# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 11 12:04:19 2022
#   Inital geometry file: a 105 line input string
#   Ligand name: (6~{R})-6-[(6-chloranyl-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: Clc1ccc2c(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
 G9X  G9X  (6~{R})-6-[(6-chloranyl-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_G9X
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
 G9X  C10   C   CH1   0  -0.403  -17.5638  66.9813  -41.4187
 G9X  C13   C   CH2   0  -0.523  -18.8244  66.8939  -42.2898
 G9X  C15   C   CR15  0  -0.087  -18.6263  67.2807  -44.8102
 G9X  C17   C   CR56  0   0.360  -17.8778  65.3226  -45.5536
 G9X  C20   C   CR6   0  -0.065  -17.1298  63.0899  -45.6575
 G9X  C21   C   CR16  0  -0.225  -17.2874  62.9516  -44.2715
 G9X  C22   C   CR16  0  -0.385  -17.7423  64.0170  -43.5205
 G9X  C01   C   CR16  0  -0.261  -16.8431  65.8641  -36.6749
 G9X  C02   C   CR16  0  -0.234  -15.4740  65.7022  -36.8418
 G9X  C03   C   CR16  0  -0.308  -14.8738  66.0850  -38.0300
 G9X  C04   C   CR6   0   0.128  -15.6103  66.6112  -39.0915
 G9X  C05   C   CR6   0  -0.042  -16.9945  66.7648  -38.9184
 G9X  C06   C   CR16  0  -0.269  -17.5891  66.4052  -37.7054
 G9X  C07   C   CH2   0  -0.534  -14.8589  67.0395  -40.3284
 G9X  C08   C   CH2   0  -0.466  -15.4024  68.2975  -41.0063
 G9X  C09   C   CH2   0  -0.401  -16.5699  68.0235  -41.9492
 G9X  C11   C   C     0   0.372  -17.9063  67.2882  -39.9791
 G9X  O12   O   O     0  -0.393  -18.9114  67.8976  -39.6782
 G9X  C14   C   CR5   0   0.034  -18.5245  66.4974  -43.6963
 G9X  N16   N   NR15  0  -0.689  -18.2415  66.5807  -45.9217
 G9X  C18   C   CR56  0   0.034  -18.0433  65.2271  -44.1531
 G9X  C19   C   CR16  0  -0.267  -17.4187  64.2592  -46.3282
 G9X  H101  H   HCH1  0   0.273  -17.0626  66.0075  -41.4326
 G9X  H132  H   HCH2  0   0.246  -19.3359  67.8584  -42.2889
 G9X  H131  H   HCH2  0   0.247  -19.5169  66.1746  -41.8424
 G9X  H151  H   HCR5  0   0.282  -18.9503  68.3066  -44.8940
 G9X  H211  H   HCR6  0   0.267  -17.0504  62.0101  -43.7951
 G9X  H221  H   HCR6  0   0.250  -17.8636  63.9029  -42.4503
 G9X  H011  H   HCR6  0   0.257  -17.3225  65.5754  -35.7489
 G9X  H021  H   HCR6  0   0.260  -14.8716  65.2879  -36.0436
 G9X  H031  H   HCR6  0   0.254  -13.8007  65.9813  -38.1391
 G9X  H061  H   HCR6  0   0.258  -18.6565  66.5340  -37.5812
 G9X  H071  H   HCH2  0   0.256  -14.8258  66.2146  -41.0495
 G9X  H072  H   HCH2  0   0.262  -13.8207  67.2083  -40.0375
 G9X  H081  H   HCH2  0   0.251  -14.5993  68.7691  -41.5752
 G9X  H082  H   HCH2  0   0.235  -15.6878  69.0219  -40.2376
 G9X  H091  H   HCH2  0   0.245  -16.1856  67.6569  -42.9033
 G9X  H092  H   HCH2  0   0.236  -17.1022  68.9542  -42.1639
 G9X  H161  H   HNR5  0   0.410  -18.2379  66.9414  -46.8613
 G9X  H191  H   HCR6  0   0.279  -17.2953  64.3465  -47.3995
 G9X  CL2   CL  CL    0  -0.142  -16.5427  61.7266  -46.5636

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
 G9X  CL2  C20   single    1.739  0.020  1.739
 G9X  C19  C20   aromatic  1.379  0.020  1.379
 G9X  C19  C17   aromatic  1.393  0.020  1.393
 G9X  N16  C17   aromatic  1.360  0.020  1.360
 G9X  N16  C15   aromatic  1.369  0.020  1.369
 G9X  C20  C21   aromatic  1.402  0.020  1.402
 G9X  C17  C18   aromatic  1.413  0.020  1.413
 G9X  C15  C14   aromatic  1.366  0.020  1.366
 G9X  C21  C22   aromatic  1.381  0.020  1.381
 G9X  C18  C14   aromatic  1.433  0.020  1.433
 G9X  C18  C22   aromatic  1.398  0.020  1.398
 G9X  C14  C13   single    1.492  0.020  1.492
 G9X  C13  C10   single    1.535  0.020  1.535
 G9X  C09  C10   single    1.535  0.020  1.535
 G9X  C09  C08   single    1.525  0.020  1.525
 G9X  C10  C11   single    1.511  0.020  1.511
 G9X  C08  C07   single    1.529  0.020  1.529
 G9X  C07  C04   single    1.509  0.020  1.509
 G9X  C11  O12   double    1.213  0.020  1.213
 G9X  C11  C05   single    1.493  0.020  1.493
 G9X  C04  C05   aromatic  1.403  0.020  1.403
 G9X  C04  C03   aromatic  1.395  0.020  1.395
 G9X  C05  C06   aromatic  1.398  0.020  1.398
 G9X  C03  C02   aromatic  1.385  0.020  1.385
 G9X  C06  C01   aromatic  1.382  0.020  1.382
 G9X  C02  C01   aromatic  1.389  0.020  1.389
 G9X  C10  H101  single    0.970  0.020  1.090
 G9X  C13  H132  single    0.970  0.020  1.090
 G9X  C13  H131  single    0.970  0.020  1.090
 G9X  C15  H151  single    0.930  0.020  1.080
 G9X  C21  H211  single    0.930  0.020  1.080
 G9X  C22  H221  single    0.930  0.020  1.080
 G9X  C01  H011  single    0.930  0.020  1.080
 G9X  C02  H021  single    0.930  0.020  1.080
 G9X  C03  H031  single    0.930  0.020  1.080
 G9X  C06  H061  single    0.930  0.020  1.080
 G9X  C07  H071  single    0.970  0.020  1.090
 G9X  C07  H072  single    0.970  0.020  1.090
 G9X  C08  H081  single    0.970  0.020  1.090
 G9X  C08  H082  single    0.970  0.020  1.090
 G9X  C09  H091  single    0.970  0.020  1.090
 G9X  C09  H092  single    0.970  0.020  1.090
 G9X  N16  H161  single    0.860  0.020  1.020
 G9X  C19  H191  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
 G9X  H101  C10  C11   107.24  3.000
 G9X  H101  C10  C09   107.64  3.000
 G9X  C11   C10  C09   109.76  3.000
 G9X  H101  C10  C13   108.54  3.000
 G9X  C11   C10  C13   111.48  3.000
 G9X  C09   C10  C13   111.99  3.000
 G9X  H131  C13  H132  106.50  3.000
 G9X  H131  C13  C14   109.76  3.000
 G9X  H132  C13  C14   109.25  3.000
 G9X  H131  C13  C10   108.98  3.000
 G9X  H132  C13  C10   109.51  3.000
 G9X  C14   C13  C10   112.66  3.000
 G9X  H151  C15  N16   120.50  3.000
 G9X  H151  C15  C14   129.13  3.000
 G9X  N16   C15  C14   110.37  3.000
 G9X  C19   C17  C18   122.53  3.000
 G9X  C18   C17  N16   107.41  3.000
 G9X  C19   C17  N16   130.05  3.000
 G9X  CL2   C20  C19   118.83  3.000
 G9X  C19   C20  C21   122.76  3.000
 G9X  CL2   C20  C21   118.41  3.000
 G9X  H211  C21  C22   120.30  3.000
 G9X  H211  C21  C20   119.79  3.000
 G9X  C22   C21  C20   119.92  3.000
 G9X  H221  C22  C18   120.93  3.000
 G9X  H221  C22  C21   119.55  3.000
 G9X  C18   C22  C21   119.52  3.000
 G9X  H011  C01  C06   120.22  3.000
 G9X  H011  C01  C02   120.57  3.000
 G9X  C06   C01  C02   119.21  3.000
 G9X  H021  C02  C03   119.81  3.000
 G9X  H021  C02  C01   120.31  3.000
 G9X  C03   C02  C01   119.88  3.000
 G9X  H031  C03  C04   118.84  3.000
 G9X  H031  C03  C02   119.28  3.000
 G9X  C04   C03  C02   121.88  3.000
 G9X  C07   C04  C05   124.13  3.000
 G9X  C05   C04  C03   117.92  3.000
 G9X  C07   C04  C03   117.89  3.000
 G9X  C11   C05  C06   116.54  3.000
 G9X  C06   C05  C04   119.89  3.000
 G9X  C11   C05  C04   123.57  3.000
 G9X  H061  C06  C05   119.23  3.000
 G9X  H061  C06  C01   119.56  3.000
 G9X  C05   C06  C01   121.20  3.000
 G9X  H072  C07  H071  105.25  3.000
 G9X  H072  C07  C08   109.21  3.000
 G9X  H071  C07  C08   109.77  3.000
 G9X  H072  C07  C04   107.41  3.000
 G9X  H071  C07  C04   109.91  3.000
 G9X  C08   C07  C04   114.83  3.000
 G9X  H082  C08  H081  105.79  3.000
 G9X  H082  C08  C09   110.71  3.000
 G9X  H081  C08  C09   108.58  3.000
 G9X  H082  C08  C07   109.02  3.000
 G9X  H081  C08  C07   108.97  3.000
 G9X  C09   C08  C07   113.47  3.000
 G9X  H092  C09  H091  106.59  3.000
 G9X  H092  C09  C08   109.94  3.000
 G9X  H091  C09  C08   109.33  3.000
 G9X  H092  C09  C10   109.30  3.000
 G9X  H091  C09  C10   107.57  3.000
 G9X  C08   C09  C10   113.83  3.000
 G9X  O12   C11  C05   120.37  3.000
 G9X  C05   C11  C10   117.84  3.000
 G9X  O12   C11  C10   121.73  3.000
 G9X  C18   C14  C15   105.87  3.000
 G9X  C18   C14  C13   127.13  3.000
 G9X  C15   C14  C13   126.99  3.000
 G9X  H161  N16  C17   125.66  3.000
 G9X  H161  N16  C15   125.16  3.000
 G9X  C17   N16  C15   109.17  3.000
 G9X  C14   C18  C22   134.04  3.000
 G9X  C22   C18  C17   118.79  3.000
 G9X  C14   C18  C17   107.17  3.000
 G9X  H191  C19  C20   121.75  3.000
 G9X  H191  C19  C17   121.77  3.000
 G9X  C20   C19  C17   116.48  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
 G9X  CONST_01  C19   C17  N16  C15   180.00   0.0  0
 G9X  CONST_02  C18   C17  N16  C15     0.00   0.0  0
 G9X  CONST_03  C17   C18  C14  C15     0.00   0.0  0
 G9X  CONST_04  C22   C18  C14  C15   180.00   0.0  0
 G9X  CONST_05  C21   C20  C19  C17     0.00   0.0  0
 G9X  CONST_06  C14   C15  N16  C17     0.00   0.0  0
 G9X  CONST_07  C21   C22  C18  C17     0.00   0.0  0
 G9X  CONST_08  N16   C17  C19  C20   180.00   0.0  0
 G9X  CONST_09  C18   C17  C19  C20     0.00   0.0  0
 G9X  CONST_10  C18   C22  C21  C20     0.00   0.0  0
 G9X  CONST_11  C14   C18  C22  C21   180.00   0.0  0
 G9X  CONST_12  C19   C20  C21  C22     0.00   0.0  0
 G9X  CONST_13  C19   C17  C18  C22     0.00   0.0  0
 G9X  CONST_14  N16   C17  C18  C22   180.00   0.0  0
 G9X  CONST_15  C04   C03  C02  C01     0.00   0.0  0
 G9X  CONST_16  C05   C06  C01  C02     0.00   0.0  0
 G9X  CONST_17  C06   C01  C02  C03     0.00   0.0  0
 G9X  CONST_18  C19   C17  C18  C14   180.00   0.0  0
 G9X  CONST_19  N16   C17  C18  C14     0.00   0.0  0
 G9X  CONST_20  C18   C14  C15  N16     0.00   0.0  0
 G9X  CONST_21  N16   C15  C14  C13   180.00   0.0  0
 G9X  CONST_22  C17   C18  C14  C13   180.00   0.0  0
 G9X  CONST_23  C22   C18  C14  C13     0.00   0.0  0
 G9X  CONST_24  CL2   C20  C19  C17   180.00   0.0  0
 G9X  CONST_25  CL2   C20  C21  C22   180.00   0.0  0
 G9X  CONST_26  H151  C15  N16  C17   180.00   0.0  0
 G9X  CONST_27  H221  C22  C18  C17   180.00   0.0  0
 G9X  CONST_28  H191  C19  C20  C21   180.00   0.0  0
 G9X  CONST_29  H031  C03  C02  C01   180.00   0.0  0
 G9X  CONST_30  H061  C06  C01  C02   180.00   0.0  0
 G9X  CONST_31  H011  C01  C02  C03   180.00   0.0  0
 G9X  CONST_32  H021  C02  C03  C04   180.00   0.0  0
 G9X  CONST_33  H161  N16  C15  C14   180.00   0.0  0
 G9X  CONST_34  H211  C21  C22  C18   180.00   0.0  0
 G9X  Var_01    C15   C14  C13  C10  -110.64  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
 G9X  chir_01  C10  C13  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
 G9X  plan-1  C13   0.020
 G9X  plan-1  C15   0.020
 G9X  plan-1  C17   0.020
 G9X  plan-1  C20   0.020
 G9X  plan-1  C21   0.020
 G9X  plan-1  C22   0.020
 G9X  plan-1  C14   0.020
 G9X  plan-1  N16   0.020
 G9X  plan-1  C18   0.020
 G9X  plan-1  C19   0.020
 G9X  plan-1  H151  0.020
 G9X  plan-1  H211  0.020
 G9X  plan-1  H221  0.020
 G9X  plan-1  H161  0.020
 G9X  plan-1  H191  0.020
 G9X  plan-1  CL2   0.020
 G9X  plan-2  C01   0.020
 G9X  plan-2  C02   0.020
 G9X  plan-2  C03   0.020
 G9X  plan-2  C04   0.020
 G9X  plan-2  C05   0.020
 G9X  plan-2  C06   0.020
 G9X  plan-2  C07   0.020
 G9X  plan-2  C11   0.020
 G9X  plan-2  H011  0.020
 G9X  plan-2  H021  0.020
 G9X  plan-2  H031  0.020
 G9X  plan-2  H061  0.020
 G9X  plan-3  C10   0.020
 G9X  plan-3  C05   0.020
 G9X  plan-3  C11   0.020
 G9X  plan-3  O12   0.020

