# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 14 06:29:07 2020
#   Inital geometry file: a 127 line input string
#   Ligand name: 3-[(3~{R})-3-[(4-fluorophenyl)sulfonylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)CCn1c2CC[C@H](Cc2c3ccccc13)N[S](=O)(=O)c4ccc(F)cc4
#
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
 A8X  A8X  '3-[(3~{R})-3-[(4-fluorophenyl)sulfonylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]propanoic acid'  ligand  49  29  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_A8X
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
 A8X  F    F  F      0  -0.302   4.9318  -3.6640  -0.5169
 A8X  C11  C  CH2    0  -0.489  -0.3040   2.3701  -0.3022
 A8X  C12  C  CH1    0  -0.096   0.8696   1.3978  -0.1754
 A8X  C16  C  CR6    0   0.550   4.6025  -2.3997  -0.2393
 A8X  C15  C  CR16   0  -0.397   3.8048  -2.1451   0.8604
 A8X  C14  C  CR16   0  -0.217   3.4648  -0.8319   1.1433
 A8X  C17  C  CR16   0  -0.399   5.0766  -1.3942  -1.0632
 A8X  C18  C  CR16   0  -0.215   4.7327  -0.0847  -0.7773
 A8X  C13  C  CR6    0  -0.214   3.9284   0.1883   0.3230
 A8X  S    S  S      0   1.373   3.4133   1.8561   0.6224
 A8X  O2   O  OS     0  -0.653   2.9538   1.9243   1.9998
 A8X  O3   O  OS     0  -0.657   4.4617   2.7479   0.1558
 A8X  N1   N  NC1    0  -0.741   2.1178   2.1436  -0.3370
 A8X  C19  C  CH2    0  -0.448   0.7478   0.2474  -1.1775
 A8X  C20  C  CH2    0  -0.521  -0.4895  -0.6087  -0.9091
 A8X  C3   C  CR5    0   0.324  -1.6580   0.2726  -0.6424
 A8X  C4   C  CR5    0  -0.043  -1.5863   1.6099  -0.3700
 A8X  C5   C  CR56   0   0.045  -2.9257   2.0603  -0.1688
 A8X  C10  C  CR56   0   0.343  -3.7596   0.9291  -0.3302
 A8X  C9   C  CR16   0  -0.318  -5.1436   1.0105  -0.1896
 A8X  C8   C  CR16   0  -0.286  -5.6874   2.2476   0.1085
 A8X  C7   C  CR16   0  -0.273  -4.8760   3.3815   0.2688
 A8X  C6   C  CR16   0  -0.383  -3.5026   3.2978   0.1326
 A8X  N    N  NR5    0  -0.590  -2.9659  -0.1455  -0.6293
 A8X  C2   C  CH2    0  -0.311  -3.4272  -1.5153  -0.7419
 A8X  C1   C  CH2    0  -0.593  -3.5309  -2.2109   0.6065
 A8X  C    C  C      0   0.419  -4.0376  -3.6627   0.5338
 A8X  O    O  O      0  -0.607  -4.2324  -4.1449  -0.5992
 A8X  O1   O  OC    -1  -0.624  -4.2039  -4.2384   1.6273
 A8X  H3   H  HCH1   0   0.268   0.8552   0.9853   0.8377
 A8X  H4   H  HCR6   0   0.297   3.4570  -2.9539   1.4888
 A8X  H5   H  HCR6   0   0.296   2.8438  -0.6179   2.0021
 A8X  H6   H  HCR6   0   0.297   5.7037  -1.6278  -1.9130
 A8X  H7   H  HCR6   0   0.295   5.0984   0.7097  -1.4136
 A8X  H8   H  HNC1   0   0.413   2.3737   2.3517  -1.2967
 A8X  H9   H  HCH2   0   0.244   0.6980   0.6632  -2.1888
 A8X  H10  H  HCH2   0   0.252   1.6356  -0.3852  -1.1377
 A8X  H11  H  HCH2   0   0.264  -0.6702  -1.2634  -1.7655
 A8X  H12  H  HCH2   0   0.256  -0.3130  -1.2726  -0.0555
 A8X  H13  H  HCR6   0   0.257  -5.7794   0.1417  -0.3064
 A8X  H14  H  HCR6   0   0.246  -6.7598   2.3410   0.2220
 A8X  H15  H  HCR6   0   0.242  -5.3354   4.3328   0.5055
 A8X  H16  H  HCR6   0   0.238  -2.8828   4.1773   0.2612
 A8X  H17  H  HCH2   0   0.250  -4.3936  -1.5042  -1.2472
 A8X  H18  H  HCH2   0   0.251  -2.7457  -2.0513  -1.4011
 A8X  H19  H  HCH2   0   0.236  -2.5509  -2.2100   1.0967
 A8X  H20  H  HCH2   0   0.234  -4.1872  -1.6386   1.2700
 A8X  H1   H  HCH2   0   0.249  -0.2965   3.0548   0.5501
 A8X  H2   H  HCH2   0   0.237  -0.1666   2.9917  -1.1950

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
 A8X  C17  C18  aromatic  1.384  0.020  1.384
 A8X  C17  C16  aromatic  1.384  0.020  1.384
 A8X  C18  C13  aromatic  1.390  0.020  1.390
 A8X  O3   S    double    1.453  0.020  1.453
 A8X  F    C16  single    1.336  0.020  1.336
 A8X  C16  C15  aromatic  1.382  0.020  1.382
 A8X  C13  S    single    1.771  0.020  1.771
 A8X  C13  C14  aromatic  1.389  0.020  1.389
 A8X  S    N1   single    1.638  0.020  1.638
 A8X  S    O2   double    1.454  0.020  1.454
 A8X  N1   C12  single    1.463  0.020  1.463
 A8X  C15  C14  aromatic  1.386  0.020  1.386
 A8X  C19  C12  single    1.530  0.020  1.530
 A8X  C19  C20  single    1.528  0.020  1.528
 A8X  C12  C11  single    1.529  0.020  1.529
 A8X  C11  C4   single    1.492  0.020  1.492
 A8X  C20  C3   single    1.488  0.020  1.488
 A8X  C4   C3   aromatic  1.367  0.020  1.367
 A8X  C4   C5   aromatic  1.427  0.020  1.427
 A8X  C3   N    aromatic  1.373  0.020  1.373
 A8X  C2   N    single    1.450  0.020  1.450
 A8X  C2   C1   single    1.521  0.020  1.521
 A8X  C5   C6   aromatic  1.398  0.020  1.398
 A8X  C5   C10  aromatic  1.415  0.020  1.415
 A8X  N    C10  aromatic  1.369  0.020  1.369
 A8X  C6   C7   aromatic  1.383  0.020  1.383
 A8X  C1   C    single    1.539  0.020  1.539
 A8X  C10  C9   aromatic  1.394  0.020  1.394
 A8X  O    C    deloc     1.247  0.020  1.247
 A8X  C    O1   deloc     1.247  0.020  1.247
 A8X  C7   C8   aromatic  1.403  0.020  1.403
 A8X  C9   C8   aromatic  1.384  0.020  1.384
 A8X  C11  H1   single    0.970  0.020  1.090
 A8X  C11  H2   single    0.970  0.020  1.090
 A8X  C12  H3   single    0.970  0.020  1.090
 A8X  C15  H4   single    0.930  0.020  1.080
 A8X  C14  H5   single    0.930  0.020  1.080
 A8X  C17  H6   single    0.930  0.020  1.080
 A8X  C18  H7   single    0.930  0.020  1.080
 A8X  N1   H8   single    0.890  0.020  1.040
 A8X  C19  H9   single    0.970  0.020  1.090
 A8X  C19  H10  single    0.970  0.020  1.090
 A8X  C20  H11  single    0.970  0.020  1.090
 A8X  C20  H12  single    0.970  0.020  1.090
 A8X  C9   H13  single    0.930  0.020  1.080
 A8X  C8   H14  single    0.930  0.020  1.080
 A8X  C7   H15  single    0.930  0.020  1.080
 A8X  C6   H16  single    0.930  0.020  1.080
 A8X  C2   H17  single    0.970  0.020  1.090
 A8X  C2   H18  single    0.970  0.020  1.090
 A8X  C1   H19  single    0.970  0.020  1.090
 A8X  C1   H20  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
 A8X  H2   C11  H1   106.19  3.000
 A8X  H2   C11  C4   111.07  3.000
 A8X  H1   C11  C4   111.12  3.000
 A8X  H2   C11  C12  109.38  3.000
 A8X  H1   C11  C12  109.17  3.000
 A8X  C4   C11  C12  109.83  3.000
 A8X  H3   C12  C19  108.78  3.000
 A8X  H3   C12  N1   107.80  3.000
 A8X  C19  C12  N1   112.26  3.000
 A8X  H3   C12  C11  107.84  3.000
 A8X  C19  C12  C11  111.26  3.000
 A8X  N1   C12  C11  108.75  3.000
 A8X  C17  C16  C15  122.52  3.000
 A8X  C15  C16  F    118.82  3.000
 A8X  C17  C16  F    118.66  3.000
 A8X  H4   C15  C14  120.74  3.000
 A8X  H4   C15  C16  120.66  3.000
 A8X  C14  C15  C16  118.59  3.000
 A8X  H5   C14  C13  121.03  3.000
 A8X  H5   C14  C15  119.39  3.000
 A8X  C13  C14  C15  119.59  3.000
 A8X  H6   C17  C18  120.72  3.000
 A8X  H6   C17  C16  120.63  3.000
 A8X  C18  C17  C16  118.65  3.000
 A8X  H7   C18  C13  121.14  3.000
 A8X  H7   C18  C17  119.31  3.000
 A8X  C13  C18  C17  119.56  3.000
 A8X  S    C13  C18  119.15  3.000
 A8X  S    C13  C14  119.66  3.000
 A8X  C18  C13  C14  121.09  3.000
 A8X  N1   S    O3   105.95  3.000
 A8X  N1   S    O2   107.27  3.000
 A8X  O3   S    O2   120.23  3.000
 A8X  O2   S    C13  107.23  3.000
 A8X  N1   S    C13  107.24  3.000
 A8X  O3   S    C13  108.29  3.000
 A8X  H8   N1   S    112.99  3.000
 A8X  H8   N1   C12  115.10  3.000
 A8X  S    N1   C12  121.38  3.000
 A8X  H10  C19  H9   106.92  3.000
 A8X  H10  C19  C20  109.12  3.000
 A8X  H9   C19  C20  109.77  3.000
 A8X  H10  C19  C12  110.32  3.000
 A8X  H9   C19  C12  108.84  3.000
 A8X  C20  C19  C12  111.74  3.000
 A8X  H12  C20  H11  105.91  3.000
 A8X  H12  C20  C3   110.23  3.000
 A8X  H11  C20  C3   111.44  3.000
 A8X  H12  C20  C19  110.23  3.000
 A8X  H11  C20  C19  109.38  3.000
 A8X  C3   C20  C19  109.60  3.000
 A8X  N    C3   C4   110.24  3.000
 A8X  N    C3   C20  124.71  3.000
 A8X  C4   C3   C20  125.04  3.000
 A8X  C5   C4   C3   106.71  3.000
 A8X  C5   C4   C11  129.73  3.000
 A8X  C3   C4   C11  123.55  3.000
 A8X  C6   C5   C10  119.29  3.000
 A8X  C10  C5   C4   106.54  3.000
 A8X  C6   C5   C4   134.17  3.000
 A8X  N    C10  C9   130.06  3.000
 A8X  C9   C10  C5   121.82  3.000
 A8X  N    C10  C5   108.11  3.000
 A8X  H13  C9   C8   120.65  3.000
 A8X  H13  C9   C10  121.69  3.000
 A8X  C8   C9   C10  117.66  3.000
 A8X  H14  C8   C7   119.41  3.000
 A8X  H14  C8   C9   119.28  3.000
 A8X  C7   C8   C9   121.31  3.000
 A8X  H15  C7   C6   119.75  3.000
 A8X  H15  C7   C8   119.31  3.000
 A8X  C6   C7   C8   120.94  3.000
 A8X  H16  C6   C7   120.48  3.000
 A8X  H16  C6   C5   120.53  3.000
 A8X  C7   C6   C5   118.99  3.000
 A8X  C2   N    C10  125.04  3.000
 A8X  C10  N    C3   108.38  3.000
 A8X  C2   N    C3   126.16  3.000
 A8X  H18  C2   H17  106.20  3.000
 A8X  H18  C2   C1   110.74  3.000
 A8X  H17  C2   C1   110.79  3.000
 A8X  H18  C2   N    108.24  3.000
 A8X  H17  C2   N    107.96  3.000
 A8X  C1   C2   N    112.64  3.000
 A8X  H20  C1   H19  105.35  3.000
 A8X  H20  C1   C    108.92  3.000
 A8X  H19  C1   C    108.44  3.000
 A8X  H20  C1   C2   109.82  3.000
 A8X  H19  C1   C2   109.59  3.000
 A8X  C    C1   C2   114.33  3.000
 A8X  O1   C    O    126.69  3.000
 A8X  O1   C    C1   115.97  3.000
 A8X  O    C    C1   117.33  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
 A8X  CONST_01  C13  C18  C17  C16    0.00   0.0  0
 A8X  CONST_02  C13  C14  C15  C16    0.00   0.0  0
 A8X  CONST_03  C18  C17  C16  C15    0.00   0.0  0
 A8X  CONST_04  C18  C13  C14  C15    0.00   0.0  0
 A8X  CONST_05  C17  C18  C13  C14    0.00   0.0  0
 A8X  CONST_06  C17  C16  C15  C14    0.00   0.0  0
 A8X  CONST_07  C6   C5   C4   C3   180.00   0.0  0
 A8X  CONST_08  C10  C5   C4   C3     0.00   0.0  0
 A8X  CONST_09  C5   C10  N    C3     0.00   0.0  0
 A8X  CONST_10  C9   C10  N    C3   180.00   0.0  0
 A8X  CONST_11  C10  N    C3   C4     0.00   0.0  0
 A8X  CONST_12  C7   C6   C5   C4   180.00   0.0  0
 A8X  CONST_13  N    C10  C5   C4     0.00   0.0  0
 A8X  CONST_14  C9   C10  C5   C4   180.00   0.0  0
 A8X  CONST_15  N    C3   C4   C5     0.00   0.0  0
 A8X  CONST_16  C8   C7   C6   C5     0.00   0.0  0
 A8X  CONST_17  C8   C9   C10  C5     0.00   0.0  0
 A8X  CONST_18  C7   C6   C5   C10    0.00   0.0  0
 A8X  CONST_19  C7   C8   C9   C10    0.00   0.0  0
 A8X  CONST_20  C6   C5   C10  C9     0.00   0.0  0
 A8X  CONST_21  C6   C7   C8   C9     0.00   0.0  0
 A8X  CONST_22  N    C10  C9   C8   180.00   0.0  0
 A8X  CONST_23  N    C10  C5   C6   180.00   0.0  0
 A8X  CONST_24  C18  C17  C16  F    180.00   0.0  0
 A8X  CONST_25  C14  C15  C16  F    180.00   0.0  0
 A8X  CONST_26  S    C13  C14  C15  180.00   0.0  0
 A8X  CONST_27  S    C13  C18  C17  180.00   0.0  0
 A8X  CONST_28  C2   N    C3   C20    0.00   0.0  0
 A8X  CONST_29  C2   N    C3   C4   180.00   0.0  0
 A8X  CONST_30  C2   N    C10  C5   180.00   0.0  0
 A8X  CONST_31  C2   N    C10  C9     0.00   0.0  0
 A8X  CONST_32  H7   C18  C17  C16  180.00   0.0  0
 A8X  CONST_33  H5   C14  C15  C16  180.00   0.0  0
 A8X  CONST_34  H6   C17  C16  C15  180.00   0.0  0
 A8X  CONST_35  H4   C15  C16  C17  180.00   0.0  0
 A8X  CONST_36  H16  C6   C5   C4     0.00   0.0  0
 A8X  CONST_37  H15  C7   C6   C5   180.00   0.0  0
 A8X  CONST_38  H13  C9   C10  C5   180.00   0.0  0
 A8X  CONST_39  H14  C8   C9   C10  180.00   0.0  0
 A8X  Var_01    C3   C20  C19  C12   44.46  30.0  1
 A8X  Var_02    C3   C4   C11  C12  -16.20  30.0  1
 A8X  Var_03    C4   C3   C20  C19  -14.03  30.0  1
 A8X  Var_04    C13  S    N1   C12   63.20  30.0  2
 A8X  Var_05    O3   S    C13  C14  151.63  30.0  2
 A8X  Var_06    C1   C2   N    C3    88.89  30.0  3
 A8X  Var_07    C    C1   C2   N    179.14  30.0  3
 A8X  Var_08    O    C    C1   C2     4.14  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
 A8X  chir_01  C12  N1  C19  C11  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
 A8X  plan-1  F    0.020
 A8X  plan-1  C16  0.020
 A8X  plan-1  C15  0.020
 A8X  plan-1  C14  0.020
 A8X  plan-1  C17  0.020
 A8X  plan-1  C18  0.020
 A8X  plan-1  C13  0.020
 A8X  plan-1  S    0.020
 A8X  plan-1  H4   0.020
 A8X  plan-1  H5   0.020
 A8X  plan-1  H6   0.020
 A8X  plan-1  H7   0.020
 A8X  plan-2  C11  0.020
 A8X  plan-2  C20  0.020
 A8X  plan-2  C3   0.020
 A8X  plan-2  C4   0.020
 A8X  plan-2  C5   0.020
 A8X  plan-2  C10  0.020
 A8X  plan-2  C9   0.020
 A8X  plan-2  C8   0.020
 A8X  plan-2  C7   0.020
 A8X  plan-2  C6   0.020
 A8X  plan-2  N    0.020
 A8X  plan-2  C2   0.020
 A8X  plan-2  H13  0.020
 A8X  plan-2  H14  0.020
 A8X  plan-2  H15  0.020
 A8X  plan-2  H16  0.020
 A8X  plan-3  C1   0.020
 A8X  plan-3  C    0.020
 A8X  plan-3  O    0.020
 A8X  plan-3  O1   0.020

