# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 10:08:32 2021
#   Inital geometry file: a 140 line input string
#   Ligand name: 4-[2-[(2~{R})-2-[3-propyl-6-(trifluoromethyloxy)-1~{H}-indol-2-yl]piperidin-1-yl]ethyl]morpholine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCc1c([nH]c2cc(OC(F)(F)F)ccc12)[C@H]3CCCCN3CCN4CCOCC4
#
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
 OHW  OHW  4-[2-[(2~{R})-2-[3-propyl-6-(trifluoromethyloxy)-1~{H}-indol-2-yl]piperidin-1-yl]ethyl]morpholine  ligand  63  31  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OHW
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
 OHW  C3   C  CH2   0  -0.545  -17.4717  32.7614  -60.5751
 OHW  C2   C  CH2   0  -0.419  -16.5247  33.9014  -60.1854
 OHW  C1   C  CH3   0  -0.666  -15.8340  33.6745  -58.8492
 OHW  N1   N  NT    0  -0.439  -16.8682  29.1791  -57.8282
 OHW  C6   C  CH1   0  -0.110  -17.5651  30.1080  -58.7068
 OHW  C5   C  CR5   0   0.267  -16.7671  30.3646  -59.9492
 OHW  C4   C  CR5   0   0.002  -16.7752  31.4548  -60.7772
 OHW  C7   C  CH2   0  -0.427  -18.9219  29.5356  -59.1510
 OHW  O1   O  O2    0  -0.481  -11.7005  27.3182  -59.9512
 OHW  C16  C  CH2   0  -0.301  -13.4310  26.8012  -58.3445
 OHW  C17  C  CR56  0   0.326  -15.5140  29.7798  -61.6979
 OHW  C18  C  CR16  0  -0.371  -14.7247  29.1106  -62.6290
 OHW  C15  C  CH2   0  -0.194  -12.7533  26.4309  -59.6489
 OHW  C14  C  CH2   0  -0.199  -12.1787  28.6413  -60.0387
 OHW  C19  C  CR6   0   0.278  -14.3833  29.8125  -63.7661
 OHW  C10  C  CH2   0  -0.288  -17.6832  28.7520  -56.6993
 OHW  C9   C  CH2   0  -0.438  -18.9974  28.1237  -57.1207
 OHW  C8   C  CH2   0  -0.446  -19.7831  29.0997  -57.9783
 OHW  C13  C  CH2   0  -0.312  -12.8782  29.0748  -58.7656
 OHW  O2   O  O2    0  -0.528  -13.6360  29.1669  -64.7543
 OHW  C12  C  CH2   0  -0.273  -14.5802  28.5530  -57.1621
 OHW  N2   N  NT    0  -0.424  -13.9518  28.1572  -58.4141
 OHW  C20  C  CT    0   1.071  -12.3048  29.2336  -64.6711
 OHW  C21  C  CR16  0  -0.308  -14.8131  31.1199  -64.0112
 OHW  C22  C  CR16  0  -0.379  -15.6144  31.7627  -63.0867
 OHW  C23  C  CR56  0   0.062  -15.9701  31.1009  -61.9085
 OHW  F1   F  F     0  -0.280  -11.8015  28.6141  -65.7291
 OHW  F2   F  F     0  -0.301  -11.8447  30.4868  -64.6629
 OHW  F3   F  F     0  -0.301  -11.8189  28.6408  -63.5765
 OHW  N3   N  NR15  0  -0.732  -16.0221  29.3539  -60.5080
 OHW  H1   H  HCH2  0   0.233  -18.2414  32.6617  -59.8052
 OHW  H2   H  HCH2  0   0.237  -18.0001  33.0393  -61.4922
 OHW  H3   H  HCH2  0   0.217  -15.7737  34.0360  -60.9692
 OHW  H4   H  HCH2  0   0.223  -17.0975  34.8320  -60.1495
 OHW  H5   H  HCH3  0   0.228  -15.1962  34.5188  -58.5848
 OHW  H6   H  HCH3  0   0.214  -16.5623  33.5438  -58.0461
 OHW  H7   H  HCH3  0   0.223  -15.2059  32.7829  -58.8739
 OHW  H9   H  HCH1  0   0.214  -17.7530  31.0743  -58.2059
 OHW  H10  H  HCH2  0   0.242  -19.4328  30.2936  -59.7489
 OHW  H11  H  HCH2  0   0.224  -18.7407  28.6811  -59.8105
 OHW  H13  H  HCH2  0   0.200  -12.7116  26.6820  -57.5164
 OHW  H14  H  HCR6  0   0.282  -14.4199  28.0815  -62.4881
 OHW  H15  H  HCH2  0   0.199  -13.4975  26.4245  -60.4595
 OHW  H16  H  HCH2  0   0.239  -12.3288  25.4282  -59.5792
 OHW  H17  H  HCH2  0   0.238  -11.3233  29.2907  -60.2300
 OHW  H18  H  HCH2  0   0.208  -12.8679  28.7432  -60.8849
 OHW  H19  H  HCH2  0   0.239  -17.1078  28.0325  -56.1117
 OHW  H20  H  HCH2  0   0.191  -17.8896  29.6019  -56.0245
 OHW  H21  H  HCH2  0   0.234  -19.5572  27.8377  -56.2277
 OHW  H22  H  HCH2  0   0.218  -18.8017  27.2064  -57.6840
 OHW  H23  H  HCH2  0   0.215  -20.0664  29.9732  -57.3815
 OHW  H24  H  HCH2  0   0.236  -20.7107  28.6499  -58.3384
 OHW  H25  H  HCH2  0   0.206  -12.1391  29.1490  -57.9491
 OHW  H26  H  HCH2  0   0.240  -13.2811  30.0786  -58.9217
 OHW  H27  H  HCH2  0   0.238  -15.0889  27.6816  -56.7436
 OHW  H28  H  HCH2  0   0.204  -13.8196  28.8443  -56.4212
 OHW  H32  H  HCR6  0   0.266  -14.5335  31.6136  -64.9325
 OHW  H33  H  HCR6  0   0.249  -15.9589  32.7701  -63.2834
 OHW  H34  H  HNR5  0   0.397  -15.6652  28.5743  -59.9637
 OHW  C11  C  CH2   0  -0.315  -15.5895  29.6800  -57.3377
 OHW  H12  H  HCH2  0   0.244  -14.2553  26.1081  -58.1607
 OHW  H29  H  HCH2  0   0.251  -15.1883  30.4263  -58.0279
 OHW  H30  H  HCH2  0   0.223  -15.7152  30.2072  -56.3805

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
 OHW  F2   C20  single    1.335  0.020  1.335
 OHW  F1   C20  single    1.325  0.020  1.325
 OHW  C20  O2   single    1.335  0.020  1.335
 OHW  C20  F3   single    1.336  0.020  1.336
 OHW  O2   C19  single    1.397  0.020  1.397
 OHW  C21  C19  aromatic  1.398  0.020  1.398
 OHW  C21  C22  aromatic  1.382  0.020  1.382
 OHW  C19  C18  aromatic  1.379  0.020  1.379
 OHW  C22  C23  aromatic  1.397  0.020  1.397
 OHW  C18  C17  aromatic  1.392  0.020  1.392
 OHW  C23  C17  aromatic  1.413  0.020  1.413
 OHW  C23  C4   aromatic  1.433  0.020  1.433
 OHW  C17  N3   aromatic  1.362  0.020  1.362
 OHW  C2   C3   single    1.532  0.020  1.532
 OHW  C2   C1   single    1.521  0.020  1.521
 OHW  C4   C3   single    1.494  0.020  1.494
 OHW  C4   C5   aromatic  1.369  0.020  1.369
 OHW  N3   C5   aromatic  1.374  0.020  1.374
 OHW  C5   C6   single    1.499  0.020  1.499
 OHW  C15  O1   single    1.410  0.020  1.410
 OHW  C15  C16  single    1.516  0.020  1.516
 OHW  O1   C14  single    1.410  0.020  1.410
 OHW  C14  C13  single    1.516  0.020  1.516
 OHW  C7   C6   single    1.538  0.020  1.538
 OHW  C7   C8   single    1.519  0.020  1.519
 OHW  C16  N2   single    1.454  0.020  1.454
 OHW  C6   N1   single    1.456  0.020  1.456
 OHW  N2   C13  single    1.455  0.020  1.455
 OHW  N2   C12  single    1.456  0.020  1.456
 OHW  N1   C11  single    1.458  0.020  1.458
 OHW  N1   C10  single    1.456  0.020  1.456
 OHW  C8   C9   single    1.518  0.020  1.518
 OHW  C11  C12  single    1.523  0.020  1.523
 OHW  C9   C10  single    1.516  0.020  1.516
 OHW  C3   H1   single    0.970  0.020  1.090
 OHW  C3   H2   single    0.970  0.020  1.090
 OHW  C2   H3   single    0.970  0.020  1.090
 OHW  C2   H4   single    0.970  0.020  1.090
 OHW  C1   H5   single    0.970  0.020  1.090
 OHW  C1   H6   single    0.970  0.020  1.090
 OHW  C1   H7   single    0.970  0.020  1.090
 OHW  C6   H9   single    0.970  0.020  1.090
 OHW  C7   H10  single    0.970  0.020  1.090
 OHW  C7   H11  single    0.970  0.020  1.090
 OHW  C16  H12  single    0.970  0.020  1.090
 OHW  C16  H13  single    0.970  0.020  1.090
 OHW  C18  H14  single    0.930  0.020  1.080
 OHW  C15  H15  single    0.970  0.020  1.090
 OHW  C15  H16  single    0.970  0.020  1.090
 OHW  C14  H17  single    0.970  0.020  1.090
 OHW  C14  H18  single    0.970  0.020  1.090
 OHW  C10  H19  single    0.970  0.020  1.090
 OHW  C10  H20  single    0.970  0.020  1.090
 OHW  C9   H21  single    0.970  0.020  1.090
 OHW  C9   H22  single    0.970  0.020  1.090
 OHW  C8   H23  single    0.970  0.020  1.090
 OHW  C8   H24  single    0.970  0.020  1.090
 OHW  C13  H25  single    0.970  0.020  1.090
 OHW  C13  H26  single    0.970  0.020  1.090
 OHW  C12  H27  single    0.970  0.020  1.090
 OHW  C12  H28  single    0.970  0.020  1.090
 OHW  C11  H29  single    0.970  0.020  1.090
 OHW  C11  H30  single    0.970  0.020  1.090
 OHW  C21  H32  single    0.930  0.020  1.080
 OHW  C22  H33  single    0.930  0.020  1.080
 OHW  N3   H34  single    0.860  0.020  1.020

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
 OHW  H2   C3   H1   105.87  3.000
 OHW  H2   C3   C4   109.50  3.000
 OHW  H1   C3   C4   110.10  3.000
 OHW  H2   C3   C2   108.82  3.000
 OHW  H1   C3   C2   108.89  3.000
 OHW  C4   C3   C2   113.38  3.000
 OHW  H4   C2   H3   106.17  3.000
 OHW  H4   C2   C1   109.63  3.000
 OHW  H3   C2   C1   109.63  3.000
 OHW  H4   C2   C3   108.53  3.000
 OHW  H3   C2   C3   109.49  3.000
 OHW  C1   C2   C3   113.14  3.000
 OHW  H7   C1   H6   107.63  3.000
 OHW  H7   C1   H5   107.55  3.000
 OHW  H6   C1   H5   107.72  3.000
 OHW  H7   C1   C2   111.32  3.000
 OHW  H6   C1   C2   111.16  3.000
 OHW  H5   C1   C2   111.29  3.000
 OHW  C11  N1   C10  109.32  3.000
 OHW  C10  N1   C6   112.77  3.000
 OHW  C11  N1   C6   113.79  3.000
 OHW  H9   C6   C7   107.85  3.000
 OHW  H9   C6   C5   108.47  3.000
 OHW  C7   C6   C5   107.10  3.000
 OHW  H9   C6   N1   111.46  3.000
 OHW  C7   C6   N1   111.04  3.000
 OHW  C5   C6   N1   110.77  3.000
 OHW  N3   C5   C4   110.06  3.000
 OHW  N3   C5   C6   119.98  3.000
 OHW  C4   C5   C6   129.39  3.000
 OHW  C23  C4   C5   106.11  3.000
 OHW  C5   C4   C3   128.12  3.000
 OHW  C23  C4   C3   125.78  3.000
 OHW  H11  C7   H10  106.82  3.000
 OHW  H11  C7   C8   109.58  3.000
 OHW  H10  C7   C8   110.89  3.000
 OHW  H11  C7   C6   108.57  3.000
 OHW  H10  C7   C6   108.20  3.000
 OHW  C8   C7   C6   112.58  3.000
 OHW  C14  O1   C15  110.53  3.000
 OHW  H13  C16  H12  107.28  3.000
 OHW  H13  C16  N2   111.72  3.000
 OHW  H12  C16  N2   109.24  3.000
 OHW  H13  C16  C15  109.14  3.000
 OHW  H12  C16  C15  109.10  3.000
 OHW  N2   C16  C15  110.28  3.000
 OHW  N3   C17  C23  107.58  3.000
 OHW  N3   C17  C18  130.20  3.000
 OHW  C23  C17  C18  122.18  3.000
 OHW  H14  C18  C19  121.43  3.000
 OHW  H14  C18  C17  121.98  3.000
 OHW  C19  C18  C17  116.56  3.000
 OHW  H16  C15  H15  107.74  3.000
 OHW  H16  C15  C16  110.09  3.000
 OHW  H15  C15  C16  109.45  3.000
 OHW  H16  C15  O1   107.56  3.000
 OHW  H15  C15  O1   110.54  3.000
 OHW  C16  C15  O1   111.39  3.000
 OHW  H18  C14  H17  107.60  3.000
 OHW  H18  C14  C13  109.37  3.000
 OHW  H17  C14  C13  109.80  3.000
 OHW  H18  C14  O1   110.40  3.000
 OHW  H17  C14  O1   107.67  3.000
 OHW  C13  C14  O1   111.89  3.000
 OHW  C21  C19  O2   118.21  3.000
 OHW  C21  C19  C18  122.98  3.000
 OHW  O2   C19  C18  118.71  3.000
 OHW  H20  C10  H19  106.05  3.000
 OHW  H20  C10  C9   109.07  3.000
 OHW  H19  C10  C9   109.46  3.000
 OHW  H20  C10  N1   110.63  3.000
 OHW  H19  C10  N1   108.37  3.000
 OHW  C9   C10  N1   113.02  3.000
 OHW  H22  C9   H21  107.04  3.000
 OHW  H22  C9   C8   109.92  3.000
 OHW  H21  C9   C8   111.41  3.000
 OHW  H22  C9   C10  109.60  3.000
 OHW  H21  C9   C10  108.99  3.000
 OHW  C8   C9   C10  109.82  3.000
 OHW  H24  C8   H23  106.77  3.000
 OHW  H24  C8   C9   111.16  3.000
 OHW  H23  C8   C9   109.80  3.000
 OHW  H24  C8   C7   110.20  3.000
 OHW  H23  C8   C7   109.79  3.000
 OHW  C9   C8   C7   109.10  3.000
 OHW  H26  C13  H25  106.90  3.000
 OHW  H26  C13  N2   109.98  3.000
 OHW  H25  C13  N2   110.95  3.000
 OHW  H26  C13  C14  108.23  3.000
 OHW  H25  C13  C14  109.36  3.000
 OHW  N2   C13  C14  111.28  3.000
 OHW  C20  O2   C19  117.78  3.000
 OHW  H28  C12  H27  105.95  3.000
 OHW  H28  C12  N2   110.64  3.000
 OHW  H27  C12  N2   108.27  3.000
 OHW  H28  C12  C11  109.85  3.000
 OHW  H27  C12  C11  109.02  3.000
 OHW  N2   C12  C11  112.84  3.000
 OHW  C12  N2   C13  110.78  3.000
 OHW  C12  N2   C16  111.53  3.000
 OHW  C13  N2   C16  109.59  3.000
 OHW  F3   C20  F2   106.62  3.000
 OHW  F3   C20  F1   107.97  3.000
 OHW  F2   C20  F1   108.23  3.000
 OHW  F3   C20  O2   113.03  3.000
 OHW  F1   C20  O2   107.79  3.000
 OHW  F2   C20  O2   113.01  3.000
 OHW  H32  C21  C22  120.48  3.000
 OHW  H32  C21  C19  119.77  3.000
 OHW  C22  C21  C19  119.74  3.000
 OHW  H33  C22  C23  120.86  3.000
 OHW  H33  C22  C21  119.71  3.000
 OHW  C23  C22  C21  119.43  3.000
 OHW  C22  C23  C17  119.09  3.000
 OHW  C17  C23  C4   107.13  3.000
 OHW  C22  C23  C4   133.76  3.000
 OHW  H34  N3   C17  125.25  3.000
 OHW  H34  N3   C5   122.49  3.000
 OHW  C17  N3   C5   109.11  3.000
 OHW  H30  C11  H29  105.32  3.000
 OHW  H30  C11  C12  109.27  3.000
 OHW  H29  C11  C12  109.57  3.000
 OHW  H30  C11  N1   110.92  3.000
 OHW  H29  C11  N1   110.13  3.000
 OHW  C12  C11  N1   111.45  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
 OHW  CONST_01  C22  C23  C4   C5    180.00   0.0  0
 OHW  CONST_02  C17  C23  C4   C5      0.00   0.0  0
 OHW  CONST_03  C18  C17  N3   C5    180.00   0.0  0
 OHW  CONST_04  C23  C17  N3   C5      0.00   0.0  0
 OHW  CONST_05  C21  C22  C23  C4    180.00   0.0  0
 OHW  CONST_06  C18  C17  C23  C4    180.00   0.0  0
 OHW  CONST_07  N3   C17  C23  C4      0.00   0.0  0
 OHW  CONST_08  C17  N3   C5   C4      0.00   0.0  0
 OHW  CONST_09  C21  C19  C18  C17     0.00   0.0  0
 OHW  CONST_10  C21  C22  C23  C17     0.00   0.0  0
 OHW  CONST_11  C22  C21  C19  C18     0.00   0.0  0
 OHW  CONST_12  C22  C23  C17  C18     0.00   0.0  0
 OHW  CONST_13  C23  C22  C21  C19     0.00   0.0  0
 OHW  CONST_14  C23  C17  C18  C19     0.00   0.0  0
 OHW  CONST_15  N3   C17  C18  C19   180.00   0.0  0
 OHW  CONST_16  N3   C17  C23  C22   180.00   0.0  0
 OHW  CONST_17  N3   C5   C4   C23     0.00   0.0  0
 OHW  CONST_18  C23  C4   C5   C6    180.00   0.0  0
 OHW  CONST_19  C17  N3   C5   C6    180.00   0.0  0
 OHW  CONST_20  C22  C23  C4   C3      0.00   0.0  0
 OHW  CONST_21  C17  C23  C4   C3    180.00   0.0  0
 OHW  CONST_22  N3   C5   C4   C3    180.00   0.0  0
 OHW  CONST_23  C6   C5   C4   C3      0.00   0.0  0
 OHW  CONST_24  O2   C19  C18  C17   180.00   0.0  0
 OHW  CONST_25  C22  C21  C19  O2    180.00   0.0  0
 OHW  CONST_27  H33  C22  C23  C4      0.00   0.0  0
 OHW  CONST_28  H32  C21  C19  C18   180.00   0.0  0
 OHW  CONST_29  H14  C18  C19  C21   180.00   0.0  0
 OHW  Var_01    C8   C9   C10  N1    -57.17  30.0  1
 OHW  Var_02    C9   C8   C7   C6    -54.56  30.0  1
 OHW  Var_03    C9   C10  N1   C6     56.41  30.0  1
 OHW  Var_04    C10  C9   C8   C7     55.26  30.0  1
 OHW  Var_05    N2   C16  C15  O1     58.51  30.0  1
 OHW  Var_06    N2   C13  C14  O1    -55.33  30.0  1
 OHW  Var_07    C14  C13  N2   C16    54.21  30.0  1
 OHW  Var_08    C13  C14  O1   C15    56.82  30.0  1
 OHW  Var_09    C13  N2   C16  C15   -55.55  30.0  1
 OHW  Var_10    H15  C15  O1   C14    63.40  30.0  1
 OHW  Var_11    C23  C4   C3   C2    -74.85  30.0  2
 OHW  Var_12    N2   C12  C11  N1     80.20  30.0  3
 OHW  Var_13    C12  C11  N1   C6   -146.63  30.0  3
 OHW  Var_14    C11  C12  N2   C16  -157.21  30.0  3
 OHW  Var_15    C21  C19  O2   C20    93.71  30.0  2
 OHW  Var_16    C4   C3   C2   C1    -63.30  30.0  3
 OHW  Var_17    F2   C20  O2   C19   -57.63  30.0  3
 OHW  Var_18    H5   C1   C2   C3   -177.94  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
 OHW  chir_01  C6  C5  C7  N1  negativ

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
 OHW  plan-1  C3   0.020
 OHW  plan-1  C6   0.020
 OHW  plan-1  C5   0.020
 OHW  plan-1  C4   0.020
 OHW  plan-1  C17  0.020
 OHW  plan-1  C18  0.020
 OHW  plan-1  C19  0.020
 OHW  plan-1  O2   0.020
 OHW  plan-1  C21  0.020
 OHW  plan-1  C22  0.020
 OHW  plan-1  C23  0.020
 OHW  plan-1  N3   0.020
 OHW  plan-1  H14  0.020
 OHW  plan-1  H32  0.020
 OHW  plan-1  H33  0.020
 OHW  plan-1  H34  0.020

