# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 20:49:12 2020
#   Inital geometry file: a 112 line input string
#   Ligand name: [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl](4-methoxyphenyl)methanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc(cc1)C(=O)c2c(sc3cc(O)ccc23)c4ccc(O)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
 X1H  X1H  '[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl](4-methoxyphenyl)methanone'  ligand  43  27  .  2021-08-24  2021-08-24  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_X1H
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
 X1H  C22   C  CH3   0  -0.440  -4.5422  -3.3128  -1.8925
 X1H  O3    O  O2    0  -0.461  -4.2605  -3.2037  -0.5088
 X1H  C21   C  CR6   0   0.393  -3.1047  -2.6476  -0.1269
 X1H  C20   C  CR16  0  -0.334  -2.8833  -2.5710   1.2541
 X1H  C18   C  CR16  0  -0.250  -1.7206  -2.0160   1.7366
 X1H  C19   C  CR16  0  -0.368  -2.1394  -2.1587  -1.0065
 X1H  C17   C  CR16  0  -0.245  -0.9833  -1.5856  -0.5038
 X1H  C16   C  CR6   0  -0.046  -0.7541  -1.5001   0.8660
 X1H  C15   C  C     0   0.317   0.4860  -0.9277   1.4224
 X1H  O1    O  O     0  -0.402   0.8680  -1.2167   2.5432
 X1H  C8    C  CR5   0   0.084   1.2996  -0.0061   0.5910
 X1H  C11   C  CR56  0   0.187   2.7334  -0.1329   0.4817
 X1H  C13   C  CR16  0  -0.315   3.5994  -1.0877   1.0258
 X1H  C14   C  CR16  0  -0.376   4.9473  -1.0390   0.7425
 X1H  C12   C  CR6   0   0.354   5.4755  -0.0402  -0.0913
 X1H  O4    O  OH1   0  -0.631   6.7892   0.0284  -0.3784
 X1H  C10   C  CR16  0  -0.370   4.6418   0.9154  -0.6502
 X1H  C9    C  CR56  0  -0.214   3.2860   0.8500  -0.3548
 X1H  S1    S  S2    0   0.240   2.0655   1.9305  -0.9379
 X1H  C7    C  CR5   0  -0.283   0.8083   1.0550  -0.1121
 X1H  C4    C  CR6   0   0.034  -0.5647   1.5464  -0.2167
 X1H  C2    C  CR16  0  -0.286  -1.3823   1.6524   0.9102
 X1H  C1    C  CR16  0  -0.314  -2.6916   2.0799   0.8065
 X1H  C3    C  CR6   0   0.353  -3.2171   2.4205  -0.4393
 X1H  O2    O  OH1   0  -0.626  -4.4974   2.8269  -0.4910
 X1H  C5    C  CR16  0  -0.367  -2.4080   2.3364  -1.5701
 X1H  C6    C  CR16  0  -0.277  -1.0985   1.9054  -1.4537
 X1H  H221  H  HCH3  0   0.234  -4.5867  -2.3339  -2.3758
 X1H  H222  H  HCH3  0   0.234  -3.8044  -3.9314  -2.4090
 X1H  H223  H  HCH3  0   0.264  -5.5163  -3.7882  -1.9707
 X1H  H20   H  HCR6  0   0.267  -3.6346  -2.9514   1.9347
 X1H  H19   H  HCR6  0   0.284  -2.2733  -2.2142  -2.0778
 X1H  H18   H  HCR6  0   0.262  -1.5657  -1.9631   2.8064
 X1H  H17   H  HCR6  0   0.268  -0.2440  -1.2177  -1.2029
 X1H  H13   H  HCR6  0   0.258   3.2251  -1.8687   1.6729
 X1H  H14   H  HCR6  0   0.277   5.6080  -1.7828   1.1731
 X1H  H4    H  HOH1  0   0.477   7.2671  -0.6890   0.0521
 X1H  H10   H  HCR6  0   0.277   5.0424   1.6852  -1.2978
 X1H  H2    H  HCR6  0   0.262  -0.9888   1.4130   1.8899
 X1H  H6    H  HCR6  0   0.261  -0.4950   1.8229  -2.3495
 X1H  H1    H  HCR6  0   0.268  -3.3104   2.1570   1.6917
 X1H  HA    H  HOH1  0   0.477  -4.7519   3.0315  -1.3980
 X1H  H5    H  HCR6  0   0.276  -2.8013   2.5980  -2.5453

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
 X1H  C22  O3    single    1.416  0.020  1.416
 X1H  O3   C21   single    1.338  0.020  1.338
 X1H  C21  C20   aromatic  1.401  0.020  1.401
 X1H  C21  C19   aromatic  1.394  0.020  1.394
 X1H  C20  C18   aromatic  1.376  0.020  1.376
 X1H  C18  C16   aromatic  1.399  0.020  1.399
 X1H  C19  C17   aromatic  1.385  0.020  1.385
 X1H  C17  C16   aromatic  1.391  0.020  1.391
 X1H  C16  C15   single    1.475  0.020  1.475
 X1H  C15  O1    double    1.219  0.020  1.219
 X1H  C15  C8    single    1.484  0.020  1.484
 X1H  C8   C11   aromatic  1.443  0.020  1.443
 X1H  C8   C7    aromatic  1.364  0.020  1.364
 X1H  C11  C13   aromatic  1.399  0.020  1.399
 X1H  C11  C9    aromatic  1.404  0.020  1.404
 X1H  C13  C14   aromatic  1.378  0.020  1.378
 X1H  C14  C12   aromatic  1.404  0.020  1.404
 X1H  C12  O4    single    1.346  0.020  1.346
 X1H  C12  C10   aromatic  1.386  0.020  1.386
 X1H  C10  C9    aromatic  1.389  0.020  1.389
 X1H  C9   S1    aromatic  1.731  0.020  1.731
 X1H  S1   C7    aromatic  1.740  0.020  1.740
 X1H  C7   C4    single    1.462  0.020  1.462
 X1H  C4   C2    aromatic  1.396  0.020  1.396
 X1H  C4   C6    aromatic  1.394  0.020  1.394
 X1H  C2   C1    aromatic  1.381  0.020  1.381
 X1H  C1   C3    aromatic  1.394  0.020  1.394
 X1H  C3   O2    single    1.344  0.020  1.344
 X1H  C3   C5    aromatic  1.393  0.020  1.393
 X1H  C5   C6    aromatic  1.384  0.020  1.384
 X1H  C22  H221  single    0.970  0.020  1.090
 X1H  C22  H222  single    0.970  0.020  1.090
 X1H  C22  H223  single    0.970  0.020  1.090
 X1H  C20  H20   single    0.930  0.020  1.080
 X1H  C19  H19   single    0.930  0.020  1.080
 X1H  C18  H18   single    0.930  0.020  1.080
 X1H  C17  H17   single    0.930  0.020  1.080
 X1H  C13  H13   single    0.930  0.020  1.080
 X1H  C14  H14   single    0.930  0.020  1.080
 X1H  O4   H4    single    0.850  0.020  0.980
 X1H  C10  H10   single    0.930  0.020  1.080
 X1H  C2   H2    single    0.930  0.020  1.080
 X1H  C6   H6    single    0.930  0.020  1.080
 X1H  C1   H1    single    0.930  0.020  1.080
 X1H  O2   HA    single    0.850  0.020  0.980
 X1H  C5   H5    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
 X1H  H223  C22  H222  108.88  3.000
 X1H  H223  C22  H221  108.88  3.000
 X1H  H222  C22  H221  109.00  3.000
 X1H  H223  C22  O3    106.40  3.000
 X1H  H222  C22  O3    111.79  3.000
 X1H  H221  C22  O3    111.79  3.000
 X1H  C21   O3   C22   118.86  3.000
 X1H  C19   C21  C20   119.56  3.000
 X1H  C19   C21  O3    124.30  3.000
 X1H  C20   C21  O3    116.14  3.000
 X1H  H20   C20  C18   120.51  3.000
 X1H  H20   C20  C21   119.40  3.000
 X1H  C18   C20  C21   120.09  3.000
 X1H  H18   C18  C16   119.88  3.000
 X1H  H18   C18  C20   119.16  3.000
 X1H  C16   C18  C20   120.95  3.000
 X1H  H19   C19  C17   118.97  3.000
 X1H  H19   C19  C21   121.42  3.000
 X1H  C17   C19  C21   119.61  3.000
 X1H  H17   C17  C16   120.17  3.000
 X1H  H17   C17  C19   118.47  3.000
 X1H  C16   C17  C19   121.35  3.000
 X1H  C15   C16  C17   122.26  3.000
 X1H  C15   C16  C18   119.28  3.000
 X1H  C17   C16  C18   118.43  3.000
 X1H  C8    C15  O1    119.38  3.000
 X1H  C8    C15  C16   119.38  3.000
 X1H  O1    C15  C16   121.23  3.000
 X1H  C7    C8   C11   112.77  3.000
 X1H  C7    C8   C15   125.04  3.000
 X1H  C11   C8   C15   122.16  3.000
 X1H  C9    C11  C13   117.76  3.000
 X1H  C9    C11  C8    111.99  3.000
 X1H  C13   C11  C8    130.19  3.000
 X1H  H13   C13  C14   119.16  3.000
 X1H  H13   C13  C11   120.76  3.000
 X1H  C14   C13  C11   120.09  3.000
 X1H  H14   C14  C12   119.65  3.000
 X1H  H14   C14  C13   119.35  3.000
 X1H  C12   C14  C13   121.00  3.000
 X1H  C10   C12  O4    117.76  3.000
 X1H  C10   C12  C14   120.24  3.000
 X1H  O4    C12  C14   121.99  3.000
 X1H  H4    O4   C12   110.53  3.000
 X1H  H10   C10  C9    121.45  3.000
 X1H  H10   C10  C12   120.59  3.000
 X1H  C9    C10  C12   117.96  3.000
 X1H  S1    C9   C10   125.95  3.000
 X1H  S1    C9   C11   111.11  3.000
 X1H  C10   C9   C11   122.94  3.000
 X1H  C7    S1   C9     92.03  3.000
 X1H  C4    C7   S1    118.38  3.000
 X1H  C4    C7   C8    129.53  3.000
 X1H  S1    C7   C8    112.06  3.000
 X1H  C6    C4   C2    118.18  3.000
 X1H  C6    C4   C7    120.64  3.000
 X1H  C2    C4   C7    121.17  3.000
 X1H  H2    C2   C1    118.75  3.000
 X1H  H2    C2   C4    120.05  3.000
 X1H  C1    C2   C4    121.20  3.000
 X1H  H1    C1   C3    119.85  3.000
 X1H  H1    C1   C2    120.16  3.000
 X1H  C3    C1   C2    120.00  3.000
 X1H  C5    C3   O2    122.70  3.000
 X1H  C5    C3   C1    119.45  3.000
 X1H  O2    C3   C1    117.85  3.000
 X1H  HA    O2   C3    110.60  3.000
 X1H  H5    C5   C6    119.63  3.000
 X1H  H5    C5   C3    120.35  3.000
 X1H  C6    C5   C3    120.02  3.000
 X1H  H6    C6   C5    118.79  3.000
 X1H  H6    C6   C4    120.05  3.000
 X1H  C5    C6   C4    121.14  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
 X1H  CONST_01  C16   C18  C20  C21     0.00   0.0  0
 X1H  CONST_02  C16   C17  C19  C21     0.00   0.0  0
 X1H  CONST_03  C17   C19  C21  C20     0.00   0.0  0
 X1H  CONST_04  C17   C16  C18  C20     0.00   0.0  0
 X1H  CONST_05  C19   C21  C20  C18     0.00   0.0  0
 X1H  CONST_06  C19   C17  C16  C18     0.00   0.0  0
 X1H  CONST_07  C14   C13  C11  C8    180.00   0.0  0
 X1H  CONST_08  C10   C9   C11  C8    180.00   0.0  0
 X1H  CONST_09  S1    C9   C11  C8      0.00   0.0  0
 X1H  CONST_10  C9    S1   C7   C8      0.00   0.0  0
 X1H  CONST_13  S1    C7   C8   C11     0.00   0.0  0
 X1H  CONST_14  C4    C7   C8   C11   180.00   0.0  0
 X1H  CONST_15  C12   C14  C13  C11     0.00   0.0  0
 X1H  CONST_16  C12   C10  C9   C11     0.00   0.0  0
 X1H  CONST_17  C7    S1   C9   C11     0.00   0.0  0
 X1H  CONST_18  C7    C8   C11  C13   180.00   0.0  0
 X1H  CONST_19  C10   C9   C11  C13     0.00   0.0  0
 X1H  CONST_20  S1    C9   C11  C13   180.00   0.0  0
 X1H  CONST_21  C10   C12  C14  C13     0.00   0.0  0
 X1H  CONST_22  C9    C11  C13  C14     0.00   0.0  0
 X1H  CONST_23  C9    C10  C12  C14     0.00   0.0  0
 X1H  CONST_24  S1    C9   C10  C12   180.00   0.0  0
 X1H  CONST_25  C7    S1   C9   C10   180.00   0.0  0
 X1H  CONST_26  C7    C8   C11  C9      0.00   0.0  0
 X1H  CONST_27  C4    C7   S1   C9    180.00   0.0  0
 X1H  CONST_30  C1    C2   C4   C7    180.00   0.0  0
 X1H  CONST_31  C5    C6   C4   C7    180.00   0.0  0
 X1H  CONST_32  C3    C1   C2   C4      0.00   0.0  0
 X1H  CONST_33  C3    C5   C6   C4      0.00   0.0  0
 X1H  CONST_34  C5    C6   C4   C2      0.00   0.0  0
 X1H  CONST_35  C5    C3   C1   C2      0.00   0.0  0
 X1H  CONST_36  C6    C4   C2   C1      0.00   0.0  0
 X1H  CONST_37  C6    C5   C3   C1      0.00   0.0  0
 X1H  CONST_38  C18   C20  C21  O3    180.00   0.0  0
 X1H  CONST_39  C17   C19  C21  O3    180.00   0.0  0
 X1H  CONST_40  C15   C16  C18  C20   180.00   0.0  0
 X1H  CONST_41  C15   C16  C17  C19   180.00   0.0  0
 X1H  CONST_42  C13   C11  C8   C15     0.00   0.0  0
 X1H  CONST_43  C9    C11  C8   C15   180.00   0.0  0
 X1H  CONST_44  S1    C7   C8   C15   180.00   0.0  0
 X1H  CONST_45  C4    C7   C8   C15     0.00   0.0  0
 X1H  CONST_46  O4    C12  C14  C13   180.00   0.0  0
 X1H  CONST_47  C9    C10  C12  O4    180.00   0.0  0
 X1H  CONST_48  O2    C3   C1   C2    180.00   0.0  0
 X1H  CONST_49  C6    C5   C3   O2    180.00   0.0  0
 X1H  CONST_50  H18   C18  C20  C21   180.00   0.0  0
 X1H  CONST_51  H17   C17  C19  C21   180.00   0.0  0
 X1H  CONST_52  H19   C19  C21  C20   180.00   0.0  0
 X1H  CONST_53  H20   C20  C21  C19   180.00   0.0  0
 X1H  CONST_54  H13   C13  C11  C8      0.00   0.0  0
 X1H  CONST_55  H14   C14  C13  C11   180.00   0.0  0
 X1H  CONST_56  H10   C10  C9   C11   180.00   0.0  0
 X1H  CONST_57  H2    C2   C4   C7      0.00   0.0  0
 X1H  CONST_58  H6    C6   C4   C7      0.00   0.0  0
 X1H  CONST_59  H1    C1   C2   C4    180.00   0.0  0
 X1H  CONST_60  H5    C5   C6   C4    180.00   0.0  0
 X1H  Var_01    C8    C15  C16  C18  -160.43  30.0  2
 X1H  Var_02    C11   C8   C15  C16  -133.89  30.0  2
 X1H  Var_03    C20   C21  O3   C22  -179.87  30.0  2
 X1H  Var_04    H221  C22  O3   C21   -61.34  30.0  3

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
 X1H  plan-1  O3   0.020
 X1H  plan-1  C21  0.020
 X1H  plan-1  C20  0.020
 X1H  plan-1  C18  0.020
 X1H  plan-1  C19  0.020
 X1H  plan-1  C17  0.020
 X1H  plan-1  C16  0.020
 X1H  plan-1  C15  0.020
 X1H  plan-1  H20  0.020
 X1H  plan-1  H19  0.020
 X1H  plan-1  H18  0.020
 X1H  plan-1  H17  0.020
 X1H  plan-2  C7   0.020
 X1H  plan-2  C4   0.020
 X1H  plan-2  C2   0.020
 X1H  plan-2  C1   0.020
 X1H  plan-2  C3   0.020
 X1H  plan-2  O2   0.020
 X1H  plan-2  C5   0.020
 X1H  plan-2  C6   0.020
 X1H  plan-2  H2   0.020
 X1H  plan-2  H6   0.020
 X1H  plan-2  H1   0.020
 X1H  plan-2  H5   0.020
 X1H  plan-3  C15  0.020
 X1H  plan-3  C8   0.020
 X1H  plan-3  C11  0.020
 X1H  plan-3  C13  0.020
 X1H  plan-3  C14  0.020
 X1H  plan-3  C12  0.020
 X1H  plan-3  O4   0.020
 X1H  plan-3  C10  0.020
 X1H  plan-3  C9   0.020
 X1H  plan-3  S1   0.020
 X1H  plan-3  C7   0.020
 X1H  plan-3  C4   0.020
 X1H  plan-3  H13  0.020
 X1H  plan-3  H14  0.020
 X1H  plan-3  H10  0.020
 X1H  plan-4  C16  0.020
 X1H  plan-4  C15  0.020
 X1H  plan-4  O1   0.020
 X1H  plan-4  C8   0.020

