# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 11 05:27:55 2022
#   Inital geometry file: a 143 line input string
#   Ligand name: (4aS,6R,8aS)-3-methoxy-11-[3-(piperidin-1-yl)propyl]-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol (non-preferred name)
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc2CN(CCCN3CCCCC3)CC[C@@]45C=C[C@H](O)C[C@@H]4Oc1c25
#
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
 G3X  G3X  '(4aS,6R,8aS)-3-methoxy-11-[3-(piperidin-1-yl)propyl]-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol (non-preferred name)'  ligand  63  29  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_G3X
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
 G3X  C1    C  C1    0  -0.145  -2.9813  -1.7470  -0.9853
 G3X  C2    C  C1    0  -0.271  -4.2543  -2.0521  -1.2109
 G3X  C3    C  CH1   0   0.007  -5.3615  -1.8547  -0.2158
 G3X  C4    C  CH2   0  -0.506  -4.8108  -1.6320   1.1819
 G3X  O5    O  O     0  -0.483  -3.9449   0.6235   0.9026
 G3X  C6    C  CR6   0   0.262  -2.6767   2.5256   0.0882
 G3X  C7    C  CR16  0  -0.387  -1.4875   2.9050  -0.5278
 G3X  C8    C  CR16  0  -0.349  -0.5316   1.9562  -0.8930
 G3X  C9    C  CH2   0  -0.408   0.2989  -0.4217  -1.0971
 G3X  N10   N  NT    0  -0.420   0.7345  -1.3111  -0.0266
 G3X  C11   C  CH2   0  -0.295  -0.1889  -2.4144   0.2000
 G3X  C12   C  CH2   0  -0.403  -1.4406  -2.0425   0.9868
 G3X  C13   C  CR56  0   0.348  -2.8568   1.1621   0.3149
 G3X  C14   C  CR56  0   0.035  -1.9085   0.2313  -0.0510
 G3X  C15   C  CR6   0   0.071  -0.7215   0.5972  -0.6698
 G3X  C16   C  CH3   0  -0.435  -3.4850   4.7386   0.2784
 G3X  O17   O  O2    0  -0.469  -3.6619   3.3525   0.4892
 G3X  O18   O  OH1   0  -0.664  -6.1847  -0.7568  -0.5731
 G3X  C19   C  CH2   0  -0.263   2.0949  -1.7853  -0.2524
 G3X  C20   C  CH2   0  -0.457   3.1527  -0.7273   0.0378
 G3X  C21   C  CH2   0  -0.250   4.5542  -1.2969  -0.1467
 G3X  N22   N  NT    0  -0.421   5.6106  -0.3802   0.2398
 G3X  C23   C  CH2   0  -0.283   5.7594   0.7229  -0.6956
 G3X  C24   C  CH2   0  -0.435   6.7947   1.7271  -0.2110
 G3X  C25   C  CH2   0  -0.438   8.1372   1.0516   0.0357
 G3X  C26   C  CH2   0  -0.437   7.9504  -0.1477   0.9560
 G3X  C27   C  CH2   0  -0.277   6.8731  -1.0779   0.4193
 G3X  C41   C  CR15  0   0.061  -3.6004  -0.7322   1.2412
 G3X  C42   C  CR5   0  -0.274  -2.4538  -1.1336   0.2852
 G3X  H1    H  H     0   0.259  -2.2535  -1.9121  -1.7723
 G3X  H2    H  H     0   0.251  -4.5353  -2.4549  -2.1794
 G3X  H3    H  HCH1  0   0.218  -5.9650  -2.7725  -0.1899
 G3X  H4    H  HCH2  0   0.260  -5.5970  -1.2613   1.8444
 G3X  H4A   H  HCH2  0   0.251  -4.5075  -2.6006   1.5880
 G3X  H7    H  HCR6  0   0.280  -1.2770   3.9484  -0.7215
 G3X  H8    H  HCR6  0   0.245   0.3838   2.3005  -1.3590
 G3X  H9    H  HCH2  0   0.257   1.1640   0.1170  -1.4846
 G3X  H9A   H  HCH2  0   0.224  -0.0891  -1.0001  -1.9533
 G3X  H11   H  HCH2  0   0.200  -0.4661  -2.9150  -0.7430
 G3X  H11A  H  HCH2  0   0.244   0.3327  -3.1662   0.7945
 G3X  H12   H  HCH2  0   0.239  -1.9467  -2.9733   1.2617
 G3X  H12A  H  HCH2  0   0.232  -1.1329  -1.5617   1.9195
 G3X  H16   H  HCH3  0   0.227  -2.6125   5.1247   0.8125
 G3X  H16A  H  HCH3  0   0.227  -3.3822   4.9805  -0.7829
 G3X  H16B  H  HCH3  0   0.258  -4.3761   5.2279   0.6637
 G3X  HO18  H  HOH1  0   0.447  -6.5680  -0.9418  -1.4364
 G3X  H19   H  HCH2  0   0.229   2.2696  -2.6261   0.4229
 G3X  H19A  H  HCH2  0   0.194   2.2321  -2.1792  -1.2736
 G3X  H20   H  HCH2  0   0.223   3.0097   0.1398  -0.6105
 G3X  H20A  H  HCH2  0   0.220   3.0369  -0.3787   1.0671
 G3X  H21   H  HCH2  0   0.222   4.6439  -2.1868   0.4835
 G3X  H21A  H  HCH2  0   0.185   4.6785  -1.6453  -1.1878
 G3X  H23   H  HCH2  0   0.180   6.0494   0.3549  -1.6976
 G3X  H23A  H  HCH2  0   0.234   4.7996   1.2284  -0.8157
 G3X  H24   H  HCH2  0   0.228   6.8911   2.5275  -0.9479
 G3X  H24A  H  HCH2  0   0.213   6.4383   2.1873   0.7156
 G3X  H25   H  HCH2  0   0.209   8.5573   0.7158  -0.9189
 G3X  H25A  H  HCH2  0   0.229   8.8525   1.7589   0.4616
 G3X  H26   H  HCH2  0   0.228   8.8845  -0.7032   1.0670
 G3X  H26A  H  HCH2  0   0.213   7.6609   0.1954   1.9539
 G3X  H27   H  HCH2  0   0.231   6.7176  -1.9034   1.1185
 G3X  H27A  H  HCH2  0   0.179   7.2238  -1.5271  -0.5285
 G3X  H41   H  HCR5  0   0.249  -3.2107  -0.7201   2.2677

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
 G3X  C2   C1    double    1.328  0.020  1.328
 G3X  C1   C42   single    1.506  0.020  1.506
 G3X  C1   H1    single    0.930  0.020  1.080
 G3X  C3   C2    single    1.502  0.020  1.502
 G3X  C2   H2    single    0.930  0.020  1.080
 G3X  O18  C3    single    1.418  0.020  1.418
 G3X  C3   C4    single    1.519  0.020  1.519
 G3X  C3   H3    single    0.970  0.020  1.090
 G3X  C4   C41   single    1.509  0.020  1.509
 G3X  C4   H4    single    0.970  0.020  1.090
 G3X  C4   H4A   single    0.970  0.020  1.090
 G3X  O5   C41   single    1.439  0.020  1.439
 G3X  O5   C13   single    1.349  0.020  1.349
 G3X  O17  C6    single    1.347  0.020  1.347
 G3X  C13  C6    aromatic  1.394  0.020  1.394
 G3X  C6   C7    aromatic  1.392  0.020  1.392
 G3X  C7   C8    aromatic  1.395  0.020  1.395
 G3X  C7   H7    single    0.930  0.020  1.080
 G3X  C15  C8    aromatic  1.390  0.020  1.390
 G3X  C8   H8    single    0.930  0.020  1.080
 G3X  C15  C9    single    1.504  0.020  1.504
 G3X  C9   N10   single    1.458  0.020  1.458
 G3X  C9   H9    single    0.970  0.020  1.090
 G3X  C9   H9A   single    0.970  0.020  1.090
 G3X  C11  N10   single    1.457  0.020  1.457
 G3X  N10  C19   single    1.458  0.020  1.458
 G3X  C12  C11   single    1.525  0.020  1.525
 G3X  C11  H11   single    0.970  0.020  1.090
 G3X  C11  H11A  single    0.970  0.020  1.090
 G3X  C42  C12   single    1.531  0.020  1.531
 G3X  C12  H12   single    0.970  0.020  1.090
 G3X  C12  H12A  single    0.970  0.020  1.090
 G3X  C13  C14   aromatic  1.378  0.020  1.378
 G3X  C42  C14   single    1.508  0.020  1.508
 G3X  C14  C15   aromatic  1.388  0.020  1.388
 G3X  C16  O17   single    1.413  0.020  1.413
 G3X  C16  H16   single    0.970  0.020  1.090
 G3X  C16  H16A  single    0.970  0.020  1.090
 G3X  C16  H16B  single    0.970  0.020  1.090
 G3X  O18  HO18  single    0.850  0.020  0.980
 G3X  C19  C20   single    1.524  0.020  1.524
 G3X  C19  H19   single    0.970  0.020  1.090
 G3X  C19  H19A  single    0.970  0.020  1.090
 G3X  C20  C21   single    1.524  0.020  1.524
 G3X  C20  H20   single    0.970  0.020  1.090
 G3X  C20  H20A  single    0.970  0.020  1.090
 G3X  N22  C21   single    1.451  0.020  1.451
 G3X  C21  H21   single    0.970  0.020  1.090
 G3X  C21  H21A  single    0.970  0.020  1.090
 G3X  N22  C27   single    1.454  0.020  1.454
 G3X  N22  C23   single    1.454  0.020  1.454
 G3X  C24  C23   single    1.522  0.020  1.522
 G3X  C23  H23   single    0.970  0.020  1.090
 G3X  C23  H23A  single    0.970  0.020  1.090
 G3X  C24  C25   single    1.523  0.020  1.523
 G3X  C24  H24   single    0.970  0.020  1.090
 G3X  C24  H24A  single    0.970  0.020  1.090
 G3X  C26  C25   single    1.523  0.020  1.523
 G3X  C25  H25   single    0.970  0.020  1.090
 G3X  C25  H25A  single    0.970  0.020  1.090
 G3X  C26  C27   single    1.521  0.020  1.521
 G3X  C26  H26   single    0.970  0.020  1.090
 G3X  C26  H26A  single    0.970  0.020  1.090
 G3X  C27  H27   single    0.970  0.020  1.090
 G3X  C27  H27A  single    0.970  0.020  1.090
 G3X  C41  C42   single    1.546  0.020  1.546
 G3X  C41  H41   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
 G3X  H1    C1   C42   116.05  3.000
 G3X  H1    C1   C2    119.00  3.000
 G3X  C42   C1   C2    124.92  3.000
 G3X  H2    C2   C3    116.68  3.000
 G3X  H2    C2   C1    118.99  3.000
 G3X  C3    C2   C1    124.32  3.000
 G3X  H3    C3   O18   109.51  3.000
 G3X  H3    C3   C4    107.46  3.000
 G3X  O18   C3   C4    109.20  3.000
 G3X  H3    C3   C2    108.11  3.000
 G3X  C4    C3   C2    111.21  3.000
 G3X  O18   C3   C2    111.27  3.000
 G3X  H4A   C4   H4    105.95  3.000
 G3X  H4A   C4   C41   106.92  3.000
 G3X  H4    C4   C41   110.54  3.000
 G3X  H4A   C4   C3    108.21  3.000
 G3X  H4    C4   C3    110.29  3.000
 G3X  C41   C4   C3    114.48  3.000
 G3X  C41   O5   C13   106.59  3.000
 G3X  O17   C6   C13   117.23  3.000
 G3X  C13   C6   C7    116.68  3.000
 G3X  O17   C6   C7    126.10  3.000
 G3X  H7    C7   C8    118.40  3.000
 G3X  H7    C7   C6    120.55  3.000
 G3X  C8    C7   C6    121.04  3.000
 G3X  H8    C8   C15   119.68  3.000
 G3X  H8    C8   C7    118.38  3.000
 G3X  C15   C8   C7    121.94  3.000
 G3X  H9A   C9   H9    105.20  3.000
 G3X  H9A   C9   C15   109.69  3.000
 G3X  H9    C9   C15   107.73  3.000
 G3X  H9A   C9   N10   110.78  3.000
 G3X  H9    C9   N10   108.98  3.000
 G3X  C15   C9   N10   114.03  3.000
 G3X  C19   N10  C11   111.67  3.000
 G3X  C19   N10  C9    111.30  3.000
 G3X  C11   N10  C9    112.75  3.000
 G3X  H11A  C11  H11   105.86  3.000
 G3X  H11A  C11  C12   106.22  3.000
 G3X  H11   C11  C12   110.22  3.000
 G3X  H11A  C11  N10   107.67  3.000
 G3X  H11   C11  N10   111.72  3.000
 G3X  C12   C11  N10   114.58  3.000
 G3X  H12A  C12  H12   106.84  3.000
 G3X  H12A  C12  C42   108.43  3.000
 G3X  H12   C12  C42   108.29  3.000
 G3X  H12A  C12  C11   108.45  3.000
 G3X  H12   C12  C11   107.56  3.000
 G3X  C42   C12  C11   116.84  3.000
 G3X  C14   C13  C6    121.91  3.000
 G3X  C14   C13  O5    113.64  3.000
 G3X  C6    C13  O5    124.45  3.000
 G3X  C42   C14  C15   130.35  3.000
 G3X  C15   C14  C13   121.93  3.000
 G3X  C42   C14  C13   107.66  3.000
 G3X  C14   C15  C9    121.90  3.000
 G3X  C14   C15  C8    116.50  3.000
 G3X  C9    C15  C8    121.60  3.000
 G3X  H16B  C16  H16A  108.75  3.000
 G3X  H16B  C16  H16   108.78  3.000
 G3X  H16A  C16  H16   108.73  3.000
 G3X  H16B  C16  O17   106.62  3.000
 G3X  H16A  C16  O17   111.94  3.000
 G3X  H16   C16  O17   111.92  3.000
 G3X  C16   O17  C6    117.78  3.000
 G3X  HO18  O18  C3    107.96  3.000
 G3X  H19A  C19  H19   106.11  3.000
 G3X  H19A  C19  C20   109.75  3.000
 G3X  H19   C19  C20   107.79  3.000
 G3X  H19A  C19  N10   112.06  3.000
 G3X  H19   C19  N10   107.69  3.000
 G3X  C20   C19  N10   113.10  3.000
 G3X  H20A  C20  H20   106.97  3.000
 G3X  H20A  C20  C21   109.31  3.000
 G3X  H20   C20  C21   110.20  3.000
 G3X  H20A  C20  C19   109.10  3.000
 G3X  H20   C20  C19   110.32  3.000
 G3X  C21   C20  C19   110.85  3.000
 G3X  H21A  C21  H21   106.09  3.000
 G3X  H21A  C21  N22   111.61  3.000
 G3X  H21   C21  N22   107.50  3.000
 G3X  H21A  C21  C20   109.59  3.000
 G3X  H21   C21  C20   108.04  3.000
 G3X  N22   C21  C20   113.65  3.000
 G3X  C27   N22  C23   110.78  3.000
 G3X  C23   N22  C21   112.48  3.000
 G3X  C27   N22  C21   111.22  3.000
 G3X  H23A  C23  H23   106.56  3.000
 G3X  H23A  C23  C24   109.13  3.000
 G3X  H23   C23  C24   109.25  3.000
 G3X  H23A  C23  N22   109.40  3.000
 G3X  H23   C23  N22   110.93  3.000
 G3X  C24   C23  N22   111.44  3.000
 G3X  H24A  C24  H24   106.97  3.000
 G3X  H24A  C24  C25   109.66  3.000
 G3X  H24   C24  C25   110.89  3.000
 G3X  H24A  C24  C23   109.00  3.000
 G3X  H24   C24  C23   109.20  3.000
 G3X  C25   C24  C23   111.02  3.000
 G3X  H25A  C25  H25   106.68  3.000
 G3X  H25A  C25  C26   110.76  3.000
 G3X  H25   C25  C26   109.40  3.000
 G3X  H25A  C25  C24   110.68  3.000
 G3X  H25   C25  C24   109.44  3.000
 G3X  C26   C25  C24   109.82  3.000
 G3X  H26A  C26  H26   107.03  3.000
 G3X  H26A  C26  C27   109.03  3.000
 G3X  H26   C26  C27   109.30  3.000
 G3X  H26A  C26  C25   109.67  3.000
 G3X  H26   C26  C25   110.91  3.000
 G3X  C27   C26  C25   110.80  3.000
 G3X  H27A  C27  H27   106.65  3.000
 G3X  H27A  C27  C26   109.04  3.000
 G3X  H27   C27  C26   109.69  3.000
 G3X  H27A  C27  N22   111.38  3.000
 G3X  H27   C27  N22   108.54  3.000
 G3X  C26   C27  N22   111.42  3.000
 G3X  H41   C41  C42   108.53  3.000
 G3X  H41   C41  O5    107.13  3.000
 G3X  C42   C41  O5    106.06  3.000
 G3X  H41   C41  C4    109.14  3.000
 G3X  C42   C41  C4    114.56  3.000
 G3X  O5    C41  C4    111.12  3.000
 G3X  C41   C42  C14    99.85  3.000
 G3X  C41   C42  C12   111.19  3.000
 G3X  C14   C42  C12   113.59  3.000
 G3X  C41   C42  C1    111.57  3.000
 G3X  C14   C42  C1    107.89  3.000
 G3X  C12   C42  C1    112.12  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
 G3X  CONST_01  C15  C14  C13  C6      0.00   0.0  0
 G3X  CONST_02  C15  C8   C7   C6      0.00   0.0  0
 G3X  CONST_03  C14  C13  C6   C7      0.00   0.0  0
 G3X  CONST_04  C14  C15  C8   C7      0.00   0.0  0
 G3X  CONST_05  C13  C6   C7   C8      0.00   0.0  0
 G3X  CONST_06  C13  C14  C15  C8      0.00   0.0  0
 G3X  CONST_07  O17  C6   C13  O5      0.00   0.0  0
 G3X  CONST_08  O17  C6   C7   C8    180.00   0.0  0
 G3X  CONST_09  O17  C6   C13  C14   180.00   0.0  0
 G3X  CONST_10  H8   C8   C7   C6    180.00   0.0  0
 G3X  CONST_11  H7   C7   C6   C13   180.00   0.0  0
 G3X  Var_01    C42  C1   C2   C3     -1.28  30.0  1
 G3X  Var_02    N10  C9   C15  C8    126.23  30.0  1
 G3X  Var_03    C12  C11  N10  C9    -77.88  30.0  1
 G3X  Var_04    C42  C12  C11  N10    69.12  30.0  1
 G3X  Var_05    C15  C9   N10  C11    81.90  30.0  1
 G3X  Var_06    C25  C26  C27  N22   -56.86  30.0  1
 G3X  Var_07    C25  C24  C23  N22    56.34  30.0  1
 G3X  Var_08    C26  C27  N22  C23    59.71  30.0  1
 G3X  Var_09    C26  C25  C24  C23   -52.69  30.0  1
 G3X  Var_10    C27  N22  C23  C24   -59.39  30.0  1
 G3X  Var_11    C27  C26  C25  C24    52.89  30.0  1
 G3X  Var_12    C20  C19  N10  C9     75.21  30.0  3
 G3X  Var_13    C21  C20  C19  N10   177.15  30.0  3
 G3X  Var_14    N22  C21  C20  C19  -174.31  30.0  3
 G3X  Var_15    H16  C16  O17  C6    -61.21  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
 G3X  chir_01  C3   C2   O18  C4   positiv
 G3X  chir_02  C41  O5   C4   C42  negativ
 G3X  chir_03  C42  C14  C12  C1   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
 G3X  plan-1  O5   0.020
 G3X  plan-1  C6   0.020
 G3X  plan-1  C7   0.020
 G3X  plan-1  C8   0.020
 G3X  plan-1  C9   0.020
 G3X  plan-1  C13  0.020
 G3X  plan-1  C14  0.020
 G3X  plan-1  C15  0.020
 G3X  plan-1  O17  0.020
 G3X  plan-1  C42  0.020
 G3X  plan-1  H7   0.020
 G3X  plan-1  H8   0.020

