# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 22:48:36 2020
#   Inital geometry file: a 141 line input string
#   Ligand name: (E)-3-[3,5-bis(fluoranyl)-4-[(1R,3R)-2-(2-fluoranyl-2-methyl-propyl)-3-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]phenyl]prop-2-enoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H]1Cc2c([nH]c3ccccc23)[C@H](N1CC(C)(C)F)c4c(F)cc(\C=C\C(O)=O)cc4F
#
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
 KE9  KE9  '(E)-3-[3,5-bis(fluoranyl)-4-[(1R,3R)-2-(2-fluoranyl-2-methyl-propyl)-3-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]phenyl]prop-2-enoic acid'  ligand  56  32  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_KE9
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
 KE9  C1    C  CH3    0  -0.674   3.7406  -2.0039   1.2566
 KE9  C2    C  CH1    0  -0.138   2.9085  -1.9045  -0.0259
 KE9  C4    C  CH2    0  -0.489   3.4424  -0.8135  -0.9562
 KE9  C5    C  CR5    0  -0.002   3.0509   0.5141  -0.4118
 KE9  C6    C  CR56   0   0.033   3.5857   1.8266  -0.5977
 KE9  C7    C  CR16   0  -0.378   4.6448   2.3532  -1.3447
 KE9  C8    C  CR16   0  -0.271   4.8902   3.7127  -1.2934
 KE9  C9    C  CR16   0  -0.288   4.0950   4.5625  -0.5076
 KE9  C10   C  CR16   0  -0.315   3.0414   4.0711   0.2418
 KE9  C11   C  CR56   0   0.325   2.7966   2.7013   0.1872
 KE9  N12   N  NR15   0  -0.755   1.8429   1.9473   0.8113
 KE9  C14   C  CR5    0   0.320   2.0037   0.6385   0.4445
 KE9  C15   C  CH1    0  -0.129   1.1416  -0.4786   0.9340
 KE9  N17   N  NT     0  -0.443   1.4705  -1.6986   0.1973
 KE9  C18   C  CH2    0  -0.308   0.7879  -2.8715   0.7102
 KE9  C19   C  CT     0   0.365   0.2496  -3.8319  -0.3512
 KE9  C20   C  CH3    0  -0.696  -0.5391  -4.9414   0.3210
 KE9  C21   C  CH3    0  -0.697  -0.5537  -3.1261  -1.4219
 KE9  F22   F  F      0  -0.395   1.3474  -4.4501  -0.9956
 KE9  C23   C  C      0  -0.354  -0.3197  -0.1245   0.7568
 KE9  C24   C  C      0   0.558  -1.2356  -0.1276   1.7975
 KE9  C25   C  C1     0  -0.495  -2.5729   0.1822   1.6436
 KE9  C26   C  C      0   0.182  -3.0614   0.5172   0.3829
 KE9  C27   C  C1     0  -0.505  -2.1679   0.5486  -0.6917
 KE9  C28   C  C      0   0.639  -0.8456   0.2366  -0.4825
 KE9  F29   F  F      0  -0.296  -0.0156   0.2981  -1.5273
 KE9  C30   C  C1     0  -0.254  -4.4843   0.8259   0.2383
 KE9  C31   C  C1     0  -0.427  -5.1476   0.9912  -0.9072
 KE9  C32   C  C      0   0.406  -6.6286   1.3000  -0.9628
 KE9  O33   O  OC    -1  -0.611  -7.1157   1.3696  -2.1094
 KE9  O34   O  O      0  -0.596  -7.2288   1.4563   0.1185
 KE9  F35   F  F      0  -0.306  -0.8119  -0.4618   3.0263
 KE9  H11C  H  HCH3   0   0.225   3.7873  -1.0568   1.7966
 KE9  H12C  H  HCH3   0   0.232   3.3418  -2.7548   1.9397
 KE9  H13C  H  HCH3   0   0.234   4.7637  -2.2964   1.0171
 KE9  H2    H  HCH1   0   0.250   2.9963  -2.8537  -0.5514
 KE9  H41C  H  HCH2   0   0.229   4.5283  -0.9054  -1.0444
 KE9  H42C  H  HCH2   0   0.240   3.0335  -0.9617  -1.9606
 KE9  H7    H  HCR6   0   0.239   5.2631   1.7051  -1.9541
 KE9  H8    H  HCR6   0   0.244   5.7078   4.1335  -1.8648
 KE9  H9    H  HCR6   0   0.247   4.3122   5.6228  -0.4865
 KE9  H10   H  HCR6   0   0.256   2.4313   4.7278   0.8493
 KE9  H12   H  HNR5   0   0.402   1.1339   2.3034   1.4309
 KE9  H15   H  HCH1   0   0.259   1.3288  -0.5957   2.0132
 KE9  H181  H  HCH2   0   0.235   1.4116  -3.4435   1.4122
 KE9  H182  H  HCH2   0   0.244  -0.0825  -2.5579   1.2887
 KE9  H201  H  HCH3   0   0.233  -1.4347  -4.5405   0.7961
 KE9  H202  H  HCH3   0   0.244  -0.8549  -5.6905  -0.4059
 KE9  H203  H  HCH3   0   0.238   0.0532  -5.4400   1.0901
 KE9  H211  H  HCH3   0   0.251   0.0459  -2.3661  -1.9186
 KE9  H212  H  HCH3   0   0.238  -0.9194  -3.8351  -2.1660
 KE9  H213  H  HCH3   0   0.221  -1.4200  -2.6328  -0.9791
 KE9  H25   H  H      0   0.280  -3.2318   0.1553   2.5021
 KE9  H27   H  H      0   0.275  -2.4909   0.8258  -1.6862
 KE9  H30   H  H      0   0.245  -5.0408   0.9108   1.1665
 KE9  H31   H  H      0   0.236  -4.6380   0.8924  -1.8614

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
 KE9  C1   C2    single    1.532  0.020  1.532
 KE9  C2   C4    single    1.530  0.020  1.530
 KE9  C2   N17   single    1.470  0.020  1.470
 KE9  C4   C5    single    1.487  0.020  1.487
 KE9  C5   C6    aromatic  1.429  0.020  1.429
 KE9  C5   C14   aromatic  1.358  0.020  1.358
 KE9  C6   C7    aromatic  1.399  0.020  1.399
 KE9  C6   C11   aromatic  1.416  0.020  1.416
 KE9  C7   C8    aromatic  1.382  0.020  1.382
 KE9  C8   C9    aromatic  1.404  0.020  1.404
 KE9  C9   C10   aromatic  1.383  0.020  1.383
 KE9  C10  C11   aromatic  1.393  0.020  1.393
 KE9  C11  N12   aromatic  1.367  0.020  1.367
 KE9  N12  C14   aromatic  1.369  0.020  1.369
 KE9  C14  C15   single    1.494  0.020  1.494
 KE9  C15  N17   single    1.463  0.020  1.463
 KE9  C15  C23   single    1.514  0.020  1.514
 KE9  N17  C18   single    1.451  0.020  1.451
 KE9  C18  C19   single    1.529  0.020  1.529
 KE9  C19  C20   single    1.518  0.020  1.518
 KE9  C19  C21   single    1.513  0.020  1.513
 KE9  C19  F22   single    1.415  0.020  1.415
 KE9  C23  C24   aromatic  1.386  0.020  1.386
 KE9  C23  C28   aromatic  1.394  0.020  1.394
 KE9  C24  C25   aromatic  1.381  0.020  1.381
 KE9  C24  F35   single    1.342  0.020  1.342
 KE9  C25  C26   aromatic  1.393  0.020  1.393
 KE9  C26  C27   aromatic  1.398  0.020  1.398
 KE9  C26  C30   single    1.463  0.020  1.463
 KE9  C27  C28   aromatic  1.375  0.020  1.375
 KE9  C28  F29   single    1.336  0.020  1.336
 KE9  C30  C31   double    1.334  0.020  1.334
 KE9  C31  C32   single    1.514  0.020  1.514
 KE9  C32  O33   deloc     1.248  0.020  1.248
 KE9  C32  O34   deloc     1.247  0.020  1.247
 KE9  C1   H11C  single    0.970  0.020  1.090
 KE9  C1   H12C  single    0.970  0.020  1.090
 KE9  C1   H13C  single    0.970  0.020  1.090
 KE9  C2   H2    single    0.970  0.020  1.090
 KE9  C4   H41C  single    0.970  0.020  1.090
 KE9  C4   H42C  single    0.970  0.020  1.090
 KE9  C7   H7    single    0.930  0.020  1.080
 KE9  C8   H8    single    0.930  0.020  1.080
 KE9  C9   H9    single    0.930  0.020  1.080
 KE9  C10  H10   single    0.930  0.020  1.080
 KE9  N12  H12   single    0.860  0.020  1.020
 KE9  C15  H15   single    0.970  0.020  1.090
 KE9  C18  H181  single    0.970  0.020  1.090
 KE9  C18  H182  single    0.970  0.020  1.090
 KE9  C20  H201  single    0.970  0.020  1.090
 KE9  C20  H202  single    0.970  0.020  1.090
 KE9  C20  H203  single    0.970  0.020  1.090
 KE9  C21  H211  single    0.970  0.020  1.090
 KE9  C21  H212  single    0.970  0.020  1.090
 KE9  C21  H213  single    0.970  0.020  1.090
 KE9  C25  H25   single    0.930  0.020  1.080
 KE9  C27  H27   single    0.930  0.020  1.080
 KE9  C30  H30   single    0.930  0.020  1.080
 KE9  C31  H31   single    0.930  0.020  1.080

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
 KE9  H13C  C1   H12C  107.21  3.000
 KE9  H13C  C1   H11C  107.53  3.000
 KE9  H12C  C1   H11C  107.65  3.000
 KE9  H13C  C1   C2    110.07  3.000
 KE9  H12C  C1   C2    111.74  3.000
 KE9  H11C  C1   C2    112.41  3.000
 KE9  H2    C2   N17   105.93  3.000
 KE9  H2    C2   C4    107.47  3.000
 KE9  N17   C2   C4    109.51  3.000
 KE9  H2    C2   C1    107.68  3.000
 KE9  N17   C2   C1    114.42  3.000
 KE9  C4    C2   C1    111.45  3.000
 KE9  H42C  C4   H41C  106.60  3.000
 KE9  H42C  C4   C5    111.00  3.000
 KE9  H41C  C4   C5    111.47  3.000
 KE9  H42C  C4   C2    109.33  3.000
 KE9  H41C  C4   C2    109.61  3.000
 KE9  C5    C4   C2    108.79  3.000
 KE9  C14   C5   C6    106.63  3.000
 KE9  C14   C5   C4    121.02  3.000
 KE9  C6    C5   C4    132.34  3.000
 KE9  C11   C6   C7    119.05  3.000
 KE9  C11   C6   C5    106.66  3.000
 KE9  C7    C6   C5    134.29  3.000
 KE9  H7    C7   C8    120.52  3.000
 KE9  H7    C7   C6    120.48  3.000
 KE9  C8    C7   C6    119.00  3.000
 KE9  H8    C8   C9    119.19  3.000
 KE9  H8    C8   C7    119.78  3.000
 KE9  C9    C8   C7    121.02  3.000
 KE9  H9    C9   C10   119.35  3.000
 KE9  H9    C9   C8    119.35  3.000
 KE9  C10   C9   C8    121.30  3.000
 KE9  H10   C10  C11   121.30  3.000
 KE9  H10   C10  C9    121.18  3.000
 KE9  C11   C10  C9    117.52  3.000
 KE9  N12   C11  C10   130.35  3.000
 KE9  N12   C11  C6    107.54  3.000
 KE9  C10   C11  C6    122.12  3.000
 KE9  H12   N12  C14   125.88  3.000
 KE9  H12   N12  C11   125.27  3.000
 KE9  C14   N12  C11   108.85  3.000
 KE9  C15   C14  N12   124.02  3.000
 KE9  C15   C14  C5    125.66  3.000
 KE9  N12   C14  C5    110.32  3.000
 KE9  H15   C15  C23   107.67  3.000
 KE9  H15   C15  N17   111.50  3.000
 KE9  C23   C15  N17   110.68  3.000
 KE9  H15   C15  C14   107.61  3.000
 KE9  C23   C15  C14   110.11  3.000
 KE9  N17   C15  C14   109.21  3.000
 KE9  C18   N17  C15   112.98  3.000
 KE9  C18   N17  C2    113.63  3.000
 KE9  C15   N17  C2    114.42  3.000
 KE9  H182  C18  H181  105.27  3.000
 KE9  H182  C18  C19   105.53  3.000
 KE9  H181  C18  C19   108.42  3.000
 KE9  H182  C18  N17   109.30  3.000
 KE9  H181  C18  N17   112.29  3.000
 KE9  C19   C18  N17   115.34  3.000
 KE9  F22   C19  C21   107.06  3.000
 KE9  F22   C19  C20   106.58  3.000
 KE9  C21   C19  C20   112.23  3.000
 KE9  F22   C19  C18   108.50  3.000
 KE9  C21   C19  C18   112.64  3.000
 KE9  C20   C19  C18   109.54  3.000
 KE9  H203  C20  H202  108.25  3.000
 KE9  H203  C20  H201  107.86  3.000
 KE9  H202  C20  H201  107.77  3.000
 KE9  H203  C20  C19   111.34  3.000
 KE9  H202  C20  C19   110.93  3.000
 KE9  H201  C20  C19   110.55  3.000
 KE9  H213  C21  H212  107.74  3.000
 KE9  H213  C21  H211  107.88  3.000
 KE9  H212  C21  H211  109.11  3.000
 KE9  H213  C21  C19   110.20  3.000
 KE9  H212  C21  C19   110.94  3.000
 KE9  H211  C21  C19   110.87  3.000
 KE9  C28   C23  C24   114.76  3.000
 KE9  C28   C23  C15   121.92  3.000
 KE9  C24   C23  C15   123.32  3.000
 KE9  F35   C24  C25   117.61  3.000
 KE9  F35   C24  C23   118.64  3.000
 KE9  C25   C24  C23   123.74  3.000
 KE9  H25   C25  C26   120.68  3.000
 KE9  H25   C25  C24   119.69  3.000
 KE9  C26   C25  C24   119.62  3.000
 KE9  C30   C26  C27   122.74  3.000
 KE9  C30   C26  C25   118.76  3.000
 KE9  C27   C26  C25   118.49  3.000
 KE9  H27   C27  C28   119.03  3.000
 KE9  H27   C27  C26   121.45  3.000
 KE9  C28   C27  C26   119.52  3.000
 KE9  F29   C28  C27   117.92  3.000
 KE9  F29   C28  C23   118.23  3.000
 KE9  C27   C28  C23   123.85  3.000
 KE9  H30   C30  C31   118.01  3.000
 KE9  H30   C30  C26   115.51  3.000
 KE9  C31   C30  C26   126.48  3.000
 KE9  H31   C31  C32   116.44  3.000
 KE9  H31   C31  C30   120.65  3.000
 KE9  C32   C31  C30   122.91  3.000
 KE9  O34   C32  O33   127.03  3.000
 KE9  O34   C32  C31   117.69  3.000
 KE9  O33   C32  C31   115.28  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
 KE9  CONST_01  C8    C7   C6   C5    180.00   0.0  0
 KE9  CONST_02  C10   C11  C6   C5    180.00   0.0  0
 KE9  CONST_03  N12   C11  C6   C5      0.00   0.0  0
 KE9  CONST_04  C11   N12  C14  C5      0.00   0.0  0
 KE9  CONST_05  N12   C14  C5   C6      0.00   0.0  0
 KE9  CONST_06  C9    C8   C7   C6      0.00   0.0  0
 KE9  CONST_07  C9    C10  C11  C6      0.00   0.0  0
 KE9  CONST_08  C14   N12  C11  C6      0.00   0.0  0
 KE9  CONST_09  C14   C5   C6   C7    180.00   0.0  0
 KE9  CONST_10  C10   C11  C6   C7      0.00   0.0  0
 KE9  CONST_11  N12   C11  C6   C7    180.00   0.0  0
 KE9  CONST_12  C10   C9   C8   C7      0.00   0.0  0
 KE9  CONST_13  C11   C6   C7   C8      0.00   0.0  0
 KE9  CONST_14  C11   C10  C9   C8      0.00   0.0  0
 KE9  CONST_15  N12   C11  C10  C9    180.00   0.0  0
 KE9  CONST_16  C14   N12  C11  C10   180.00   0.0  0
 KE9  CONST_17  C14   C5   C6   C11     0.00   0.0  0
 KE9  CONST_18  C26   C25  C24  C23     0.00   0.0  0
 KE9  CONST_19  C26   C27  C28  C23     0.00   0.0  0
 KE9  CONST_20  C27   C28  C23  C24     0.00   0.0  0
 KE9  CONST_21  C27   C26  C25  C24     0.00   0.0  0
 KE9  CONST_22  C28   C23  C24  C25     0.00   0.0  0
 KE9  CONST_23  C28   C27  C26  C25     0.00   0.0  0
 KE9  CONST_24  C25   C24  C23  C15   180.00   0.0  0
 KE9  CONST_25  C27   C28  C23  C15   180.00   0.0  0
 KE9  CONST_26  F35   C24  C23  C15     0.00   0.0  0
 KE9  CONST_27  F29   C28  C23  C15     0.00   0.0  0
 KE9  CONST_28  F29   C28  C23  C24   180.00   0.0  0
 KE9  CONST_29  C30   C26  C25  C24   180.00   0.0  0
 KE9  CONST_30  F35   C24  C25  C26   180.00   0.0  0
 KE9  CONST_31  F29   C28  C27  C26   180.00   0.0  0
 KE9  CONST_32  F35   C24  C23  C28   180.00   0.0  0
 KE9  CONST_33  C30   C26  C27  C28   180.00   0.0  0
 KE9  CONST_34  H7    C7   C6   C5      0.00   0.0  0
 KE9  CONST_35  H12   N12  C14  C5    180.00   0.0  0
 KE9  CONST_36  H8    C8   C7   C6    180.00   0.0  0
 KE9  CONST_37  H10   C10  C11  C6    180.00   0.0  0
 KE9  CONST_38  H9    C9   C8   C7    180.00   0.0  0
 KE9  CONST_39  H25   C25  C24  C23   180.00   0.0  0
 KE9  CONST_40  H27   C27  C28  C23   180.00   0.0  0
 KE9  Var_01    C6    C5   C4   C2    157.70  30.0  1
 KE9  Var_02    C19   C18  N17  C2    -88.58  30.0  3
 KE9  Var_03    C31   C30  C26  C25  -170.55  30.0  2
 KE9  Var_04    C32   C31  C30  C26   179.53   0.0  2
 KE9  Var_05    C20   C19  C18  N17  -175.13  30.0  3
 KE9  Var_06    O33   C32  C31  C30  -177.06  30.0  2
 KE9  Var_07    H201  C20  C19  C18    65.80  30.0  3
 KE9  Var_08    H211  C21  C19  C18    58.31  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
 KE9  chir_01  C2   C1   C4   N17  positiv
 KE9  chir_02  C15  N17  C23  C14  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
 KE9  plan-1  C15  0.020
 KE9  plan-1  C23  0.020
 KE9  plan-1  C24  0.020
 KE9  plan-1  C25  0.020
 KE9  plan-1  C26  0.020
 KE9  plan-1  C27  0.020
 KE9  plan-1  C28  0.020
 KE9  plan-1  F29  0.020
 KE9  plan-1  C30  0.020
 KE9  plan-1  F35  0.020
 KE9  plan-1  H25  0.020
 KE9  plan-1  H27  0.020
 KE9  plan-2  C4   0.020
 KE9  plan-2  C5   0.020
 KE9  plan-2  C6   0.020
 KE9  plan-2  C7   0.020
 KE9  plan-2  C8   0.020
 KE9  plan-2  C9   0.020
 KE9  plan-2  C10  0.020
 KE9  plan-2  C11  0.020
 KE9  plan-2  N12  0.020
 KE9  plan-2  C14  0.020
 KE9  plan-2  C15  0.020
 KE9  plan-2  H7   0.020
 KE9  plan-2  H8   0.020
 KE9  plan-2  H9   0.020
 KE9  plan-2  H10  0.020
 KE9  plan-2  H12  0.020
 KE9  plan-3  C31  0.020
 KE9  plan-3  C32  0.020
 KE9  plan-3  O33  0.020
 KE9  plan-3  O34  0.020
 KE9  plan-4  C26  0.020
 KE9  plan-4  C30  0.020
 KE9  plan-4  C31  0.020
 KE9  plan-4  C32  0.020
 KE9  plan-4  H30  0.020
 KE9  plan-4  H31  0.020

