# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 11:23:00 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: (2S)-3-(3-hydroxyphenyl)-2-(4-iodophenyl)-4-methyl-2H-1-benzopyran-6-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC1=C([C@@H](Oc2ccc(O)cc12)c3ccc(I)cc3)c4cccc(O)c4
#
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
 G9J  G9J  (2S)-3-(3-hydroxyphenyl)-2-(4-iodophenyl)-4-methyl-2H-1-benzopyran-6-ol  ligand  43  26  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_G9J
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
 G9J  C1   C  CH3   0  -0.766   3.5643  -0.9883   2.0230
 G9J  C2   C  CR6   0   0.121   2.7814  -0.9734   0.7458
 G9J  C3   C  CR6   0  -0.057   2.5487   0.1298   0.0141
 G9J  C4   C  CR16  0  -0.116   1.7704   0.0158  -1.2706
 G9J  O5   O  O     0  -0.478   1.9490  -1.2494  -1.8925
 G9J  C6   C  CR66  0   0.313   1.8171  -2.3219  -1.0731
 G9J  C7   C  CR66  0   0.017   2.2347  -2.2438   0.2564
 G9J  C8   C  CR16  0  -0.477   2.1310  -3.3794   1.0594
 G9J  C9   C  CR6   0   0.379   1.6255  -4.5691   0.5496
 G9J  C10  C  CR16  0  -0.348   1.2311  -4.6333  -0.7841
 G9J  C11  C  CR16  0  -0.336   1.3243  -3.5088  -1.5894
 G9J  O12  O  OH1   0  -0.641   1.4974  -5.6862   1.3004
 G9J  C13  C  CR6   0   0.121   0.2915   0.3118  -1.1012
 G9J  C14  C  CR16  0  -0.289  -0.4387   0.7158  -2.2155
 G9J  C15  C  CR16  0  -0.215  -1.8020   0.9543  -2.1348
 G9J  C16  C  CR6   0  -0.232  -2.4428   0.7827  -0.9153
 G9J  C17  C  CR16  0  -0.206  -1.7393   0.3832   0.2101
 G9J  C18  C  CR16  0  -0.272  -0.3733   0.1519   0.1084
 G9J  I19  I  I     0   0.056  -4.5102   1.1433  -0.7722
 G9J  C20  C  CR6   0   0.089   2.9245   1.4998   0.4142
 G9J  C21  C  CR16  0  -0.328   2.5128   2.0175   1.6407
 G9J  C22  C  CR16  0  -0.227   2.8463   3.3192   1.9888
 G9J  C23  C  CR16  0  -0.348   3.5833   4.1197   1.1319
 G9J  C24  C  CR6   0   0.381   3.9934   3.6095  -0.0987
 G9J  C25  C  CR16  0  -0.450   3.6576   2.3076  -0.4555
 G9J  O26  O  OH1   0  -0.632   4.7141   4.4160  -0.9024
 G9J  H1   H  HCH3  0   0.253   4.2888  -1.8040   2.0201
 G9J  H2   H  HCH3  0   0.263   4.1036  -0.0574   2.1798
 G9J  H3   H  HCH3  0   0.251   2.9142  -1.1419   2.8877
 G9J  H4   H  HCR6  0   0.273   2.1716   0.7269  -1.9969
 G9J  H5   H  HCR6  0   0.273   2.4420  -3.3326   2.0967
 G9J  H6   H  HCR6  0   0.267   0.8425  -5.5592  -1.1886
 G9J  H7   H  HCR6  0   0.266   1.0166  -3.5576  -2.6262
 G9J  H8   H  HOH1  0   0.473   1.7862  -5.5167   2.2037
 G9J  H9   H  HCR6  0   0.268   0.0612   0.8539  -3.1670
 G9J  H10  H  HCR6  0   0.281  -2.3441   1.2727  -3.0147
 G9J  H11  H  HCR6  0   0.280  -2.2325   0.2508   1.1634
 G9J  H12  H  HCR6  0   0.267   0.1664  -0.1514   0.9964
 G9J  H13  H  HCR6  0   0.253   1.9210   1.4105   2.3127
 G9J  H14  H  HCR6  0   0.260   2.5206   3.7194   2.9401
 G9J  H15  H  HCR6  0   0.265   3.8403   5.1351   1.4061
 G9J  H16  H  HCR6  0   0.273   3.9856   1.9119  -1.4114
 G9J  H17  H  HOH1  0   0.475   4.9379   3.9627  -1.7228

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
 G9J  I19  C16  single    2.103  0.020  2.103
 G9J  C16  C15  aromatic  1.388  0.020  1.388
 G9J  C16  C17  aromatic  1.386  0.020  1.386
 G9J  C15  C14  aromatic  1.386  0.020  1.386
 G9J  C17  C18  aromatic  1.389  0.020  1.389
 G9J  C14  C13  aromatic  1.392  0.020  1.392
 G9J  C18  C13  aromatic  1.390  0.020  1.390
 G9J  C13  C4   single    1.518  0.020  1.518
 G9J  C22  C21  aromatic  1.388  0.020  1.388
 G9J  C22  C23  aromatic  1.385  0.020  1.385
 G9J  C21  C20  aromatic  1.393  0.020  1.393
 G9J  C4   O5   single    1.421  0.020  1.421
 G9J  C4   C3   single    1.506  0.020  1.506
 G9J  C23  C24  aromatic  1.394  0.020  1.394
 G9J  O5   C6   single    1.356  0.020  1.356
 G9J  C20  C3   single    1.476  0.020  1.476
 G9J  C20  C25  aromatic  1.395  0.020  1.395
 G9J  C3   C2   double    1.344  0.020  1.344
 G9J  C6   C11  aromatic  1.385  0.020  1.385
 G9J  C6   C7   aromatic  1.396  0.020  1.396
 G9J  C11  C10  aromatic  1.386  0.020  1.386
 G9J  C2   C7   single    1.467  0.020  1.467
 G9J  C2   C1   single    1.498  0.020  1.498
 G9J  C7   C8   aromatic  1.395  0.020  1.395
 G9J  C10  C9   aromatic  1.392  0.020  1.392
 G9J  C24  C25  aromatic  1.391  0.020  1.391
 G9J  C24  O26  single    1.347  0.020  1.347
 G9J  C8   C9   aromatic  1.390  0.020  1.390
 G9J  C9   O12  single    1.352  0.020  1.352
 G9J  C1   H1   single    0.970  0.020  1.090
 G9J  C1   H2   single    0.970  0.020  1.090
 G9J  C1   H3   single    0.970  0.020  1.090
 G9J  C4   H4   single    0.970  0.020  1.090
 G9J  C8   H5   single    0.930  0.020  1.080
 G9J  C10  H6   single    0.930  0.020  1.080
 G9J  C11  H7   single    0.930  0.020  1.080
 G9J  O12  H8   single    0.850  0.020  0.980
 G9J  C14  H9   single    0.930  0.020  1.080
 G9J  C15  H10  single    0.930  0.020  1.080
 G9J  C17  H11  single    0.930  0.020  1.080
 G9J  C18  H12  single    0.930  0.020  1.080
 G9J  C21  H13  single    0.930  0.020  1.080
 G9J  C22  H14  single    0.930  0.020  1.080
 G9J  C23  H15  single    0.930  0.020  1.080
 G9J  C25  H16  single    0.930  0.020  1.080
 G9J  O26  H17  single    0.850  0.020  0.980

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
 G9J  H3   C1   H2   107.54  3.000
 G9J  H3   C1   H1   106.98  3.000
 G9J  H2   C1   H1   108.14  3.000
 G9J  H3   C1   C2   111.41  3.000
 G9J  H2   C1   C2   111.94  3.000
 G9J  H1   C1   C2   110.62  3.000
 G9J  C7   C2   C3   117.68  3.000
 G9J  C7   C2   C1   118.07  3.000
 G9J  C3   C2   C1   124.25  3.000
 G9J  C20  C3   C4   115.66  3.000
 G9J  C20  C3   C2   124.76  3.000
 G9J  C4   C3   C2   119.45  3.000
 G9J  H4   C4   C13  107.76  3.000
 G9J  H4   C4   O5   104.02  3.000
 G9J  C13  C4   O5   110.17  3.000
 G9J  H4   C4   C3   109.14  3.000
 G9J  O5   C4   C3   112.07  3.000
 G9J  C13  C4   C3   113.18  3.000
 G9J  C6   O5   C4   115.30  3.000
 G9J  C11  C6   C7   120.63  3.000
 G9J  C7   C6   O5   120.15  3.000
 G9J  C11  C6   O5   119.15  3.000
 G9J  C8   C7   C6   118.73  3.000
 G9J  C8   C7   C2   122.73  3.000
 G9J  C6   C7   C2   118.53  3.000
 G9J  H5   C8   C9   119.50  3.000
 G9J  H5   C8   C7   119.64  3.000
 G9J  C9   C8   C7   120.86  3.000
 G9J  O12  C9   C10  117.84  3.000
 G9J  O12  C9   C8   122.55  3.000
 G9J  C10  C9   C8   119.61  3.000
 G9J  H6   C10  C11  120.06  3.000
 G9J  H6   C10  C9   119.94  3.000
 G9J  C11  C10  C9   120.00  3.000
 G9J  H7   C11  C10  120.04  3.000
 G9J  H7   C11  C6   119.79  3.000
 G9J  C10  C11  C6   120.17  3.000
 G9J  H8   O12  C9   110.30  3.000
 G9J  C18  C13  C14  118.64  3.000
 G9J  C18  C13  C4   122.74  3.000
 G9J  C14  C13  C4   118.58  3.000
 G9J  H9   C14  C15  118.86  3.000
 G9J  H9   C14  C13  119.86  3.000
 G9J  C15  C14  C13  121.28  3.000
 G9J  H10  C15  C16  121.31  3.000
 G9J  H10  C15  C14  119.76  3.000
 G9J  C16  C15  C14  118.93  3.000
 G9J  I19  C16  C17  119.54  3.000
 G9J  C17  C16  C15  120.97  3.000
 G9J  I19  C16  C15  119.49  3.000
 G9J  H11  C17  C18  119.51  3.000
 G9J  H11  C17  C16  121.31  3.000
 G9J  C18  C17  C16  119.19  3.000
 G9J  H12  C18  C17  118.48  3.000
 G9J  H12  C18  C13  120.52  3.000
 G9J  C17  C18  C13  121.00  3.000
 G9J  C25  C20  C21  119.26  3.000
 G9J  C25  C20  C3   120.15  3.000
 G9J  C21  C20  C3   120.55  3.000
 G9J  H13  C21  C22  120.12  3.000
 G9J  H13  C21  C20  119.99  3.000
 G9J  C22  C21  C20  119.88  3.000
 G9J  H14  C22  C23  119.36  3.000
 G9J  H14  C22  C21  119.66  3.000
 G9J  C23  C22  C21  120.97  3.000
 G9J  H15  C23  C24  119.80  3.000
 G9J  H15  C23  C22  120.77  3.000
 G9J  C24  C23  C22  119.42  3.000
 G9J  O26  C24  C25  122.43  3.000
 G9J  O26  C24  C23  117.70  3.000
 G9J  C25  C24  C23  119.87  3.000
 G9J  H16  C25  C24  119.62  3.000
 G9J  H16  C25  C20  119.78  3.000
 G9J  C24  C25  C20  120.59  3.000
 G9J  H17  O26  C24  110.52  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
 G9J  CONST_01  C9   C10  C11  C6      0.00   0.0  0
 G9J  CONST_02  C9   C8   C7   C6      0.00   0.0  0
 G9J  CONST_03  C10  C11  C6   C7      0.00   0.0  0
 G9J  CONST_04  C10  C9   C8   C7      0.00   0.0  0
 G9J  CONST_05  C11  C6   C7   C8      0.00   0.0  0
 G9J  CONST_06  C11  C10  C9   C8      0.00   0.0  0
 G9J  CONST_07  C16  C15  C14  C13     0.00   0.0  0
 G9J  CONST_08  C16  C17  C18  C13     0.00   0.0  0
 G9J  CONST_09  C17  C16  C15  C14     0.00   0.0  0
 G9J  CONST_10  C17  C18  C13  C14     0.00   0.0  0
 G9J  CONST_11  C18  C17  C16  C15     0.00   0.0  0
 G9J  CONST_12  C18  C13  C14  C15     0.00   0.0  0
 G9J  CONST_13  C23  C22  C21  C20     0.00   0.0  0
 G9J  CONST_14  C23  C24  C25  C20     0.00   0.0  0
 G9J  CONST_15  C24  C23  C22  C21     0.00   0.0  0
 G9J  CONST_16  C24  C25  C20  C21     0.00   0.0  0
 G9J  CONST_17  C25  C20  C21  C22     0.00   0.0  0
 G9J  CONST_18  C25  C24  C23  C22     0.00   0.0  0
 G9J  CONST_19  C22  C21  C20  C3    180.00   0.0  0
 G9J  CONST_20  C24  C25  C20  C3    180.00   0.0  0
 G9J  CONST_21  C15  C14  C13  C4    180.00   0.0  0
 G9J  CONST_22  C17  C18  C13  C4    180.00   0.0  0
 G9J  CONST_23  O12  C9   C8   C7    180.00   0.0  0
 G9J  CONST_24  O12  C9   C10  C11   180.00   0.0  0
 G9J  CONST_25  I19  C16  C15  C14   180.00   0.0  0
 G9J  CONST_26  I19  C16  C17  C18   180.00   0.0  0
 G9J  CONST_27  O26  C24  C25  C20   180.00   0.0  0
 G9J  CONST_28  O26  C24  C23  C22   180.00   0.0  0
 G9J  CONST_29  H5   C8   C7   C2      0.00   0.0  0
 G9J  CONST_30  H13  C21  C20  C3      0.00   0.0  0
 G9J  CONST_31  H16  C25  C20  C3      0.00   0.0  0
 G9J  CONST_32  H9   C14  C13  C4      0.00   0.0  0
 G9J  CONST_33  H12  C18  C13  C4      0.00   0.0  0
 G9J  CONST_34  H7   C11  C6   O5      0.00   0.0  0
 G9J  CONST_35  H6   C10  C11  C6    180.00   0.0  0
 G9J  CONST_36  H10  C15  C14  C13   180.00   0.0  0
 G9J  CONST_37  H11  C17  C18  C13   180.00   0.0  0
 G9J  CONST_38  H14  C22  C21  C20   180.00   0.0  0
 G9J  CONST_39  H15  C23  C22  C21   180.00   0.0  0
 G9J  Var_01    C21  C20  C3   C2    -54.29  30.0  3
 G9J  Var_02    C6   C7   C2   C3     16.38  30.0  1
 G9J  Var_03    C11  C6   O5   C4    148.51  30.0  1
 G9J  Var_04    C7   C2   C3   C4     -1.09  30.0  1
 G9J  Var_05    H1   C1   C2   C3   -133.14  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 G9J  chir_01  C4  C13  O5  C3  positiv

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
 G9J  plan-1  C4   0.020
 G9J  plan-1  C13  0.020
 G9J  plan-1  C14  0.020
 G9J  plan-1  C15  0.020
 G9J  plan-1  C16  0.020
 G9J  plan-1  C17  0.020
 G9J  plan-1  C18  0.020
 G9J  plan-1  I19  0.020
 G9J  plan-1  H9   0.020
 G9J  plan-1  H10  0.020
 G9J  plan-1  H11  0.020
 G9J  plan-1  H12  0.020
 G9J  plan-2  C3   0.020
 G9J  plan-2  C20  0.020
 G9J  plan-2  C21  0.020
 G9J  plan-2  C22  0.020
 G9J  plan-2  C23  0.020
 G9J  plan-2  C24  0.020
 G9J  plan-2  C25  0.020
 G9J  plan-2  O26  0.020
 G9J  plan-2  H13  0.020
 G9J  plan-2  H14  0.020
 G9J  plan-2  H15  0.020
 G9J  plan-2  H16  0.020
 G9J  plan-3  C2   0.020
 G9J  plan-3  O5   0.020
 G9J  plan-3  C6   0.020
 G9J  plan-3  C7   0.020
 G9J  plan-3  C8   0.020
 G9J  plan-3  C9   0.020
 G9J  plan-3  C10  0.020
 G9J  plan-3  C11  0.020
 G9J  plan-3  O12  0.020
 G9J  plan-3  H5   0.020
 G9J  plan-3  H6   0.020
 G9J  plan-3  H7   0.020

