# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 11 12:01:48 2022
#   Inital geometry file: a 105 line input string
#   Ligand name: (6~{R})-6-[(6-bromanyl-1~{H}-indol-3-yl)methyl]-6,7,8,9-tetrahydrobenzo[7]annulen-5-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Brc1ccc2c(C[C@H]3CCCc4ccccc4C3=O)c[nH]c2c1
#
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
 G9U  G9U  (6~{R})-6-[(6-bromanyl-1~{H}-indol-3-yl)methyl]-6,7,8,9-tetrahydrobenzo[7]annulen-5-one  ligand  41  23  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_G9U
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
 G9U  C10  C   CH1   0  -0.407  -17.4994  67.1099  -41.3979
 G9U  C13  C   CR5   0   0.032  -18.4560  66.6657  -43.6836
 G9U  C15  C   CR56  0   0.365  -17.8167  65.4447  -45.5132
 G9U  C17  C   CR16  0  -0.274  -17.3645  64.3616  -46.2647
 G9U  C20  C   CR16  0  -0.376  -17.7258  64.1727  -43.4579
 G9U  C01  C   CR16  0  -0.261  -16.9160  66.1092  -36.6066
 G9U  C02  C   CR16  0  -0.234  -15.5671  65.8152  -36.7556
 G9U  C03  C   CR16  0  -0.309  -14.9281  66.0950  -37.9521
 G9U  C04  C   CR6   0   0.128  -15.6078  66.6440  -39.0397
 G9U  C05  C   CR6   0  -0.042  -16.9730  66.9310  -38.8848
 G9U  C06  C   CR16  0  -0.269  -17.6036  66.6766  -37.6634
 G9U  C07  C   CH2   0  -0.536  -14.8150  66.9488  -40.2864
 G9U  C08  C   CH2   0  -0.465  -15.2278  68.2331  -41.0065
 G9U  C09  C   CH2   0  -0.402  -16.4121  68.0426  -41.9486
 G9U  C11  C   C     0   0.374  -17.8310  67.4883  -39.9732
 G9U  O01  O   O     0  -0.394  -18.7905  68.1804  -39.7037
 G9U  C12  C   CH2   0  -0.521  -18.7501  67.1017  -42.2869
 G9U  C14  C   CR15  0  -0.086  -18.5309  67.4304  -44.8127
 G9U  N01  N   NR15  0  -0.688  -18.1528  66.7026  -45.9078
 G9U  C16  C   CR56  0   0.033  -17.9986  65.3775  -44.1131
 G9U  C18  C   CR6   0  -0.139  -17.0966  63.2000  -45.5704
 G9U  C19  C   CR16  0  -0.240  -17.2752  63.0876  -44.1836
 G9U  BR1  BR  BR    0  -0.066  -16.4555  61.6939  -46.5236
 G9U  H11  H   HCH1  0   0.273  -17.0843  66.0969  -41.3751
 G9U  H16  H   HCR6  0   0.281  -17.2302  64.4382  -47.3359
 G9U  H18  H   HCR6  0   0.251  -17.8636  64.0755  -42.3881
 G9U  H01  H   HCR6  0   0.257  -17.4245  65.9018  -35.6744
 G9U  H02  H   HCR6  0   0.260  -15.0097  65.3781  -35.9371
 G9U  H03  H   HCR6  0   0.254  -13.8686  65.8887  -38.0483
 G9U  H04  H   HCR6  0   0.258  -18.6548  66.9085  -37.5524
 G9U  H06  H   HCH2  0   0.256  -14.8690  66.1011  -40.9792
 G9U  H05  H   HCH2  0   0.262  -13.7647  67.0179  -39.9985
 G9U  H08  H   HCH2  0   0.251  -14.3798  68.6077  -41.5822
 G9U  H07  H   HCH2  0   0.235  -15.4471  69.0040  -40.2619
 G9U  H10  H   HCH2  0   0.246  -16.0608  67.6133  -42.8890
 G9U  H09  H   HCH2  0   0.236  -16.8554  69.0119  -42.1926
 G9U  H12  H   HCH2  0   0.246  -19.1899  68.1006  -42.3084
 G9U  H13  H   HCH2  0   0.247  -19.4988  66.4400  -41.8408
 G9U  H14  H   HCR5  0   0.282  -18.8294  68.4621  -44.9177
 G9U  H15  H   HNR5  0   0.410  -18.1291  67.0476  -46.8530
 G9U  H17  H   HCR6  0   0.268  -17.0606  62.1553  -43.6790

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
 G9U  BR1  C18  single    1.894  0.020  1.894
 G9U  C17  C18  aromatic  1.380  0.020  1.380
 G9U  C17  C15  aromatic  1.394  0.020  1.394
 G9U  N01  C15  aromatic  1.361  0.020  1.361
 G9U  N01  C14  aromatic  1.368  0.020  1.368
 G9U  C18  C19  aromatic  1.403  0.020  1.403
 G9U  C15  C16  aromatic  1.413  0.020  1.413
 G9U  C14  C13  aromatic  1.366  0.020  1.366
 G9U  C19  C20  aromatic  1.381  0.020  1.381
 G9U  C16  C13  aromatic  1.433  0.020  1.433
 G9U  C16  C20  aromatic  1.398  0.020  1.398
 G9U  C13  C12  single    1.492  0.020  1.492
 G9U  C12  C10  single    1.534  0.020  1.534
 G9U  C09  C10  single    1.535  0.020  1.535
 G9U  C09  C08  single    1.525  0.020  1.525
 G9U  C10  C11  single    1.511  0.020  1.511
 G9U  C08  C07  single    1.529  0.020  1.529
 G9U  C07  C04  single    1.509  0.020  1.509
 G9U  C11  O01  double    1.213  0.020  1.213
 G9U  C11  C05  single    1.494  0.020  1.494
 G9U  C04  C05  aromatic  1.404  0.020  1.404
 G9U  C04  C03  aromatic  1.395  0.020  1.395
 G9U  C05  C06  aromatic  1.398  0.020  1.398
 G9U  C03  C02  aromatic  1.385  0.020  1.385
 G9U  C06  C01  aromatic  1.383  0.020  1.383
 G9U  C02  C01  aromatic  1.389  0.020  1.389
 G9U  C10  H11  single    0.970  0.020  1.090
 G9U  C17  H16  single    0.930  0.020  1.080
 G9U  C20  H18  single    0.930  0.020  1.080
 G9U  C01  H01  single    0.930  0.020  1.080
 G9U  C02  H02  single    0.930  0.020  1.080
 G9U  C03  H03  single    0.930  0.020  1.080
 G9U  C06  H04  single    0.930  0.020  1.080
 G9U  C07  H06  single    0.970  0.020  1.090
 G9U  C07  H05  single    0.970  0.020  1.090
 G9U  C08  H08  single    0.970  0.020  1.090
 G9U  C08  H07  single    0.970  0.020  1.090
 G9U  C09  H10  single    0.970  0.020  1.090
 G9U  C09  H09  single    0.970  0.020  1.090
 G9U  C12  H12  single    0.970  0.020  1.090
 G9U  C12  H13  single    0.970  0.020  1.090
 G9U  C14  H14  single    0.930  0.020  1.080
 G9U  N01  H15  single    0.860  0.020  1.020
 G9U  C19  H17  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
 G9U  H11  C10  C12  108.43  3.000
 G9U  H11  C10  C11  107.18  3.000
 G9U  C12  C10  C11  111.64  3.000
 G9U  H11  C10  C09  107.52  3.000
 G9U  C11  C10  C09  109.97  3.000
 G9U  C12  C10  C09  111.89  3.000
 G9U  C16  C13  C14  105.85  3.000
 G9U  C16  C13  C12  127.31  3.000
 G9U  C14  C13  C12  126.82  3.000
 G9U  C16  C15  N01  107.43  3.000
 G9U  C16  C15  C17  122.61  3.000
 G9U  N01  C15  C17  129.96  3.000
 G9U  H16  C17  C18  122.25  3.000
 G9U  H16  C17  C15  121.27  3.000
 G9U  C18  C17  C15  116.48  3.000
 G9U  H18  C20  C19  119.35  3.000
 G9U  H18  C20  C16  121.02  3.000
 G9U  C19  C20  C16  119.63  3.000
 G9U  H01  C01  C06  120.23  3.000
 G9U  H01  C01  C02  120.56  3.000
 G9U  C06  C01  C02  119.21  3.000
 G9U  H02  C02  C03  119.81  3.000
 G9U  H02  C02  C01  120.31  3.000
 G9U  C03  C02  C01  119.88  3.000
 G9U  H03  C03  C04  118.82  3.000
 G9U  H03  C03  C02  119.29  3.000
 G9U  C04  C03  C02  121.88  3.000
 G9U  C07  C04  C05  124.13  3.000
 G9U  C05  C04  C03  117.93  3.000
 G9U  C07  C04  C03  117.89  3.000
 G9U  C11  C05  C06  116.45  3.000
 G9U  C06  C05  C04  119.86  3.000
 G9U  C11  C05  C04  123.68  3.000
 G9U  H04  C06  C05  119.25  3.000
 G9U  H04  C06  C01  119.52  3.000
 G9U  C05  C06  C01  121.22  3.000
 G9U  H05  C07  H06  105.26  3.000
 G9U  H05  C07  C08  109.32  3.000
 G9U  H06  C07  C08  109.79  3.000
 G9U  H05  C07  C04  107.50  3.000
 G9U  H06  C07  C04  109.89  3.000
 G9U  C08  C07  C04  114.64  3.000
 G9U  H07  C08  H08  105.84  3.000
 G9U  H07  C08  C09  110.66  3.000
 G9U  H08  C08  C09  108.69  3.000
 G9U  H07  C08  C07  108.99  3.000
 G9U  H08  C08  C07  109.08  3.000
 G9U  C09  C08  C07  113.30  3.000
 G9U  H09  C09  H10  106.66  3.000
 G9U  H09  C09  C08  110.00  3.000
 G9U  H10  C09  C08  109.35  3.000
 G9U  H09  C09  C10  109.36  3.000
 G9U  H10  C09  C10  107.34  3.000
 G9U  C08  C09  C10  113.85  3.000
 G9U  O01  C11  C05  120.34  3.000
 G9U  C05  C11  C10  117.87  3.000
 G9U  O01  C11  C10  121.73  3.000
 G9U  H13  C12  H12  106.60  3.000
 G9U  H13  C12  C13  109.85  3.000
 G9U  H12  C12  C13  109.16  3.000
 G9U  H13  C12  C10  108.95  3.000
 G9U  H12  C12  C10  109.57  3.000
 G9U  C13  C12  C10  112.53  3.000
 G9U  H14  C14  N01  120.48  3.000
 G9U  H14  C14  C13  129.12  3.000
 G9U  N01  C14  C13  110.41  3.000
 G9U  H15  N01  C14  125.15  3.000
 G9U  H15  N01  C15  125.70  3.000
 G9U  C14  N01  C15  109.15  3.000
 G9U  C20  C16  C15  118.69  3.000
 G9U  C20  C16  C13  134.14  3.000
 G9U  C15  C16  C13  107.17  3.000
 G9U  BR1  C18  C19  118.48  3.000
 G9U  C19  C18  C17  122.71  3.000
 G9U  BR1  C18  C17  118.81  3.000
 G9U  H17  C19  C18  120.33  3.000
 G9U  H17  C19  C20  119.79  3.000
 G9U  C18  C19  C20  119.87  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
 G9U  CONST_01  C15  N01  C14  C13     0.00   0.0  0
 G9U  CONST_02  C17  C15  C16  C13   180.00   0.0  0
 G9U  CONST_03  N01  C15  C16  C13     0.00   0.0  0
 G9U  CONST_04  C19  C20  C16  C13   180.00   0.0  0
 G9U  CONST_05  C19  C18  C17  C15     0.00   0.0  0
 G9U  CONST_06  C14  C13  C16  C15     0.00   0.0  0
 G9U  CONST_07  C19  C20  C16  C15     0.00   0.0  0
 G9U  CONST_08  C20  C19  C18  C17     0.00   0.0  0
 G9U  CONST_09  C14  N01  C15  C17   180.00   0.0  0
 G9U  CONST_10  C20  C16  C15  C17     0.00   0.0  0
 G9U  CONST_11  N01  C15  C16  C20   180.00   0.0  0
 G9U  CONST_12  C14  C13  C16  C20   180.00   0.0  0
 G9U  CONST_13  C04  C03  C02  C01     0.00   0.0  0
 G9U  CONST_14  C05  C06  C01  C02     0.00   0.0  0
 G9U  CONST_15  C06  C01  C02  C03     0.00   0.0  0
 G9U  CONST_16  C16  C15  N01  C14     0.00   0.0  0
 G9U  CONST_17  C18  C17  C15  N01   180.00   0.0  0
 G9U  CONST_18  C16  C13  C14  N01     0.00   0.0  0
 G9U  CONST_19  C18  C17  C15  C16     0.00   0.0  0
 G9U  CONST_20  C18  C19  C20  C16     0.00   0.0  0
 G9U  CONST_21  BR1  C18  C17  C15   180.00   0.0  0
 G9U  CONST_22  C12  C13  C16  C15   180.00   0.0  0
 G9U  CONST_23  BR1  C18  C19  C20   180.00   0.0  0
 G9U  CONST_24  C12  C13  C16  C20     0.00   0.0  0
 G9U  CONST_25  N01  C14  C13  C12   180.00   0.0  0
 G9U  CONST_26  H15  N01  C14  C13   180.00   0.0  0
 G9U  CONST_27  H18  C20  C16  C13     0.00   0.0  0
 G9U  CONST_28  H14  C14  N01  C15   180.00   0.0  0
 G9U  CONST_29  H17  C19  C18  C17   180.00   0.0  0
 G9U  CONST_30  H03  C03  C02  C01   180.00   0.0  0
 G9U  CONST_31  H04  C06  C01  C02   180.00   0.0  0
 G9U  CONST_32  H01  C01  C02  C03   180.00   0.0  0
 G9U  CONST_33  H02  C02  C03  C04   180.00   0.0  0
 G9U  CONST_34  H16  C17  C15  N01     0.00   0.0  0
 G9U  Var_01    C14  C13  C12  C10  -113.17  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
 G9U  chir_01  C10  C12  C09  C11  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
 G9U  plan-1  C13  0.020
 G9U  plan-1  C15  0.020
 G9U  plan-1  C17  0.020
 G9U  plan-1  C20  0.020
 G9U  plan-1  C12  0.020
 G9U  plan-1  C14  0.020
 G9U  plan-1  N01  0.020
 G9U  plan-1  C16  0.020
 G9U  plan-1  C18  0.020
 G9U  plan-1  C19  0.020
 G9U  plan-1  BR1  0.020
 G9U  plan-1  H16  0.020
 G9U  plan-1  H18  0.020
 G9U  plan-1  H14  0.020
 G9U  plan-1  H15  0.020
 G9U  plan-1  H17  0.020
 G9U  plan-2  C01  0.020
 G9U  plan-2  C02  0.020
 G9U  plan-2  C03  0.020
 G9U  plan-2  C04  0.020
 G9U  plan-2  C05  0.020
 G9U  plan-2  C06  0.020
 G9U  plan-2  C07  0.020
 G9U  plan-2  C11  0.020
 G9U  plan-2  H01  0.020
 G9U  plan-2  H02  0.020
 G9U  plan-2  H03  0.020
 G9U  plan-2  H04  0.020
 G9U  plan-3  C10  0.020
 G9U  plan-3  C05  0.020
 G9U  plan-3  C11  0.020
 G9U  plan-3  O01  0.020

