# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Aug  3 00:37:44 2022
#   Inital geometry file: a 81 line input string
#   Ligand name: 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-hydroxybenzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1ccc(C)n1c2ccc(O)cc2C(O)=O
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 WOV  WOV  "2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-hydroxybenzoic acid"  ligand  29  17  .  2022-08-11  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_WOV
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 WOV  C1   C  CR5    0   0.287  35.8231  34.4443  23.7780
 WOV  C2   C  CR15   0  -0.396  34.9972  35.2304  23.0165
 WOV  C3   C  CR15   0  -0.404  34.5612  34.4510  21.9103
 WOV  C4   C  CR5    0   0.309  35.1336  33.2105  22.0251
 WOV  C5   C  CH3    0  -0.743  35.0488  32.0213  21.1376
 WOV  O1   O  OC    -1  -0.589  39.7033  33.6602  23.2183
 WOV  C6   C  CR6    0   0.220  36.6407  32.1157  23.6577
 WOV  C7   C  CR6    0  -0.011  38.0187  32.0388  23.4532
 WOV  C8   C  CR16   0  -0.398  38.7182  30.9771  24.0139
 WOV  O2   O  O      0  -0.574  38.4069  33.2078  21.4517
 WOV  C9   C  CR6    0   0.369  38.0610  29.9739  24.7211
 WOV  C10  C  CR16   0  -0.407  36.6840  30.0549  24.9139
 WOV  C11  C  CR16   0  -0.240  35.9900  31.1343  24.3925
 WOV  C12  C  C      0   0.365  38.7758  33.0743  22.6307
 WOV  O    O  OH1    0  -0.630  38.8042  28.9582  25.2035
 WOV  N    N  NR5    0  -0.573  35.8941  33.2162  23.1664
 WOV  C    C  CH3    0  -0.743  36.5538  34.7445  25.0387
 WOV  H1   H  HCR5   0   0.228  34.7337  36.2545  23.2346
 WOV  H2   H  HCR5   0   0.228  33.9050  34.7641  21.1122
 WOV  H3   H  HCH3   0   0.239  36.0331  31.7403  20.7587
 WOV  H4   H  HCH3   0   0.237  34.6341  31.1480  21.6451
 WOV  H5   H  HCH3   0   0.247  34.4094  32.2440  20.2850
 WOV  H7   H  HCR6   0   0.255  39.7925  30.9117  23.8868
 WOV  H8   H  HCR6   0   0.268  36.1582  29.2904  25.4744
 WOV  H9   H  HCR6   0   0.260  34.9232  31.2162  24.5614
 WOV  H10  H  HOH1   0   0.472  38.2493  28.3306  25.6802
 WOV  H11  H  HCH3   0   0.238  36.2684  34.0750  25.8531
 WOV  H12  H  HCH3   0   0.239  37.6356  34.6600  24.9167
 WOV  H13  H  HCH3   0   0.249  36.3343  35.7627  25.3560

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 WOV  C5   C4   single    1.486  0.020  1.486
 WOV  O2   C12  deloc     1.243  0.020  1.243
 WOV  C3   C4   aromatic  1.371  0.020  1.371
 WOV  C3   C2   aromatic  1.422  0.020  1.422
 WOV  C4   N    aromatic  1.371  0.020  1.371
 WOV  C12  O1   deloc     1.245  0.020  1.245
 WOV  C12  C7   single    1.524  0.020  1.524
 WOV  C2   C1   aromatic  1.371  0.020  1.371
 WOV  N    C6   single    1.418  0.020  1.418
 WOV  N    C1   aromatic  1.374  0.020  1.374
 WOV  C7   C6   aromatic  1.395  0.020  1.395
 WOV  C7   C8   aromatic  1.390  0.020  1.390
 WOV  C6   C11  aromatic  1.388  0.020  1.388
 WOV  C1   C    single    1.488  0.020  1.488
 WOV  C8   C9   aromatic  1.392  0.020  1.392
 WOV  C11  C10  aromatic  1.385  0.020  1.385
 WOV  C9   C10  aromatic  1.393  0.020  1.393
 WOV  C9   O    single    1.348  0.020  1.348
 WOV  C2   H1   single    0.930  0.020  1.080
 WOV  C3   H2   single    0.930  0.020  1.080
 WOV  C5   H3   single    0.970  0.020  1.090
 WOV  C5   H4   single    0.970  0.020  1.090
 WOV  C5   H5   single    0.970  0.020  1.090
 WOV  C8   H7   single    0.930  0.020  1.080
 WOV  C10  H8   single    0.930  0.020  1.080
 WOV  C11  H9   single    0.930  0.020  1.080
 WOV  O    H10  single    0.850  0.020  0.980
 WOV  C    H11  single    0.970  0.020  1.090
 WOV  C    H12  single    0.970  0.020  1.090
 WOV  C    H13  single    0.970  0.020  1.090

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 WOV  C    C1   N    122.16  3.000
 WOV  C    C1   C2   130.60  3.000
 WOV  N    C1   C2   107.24  3.000
 WOV  H1   C2   C3   127.03  3.000
 WOV  H1   C2   C1   125.36  3.000
 WOV  C3   C2   C1   107.61  3.000
 WOV  H2   C3   C4   125.32  3.000
 WOV  H2   C3   C2   127.06  3.000
 WOV  C4   C3   C2   107.62  3.000
 WOV  N    C4   C5   122.13  3.000
 WOV  N    C4   C3   107.31  3.000
 WOV  C5   C4   C3   130.55  3.000
 WOV  H5   C5   H4   107.72  3.000
 WOV  H5   C5   H3   108.08  3.000
 WOV  H4   C5   H3   107.33  3.000
 WOV  H5   C5   C4   109.73  3.000
 WOV  H4   C5   C4   112.59  3.000
 WOV  H3   C5   C4   111.22  3.000
 WOV  N    C6   C11  119.04  3.000
 WOV  C11  C6   C7   120.11  3.000
 WOV  N    C6   C7   120.81  3.000
 WOV  C12  C7   C8   119.14  3.000
 WOV  C8   C7   C6   118.70  3.000
 WOV  C12  C7   C6   122.16  3.000
 WOV  H7   C8   C9   118.95  3.000
 WOV  H7   C8   C7   119.85  3.000
 WOV  C9   C8   C7   121.19  3.000
 WOV  O    C9   C10  122.65  3.000
 WOV  O    C9   C8   117.68  3.000
 WOV  C10  C9   C8   119.68  3.000
 WOV  H8   C10  C11  120.08  3.000
 WOV  H8   C10  C9   120.67  3.000
 WOV  C11  C10  C9   119.25  3.000
 WOV  H9   C11  C10  119.59  3.000
 WOV  H9   C11  C6   119.39  3.000
 WOV  C10  C11  C6   121.02  3.000
 WOV  O2   C12  C7   115.96  3.000
 WOV  C7   C12  O1   115.81  3.000
 WOV  O2   C12  O1   128.22  3.000
 WOV  H10  O    C9   110.49  3.000
 WOV  C6   N    C4   125.25  3.000
 WOV  C6   N    C1   124.53  3.000
 WOV  C4   N    C1   110.21  3.000
 WOV  H13  C    H12  107.73  3.000
 WOV  H13  C    H11  107.65  3.000
 WOV  H12  C    H11  107.14  3.000
 WOV  H13  C    C1   109.68  3.000
 WOV  H12  C    C1   112.11  3.000
 WOV  H11  C    C1   112.33  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 WOV  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 WOV  CONST_02  C3   C4   N    C1      0.00   0.0  0
 WOV  CONST_05  N    C4   C3   C2      0.00   0.0  0
 WOV  CONST_06  C4   N    C1   C2      0.00   0.0  0
 WOV  CONST_07  C6   N    C1   C2    180.00   0.0  0
 WOV  CONST_08  C6   N    C4   C3    180.00   0.0  0
 WOV  CONST_09  N    C1   C2   C3      0.00   0.0  0
 WOV  CONST_12  C9   C8   C7   C6      0.00   0.0  0
 WOV  CONST_13  C9   C10  C11  C6      0.00   0.0  0
 WOV  CONST_14  C10  C11  C6   C7      0.00   0.0  0
 WOV  CONST_15  C10  C9   C8   C7      0.00   0.0  0
 WOV  CONST_16  N    C6   C7   C8    180.00   0.0  0
 WOV  CONST_17  C11  C6   C7   C8      0.00   0.0  0
 WOV  CONST_18  C11  C10  C9   C8      0.00   0.0  0
 WOV  CONST_19  N    C6   C11  C10   180.00   0.0  0
 WOV  CONST_20  C5   C4   N    C1    180.00   0.0  0
 WOV  CONST_21  C5   C4   C3   C2    180.00   0.0  0
 WOV  CONST_22  C    C1   C2   C3    180.00   0.0  0
 WOV  CONST_23  C    C1   N    C4    180.00   0.0  0
 WOV  CONST_24  C6   N    C4   C5      0.00   0.0  0
 WOV  CONST_25  C    C1   N    C6      0.00   0.0  0
 WOV  CONST_26  O    C9   C8   C7    180.00   0.0  0
 WOV  CONST_27  C12  C7   C8   C9    180.00   0.0  0
 WOV  CONST_28  C12  C7   C6   C11   180.00   0.0  0
 WOV  CONST_29  O    C9   C10  C11   180.00   0.0  0
 WOV  CONST_30  N    C6   C7   C12     0.00   0.0  0
 WOV  CONST_31  H2   C3   C2   C1    180.00   0.0  0
 WOV  CONST_32  H1   C2   C3   C4    180.00   0.0  0
 WOV  CONST_33  H7   C8   C7   C6    180.00   0.0  0
 WOV  CONST_34  H8   C10  C11  C6    180.00   0.0  0
 WOV  CONST_35  H9   C11  C6   C7    180.00   0.0  0
 WOV  CONST_36  H8   C10  C9   C8    180.00   0.0  0
 WOV  CONST_37  H9   C11  C10  C9    180.00   0.0  0
 WOV  CONST_38  H7   C8   C9   C10   180.00   0.0  0
 WOV  CONST_39  H2   C3   C4   N     180.00   0.0  0
 WOV  CONST_40  H9   C11  C6   N       0.00   0.0  0
 WOV  CONST_41  H1   C2   C1   N     180.00   0.0  0
 WOV  Var_01    C6   C7   C12  O1    122.47  30.0  2
 WOV  Var_02    C8   C7   C12  O1    -57.89  30.0  2
 WOV  Var_03    O2   C12  C7   C6    -58.90  30.0  2
 WOV  Var_04    O2   C12  C7   C8    120.73  30.0  2
 WOV  Var_05    H11  C    C1   C2    120.93  30.0  2
 WOV  Var_06    H12  C    C1   C2   -118.36  30.0  2
 WOV  Var_07    H13  C    C1   C2      1.27  30.0  2
 WOV  Var_08    H3   C5   C4   C3    119.16  30.0  2
 WOV  Var_09    H4   C5   C4   C3   -120.33  30.0  2
 WOV  Var_10    H5   C5   C4   C3     -0.37  30.0  2
 WOV  Var_11    H3   C5   C4   N     -59.35  30.0  2
 WOV  Var_12    H4   C5   C4   N      61.16  30.0  2
 WOV  Var_13    H5   C5   C4   N    -178.88  30.0  2
 WOV  Var_14    H11  C    C1   N     -58.89  30.0  2
 WOV  Var_15    H12  C    C1   N      61.82  30.0  2
 WOV  Var_16    H13  C    C1   N    -178.55  30.0  2

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 WOV  plan-1  C1   0.020
 WOV  plan-1  C2   0.020
 WOV  plan-1  C3   0.020
 WOV  plan-1  C4   0.020
 WOV  plan-1  C5   0.020
 WOV  plan-1  C6   0.020
 WOV  plan-1  N    0.020
 WOV  plan-1  C    0.020
 WOV  plan-1  H1   0.020
 WOV  plan-1  H2   0.020
 WOV  plan-2  C6   0.020
 WOV  plan-2  C7   0.020
 WOV  plan-2  C8   0.020
 WOV  plan-2  C9   0.020
 WOV  plan-2  C10  0.020
 WOV  plan-2  C11  0.020
 WOV  plan-2  C12  0.020
 WOV  plan-2  O    0.020
 WOV  plan-2  N    0.020
 WOV  plan-2  H7   0.020
 WOV  plan-2  H8   0.020
 WOV  plan-2  H9   0.020
 WOV  plan-3  O1   0.020
 WOV  plan-3  C7   0.020
 WOV  plan-3  O2   0.020
 WOV  plan-3  C12  0.020

