH1:2]!@;-[c:3][nX2:4]",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH0:2]!@;-[c:3]([cH1])[cH1:4]",
        [1.0, 0.0, 1.0, 13.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH1:2]!@;-[c:3]([cH1])[cH1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.9, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH0:2]!@;-[c:3]([cH1])[cH0:4]",
        [1.0, 0.0, 1.0, 50.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH1:2]!@;-[c:3]([cH1])[cH0:4]",
        [1.0, 1.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH0:2]!@;-[c:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 17.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH1:2]!@;-[c:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 10.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][N:2]!@;-[c:3][a:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O-:1][N+:2](=O)!@;-[c:3]([cH,nX2H0])[cH,nX2H0:4]",
        [1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O-:1][N+:2](=O)!@;-[c:3]([cH0])[cH,nX2H0:4]",
        [
            -1.0, -0.2, 1.0, -5.7, 1.0, -0.2, -1.0, -3.2, 1.0, 0.1, 1.0, -1.3,
        ],
    ),
    (
        "[O-:1][N+:2](=O)!@;-[c:3]([cH0])[cH0:4]",
        [
            -1.0, -0.4, 1.0, 0.3, 1.0, -0.1, -1.0, 0.6, 1.0, -0.1, -1.0, 0.2,
        ],
    ),
    (
        "[O-:1][N+:2](=O)!@;-[c:3][a:4]",
        [1.0, 0.0, -1.0, 11.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[NX3H1:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, 1.0, 2.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH1])!@;-[NX3H1:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([nX2H0])!@;-[NX3H1:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 40.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[NX3H1:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, -1.0, 1.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c:2]([nX2H0])!@;-[NX3H1:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c:2]([nX3H1])!@;-[NX3H1:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, -1.0, 27.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a:2]!@;-[NH1:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, -1.0, 6.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][NH:2]!@;-[C:3](=[NH2:4])[NH2]",
        [
            1.0, 0.0, -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[NH2][C:1](=[NH2])[NH:2]!@;-[CH2:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[NX2:3]=[$(C([NX3])n):4]",
        [
            -1.0, -0.1, 1.0, 1.9, -1.0, -0.1, -1.0, -1.9, -1.0, 0.1, 1.0, 0.0,
        ],
    ),
    (
        "[nX2:1][c:2]!@;-[NX2:3]=[$(C([NX3])N):4]",
        [1.0, 0.0, -1.0, 6.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[NX2:3]=[$(C([NX3])N):4]",
        [
            -1.0, -0.1, 1.0, 1.9, -1.0, -0.1, -1.0, -1.9, -1.0, 0.1, 1.0, 0.0,
        ],
    ),
    (
        "[cH1:1][c:2]!@;-[NX2:3]=[$(C([NX3])N):4]",
        [
            1.0, -0.4, -1.0, -0.9, 1.0, -0.4, 1.0, 1.1, 1.0, -0.2, 1.0, -0.1,
        ],
    ),
    (
        "[O:1]=[C:2]([NH1])!@;-[NX3H1:3](C=O)[H:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[O:1]=[C:2]!@;-[NX3H1:3](C=O)[H:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]!@;-[NX3:3](C=O)[*:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX3:3]=[NX2:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[CX3:3]=[*H0:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[CX3:3]=[*H1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX3:3]=[*H2:4]",
        [1.0, 0.0, -1.0, 68.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX3:3]=[*H1:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX3:3]=[*H0:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[CX3H1:3]=[*:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX3H1:3]=[*:4]",
        [1.0, 84.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)):1][NX3H0:2]!@;-[CX4H2:3][$([c]([cH,nX2H0])[cH,nX2H0]):4]",
        [1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX4H2:3][$([c]([cH,nX2H0])[cH,nX2H0]):4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[CX4H2:3][!#1:4]",
        [1.0, 0.0, 1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX4H2:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[CX4H1:3][H:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX4H1:3][H:4]",
        [-1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[CX4H0:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[CX4H0:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3:2]!@;-[!#1:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.8, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)([$([NX3H1]),$([NX3H2])])[NX3H1]):1][NX3H1:2]!@;-[c:3]([nH1])[nH0:4]",
        [1.0, 84.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)([$([NX3H1]),$([NX3H2])])[NX3H1]):1][NX3H1:2]!@;-[c:3]([nH0])[cH1:4]",
        [1.0, 84.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)):1][NX3H1:2]!@;-[$([a]([nH0,o])):3][cH1:4]",
        [-1.0, 53.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)([$([NX3H1]),$([NX3H2])])[NX3H1]):1][NX3H1:2]!@;-[c&r6:3][nH0&r6:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)):1][NX3H1:2]!@;-[c:3]([cH])[nX2H0:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[c:3]([s,o])[n:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[c:3]([s,o])[n:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)):1][NX3:2]!@;-[a:3](s)[a:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3:2]!@;-[a:3][nH:4]",
        [-1.0, 53.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[c:3]([cH0]Cl)[cH:4]",
        [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[c:3]([cH0]F)[cH:4]",
        [-1.0, 11.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3:2]!@;-[$([a]([cH1])):3][$([aH0](!@O)):4]",
        [1.0, 38.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3:2]!@;-[a:3][aH0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[c:3]([cH1])[cH1:4]",
        [1.0, 0.0, -1.0, 2.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[c:3]([cH1])[cH1:4]",
        [1.0, 0.0, 1.0, 2.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[c:3]([cH0])[cH:4]",
        [1.0, 0.0, 1.0, 2.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[c:3]([cH0])[cH:4]",
        [-1.0, 9.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0:2]!@;-[c:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 2.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1:2]!@;-[c:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 2.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O,S:1]=[C:2]([$([NX3H1]),$([NX3H2])])!@;-[$([NX3]c[nH0]):3][H:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]!@;-[$([NX3](c([nH1])n)):3][H:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2](c)!@;-[$([NX3](c([nX2H0])([nX2H0]))):3][H:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2]([$([NX3H1]C)])!@;-[NX3H1:3][!#1:4]",
        [-1.0, 51.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([!$([NH1])])!@;-[NX3H1:3]([H:4])[$(c([nX2H0])([nX2H0]))]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O,S:1]=[C:2]([$([NX3H1]),$([NX3H2])])!@;-[$([NX3](cn)):3][H:4]",
        [1.0, 0.0, -1.0, 50.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]!@;-[NX3H0:3]([a:4])[A]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2](a)!@;-[NX3H0:3][!#1:4]",
        [1.0, 0.0, -1.0, 13.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2]!@;-[NX3H0:3][!#1:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2]!@;-[NX3H1:3][!#1:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[CH0:1][NX3:2]([CH0])!@;-[c:3][a:4]",
        [1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CH0:1][NX3:2]([CH1])!@;-[c:3][a:4]",
        [1.0, 0.0, 1.0, 1.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1,nX2H0:1][c:2]([cH1,nX2H0])!@;-[NX3&r:3][*:4]",
        [1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[NX3H1:3][$([CX4&r]([C;r])([C;r])):4]",
        [1.0, 0.0, -1.0, 6.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[NX3:3][CX4:4]",
        [1.0, 0.0, -1.0, 6.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH,nX2H0])!@;-[NX3H1:3][CX4:4]",
        [1.0, 73.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH,nX2H0])!@;-[NX3H0:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[NX3:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c:2](c)!@;-[NX3:3][CX4:4]",
        [
            1.0, 0.0, -1.0, 0.5, 1.0, 0.0, -1.0, 0.8, 1.0, 0.0, 1.0, -0.6,
        ],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[NX3:3][a:4]",
        [1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH0])!@;-[NX3:3][a:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[NX3:3][a:4]",
        [1.0, 0.0, 1.0, 1.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][a:2]!@;-[NX3H0:3][$([CX3]=O):4]",
        [1.0, 0.0, 1.0, 2.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][a:2]!@;-[NX3H1:3][$([CX3]=O):4]",
        [
            -1.0, -1.6, -1.0, -0.6, 1.0, 0.6, 1.0, 0.0, -1.0, 0.1, 1.0, -0.5,
        ],
    ),
    (
        "[nX2H0:1][a:2]([nX2H0])!@;-[NX3H0:3][$([CX3]=O):4]",
        [1.0, 72.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][$(a([!nX2H0])([nX2H0])!@;-[NX3H1]):2]!@[NX3H1:3][$([CX3](a)=O):4]",
        [1.0, 72.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][a:2]!@;-[NX3H1:3][$([CX3]=O):4]",
        [1.0, 0.0, -1.0, 34.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a:2]!@;-[NX3H1:3][$([CX3]=O):4]",
        [1.0, 0.0, -1.0, 3.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a:2]!@;-[NX3:3][CX4H0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a:2]!@;-[NX3:3][!#1:4]",
        [
            1.0, 0.0, 1.0, -0.7, 1.0, 0.0, 1.0, -0.5, 1.0, 0.0, 1.0, -0.6,
        ],
    ),
    (
        "[O:1]=[CX3:2]!@;-[nX3:3]([aH0:4])([aH0])",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2]!@;-[nX3:3][aH1:4]",
        [1.0, 0.0, -1.0, 18.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][CX3:2](=S)!@;-[NX3:3][a:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX3:2](=S)!@;-[NX3H0:3][!#1:4]",
        [1.0, 0.0, -1.0, 22.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX3:2](=S)!@;-[NX3H1:3][!#1:4]",
        [1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CH2:2]!@;-[n:3][cH0:4]",
        [1.0, 0.0, 1.0, 6.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CH2:2]!@;-[n:3][a:4]",
        [1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][n:2]!@;-[CX3H0:3]~[$([n,N](-a)):4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX4:1][CX4H2:2]!@;-[NX3:3][CX4:4]",
        [1.0, 4.0, 1.0, 3.1, 1.0, 3.9, -1.0, -0.8, 1.0, 0.0, 1.0, 0.7],
    ),
    (
        "[C:1][CX4H2:2]!@;-[NX3:3][C:4]",
        [1.0, 4.0, 1.0, 3.1, 1.0, 3.9, -1.0, -0.8, 1.0, 0.0, 1.0, 0.7],
    ),
    (
        "[C:1][CX4:2]!@;-[NX3:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2:2]!@;-[NX3H1:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2:2]!@;-[NX3:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H1:2]!@;-[NX3:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4:2]!@;-[NX3:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][$(S(=O)=O):2]!@;-[nX3:3]([aH1])[aH1:4]",
        [1.0, 0.0, 1.0, 20.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][$(S(=O)=O):2]!@;-[nX3:3][aH0:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][S:2](=O)(=O)!@;-[NX2H0-:3]-[*:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][$(S(=O)=O):2]!@;-[NX3H0&r:3][*:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][$(S(=O)=O):2]!@;-[NX3H1:3][c:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][$(S(=O)=O):2]!@;-[NX3H0:3][c:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][$(S(=O)=O):2]!@;-[NX3H1:3][C:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][$(S(=O)=O):2]!@;-[NX3H0:3][C:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][$(S(=O)=O):2]!@;-[NX3H1:3][c:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][$(S(=O)=O):2]!@;-[NX3H0:3][c:4]",
        [1.0, 0.0, 1.0, 4.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][$(S(=O)=O):2]!@;-[NX3H1:3][C:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][$(S(=O)=O):2]!@;-[NX3H0:3][C:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][$(S(=O)=O):2]!@;-[NX3H1:3][*:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][$(S(=O)=O):2]!@;-[NX3H0:3][*:4]",
        [1.0, 0.0, 1.0, 3.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX3:2]!@;-[SX2:3][!#1:4]",
        [1.0, 0.0, -1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4:2]!@;-[SX2:3][!#1:4]",
        [
            -1.0, -0.8, -1.0, -0.8, -1.0, -1.5, -1.0, 0.4, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[!#1:1][CX3:2]!@;-[SX3:3][!#1:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4:2]!@;-[SX3:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 10.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX3:2]!@;-[SX4:3][!#1:4]",
        [1.0, 0.0, 1.0, 3.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[H:1][CX4H1:2]!@;-[SX4:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4:2]!@;-[SX4:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH1:1][c:2]([aH1])!@;-[SX2:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH1:1][c:2]([aH0])!@;-[SX2:3][*R:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH1:1][c:2]([aH0])!@;-[SX2:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH0:1][c:2]([aH0])!@;-[SX2:3][!#1:4]",
        [
            1.0, -0.2, 1.0, 0.4, 1.0, 0.0, -1.0, 1.9, 1.0, 0.0, 1.0, -1.1,
        ],
    ),
    (
        "[!#1:1][c:2]!@;-[SX2:3][!#1:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][c:2]!@;-[SX3:3][!#1:4]",
        [1.0, 0.0, 1.0, 1.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH1:1][c:2]([aH1])!@;-[SX4:3][!#1:4]",
        [1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH0:1][c:2]([aH1])!@;-[SX4:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH0:1][c:2]([aH0])!@;-[SX4:3][!#1:4]",
        [1.0, 0.0, 1.0, 3.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2]([NH1])!@;-[CH2:3][CX3:4]=O",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2]([NH1])!@;-[CH2:3][C:4]",
        [-1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]([C])([H])):1]=[CX3:2]([C])!@;-[CH2:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]([C])([H])):1]=[CX3:2]([H])!@;-[CH1:3](C)[C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]([C])([H])):1]=[CX3:2]([H])!@;-[CH2:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[N:1][C:2](=O)!@;-[CX4H2:3][CX4H2:4]",
        [1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "N[C:2](=[O:1])!@;-[CH2:3][N:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[CX4H1:3][H:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H2:1]=[CX3:2]!@;-[CX3:3]=[C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3:2]!@;-[CH2:3][OX2:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3:2]!@;-[CH1:3](C)[C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3:2]!@;-[CH2:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3:2]!@;-[CH2:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3:2]!@;-[CH2:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2](O)!@;-[CX3:3]([$([NH1,NH2,CH2])])=[O:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2]!@;-[CX3:3]=[O:4]",
        [1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3R:1]=[CX3R:2]!@;-[CX3:3]=[CX3:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H0:1]=[CX3H0:2]!@;-[CX3:3]=[CX3H0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H0:1]=[CX3H0:2]!@;-[CX3H0:3]=[CX3:4]",
        [1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H0:1]=[CX3:2]!@;-[CX3H0:3]=[CX3:4]",
        [1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H0:1]=[CX3H0:2]!@;-[CX3:3]=[CX3:4]",
        [1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3:2]!@;-[CX3:3]=[CX3:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*^2:1]~[C^2:2]([!H])!@;-[C^2:3]~[*^2:4]",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*^2:1]~[C^2:2]!@;-[C^2:3]~[*^2:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3:2]!@;-[CX4&r3:3]!@[!#1:4]",
        [
            -1.0, -0.7, -1.0, 0.5, 1.0, -0.3, -1.0, 0.3, -1.0, -0.2, -1.0, 0.2,
        ],
    ),
    (
        "[O:1]=[CX3:2]!@;-[CX4H1&r3:3][H:4]",
        [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4H2:2]!@;-[CX4H2:3][N&r:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4H2:2]!@;-[CX4H2:3][N:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4:2]!@;-[CX4:3][N:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4H2:2]!@;-[CX4H2:3][OX2:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4:2]!@;-[CX4:3][OX2:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4&r:2]!@;-[CX4&r:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2:2]!@;-[CX4H2:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4:2]!@;-[CX4:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4H2:2]!@;-[CX3:3]([$([NX3H1,NX3H2])])=[O:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OH1:1][CX4:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[NH1:1][CX4:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1][CX4:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[N:1][CX4:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 1.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4H2:2]!@;-[CX3:3]=[O:4]",
        [
            1.0, -1.0, 1.0, -0.5, 1.0, -0.2, 1.0, -0.3, 1.0, 0.0, 1.0, -0.3,
        ],
    ),
    (
        "[c:1][CX4H2:2]!@;-[CX3:3]=[O:4]",
        [
            -1.0, 0.9, 1.0, -0.3, 1.0, -0.2, 1.0, -0.5, -1.0, 0.1, 1.0, 0.2,
        ],
    ),
    (
        "[!#1:1][CX4H2:2]!@;-[CX3:3]=[O:4]",
        [
            1.0, 0.0, 1.0, -0.7, 1.0, 0.0, 1.0, -0.5, 1.0, 0.0, 1.0, -0.6,
        ],
    ),
    (
        "[c:1][CX4:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4:2]!@;-[CX3:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4:2]!@;-[CX3:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4:2]!@;-[CX3:3][c:4]",
        [
            -1.0, -4.4, 1.0, 4.0, -1.0, -3.9, -1.0, -1.0, 1.0, 0.6, -1.0, -0.4,
        ],
    ),
    (
        "[C:1][CX4:2]!@;-[CX3:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4:2]!@;-[CX3H0:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[H:1][CX4H1:2]!@;-[CX3:3][!#1:4]",
        [1.0, 0.0, -1.0, 1.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2:2]!@;-[CX3:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.8, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]([$([NX3H2]),$([NX3H1])])):1][a:2]!@;-[a:3][nX2:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nH0:1][c&r6:2]([nH0])!@;-[c&r6:3]([nH0])[nH0:4]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nH0&r6:1][c&r6:2]([nH0&r6])!@;-[c&r6:3]([cH1&r6])[nH0&r6:4]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nH0&r6:1][c&r6:2]([nH0&r6])!@;-[c&r6:3]([cH1&r6])[cH1&r6:4]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c:2]!@;-[c:3][$(c!@c):4]",
        [
            1.0, 0.1, 1.0, 0.9, 1.0, 0.1, -1.0, -0.4, 1.0, 0.0, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[c:3]([cH0:4])[cH0]",
        [1.0, 0.0, 1.0, 3.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[c:3]([cH0:4])[cH1]",
        [1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH1])!@;-[c:3]([cH0:4])[cH1]",
        [1.0, 0.0, 1.0, 3.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[c:3]([cH1:4])[cH1]",
        [1.0, 0.0, 1.0, 3.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH1])!@;-[c:3]([cH1:4])[cH1]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.6, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[c:3]([cH1:4])[cH1]",
        [
            -1.0, -0.7, 1.0, -8.0, 1.0, 0.0, 1.0, 4.4, 1.0, 0.0, 1.0, -1.5,
        ],
    ),
    (
        "[nX2H0:1][c:2]!@;-[c:3][nX3H1:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c:2]([!nX2H0])!@;-[c:3]([!nX2H0])[nX2H0:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][$(c([nX2H0])(a(a)(a))!@;-c[nX2H0]):2]!@[c:3][nX2H0:4]",
        [1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][$([c&r6](c[OH])):2]!@;-[$([c&r6](c[OH])):3][nX2H0:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c:2]!@;-[c:3][s,o,nX3H1:4]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[c:3][nX2H0:4]",
        [1.0, 0.0, 1.0, 1.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[c:3]([cH0])[nX2H0:4]",
        [
            -1.0, 0.9, -1.0, -1.0, 1.0, -0.8, -1.0, 0.2, -1.0, 0.3, 1.0, -0.2,
        ],
    ),
    (
        "[c:1][c:2]!@;-[c:3]([cH0])[nX2H0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.1, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c:2]([cH0])!@;-[c:3][nX2H0:4]",
        [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]!@;-[c:3]([cH1])[nX2H0:4]",
        [1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c&r5:2]!@;-[c&r5:3][c:4]",
        [1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c&r6:2]!@;-[c&r5:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.1, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c&r6:2]!@;-[c&r6:3][cH0:4]",
        [1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c&r6:2]!@;-[c&r6:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.1, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c:2]!@;-[c:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.1, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2&r6:1][cH0&r6:2]([cH1&r6])!@;-[CX4H2:3][O!H:4]",
        [1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H0:3][a:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H0:3][N,O,S:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H0:3][CX3:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 12.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H0:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H0:3][*:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H2:3][a:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H2:3][CX3:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[CX4H2:3][$([CX4H1]C(=O)O):4]",
        [1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[CX4H2:3][CX4:4]",
        [1.0, 0.0, 1.0, 3.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H2:3][CX4:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H2:3][N,O,S:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H2:3][!#1:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H1:3][a:4]",
        [1.0, 0.9, 1.0, 1.2, 1.0, 0.6, 1.0, 0.4, 1.0, 0.0, 1.0, 0.1],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H1:3][CX4:4]",
        [1.0, 0.0, 1.0, 1.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H1:3][CX3:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H1:3][N,O,S:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]!@;-[CX4H1:3][H:4]",
        [1.0, 0.0, -1.0, 4.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H0:3][a:4]",
        [
            1.0, 0.0, -1.0, -0.3, -1.0, -0.1, 1.0, 0.1, 1.0, 0.0, -1.0, 0.1,
        ],
    ),
    (
        "[a:1][c:2]!@;-[CX4H0:3][CX3:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H0:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H0:3][N,O:4]",
        [1.0, 0.0, -1.0, 0.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H2:3][a:4]",
        [1.0, 0.0, 1.0, 1.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H2:3][CX3:4]",
        [1.0, 0.0, 1.0, 1.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[n,o,s:1][c:2]!@;-[CX4H2:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H2:3][!#1:4]",
        [1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H1:3][N,O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H1:3][a:4]",
        [1.0, 0.0, 1.0, 0.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[CX4H1:3][H:4]",
        [1.0, 0.0, -1.0, 0.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c:2]!@;-[C:3](=[N:4])(-[NH1,NH2])",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[C:3](=[$([N][CX4]):4])([$(N[CX4])])",
        [1.0, 0.0, -1.0, 0.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[C:3](=[$([NH0][CX4]):4])(-N)",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[C:3](=[$([N][!#1]):4])([$(N(C)[!#1])])",
        [
            1.0, 0.0, -1.0, 0.6, 1.0, 0.0, 1.0, 0.3, 1.0, 0.0, -1.0, -0.1,
        ],
    ),
    (
        "[a:1][c:2]!@;-[C:3](=[$([N][!#1]):4])([$(N(C)~[!#1])])",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[C:3](=[N:4])(-N)",
        [
            1.0, 0.0, -1.0, 0.6, 1.0, 0.0, 1.0, 0.3, 1.0, 0.0, -1.0, -0.1,
        ],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[c:3][$(aC(=O)(O)):4]",
        [1.0, 0.0, -1.0, 0.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[c:3][nX3H1:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[c:3][nX2H0:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[c:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[c:3]([cH1])[$([cH0][NH1,NH2]):4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[c:3]([cH1])[cH0:4]",
        [1.0, 0.0, -1.0, 7.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[c:3]([cH1])[cH1:4]",
        [1.0, 0.0, -1.0, 7.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]([O-])!@;-[c:3][a:4]",
        [1.0, 0.0, -1.0, 25.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([c]([NH1,NH2])):1][c:2]!@;-[CX3:3]([!O])=[O:4]",
        [-1.0, 14.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(a[OH1]):1][a:2]!@;-[CX3:3]([NX3H0,CX4H0,c])=[O:4]",
        [-1.0, 14.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(a[NH1,NH2]):1][a:2]!@;-[CX3:3]([NX3H0,CX4H0,c])=[O:4]",
        [-1.0, 36.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH1])!@;-[CX3:3](c)=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[CX3:3](c)=[O:4]",
        [
            -1.0, -0.1, -1.0, 2.4, 1.0, -0.4, -1.0, -1.0, 1.0, 0.1, -1.0, -0.5,
        ],
    ),
    (
        "[a:1][a:2]!@;-[CX3:3](a)=[O:4]",
        [-1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](=O)):1][c:2]([cH1])!@;-[CX3:3]([NX3H1,NX3H2])=[O:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nH0&r6:1][c&r6:2]([cH1&r6])!@;-[C:3]([NH1,NH2])=[O:4]",
        [1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[s:1][c:2]!@;-[C:3]([NH1])=[O:4]",
        [1.0, 0.0, -1.0, 36.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]Cl):1][c:2]([cH1])!@;-[CX3:3]([NX3H1])=[O:4]",
        [
            1.0, 0.1, 1.0, 0.9, 1.0, 0.1, -1.0, -0.4, 1.0, 0.0, -1.0, 0.3,
        ],
    ),
    (
        "[$([cH0]F):1][c:2]([cH1])!@;-[CX3:3]([NX3H1])=[O:4]",
        [1.0, 6.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0][OH0]):1][c:2]([cH1])!@;-[C:3](=O)[NH1:4]",
        [-1.0, 60.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0][OH1]):1][c:2]([cH1])!@;-[C:3](=O)[NH1:4]",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH1])!@;-[CX3:3]([NX3H1])=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 1.2],
    ),
    (
        "[cH0:1][c:2]([cH1])!@;-[CX3:3]([NX3H0])=[O:4]",
        [1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[C:3]([NH1,NH2])=[O:4]",
        [1.0, 0.0, -1.0, 1.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c:2]!@;-[C:3]([NH0])=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 1.2],
    ),
    (
        "[a:1][c:2]!@;-[C:3]([NH1,NH2])=[O:4]",
        [1.0, 0.0, -1.0, 2.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[s:1][c:2]([aX2,cH1])!@;-[CX3:3](O)=[O:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[s:1][c:2]([aX2,cH1])!@;-[CX3:3]=[O:4]",
        [-1.0, 60.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](F)):1][c:2]([cH1])!@;-[CX3:3]([O,N])=[O:4]",
        [1.0, 0.0, -1.0, 1.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]F):1][c:2]([cH1])!@;-[CX3:3]=[O:4]",
        [1.0, 6.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](Cl)):1][c:2]([cH1])!@;-[CX3:3]([CX3H])=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](Cl)):1][c:2]([cH1])!@;-[CX3H:3]=[O:4]",
        [1.0, 6.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](Cl)):1][c:2]([cH1])!@;-[CX3:3](O)=[O:4]",
        [1.0, 0.0, -1.0, 1.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX3H1:1][a:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c:2]([cH1])!@;-[CX3H1:3]=[O:4]",
        [1.0, 66.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0&r6:1][c&r6:2]([c&r6])!@;-[CX3:3]([!O])=[O:4]",
        [1.0, 6.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][a:2]([nX2H0])!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 36.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]!@;-[*^2]):1][c:2]([cH1])!@[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH1])!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[CX3:3]([CX3H0])=[O:4]",
        [1.0, 0.0, -1.0, 5.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a:2]!@;-[CX3:3]=[O:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([nX2])!@;-[CX3:3]=[NX3:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([nX3H1])!@;-[CX3:3]=[NX2:4]",
        [1.0, 97.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([nX2])!@;-[CX3:3]=[NX2:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([$([cH0][OH1])])!@;-[CX3:3]=[NX2:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH0])!@;-[CX3x0:3]=[NX2:4]",
        [1.0, 0.0, -1.0, 36.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c:2]([cH1])!@;-[CX3:3]=[NX2:4]",
        [1.0, 0.0, -1.0, 9.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c:2]([cH0])!@;-[CX3!r:3]=[NX2!r:4]",
        [
            1.0, 0.0, 1.0, -0.7, 1.0, 0.0, 1.0, -0.5, 1.0, 0.0, 1.0, -0.6,
        ],
    ),
    (
        "[a:1][c:2]!@;-[CX3:3]=[CX3H0:4]",
        [1.0, 0.0, -1.0, 0.7, 1.0, 0.0, 1.0, 0.6, 1.0, 0.0, 1.0, -0.5],
    ),
    (
        "[a:1][a:2]!@;-[CX3:3]=[CX3H2:4]",
        [1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a:2]!@;-[CX3:3]=[CX3H1:4]",
        [1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][SX2:2]!@;-[SX2:3][*:4]",
        [1.0, 0.0, 1.0, 12.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][X3,X2:2]=[X3,X2:3][*:4]",
        [
            1.0, 0.0, -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    // ─── Additional patterns: amides, sulfoxides, phosphorus ─────────────
    // Amide C(=O)-NH rotation: strong 2-fold barrier (planar trans preferred)
    (
        "[O:1]=[C:2]!@;-[NH1:3][*:4]",
        [-1.0, 50.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C:2]!@;-[NH2:3][H:4]",
        [-1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    // Amide C(=O)-N(C)(C) (tertiary amide)
    (
        "[O:1]=[C:2]!@;-[NX3H0:3][*:4]",
        [-1.0, 40.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    // Sulfonamide S(=O)(=O)-N
    (
        "[O:1]=[S:2](=O)!@;-[N:3][*:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    // Sulfoxide S(=O) rotation
    (
        "[O:1]=[SX3:2]!@;-[C:3][*:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    // Sulfone S(=O)(=O) rotation
    (
        "[*:1][SX4:2](=O)(=O)!@;-[C:3][*:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    // Phosphonate P(=O) rotation
    (
        "[O:1]=[PX4:2]!@;-[O:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    // 1,5-allylic: C=C-C-C-X
    (
        "[*:1][CX3:2](=C)!@;-[CX4:3][*:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
];

/// Small ring torsion preferences (105 patterns)
pub const TORSION_PREFS_SMALL_RINGS: &[(&str, [f32; 12])] = &[
    ("[x3;r{-8}:1]@;~[A;x3;r3:2]@;-[A;x2;r3:3]@;~[!#1;r{-8}:4]", [1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{-8}:1]@;~[A;r3:2]@;-[A;r3:3]@;~[!#1;r{-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{-4}:1]1@[C;r{-4}:2]@;-[C;r{-4}:3]@[!#1;r{-4}:4]1", [-1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{-4}:1]@[A;r{-4}:2]@;-[!#1;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 2.0]),
    ("[!#1;r{5-8}:1]@[C^2;r{5-8}:2]@;-[C^2;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r5:1]@;=,:[C^2;r5:2]@;-[C;r5:3]@[!#1;r5:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 15.0]),
    ("[!#1;r{5-6}:1]@;=,:[C^2;r{5-6}:2]@;-[C;r{5-6}:3]@[!#1;r{5-6}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[!#1;r{5-8}:1]@;=,:[C^2;r{5-8}:2]@;-[C;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[C^2;r5:2]@;-[C;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C^2;r{5-6}:2]@;-[C;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C^2;r{5-8}:2]@;-[C;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;R3;r{5-8}:1]@[CX4;R2;r{5-8}:2]@;-[CX4;R2;r{5-8}:3]@[!#1;R3;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;R2;r5:1]@[CX4;R1;r5:2]@;-[CX4;R1;r5:3]@[!#1;R2;r5:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[!#1;R2;r{5-6}:1]@[CX4;R1;r{5-6}:2]@;-[CX4;R1;r{5-6}:3]@[!#1;R2;r{5-6}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1]1@[x3;r5:1]@[CX4;x2;r5:2]@;-[CX4;x3;r5:3]@[!#1;r5:4]1", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[!#1]1@[x3;r5:1]@[CX4;r5:2]@;-[CX4;r5:3]@[x3;r5:4]1", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[!#1]1@[x3;r{5-6}:1]@[CX4;r5:2]@;-[CX4;r5:3]@[x3;r{5-6}:4]@[!#1]1", [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1]1@[x3;C^2,c,r3;r{5-6}:1]@[CX4;r{5-6}:2]@;-[CX4;r{5-6}:3]@[x3;r{5-6}:4]@[!#1]1", [1.0, 0.0, 1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1]1@[x3;r{5-6}:1]@[CX4;r{5-6}:2]@;-[CX4;r{5-6}:3]@[x3;r{5-6}:4]@[!#1]1", [1.0, 0.0, 1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[CX4;r{5-7}:1]1@[CX4;r{5-7}:2]@;-[CX4;x3;r{5-7}:3]@[!#1;r{5-7}:4]@[!#1]@[!#1]@[!#1]1", [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[CX4;r{5-8}:1]1@[CX4;r{5-8}:2]@;-[CX4;x3;r{5-8}:3]@[!#1;r{5-8}:4]@[!#1]@[!#1]@[!#1]@[!#1]1", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[C^2,a;r{5-8}:1]@[CX4;x2;r5:2]@;-[CX4;x2;r5:3]@[!#1;r{5-8}:4][C^2,a]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[CX4;x3;r{5-8}:2]@;-[CX4;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1]1@[!#1;R1;r5:1]@[CX4;R2;r5:2]@;-[CX4;R2;r5:3]@[!#1;R1;r5:4]1", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[C^2,a;r{5-8}][C^2,a;r{5-8}:1]@[CX4;r{5-8}:2]@;-[CX4;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r5:1]@[CX4;r5:2]@;-[CX4;r5:3]@[!#1;r5:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[C^2,c,x4;r{5-8}:1]@[CX4;r{5-8}:2]@;-[CX4;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-8}:2]@;-[CX4;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C;r{5-8}:2]@;-[C;r{5-8}:3]@[!#1;r{5-8}:4]", [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C;r5:2]@;-[a;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 15.0]),
    ("[!#1;r{5-8}:1]@[C;r{5-6}:2]@;-[a;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C;r{5-8}:2]@;-[a;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0]),
    ("[a;r5:1]@[c;r5:2]@;-[N;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[a;r{5-6}:1]@[c;r{5-6}:2]@;-[N;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[a;r{5-8}:1]@[c;r{5-8}:2]@;-[N;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C^2;r{5-8}:2]@;-[N;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C;r{5-8}:2]@;-[NX2;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[CX4;r5:2]@;-[ND3;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[ND3;r{5-6}:3]@[C;r{5-8}:4]=O", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0]),
    ("[C^2,c,r5;r{5-8}:1]@[CX4;r{5-6}:2]@;-[ND3;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[ND3;r{5-6}:3]@[!#1;r{5-8}:4]@[C^2,c,r5;r{5-8}]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[ND3;r{5-6}:3]@[!#1;!#6;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[ND3;r{5-6}:3]@[C^2,c;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[ND3;r{5-6}:3]([C^2,c])[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[ND3;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-8}:2]@;-[ND3;r{5-8}:3]@[C;r{5-8}:4]=O", [1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-8}:2]@;-[ND3;r{5-8}:3](C=O)[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-8}:2]@;-[ND3;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-8}:2]@;-[N;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[C;r{5-8}:2]@;-[N;r{5-8}:3]@[!#1;r{5-8}:4]", [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C^2,c;r{5-8}:2]@;-[O;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r5:2]@;-[O;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[O;r{5-6}:3]@[C^2,c;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[O;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C;r{5-8}:2]@;-[O;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[C^2,c;r{5-8}:2]@;-[S;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r5:2]@;-[S;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-6}:2]@;-[S;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[CX4;r{5-8}:2]@;-[S;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[C;r{5-8}:2]@;-[S;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[NX2;r{5-8}:2]@;-[N;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1^2,a;r{5-8}:1]@[N;r{5-6}:2]@;-[N;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 3.0]),
    ("[!#1;R2,R3;r{5-8}:1]@[N;r{5-6}:2]@;-[N;r{5-6}:3]@[!#1;R2,R3;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[N;r5:2]@;-[N;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r{5-6}:2]@;-[N;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r{5-8}:2]@;-[N;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r{5-6}:2]@;-[a;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r{5-8}:2]@;-[a;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[NX2;r{5-8}:2]@;-[O;r{5-8}:3]@[!#1;r{5-8}:4]", [-1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;R2,R3;r{5-8}:1]@[N;r{5-6}:2]@;-[O;r{5-6}:3]@[!#1;R2,R3;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@[N;r5:2]@;-[O;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 3.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r{5-6}:2]@;-[O;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r{5-8}:2]@;-[O;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[NX2;r{5-8}:2]@;-[S;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r5:2]@;-[S;r5:3]@[!#1;r{5-8}:4]", [-1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r{5-6}:2]@;-[S;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[N;r{5-8}:2]@;-[S;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 5.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[O;r{5-8}:2]@;-[O;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 3.0]),
    ("[!#1;r{5-8}:1]@[O;r{5-8}:2]@;-[S;r{5-8}:3]@;=,:[!#1;r{5-8}:4]", [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[O;r5:2]@;-[S;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[O;r{5-6}:2]@;-[S;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[O;r{5-8}:2]@;-[S;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 10.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[O;r{5-6}:2]@;-[a;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[O;r{5-8}:2]@;-[a;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[S;r5:2]@;-[S;r5:3]@[!#1;r{5-8}:4]", [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[S;r{5-6}:2]@;-[S;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[S;r{5-8}:2]@;-[S;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[S;r5:2]@;-[a;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[S;r{5-6}:2]@;-[a;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[S;r{5-8}:2]@;-[a;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-8}:2]@;-[C^2,c;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r5:2]@;-[CX4;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-6}:2]@;-[CX4;r{5-6}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-8}:2]@;-[C;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-8}:2]@;-[NX2;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-8}:2]@;-[N;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@;=[P;r{5-8}:2]@;-[O;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 20.0]),
    ("[!#1;r{5-8}:1]@[P;r5:2]@;-[O;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-6}:2]@;-[O;r{5-6}:3]@[!#1;r{5-8}:4]", [-1.0, 10.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-8}:2]@;-[O;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r5:2]@;-[S,P;r5:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-6}:2]@;-[S,P;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-8}:2]@;-[S,P;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 5.0]),
    ("[!#1;r{5-8}:1]@[P;r{5-8}:2]@;-[a;r{5-8}:3]@[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 10.0]),
    ("[!#1;r{5-8}:1]@;~[A;r{5-8}:2]@;-[A,a;r{5-8}:3]@;~[!#1;r{5-8}:4]", [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 20.0]),
];

/// Macrocycle torsion preferences (367 patterns)
pub const TORSION_PREFS_MACROCYCLES: &[(&str, [f32; 12])] = &[
    (
        "[C:1][C;r{9-}:2](=O)@;-[NX3H0;r:3][CX4H1:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][C;r{9-}:2](=O)@;-[NX3H1;r:3][CX4H1:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][C;r{9-}:2](=O)@;-[NX3H0;r:3][CX4H2:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]@;-[O;r{9-}:3]~[CH0:4]",
        [-1.0, 78.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([N])@;-[O;r{9-}:3]~[C:4]",
        [-1.0, 79.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]@;-[O;r{9-}:3]~[C:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[O:1]=[C;r{9-}:2]@;-[O;r{9-}:3]~[!#1:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[$(C=O):1][O;r{9-}:2]@;-[c;r{9-}:3]~[*:4]",
        [1.0, 0.0, 1.0, 0.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][O;r{9-}:2]@;-[CX3;r{9-}:3]~[*:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][O;r{9-}:2]@;-[CH1;r{9-}:3][H:4]",
        [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][O;r{9-}:2]@;-[CH2;r{9-}:3]~[C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[H:1][CX4H1;r{9-}:2]@;-[O;r{9-}:3][CX4:4]",
        [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CH2;r{9-}:2]@;-[O;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][CX4;r{9-}:2]@;-[O;r{9-}:3][$([CX3](=[!O])):4]",
        [1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1][CX4;r{9-}:2]@;-[O;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 8.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][CX4;r{9-}:2]@;-[O;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[O;r{9-}:3][S:4]",
        [1.0, 0.0, 1.0, 3.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][S:4]",
        [1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][S:4]",
        [1.0, 0.0, 1.0, 11.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[O;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 2.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][P:4]",
        [1.0, 0.0, 1.0, 2.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][p:4]",
        [1.0, 0.0, 1.0, 11.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH:1][c;r{9-}:2]([cH])@;-[O;r{9-}:3][$(C([F])([F])[F]):4]",
        [1.0, 0.0, 1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][CX4H0:4]",
        [1.0, 0.0, 1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]([a])@;-[O;r{9-}:3][CX4H0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1,n:1][c;r{9-}:2]@;-[O;r{9-}:3][CRH1:4]",
        [1.0, 0.0, -1.0, 5.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1,n:1][c;r{9-}:2]@;-[O;r{9-}:3][CH1:4]",
        [1.0, 0.0, -1.0, 7.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][CX4H0:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[cH0:1][c;r{9-}:2]([nX2])@;-[O;r{9-}:3][C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2:1][c;r{9-}:2]([nX2])@;-[O;r{9-}:3][C:4]",
        [1.0, 0.0, -1.0, 44.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2:1][c;r{9-}:2]([nX3])@;-[O;r{9-}:3][C:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[cH1:1][c;r{9-}:2]([nX3])@;-[O;r{9-}:3][C:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[cH1:1][c;r{9-}:2]([nX2])@;-[O;r{9-}:3][C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]([CX3])):1][c;r{9-}:2]([cH1])@;-[O;r{9-}:3][C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2](cO)@;-[O;r{9-}:3][C:4]",
        [-1.0, 61.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(cO):1][c;r{9-}:2](cO)@;-[O;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[O;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 6.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH1])@;-[O;r{9-}:3][C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[O;r{9-}:3][C:4]",
        [1.0, 0.0, -1.0, 19.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[O;r{9-}:3][CX3H0:4]",
        [1.0, 0.0, 1.0, 1.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH0:1][c;r{9-}:2]@;-[OX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, -1.0, 7.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H0;r{9-}:2]@;-[OX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[H:1][CX4H1;r{9-}:2]@;-[OX2;r{9-}:3][!#1:4]",
        [-1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][!#1:4]",
        [1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2;r{9-}:2]@;-[OX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4;r{9-}:2]@;-[OX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]=O):1][NX3H0;r{9-}:2](C)@;-[CX4H2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]=O):1][NX3H1;r{9-}:2]@;-[CX4H2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NX3H0;r{9-}:2]@;-[CX4H2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 1.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NX3H1;r{9-}:2]@;-[CX4H2;r{9-}:3][!#1:4]",
        [
            1.0, 17.9, -1.0, -13.3, 1.0, 9.2, 1.0, 4.7, -1.0, -2.3, -1.0, -0.9,
        ],
    ),
    (
        "[$(S(=O)(=O)):1][NX3H0;r{9-}:2]@;-[CX4H1;r{9-}:3][H:4]",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NX3H1;r{9-}:2]@;-[CX4H1;r{9-}:3][H:4]",
        [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH1;r{9-}:2]@;-[c;r{9-}:3][nX2:4]",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH0;r{9-}:2]@;-[c;r{9-}:3]([cH1])[cH1:4]",
        [1.0, 0.0, 1.0, 13.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH1;r{9-}:2]@;-[c;r{9-}:3]([cH1])[cH1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.9, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH0;r{9-}:2]@;-[c;r{9-}:3]([cH1])[cH0:4]",
        [1.0, 0.0, 1.0, 50.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH1;r{9-}:2]@;-[c;r{9-}:3]([cH1])[cH0:4]",
        [1.0, 1.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH0;r{9-}:2]@;-[c;r{9-}:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 17.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][NH1;r{9-}:2]@;-[c;r{9-}:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 10.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(S(=O)(=O)):1][N;r{9-}:2]@;-[c;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O-:1][N+;r{9-}:2](=O)@;-[c;r{9-}:3]([cH,nX2H0])[cH,nX2H0:4]",
        [1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O-:1][N+;r{9-}:2](=O)@;-[c;r{9-}:3]([cH0])[cH,nX2H0:4]",
        [
            -1.0, -0.2, 1.0, -5.7, 1.0, -0.2, -1.0, -3.2, 1.0, 0.1, 1.0, -1.3,
        ],
    ),
    (
        "[O-:1][N+;r{9-}:2](=O)@;-[c;r{9-}:3]([cH0])[cH0:4]",
        [
            -1.0, -0.4, 1.0, 0.3, 1.0, -0.1, -1.0, 0.6, 1.0, -0.1, -1.0, 0.2,
        ],
    ),
    (
        "[O-:1][N+;r{9-}:2](=O)@;-[c;r{9-}:3][a:4]",
        [1.0, 0.0, -1.0, 11.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[NX3H1;r{9-}:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, 1.0, 2.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH1])@;-[NX3H1;r{9-}:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([nX2H0])@;-[NX3H1;r{9-}:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 40.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[NX3H1;r{9-}:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, -1.0, 1.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c;r{9-}:2]([nX2H0])@;-[NX3H1;r{9-}:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c;r{9-}:2]([nX3H1])@;-[NX3H1;r{9-}:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, -1.0, 27.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a;r{9-}:2]@;-[NH1;r{9-}:3][C,c:4](~[N,n])(~[N,n])",
        [1.0, 0.0, -1.0, 6.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][NH;r{9-}:2]@;-[C;r{9-}:3](=[NH2:4])[NH2]",
        [
            1.0, 0.0, -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[NH2][C:1](=[NH2])[NH;r{9-}:2]@;-[CH2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[NX2;r{9-}:3]=[$(C([NX3])n):4]",
        [
            -1.0, -0.1, 1.0, 1.9, -1.0, -0.1, -1.0, -1.9, -1.0, 0.1, 1.0, 0.0,
        ],
    ),
    (
        "[nX2:1][c;r{9-}:2]@;-[NX2;r{9-}:3]=[$(C([NX3])N):4]",
        [1.0, 0.0, -1.0, 6.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[NX2;r{9-}:3]=[$(C([NX3])N):4]",
        [
            -1.0, -0.1, 1.0, 1.9, -1.0, -0.1, -1.0, -1.9, -1.0, 0.1, 1.0, 0.0,
        ],
    ),
    (
        "[cH1:1][c;r{9-}:2]@;-[NX2;r{9-}:3]=[$(C([NX3])N):4]",
        [
            1.0, -0.4, -1.0, -0.9, 1.0, -0.4, 1.0, 1.1, 1.0, -0.2, 1.0, -0.1,
        ],
    ),
    (
        "[O:1]=[C;r{9-}:2]([NH1])@;-[NX3H1;r{9-}:3](C=O)[H:4]",
        [
            -1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0,
        ],
    ),
    (
        "[O:1]=[C;r{9-}:2]@;-[NX3H1;r{9-}:3](C=O)[H:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]@;-[NX3;r{9-}:3](C=O)[*:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX3;r{9-}:3]=[NX2:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[CX3;r{9-}:3]=[*H0:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[CX3;r{9-}:3]=[*H1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX3;r{9-}:3]=[*H2:4]",
        [1.0, 0.0, -1.0, 68.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX3;r{9-}:3]=[*H1:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX3;r{9-}:3]=[*H0:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[CX3H1;r{9-}:3]=[*:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX3H1;r{9-}:3]=[*:4]",
        [1.0, 84.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)):1][NX3H0;r{9-}:2]@;-[CX4H2;r{9-}:3][$([c]([cH,nX2H0])[cH,nX2H0]):4]",
        [1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX4H2;r{9-}:3][$([c]([cH,nX2H0])[cH,nX2H0]):4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[CX4H2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX4H2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[CX4H1;r{9-}:3][H:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX4H1;r{9-}:3][H:4]",
        [-1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[CX4H0;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[CX4H0;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3;r{9-}:2]@;-[!#1;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.8, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)([$([NX3H1]),$([NX3H2])])[NX3H1]):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([nH1])[nH0:4]",
        [1.0, 84.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)([$([NX3H1]),$([NX3H2])])[NX3H1]):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([nH0])[cH1:4]",
        [1.0, 84.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)):1][NX3H1;r{9-}:2]@;-[$([a]([nH0,o]));r{9-}:3][cH1:4]",
        [-1.0, 53.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)([$([NX3H1]),$([NX3H2])])[NX3H1]):1][NX3H1;r{9-}:2]@;-[c&r6;r{9-}:3][nH0&r6:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([cH])[nX2H0:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[c;r{9-}:3]([s,o])[n:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([s,o])[n:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([C](=O)):1][NX3;r{9-}:2]@;-[a;r{9-}:3](s)[a:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3;r{9-}:2]@;-[a;r{9-}:3][nH:4]",
        [-1.0, 53.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([cH0]Cl)[cH:4]",
        [-1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([cH0]F)[cH:4]",
        [-1.0, 11.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3;r{9-}:2]@;-[$([a]([cH1]));r{9-}:3][$([aH0](!@O)):4]",
        [1.0, 38.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3;r{9-}:2]@;-[a;r{9-}:3][aH0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([cH1])[cH1:4]",
        [1.0, 0.0, -1.0, 2.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[c;r{9-}:3]([cH1])[cH1:4]",
        [1.0, 0.0, 1.0, 2.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[c;r{9-}:3]([cH0])[cH:4]",
        [1.0, 0.0, 1.0, 2.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([cH0])[cH:4]",
        [-1.0, 9.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H0;r{9-}:2]@;-[c;r{9-}:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 2.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(C=O):1][NX3H1;r{9-}:2]@;-[c;r{9-}:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 2.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O,S:1]=[C;r{9-}:2]([$([NX3H1]),$([NX3H2])])@;-[$([NX3]c[nH0]);r{9-}:3][H:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]@;-[$([NX3](c([nH1])n));r{9-}:3][H:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2](c)@;-[$([NX3](c([nX2H0])([nX2H0])));r{9-}:3][H:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2]([$([NX3H1]C)])@;-[NX3H1;r{9-}:3][!#1:4]",
        [-1.0, 51.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([!$([NH1])])@;-[NX3H1;r{9-}:3]([H:4])[$(c([nX2H0])([nX2H0]))]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O,S:1]=[C;r{9-}:2]([$([NX3H1]),$([NX3H2])])@;-[$([NX3](cn));r{9-}:3][H:4]",
        [1.0, 0.0, -1.0, 50.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]@;-[NX3H0;r{9-}:3]([a:4])[A]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2](a)@;-[NX3H0;r{9-}:3][!#1:4]",
        [1.0, 0.0, -1.0, 13.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2]@;-[NX3H0;r{9-}:3][!#1:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2]@;-[NX3H1;r{9-}:3][!#1:4]",
        [
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        ],
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    (
        "[CH0:1][NX3;r{9-}:2]([CH0])@;-[c;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CH0:1][NX3;r{9-}:2]([CH1])@;-[c;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 1.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1,nX2H0:1][c;r{9-}:2]([cH1,nX2H0])@;-[NX3&r;r{9-}:3][*:4]",
        [1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[NX3H1;r{9-}:3][$([CX4&r]([C;r])([C;r])):4]",
        [1.0, 0.0, -1.0, 6.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[NX3;r{9-}:3][CX4:4]",
        [1.0, 0.0, -1.0, 6.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH,nX2H0])@;-[NX3H1;r{9-}:3][CX4:4]",
        [1.0, 73.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH,nX2H0])@;-[NX3H0;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[NX3;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c;r{9-}:2](c)@;-[NX3;r{9-}:3][CX4:4]",
        [
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    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[NX3;r{9-}:3][a:4]",
        [1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH0])@;-[NX3;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
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    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[NX3;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 1.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][a;r{9-}:2]@;-[NX3H0;r{9-}:3][$([CX3]=O):4]",
        [1.0, 0.0, 1.0, 2.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][a;r{9-}:2]@;-[NX3H1;r{9-}:3][$([CX3]=O):4]",
        [
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    (
        "[nX2H0:1][a;r{9-}:2]([nX2H0])@;-[NX3H0;r{9-}:3][$([CX3]=O):4]",
        [1.0, 72.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][$(a([!nX2H0])([nX2H0])@;-[NX3H1]);r{9-}:2]!@[NX3H1;r{9-}:3][$([CX3](a)=O):4]",
        [1.0, 72.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][a;r{9-}:2]@;-[NX3H1;r{9-}:3][$([CX3]=O):4]",
        [1.0, 0.0, -1.0, 34.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
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    (
        "[a:1][a;r{9-}:2]@;-[NX3H1;r{9-}:3][$([CX3]=O):4]",
        [1.0, 0.0, -1.0, 3.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
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    (
        "[a:1][a;r{9-}:2]@;-[NX3;r{9-}:3][CX4H0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a;r{9-}:2]@;-[NX3;r{9-}:3][!#1:4]",
        [
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    ),
    (
        "[O:1]=[CX3;r{9-}:2]@;-[nX3;r{9-}:3]([aH0:4])([aH0])",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
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    (
        "[O:1]=[CX3;r{9-}:2]@;-[nX3;r{9-}:3][aH1:4]",
        [1.0, 0.0, -1.0, 18.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][CX3;r{9-}:2](=S)@;-[NX3;r{9-}:3][a:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX3;r{9-}:2](=S)@;-[NX3H0;r{9-}:3][!#1:4]",
        [1.0, 0.0, -1.0, 22.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX3;r{9-}:2](=S)@;-[NX3H1;r{9-}:3][!#1:4]",
        [1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CH2;r{9-}:2]@;-[n;r{9-}:3][cH0:4]",
        [1.0, 0.0, 1.0, 6.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CH2;r{9-}:2]@;-[n;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][n;r{9-}:2]@;-[CX3H0;r{9-}:3]~[$([n,N](-a)):4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX4:1][CX4H2;r{9-}:2]@;-[NX3;r{9-}:3][CX4:4]",
        [1.0, 4.0, 1.0, 3.1, 1.0, 3.9, -1.0, -0.8, 1.0, 0.0, 1.0, 0.7],
    ),
    (
        "[C:1][CX4H2;r{9-}:2]@;-[NX3;r{9-}:3][C:4]",
        [1.0, 4.0, 1.0, 3.1, 1.0, 3.9, -1.0, -0.8, 1.0, 0.0, 1.0, 0.7],
    ),
    (
        "[C:1][CX4;r{9-}:2]@;-[NX3;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2;r{9-}:2]@;-[NX3H1;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2;r{9-}:2]@;-[NX3;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H1;r{9-}:2]@;-[NX3;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4;r{9-}:2]@;-[NX3;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][$(S(=O)=O);r{9-}:2]@;-[nX3;r{9-}:3]([aH1])[aH1:4]",
        [1.0, 0.0, 1.0, 20.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][$(S(=O)=O);r{9-}:2]@;-[nX3;r{9-}:3][aH0:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][S;r{9-}:2](=O)(=O)@;-[NX2H0-;r{9-}:3]-[*:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][$(S(=O)=O);r{9-}:2]@;-[NX3H0&r;r{9-}:3][*:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][$(S(=O)=O);r{9-}:2]@;-[NX3H1;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][$(S(=O)=O);r{9-}:2]@;-[NX3H0;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][$(S(=O)=O);r{9-}:2]@;-[NX3H1;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][$(S(=O)=O);r{9-}:2]@;-[NX3H0;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][$(S(=O)=O);r{9-}:2]@;-[NX3H1;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][$(S(=O)=O);r{9-}:2]@;-[NX3H0;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 4.1, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][$(S(=O)=O);r{9-}:2]@;-[NX3H1;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][$(S(=O)=O);r{9-}:2]@;-[NX3H0;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][$(S(=O)=O);r{9-}:2]@;-[NX3H1;r{9-}:3][*:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][$(S(=O)=O);r{9-}:2]@;-[NX3H0;r{9-}:3][*:4]",
        [1.0, 0.0, 1.0, 3.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX3;r{9-}:2]@;-[SX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, -1.0, 2.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4;r{9-}:2]@;-[SX2;r{9-}:3][!#1:4]",
        [
            -1.0, -0.8, -1.0, -0.8, -1.0, -1.5, -1.0, 0.4, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[!#1:1][CX3;r{9-}:2]@;-[SX3;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 16.0, 1.0, 5.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4;r{9-}:2]@;-[SX3;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 10.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX3;r{9-}:2]@;-[SX4;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 3.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[H:1][CX4H1;r{9-}:2]@;-[SX4;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4;r{9-}:2]@;-[SX4;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH1:1][c;r{9-}:2]([aH1])@;-[SX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH1:1][c;r{9-}:2]([aH0])@;-[SX2;r{9-}:3][*R:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH1:1][c;r{9-}:2]([aH0])@;-[SX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.9, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH0:1][c;r{9-}:2]([aH0])@;-[SX2;r{9-}:3][!#1:4]",
        [
            1.0, -0.2, 1.0, 0.4, 1.0, 0.0, -1.0, 1.9, 1.0, 0.0, 1.0, -1.1,
        ],
    ),
    (
        "[!#1:1][c;r{9-}:2]@;-[SX2;r{9-}:3][!#1:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][c;r{9-}:2]@;-[SX3;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 1.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH1:1][c;r{9-}:2]([aH1])@;-[SX4;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH0:1][c;r{9-}:2]([aH1])@;-[SX4;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[aH0:1][c;r{9-}:2]([aH0])@;-[SX4;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 3.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2]([NH1])@;-[CH2;r{9-}:3][CX3:4]=O",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2]([NH1])@;-[CH2;r{9-}:3][C:4]",
        [-1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]([C])([H])):1]=[CX3;r{9-}:2]([C])@;-[CH2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]([C])([H])):1]=[CX3;r{9-}:2]([H])@;-[CH1;r{9-}:3](C)[C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([CX3]([C])([H])):1]=[CX3;r{9-}:2]([H])@;-[CH2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[N:1][C;r{9-}:2](=O)@;-[CX4H2;r{9-}:3][CX4H2:4]",
        [1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "N[C;r{9-}:2](=[O:1])@;-[CH2;r{9-}:3][N:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[CX4H1;r{9-}:3][H:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H2:1]=[CX3;r{9-}:2]@;-[CX3;r{9-}:3]=[C:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3;r{9-}:2]@;-[CH2;r{9-}:3][OX2:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3;r{9-}:2]@;-[CH1;r{9-}:3](C)[C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3;r{9-}:2]@;-[CH2;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3;r{9-}:2]@;-[CH2;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3;r{9-}:2]@;-[CH2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2](O)@;-[CX3;r{9-}:3]([$([NH1,NH2,CH2])])=[O:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3R:1]=[CX3R;r{9-}:2]@;-[CX3;r{9-}:3]=[CX3:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H0:1]=[CX3H0;r{9-}:2]@;-[CX3;r{9-}:3]=[CX3H0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H0:1]=[CX3H0;r{9-}:2]@;-[CX3H0;r{9-}:3]=[CX3:4]",
        [1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H0:1]=[CX3;r{9-}:2]@;-[CX3H0;r{9-}:3]=[CX3:4]",
        [1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3H0:1]=[CX3H0;r{9-}:2]@;-[CX3;r{9-}:3]=[CX3:4]",
        [1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[CX3:1]=[CX3;r{9-}:2]@;-[CX3;r{9-}:3]=[CX3:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*^2:1]~[C^2;r{9-}:2]([!H])@;-[C^2;r{9-}:3]~[*^2:4]",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*^2:1]~[C^2;r{9-}:2]@;-[C^2;r{9-}:3]~[*^2:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[CX3;r{9-}:2]@;-[CX4&r3;r{9-}:3]!@[!#1:4]",
        [
            -1.0, -0.7, -1.0, 0.5, 1.0, -0.3, -1.0, 0.3, -1.0, -0.2, -1.0, 0.2,
        ],
    ),
    (
        "[O:1]=[CX3;r{9-}:2]@;-[CX4H1&r3;r{9-}:3][H:4]",
        [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4H2;r{9-}:2]@;-[CX4H2;r{9-}:3][N&r:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4H2;r{9-}:2]@;-[CX4H2;r{9-}:3][N:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4;r{9-}:2]@;-[CX4;r{9-}:3][N:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4H2;r{9-}:2]@;-[CX4H2;r{9-}:3][OX2:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4;r{9-}:2]@;-[CX4;r{9-}:3][OX2:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4&r;r{9-}:2]@;-[CX4&r;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2;r{9-}:2]@;-[CX4H2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4;r{9-}:2]@;-[CX4;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 7.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OX2:1][CX4H2;r{9-}:2]@;-[CX3;r{9-}:3]([$([NX3H1,NX3H2])])=[O:4]",
        [1.0, 0.0, -1.0, 39.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[OH1:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[NH1:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[N:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 1.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4H2;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [
            1.0, -1.0, 1.0, -0.5, 1.0, -0.2, 1.0, -0.3, 1.0, 0.0, 1.0, -0.3,
        ],
    ),
    (
        "[c:1][CX4H2;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [
            -1.0, 0.9, 1.0, -0.3, 1.0, -0.2, 1.0, -0.5, -1.0, 0.1, 1.0, 0.2,
        ],
    ),
    (
        "[!#1:1][CX4H2;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [
            1.0, 0.0, 1.0, -0.7, 1.0, 0.0, 1.0, -0.5, 1.0, 0.0, 1.0, -0.6,
        ],
    ),
    (
        "[c:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, 1.0, 0.0, -1.0, 1.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[C:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3][c:4]",
        [
            -1.0, -4.4, 1.0, 4.0, -1.0, -3.9, -1.0, -1.0, 1.0, 0.6, -1.0, -0.4,
        ],
    ),
    (
        "[C:1][CX4;r{9-}:2]@;-[CX3;r{9-}:3][C:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4;r{9-}:2]@;-[CX3H0;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[H:1][CX4H1;r{9-}:2]@;-[CX3;r{9-}:3][!#1:4]",
        [1.0, 0.0, -1.0, 1.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[!#1:1][CX4H2;r{9-}:2]@;-[CX3;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.8, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]([$([NX3H2]),$([NX3H1])])):1][a;r{9-}:2]@;-[a;r{9-}:3][nX2:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nH0:1][c&r6;r{9-}:2]([nH0])@;-[c&r6;r{9-}:3]([nH0])[nH0:4]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nH0&r6:1][c&r6;r{9-}:2]([nH0&r6])@;-[c&r6;r{9-}:3]([cH1&r6])[nH0&r6:4]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nH0&r6:1][c&r6;r{9-}:2]([nH0&r6])@;-[c&r6;r{9-}:3]([cH1&r6])[cH1&r6:4]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c;r{9-}:2]@;-[c;r{9-}:3][$(c!@c):4]",
        [
            1.0, 0.1, 1.0, 0.9, 1.0, 0.1, -1.0, -0.4, 1.0, 0.0, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[c;r{9-}:3]([cH0:4])[cH0]",
        [1.0, 0.0, 1.0, 3.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[c;r{9-}:3]([cH0:4])[cH1]",
        [1.0, 0.0, 1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH1])@;-[c;r{9-}:3]([cH0:4])[cH1]",
        [1.0, 0.0, 1.0, 3.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[c;r{9-}:3]([cH1:4])[cH1]",
        [1.0, 0.0, 1.0, 3.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH1])@;-[c;r{9-}:3]([cH1:4])[cH1]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.6, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[c;r{9-}:3]([cH1:4])[cH1]",
        [
            -1.0, -0.7, 1.0, -8.0, 1.0, 0.0, 1.0, 4.4, 1.0, 0.0, 1.0, -1.5,
        ],
    ),
    (
        "[nX2H0:1][c;r{9-}:2]@;-[c;r{9-}:3][nX3H1:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c;r{9-}:2]([!nX2H0])@;-[c;r{9-}:3]([!nX2H0])[nX2H0:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][$(c([nX2H0])(a(a)(a))@;-c[nX2H0]);r{9-}:2]!@[c;r{9-}:3][nX2H0:4]",
        [1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][$([c&r6](c[OH]));r{9-}:2]@;-[$([c&r6](c[OH]));r{9-}:3][nX2H0:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c;r{9-}:2]@;-[c;r{9-}:3][s,o,nX3H1:4]",
        [1.0, 0.0, -1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[c;r{9-}:3][nX2H0:4]",
        [1.0, 0.0, 1.0, 1.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[c;r{9-}:3]([cH0])[nX2H0:4]",
        [
            -1.0, 0.9, -1.0, -1.0, 1.0, -0.8, -1.0, 0.2, -1.0, 0.3, 1.0, -0.2,
        ],
    ),
    (
        "[c:1][c;r{9-}:2]@;-[c;r{9-}:3]([cH0])[nX2H0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.1, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c;r{9-}:2]([cH0])@;-[c;r{9-}:3][nX2H0:4]",
        [1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]@;-[c;r{9-}:3]([cH1])[nX2H0:4]",
        [1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c&r5;r{9-}:2]@;-[c&r5;r{9-}:3][c:4]",
        [1.0, 0.0, -1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c&r6;r{9-}:2]@;-[c&r5;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.1, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c&r6;r{9-}:2]@;-[c&r6;r{9-}:3][cH0:4]",
        [1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c&r6;r{9-}:2]@;-[c&r6;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.1, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[c:1][c;r{9-}:2]@;-[c;r{9-}:3][c:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.1, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2&r6:1][cH0&r6;r{9-}:2]([cH1&r6])@;-[CX4H2;r{9-}:3][O!H:4]",
        [1.0, 2.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][N,O,S:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][CX3:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 12.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][*:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][a:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][CX3:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[CX4H2;r{9-}:3][$([CX4H1]C(=O)O):4]",
        [1.0, 0.0, 1.0, 4.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[CX4H2;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 3.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][CX4:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][N,O,S:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][!#1:4]",
        [
            -1.0, -1.3, 1.0, 1.6, -1.0, -0.6, -1.0, 0.6, 1.0, -0.1, -1.0, 0.3,
        ],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H1;r{9-}:3][a:4]",
        [1.0, 0.9, 1.0, 1.2, 1.0, 0.6, 1.0, 0.4, 1.0, 0.0, 1.0, 0.1],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H1;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 1.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H1;r{9-}:3][CX3:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H1;r{9-}:3][N,O,S:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]@;-[CX4H1;r{9-}:3][H:4]",
        [1.0, 0.0, -1.0, 4.3, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][a:4]",
        [
            1.0, 0.0, -1.0, -0.3, -1.0, -0.1, 1.0, 0.1, 1.0, 0.0, -1.0, 0.1,
        ],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][CX3:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 0.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H0;r{9-}:3][N,O:4]",
        [1.0, 0.0, -1.0, 0.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 1.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][CX3:4]",
        [1.0, 0.0, 1.0, 1.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[n,o,s:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][CX4:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H2;r{9-}:3][!#1:4]",
        [1.0, 0.0, 1.0, 3.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H1;r{9-}:3][N,O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H1;r{9-}:3][a:4]",
        [1.0, 0.0, 1.0, 0.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX4H1;r{9-}:3][H:4]",
        [1.0, 0.0, -1.0, 0.7, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c;r{9-}:2]@;-[C;r{9-}:3](=[N:4])(-[NH1,NH2])",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[C;r{9-}:3](=[$([N][CX4]):4])([$(N[CX4])])",
        [1.0, 0.0, -1.0, 0.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[C;r{9-}:3](=[$([NH0][CX4]):4])(-N)",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[C;r{9-}:3](=[$([N][!#1]):4])([$(N(C)[!#1])])",
        [
            1.0, 0.0, -1.0, 0.6, 1.0, 0.0, 1.0, 0.3, 1.0, 0.0, -1.0, -0.1,
        ],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[C;r{9-}:3](=[$([N][!#1]):4])([$(N(C)~[!#1])])",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[C;r{9-}:3](=[N:4])(-N)",
        [
            1.0, 0.0, -1.0, 0.6, 1.0, 0.0, 1.0, 0.3, 1.0, 0.0, -1.0, -0.1,
        ],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[c;r{9-}:3][$(aC(=O)(O)):4]",
        [1.0, 0.0, -1.0, 0.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[c;r{9-}:3][nX3H1:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[c;r{9-}:3][nX2H0:4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[c;r{9-}:3]([cH0])[cH0:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[c;r{9-}:3]([cH1])[$([cH0][NH1,NH2]):4]",
        [1.0, 0.0, -1.0, 30.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[c;r{9-}:3]([cH1])[cH0:4]",
        [1.0, 0.0, -1.0, 7.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[c;r{9-}:3]([cH1])[cH1:4]",
        [1.0, 0.0, -1.0, 7.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[O:1]=[C;r{9-}:2]([O-])@;-[c;r{9-}:3][a:4]",
        [1.0, 0.0, -1.0, 25.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([c]([NH1,NH2])):1][c;r{9-}:2]@;-[CX3;r{9-}:3]([!O])=[O:4]",
        [-1.0, 14.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(a[OH1]):1][a;r{9-}:2]@;-[CX3;r{9-}:3]([NX3H0,CX4H0,c])=[O:4]",
        [-1.0, 14.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$(a[NH1,NH2]):1][a;r{9-}:2]@;-[CX3;r{9-}:3]([NX3H0,CX4H0,c])=[O:4]",
        [-1.0, 36.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3](c)=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 1.5, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3](c)=[O:4]",
        [
            -1.0, -0.1, -1.0, 2.4, 1.0, -0.4, -1.0, -1.0, 1.0, 0.1, -1.0, -0.5,
        ],
    ),
    (
        "[a:1][a;r{9-}:2]@;-[CX3;r{9-}:3](a)=[O:4]",
        [-1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](=O)):1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]([NX3H1,NX3H2])=[O:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nH0&r6:1][c&r6;r{9-}:2]([cH1&r6])@;-[C;r{9-}:3]([NH1,NH2])=[O:4]",
        [1.0, 20.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[s:1][c;r{9-}:2]@;-[C;r{9-}:3]([NH1])=[O:4]",
        [1.0, 0.0, -1.0, 36.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]Cl):1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]([NX3H1])=[O:4]",
        [
            1.0, 0.1, 1.0, 0.9, 1.0, 0.1, -1.0, -0.4, 1.0, 0.0, -1.0, 0.3,
        ],
    ),
    (
        "[$([cH0]F):1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]([NX3H1])=[O:4]",
        [1.0, 6.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0][OH0]):1][c;r{9-}:2]([cH1])@;-[C;r{9-}:3](=O)[NH1:4]",
        [-1.0, 60.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0][OH1]):1][c;r{9-}:2]([cH1])@;-[C;r{9-}:3](=O)[NH1:4]",
        [1.0, 0.0, -1.0, 15.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]([NX3H1])=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 1.2],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]([NX3H0])=[O:4]",
        [1.0, 0.0, 1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[C;r{9-}:3]([NH1,NH2])=[O:4]",
        [1.0, 0.0, -1.0, 1.6, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[C;r{9-}:3]([NH0])=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 1.2],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[C;r{9-}:3]([NH1,NH2])=[O:4]",
        [1.0, 0.0, -1.0, 2.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[s:1][c;r{9-}:2]([aX2,cH1])@;-[CX3;r{9-}:3](O)=[O:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[s:1][c;r{9-}:2]([aX2,cH1])@;-[CX3;r{9-}:3]=[O:4]",
        [-1.0, 60.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](F)):1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]([O,N])=[O:4]",
        [1.0, 0.0, -1.0, 1.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]F):1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 6.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](Cl)):1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]([CX3H])=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 2.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](Cl)):1][c;r{9-}:2]([cH1])@;-[CX3H;r{9-}:3]=[O:4]",
        [1.0, 6.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0](Cl)):1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3](O)=[O:4]",
        [1.0, 0.0, -1.0, 1.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX3H1:1][a;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][c;r{9-}:2]([cH1])@;-[CX3H1;r{9-}:3]=[O:4]",
        [1.0, 66.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0&r6:1][c&r6;r{9-}:2]([c&r6])@;-[CX3;r{9-}:3]([!O])=[O:4]",
        [1.0, 6.2, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[nX2H0:1][a;r{9-}:2]([nX2H0])@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 36.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[$([cH0]@;-[*^2]):1][c;r{9-}:2]([cH1])!@[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 10.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, 1.0, 0.0, 1.0, 0.0, -1.0, 3.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]([CX3H0])=[O:4]",
        [1.0, 0.0, -1.0, 5.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a;r{9-}:2]@;-[CX3;r{9-}:3]=[O:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([nX2])@;-[CX3;r{9-}:3]=[NX3:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([nX3H1])@;-[CX3;r{9-}:3]=[NX2:4]",
        [1.0, 97.4, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([nX2])@;-[CX3;r{9-}:3]=[NX2:4]",
        [1.0, 0.0, -1.0, 8.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([$([cH0][OH1])])@;-[CX3;r{9-}:3]=[NX2:4]",
        [1.0, 100.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH0])@;-[CX3x0;r{9-}:3]=[NX2:4]",
        [1.0, 0.0, -1.0, 36.8, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH1:1][c;r{9-}:2]([cH1])@;-[CX3;r{9-}:3]=[NX2:4]",
        [1.0, 0.0, -1.0, 9.5, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[cH0:1][c;r{9-}:2]([cH0])@;-[CX3!r;r{9-}:3]=[NX2!r:4]",
        [
            1.0, 0.0, 1.0, -0.7, 1.0, 0.0, 1.0, -0.5, 1.0, 0.0, 1.0, -0.6,
        ],
    ),
    (
        "[a:1][c;r{9-}:2]@;-[CX3;r{9-}:3]=[CX3H0:4]",
        [1.0, 0.0, -1.0, 0.7, 1.0, 0.0, 1.0, 0.6, 1.0, 0.0, 1.0, -0.5],
    ),
    (
        "[a:1][a;r{9-}:2]@;-[CX3;r{9-}:3]=[CX3H2:4]",
        [1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[a:1][a;r{9-}:2]@;-[CX3;r{9-}:3]=[CX3H1:4]",
        [1.0, 0.0, -1.0, 5.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
    (
        "[*:1][SX2;r{9-}:2]@;-[SX2;r{9-}:3][*:4]",
        [1.0, 0.0, 1.0, 12.9, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0, 1.0, 0.0],
    ),
];