# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May 13 12:09:12 2020
#   Inital geometry file: a 138 line input string
#   Ligand name: 3-[5-cyclopropyl-3-(3-methoxypyridin-4-yl)-2-phenyl-1H-indol-1-yl]propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cnccc1c2c3cc(ccc3n(CCC(O)=O)c2c4ccccc4)C5CC5
#
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
 L19  L19  '3-[5-cyclopropyl-3-(3-methoxypyridin-4-yl)-2-phenyl-1H-indol-1-yl]propanoic acid'  ligand  55  31  .  2022-09-22  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_L19
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
 L19  O1   O  O     0  -0.443   3.8214  -3.8043   0.7231
 L19  C22  C  C     0   0.558   3.3613  -3.4581  -0.3363
 L19  O2   O  OH1   0  -0.592   3.8328  -3.8668  -1.5073
 L19  C21  C  CH2   0  -0.591   2.1972  -2.5220  -0.4983
 L19  C20  C  CH2   0  -0.329   1.6464  -2.0449   0.8388
 L19  N1   N  NR5   0  -0.583   0.5144  -1.1619   0.6534
 L19  C13  C  CR5   0   0.359   0.5728   0.1815   0.3673
 L19  C14  C  CR6   0   0.029   1.8113   0.9588   0.4812
 L19  C15  C  CR16  0  -0.291   2.2621   1.6988  -0.6101
 L19  C16  C  CR16  0  -0.238   3.4034   2.4815  -0.5067
 L19  C17  C  CR16  0  -0.259   4.1121   2.5265   0.6858
 L19  C18  C  CR16  0  -0.245   3.6709   1.7889   1.7776
 L19  C19  C  CR16  0  -0.288   2.5261   1.0142   1.6783
 L19  C6   C  CR5   0  -0.031  -0.6660   0.6195  -0.0447
 L19  C7   C  CR56  0   0.131  -1.5321  -0.5218  -0.0338
 L19  C8   C  CR16  0  -0.481  -2.8865  -0.7132  -0.3262
 L19  C9   C  CR6   0   0.220  -3.4452  -1.9758  -0.2163
 L19  C23  C  CH1   0  -0.367  -4.8807  -2.1704  -0.5442
 L19  C24  C  CH2   0  -0.479  -5.3663  -3.4304  -1.2088
 L19  C25  C  CH2   0  -0.478  -5.7315  -3.1541   0.2117
 L19  C10  C  CR16  0  -0.373  -2.6350  -3.0522   0.2001
 L19  C11  C  CR16  0  -0.298  -1.3001  -2.8898   0.5107
 L19  C12  C  CR56  0   0.317  -0.7577  -1.6115   0.3984
 L19  C5   C  CR6   0  -0.036  -1.0389   1.9762  -0.4423
 L19  C4   C  CR16  0  -0.374  -1.7488   2.2045  -1.6163
 L19  C3   C  CR16  0  -0.090  -2.0799   3.4978  -1.9898
 L19  N    N  N     0  -0.394  -1.7433   4.5594  -1.2734
 L19  C2   C  CR16  0  -0.194  -1.0769   4.3644  -0.1406
 L19  C1   C  CR6   0   0.275  -0.7159   3.1038   0.3299
 L19  O    O  O2    0  -0.455  -0.0863   2.8915   1.4929
 L19  C    C  CH3   0  -0.432   0.5739   3.9752   2.1170
 L19  H1   H  HOH1  0   0.481   4.5830  -4.4657  -1.3739
 L19  H2   H  HCH2  0   0.293   2.5192  -1.6683  -1.1023
 L19  H3   H  HCH2  0   0.296   1.4204  -3.0267  -1.0799
 L19  H4   H  HCH2  0   0.279   1.3227  -2.8861   1.4510
 L19  H5   H  HCH2  0   0.283   2.4151  -1.5280   1.4069
 L19  H6   H  HCR6  0   0.253   1.7175   1.6601  -1.5453
 L19  H7   H  HCR6  0   0.258   3.7413   3.0529  -1.3614
 L19  H8   H  HCR6  0   0.258   5.0032   3.1354   0.7657
 L19  H9   H  HCR6  0   0.258   4.2134   1.8269   2.7133
 L19  H10  H  HCR6  0   0.261   2.1703   0.4725   2.5463
 L19  H11  H  HCR6  0   0.241  -3.4990   0.1235  -0.6432
 L19  H12  H  HCH1  0   0.257  -5.3828  -1.2592  -0.8505
 L19  H13  H  HCH2  0   0.258  -6.1319  -3.3377  -1.9679
 L19  H14  H  HCH2  0   0.250  -4.6362  -4.2068  -1.4047
 L19  H15  H  HCH2  0   0.250  -5.2530  -3.7434   0.9850
 L19  H16  H  HCH2  0   0.258  -6.7510  -2.8695   0.4380
 L19  H17  H  HCR6  0   0.246  -3.0637  -4.0437   0.2865
 L19  H18  H  HCR6  0   0.263  -0.7098  -3.7385   0.8316
 L19  H19  H  HCR6  0   0.266  -2.0204   1.3749  -2.2563
 L19  H20  H  HCR6  0   0.258  -2.6268   3.6774  -2.9084
 L19  H21  H  HCR6  0   0.271  -0.8256   5.2567   0.4219
 L19  H22  H  HCH3  0   0.256   1.1583   3.5519   2.9298
 L19  H23  H  HCH3  0   0.227   1.2509   4.4833   1.4256
 L19  H24  H  HCH3  0   0.233  -0.1291   4.7032   2.5301

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
 L19  C17  C18  aromatic  1.390  0.020  1.390
 L19  C17  C16  aromatic  1.388  0.020  1.388
 L19  C18  C19  aromatic  1.386  0.020  1.386
 L19  C16  C15  aromatic  1.388  0.020  1.388
 L19  O1   C22  double    1.206  0.020  1.206
 L19  C19  C14  aromatic  1.395  0.020  1.395
 L19  C15  C14  aromatic  1.393  0.020  1.393
 L19  C14  C13  single    1.467  0.020  1.467
 L19  C22  O2   single    1.327  0.020  1.327
 L19  C22  C21  single    1.503  0.020  1.503
 L19  C21  C20  single    1.523  0.020  1.523
 L19  C20  N1   single    1.448  0.020  1.448
 L19  C13  N1   aromatic  1.375  0.020  1.375
 L19  C13  C6   aromatic  1.377  0.020  1.377
 L19  C3   C4   aromatic  1.386  0.020  1.386
 L19  C3   N    aromatic  1.324  0.020  1.324
 L19  N1   C12  aromatic  1.373  0.020  1.373
 L19  C4   C5   aromatic  1.391  0.020  1.391
 L19  N    C2   aromatic  1.329  0.020  1.329
 L19  C5   C6   single    1.462  0.020  1.462
 L19  C5   C1   aromatic  1.404  0.020  1.404
 L19  C6   C7   aromatic  1.433  0.020  1.433
 L19  C2   C1   aromatic  1.393  0.020  1.393
 L19  C1   O    single    1.339  0.020  1.339
 L19  C12  C7   aromatic  1.405  0.020  1.405
 L19  C12  C11  aromatic  1.393  0.020  1.393
 L19  O    C    single    1.414  0.020  1.414
 L19  C7   C8   aromatic  1.399  0.020  1.399
 L19  C11  C10  aromatic  1.380  0.020  1.380
 L19  C8   C9   aromatic  1.385  0.020  1.385
 L19  C10  C9   aromatic  1.410  0.020  1.410
 L19  C9   C23  single    1.485  0.020  1.485
 L19  C23  C25  single    1.504  0.020  1.504
 L19  C23  C24  single    1.505  0.020  1.505
 L19  C25  C24  single    1.492  0.020  1.492
 L19  O2   H1   single    0.850  0.020  0.980
 L19  C21  H2   single    0.970  0.020  1.090
 L19  C21  H3   single    0.970  0.020  1.090
 L19  C20  H4   single    0.970  0.020  1.090
 L19  C20  H5   single    0.970  0.020  1.090
 L19  C15  H6   single    0.930  0.020  1.080
 L19  C16  H7   single    0.930  0.020  1.080
 L19  C17  H8   single    0.930  0.020  1.080
 L19  C18  H9   single    0.930  0.020  1.080
 L19  C19  H10  single    0.930  0.020  1.080
 L19  C8   H11  single    0.930  0.020  1.080
 L19  C23  H12  single    0.970  0.020  1.090
 L19  C24  H13  single    0.970  0.020  1.090
 L19  C24  H14  single    0.970  0.020  1.090
 L19  C25  H15  single    0.970  0.020  1.090
 L19  C25  H16  single    0.970  0.020  1.090
 L19  C10  H17  single    0.930  0.020  1.080
 L19  C11  H18  single    0.930  0.020  1.080
 L19  C4   H19  single    0.930  0.020  1.080
 L19  C3   H20  single    0.930  0.020  1.080
 L19  C2   H21  single    0.930  0.020  1.080
 L19  C    H22  single    0.970  0.020  1.090
 L19  C    H23  single    0.970  0.020  1.090
 L19  C    H24  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
 L19  C21  C22  O2   111.84  3.000
 L19  C21  C22  O1   124.70  3.000
 L19  O2   C22  O1   123.46  3.000
 L19  H1   O2   C22  110.12  3.000
 L19  H3   C21  H2   105.99  3.000
 L19  H3   C21  C20  110.76  3.000
 L19  H2   C21  C20  110.29  3.000
 L19  H3   C21  C22  108.67  3.000
 L19  H2   C21  C22  108.52  3.000
 L19  C20  C21  C22  112.38  3.000
 L19  H5   C20  H4   106.49  3.000
 L19  H5   C20  N1   109.27  3.000
 L19  H4   C20  N1   108.10  3.000
 L19  H5   C20  C21  110.62  3.000
 L19  H4   C20  C21  111.03  3.000
 L19  N1   C20  C21  111.19  3.000
 L19  C12  N1   C13  108.70  3.000
 L19  C12  N1   C20  123.26  3.000
 L19  C13  N1   C20  126.13  3.000
 L19  C6   C13  C14  127.90  3.000
 L19  C6   C13  N1   109.57  3.000
 L19  C14  C13  N1   122.52  3.000
 L19  C19  C14  C15  119.02  3.000
 L19  C15  C14  C13  119.59  3.000
 L19  C19  C14  C13  121.35  3.000
 L19  H6   C15  C16  119.87  3.000
 L19  H6   C15  C14  119.65  3.000
 L19  C16  C15  C14  120.48  3.000
 L19  H7   C16  C17  120.13  3.000
 L19  H7   C16  C15  119.72  3.000
 L19  C17  C16  C15  120.15  3.000
 L19  H8   C17  C18  120.14  3.000
 L19  H8   C17  C16  120.14  3.000
 L19  C18  C17  C16  119.72  3.000
 L19  H9   C18  C19  119.72  3.000
 L19  H9   C18  C17  120.10  3.000
 L19  C19  C18  C17  120.18  3.000
 L19  H10  C19  C18  119.57  3.000
 L19  H10  C19  C14  119.95  3.000
 L19  C18  C19  C14  120.45  3.000
 L19  C5   C6   C7   125.95  3.000
 L19  C7   C6   C13  106.75  3.000
 L19  C5   C6   C13  127.30  3.000
 L19  C12  C7   C8   119.46  3.000
 L19  C8   C7   C6   133.85  3.000
 L19  C12  C7   C6   106.68  3.000
 L19  H11  C8   C9   119.92  3.000
 L19  H11  C8   C7   120.16  3.000
 L19  C9   C8   C7   119.92  3.000
 L19  C10  C9   C23  121.36  3.000
 L19  C23  C9   C8   119.46  3.000
 L19  C10  C9   C8   119.18  3.000
 L19  H12  C23  C25  115.43  3.000
 L19  H12  C23  C24  115.43  3.000
 L19  C25  C23  C24   59.47  3.000
 L19  H12  C23  C9   113.56  3.000
 L19  C24  C23  C9   121.27  3.000
 L19  C25  C23  C9   121.43  3.000
 L19  H14  C24  H13  114.28  3.000
 L19  H14  C24  C25  118.01  3.000
 L19  H13  C24  C25  118.60  3.000
 L19  H14  C24  C23  117.54  3.000
 L19  H13  C24  C23  117.79  3.000
 L19  C25  C24  C23   60.24  3.000
 L19  H16  C25  H15  114.19  3.000
 L19  H16  C25  C24  118.57  3.000
 L19  H15  C25  C24  118.06  3.000
 L19  H16  C25  C23  117.77  3.000
 L19  H15  C25  C23  117.68  3.000
 L19  C24  C25  C23   60.29  3.000
 L19  H17  C10  C11  118.19  3.000
 L19  H17  C10  C9   119.65  3.000
 L19  C11  C10  C9   122.16  3.000
 L19  H18  C11  C12  122.07  3.000
 L19  H18  C11  C10  120.13  3.000
 L19  C12  C11  C10  117.80  3.000
 L19  C11  C12  C7   121.46  3.000
 L19  C11  C12  N1   130.25  3.000
 L19  C7   C12  N1   108.29  3.000
 L19  C1   C5   C4   116.73  3.000
 L19  C1   C5   C6   122.47  3.000
 L19  C4   C5   C6   120.80  3.000
 L19  H19  C4   C3   119.72  3.000
 L19  H19  C4   C5   120.09  3.000
 L19  C3   C4   C5   120.17  3.000
 L19  H20  C3   N    117.00  3.000
 L19  H20  C3   C4   120.22  3.000
 L19  N    C3   C4   122.78  3.000
 L19  C2   N    C3   118.10  3.000
 L19  H21  C2   C1   120.62  3.000
 L19  H21  C2   N    115.96  3.000
 L19  C1   C2   N    123.42  3.000
 L19  O    C1   C2   123.95  3.000
 L19  O    C1   C5   117.28  3.000
 L19  C2   C1   C5   118.77  3.000
 L19  C    O    C1   118.76  3.000
 L19  H24  C    H23  109.14  3.000
 L19  H24  C    H22  108.82  3.000
 L19  H23  C    H22  108.73  3.000
 L19  H24  C    O    112.14  3.000
 L19  H23  C    O    111.49  3.000
 L19  H22  C    O    106.41  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
 L19  CONST_03  C5   C6   C13  N1    180.00   0.0  0
 L19  CONST_04  C7   C6   C13  N1      0.00   0.0  0
 L19  CONST_05  C6   C7   C12  N1      0.00   0.0  0
 L19  CONST_06  C8   C7   C12  N1    180.00   0.0  0
 L19  CONST_07  C10  C11  C12  N1    180.00   0.0  0
 L19  CONST_08  C18  C19  C14  C13   180.00   0.0  0
 L19  CONST_09  C16  C15  C14  C13   180.00   0.0  0
 L19  CONST_10  C7   C12  N1   C13     0.00   0.0  0
 L19  CONST_11  C11  C12  N1   C13   180.00   0.0  0
 L19  CONST_14  C12  C7   C6   C13     0.00   0.0  0
 L19  CONST_15  C8   C7   C6   C13   180.00   0.0  0
 L19  CONST_16  C17  C18  C19  C14     0.00   0.0  0
 L19  CONST_17  C17  C16  C15  C14     0.00   0.0  0
 L19  CONST_18  C12  N1   C13  C14   180.00   0.0  0
 L19  CONST_19  C5   C6   C13  C14     0.00   0.0  0
 L19  CONST_20  C7   C6   C13  C14   180.00   0.0  0
 L19  CONST_21  C18  C17  C16  C15     0.00   0.0  0
 L19  CONST_22  C18  C19  C14  C15     0.00   0.0  0
 L19  CONST_24  C19  C18  C17  C16     0.00   0.0  0
 L19  CONST_25  C19  C14  C15  C16     0.00   0.0  0
 L19  CONST_27  C12  N1   C13  C6      0.00   0.0  0
 L19  CONST_28  C3   C4   C5   C6    180.00   0.0  0
 L19  CONST_29  C2   C1   C5   C6    180.00   0.0  0
 L19  CONST_30  C11  C12  C7   C6    180.00   0.0  0
 L19  CONST_31  C9   C8   C7   C6    180.00   0.0  0
 L19  CONST_34  C10  C11  C12  C7      0.00   0.0  0
 L19  CONST_35  C10  C9   C8   C7      0.00   0.0  0
 L19  CONST_36  C5   C6   C7   C8      0.00   0.0  0
 L19  CONST_37  C11  C12  C7   C8      0.00   0.0  0
 L19  CONST_38  C11  C10  C9   C8      0.00   0.0  0
 L19  CONST_39  C12  C7   C8   C9      0.00   0.0  0
 L19  CONST_40  C12  C11  C10  C9      0.00   0.0  0
 L19  CONST_41  C5   C6   C7   C12   180.00   0.0  0
 L19  CONST_42  N    C3   C4   C5      0.00   0.0  0
 L19  CONST_43  N    C2   C1   C5      0.00   0.0  0
 L19  CONST_44  C2   N    C3   C4      0.00   0.0  0
 L19  CONST_45  C2   C1   C5   C4      0.00   0.0  0
 L19  CONST_46  C1   C5   C4   C3      0.00   0.0  0
 L19  CONST_47  C1   C2   N    C3      0.00   0.0  0
 L19  CONST_48  C23  C9   C8   C7    180.00   0.0  0
 L19  CONST_49  C11  C10  C9   C23   180.00   0.0  0
 L19  CONST_50  C14  C13  N1   C20     0.00   0.0  0
 L19  CONST_51  C6   C13  N1   C20   180.00   0.0  0
 L19  CONST_52  C7   C12  N1   C20   180.00   0.0  0
 L19  CONST_53  C11  C12  N1   C20     0.00   0.0  0
 L19  CONST_54  O    C1   C5   C6      0.00   0.0  0
 L19  CONST_55  O    C1   C5   C4    180.00   0.0  0
 L19  CONST_56  O    C1   C2   N     180.00   0.0  0
 L19  CONST_57  H18  C11  C12  N1      0.00   0.0  0
 L19  CONST_58  H10  C19  C14  C13     0.00   0.0  0
 L19  CONST_59  H6   C15  C14  C13     0.00   0.0  0
 L19  CONST_60  H9   C18  C19  C14   180.00   0.0  0
 L19  CONST_61  H7   C16  C15  C14   180.00   0.0  0
 L19  CONST_62  H8   C17  C16  C15   180.00   0.0  0
 L19  CONST_63  H19  C4   C5   C6      0.00   0.0  0
 L19  CONST_64  H11  C8   C7   C6      0.00   0.0  0
 L19  CONST_65  H17  C10  C9   C8    180.00   0.0  0
 L19  CONST_66  H20  C3   C4   C5    180.00   0.0  0
 L19  CONST_67  H21  C2   C1   C5    180.00   0.0  0
 L19  CONST_68  H1   O2   C22  O1      0.00   0.0  0
 L19  Var_01    C25  C23  C9   C8   -144.87  30.0  2
 L19  Var_02    C24  C25  C23  C9   -110.23  30.0  1
 L19  Var_03    C13  N1   C20  C21   -81.98  30.0  2
 L19  Var_04    N1   C20  C21  C22  -179.12  30.0  3
 L19  Var_05    H22  C    O    C1   -169.88  30.0  3
 L19  Var_06    C20  C21  C22  O1      0.01  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
 L19  chir_01  C23  C9  C25  C24  both

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
 L19  plan-1  C13  0.020
 L19  plan-1  C14  0.020
 L19  plan-1  C15  0.020
 L19  plan-1  C16  0.020
 L19  plan-1  C17  0.020
 L19  plan-1  C18  0.020
 L19  plan-1  C19  0.020
 L19  plan-1  H6   0.020
 L19  plan-1  H7   0.020
 L19  plan-1  H8   0.020
 L19  plan-1  H9   0.020
 L19  plan-1  H10  0.020
 L19  plan-2  C6   0.020
 L19  plan-2  C5   0.020
 L19  plan-2  C4   0.020
 L19  plan-2  C3   0.020
 L19  plan-2  N    0.020
 L19  plan-2  C2   0.020
 L19  plan-2  C1   0.020
 L19  plan-2  O    0.020
 L19  plan-2  H19  0.020
 L19  plan-2  H20  0.020
 L19  plan-2  H21  0.020
 L19  plan-3  C20  0.020
 L19  plan-3  N1   0.020
 L19  plan-3  C13  0.020
 L19  plan-3  C14  0.020
 L19  plan-3  C6   0.020
 L19  plan-3  C7   0.020
 L19  plan-3  C8   0.020
 L19  plan-3  C9   0.020
 L19  plan-3  C23  0.020
 L19  plan-3  C10  0.020
 L19  plan-3  C11  0.020
 L19  plan-3  C12  0.020
 L19  plan-3  C5   0.020
 L19  plan-3  H11  0.020
 L19  plan-3  H17  0.020
 L19  plan-3  H18  0.020
 L19  plan-4  O1   0.020
 L19  plan-4  C22  0.020
 L19  plan-4  O2   0.020
 L19  plan-4  C21  0.020
 L19  plan-4  H1   0.020

