# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Sun Jun 14 05:18:01 2020
#   Inital geometry file: a 157 line input string
#   Ligand name: (1R,2S,4R)-N-ethyl-5,6-bis(4-hydroxyphenyl)-N-(4-methoxyphenyl)-7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN(c1ccc(OC)cc1)[S](=O)(=O)[C@H]2C[C@H]3O[C@@H]2C(=C3c4ccc(O)cc4)c5ccc(O)cc5
#
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
 OB5  OB5  (1R,2S,4R)-N-ethyl-5,6-bis(4-hydroxyphenyl)-N-(4-methoxyphenyl)-7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonamide  ligand  62  35  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_OB5
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
 OB5  C01  C  CR16  0  -0.370  -5.4168   2.0527   1.5471
 OB5  C02  C  CR6   0   0.347  -5.4311   1.0637   2.5273
 OB5  C03  C  CR16  0  -0.319  -4.4506   0.0713   2.5130
 OB5  C04  C  CR16  0  -0.298  -3.4841   0.0697   1.5250
 OB5  C05  C  CR6   0   0.005  -3.4621   1.0460   0.5248
 OB5  C06  C  CR16  0  -0.294  -4.4380   2.0420   0.5669
 OB5  O01  O  OH1   0  -0.627  -6.3541   1.0222   3.5051
 OB5  C07  C  C     0   0.065  -2.4289   1.0606  -0.5081
 OB5  C08  C  C     0   0.135  -1.8379   0.0727  -1.2032
 OB5  C09  C  CH1   0  -0.119  -0.6673   0.7498  -1.8962
 OB5  C10  C  CR6   0   0.041  -2.0757  -1.3615  -1.2848
 OB5  C11  C  CH1   0  -0.083  -1.6110   2.3022  -0.8283
 OB5  C12  C  CR16  0  -0.305  -3.3452  -1.9181  -1.0919
 OB5  C13  C  CR16  0  -0.320  -3.5587  -3.2789  -1.1882
 OB5  C14  C  CR6   0   0.345  -2.4973  -4.1358  -1.4834
 OB5  C15  C  CR16  0  -0.368  -1.2309  -3.6006  -1.6961
 OB5  C16  C  CR16  0  -0.323  -1.0316  -2.2320  -1.6042
 OB5  O02  O  OH1   0  -0.628  -2.7554  -5.4544  -1.5577
 OB5  C17  C  CH2   0  -0.443  -0.2957   2.1771  -0.0158
 OB5  C18  C  CH1   0  -0.447   0.3671   1.0022  -0.7548
 OB5  S01  S  S     0   1.362   1.9883   1.3717  -1.4228
 OB5  O03  O  O2    0  -0.451  -1.1569   2.0452  -2.1444
 OB5  N01  N  N     0  -0.690   2.9465   1.6514  -0.1140
 OB5  O04  O  OS    0  -0.657   2.4418   0.1473  -2.0691
 OB5  O05  O  OS    0  -0.656   1.9098   2.5968  -2.2052
 OB5  C19  C  CR6   0   0.284   3.5444   0.5332   0.5283
 OB5  C20  C  CH2   0  -0.304   3.3415   3.0001   0.3056
 OB5  C21  C  CR16  0  -0.244   2.9156  -0.0875   1.6044
 OB5  C22  C  CR16  0  -0.346   3.5100  -1.1578   2.2452
 OB5  C23  C  CR6   0   0.392   4.7580  -1.6232   1.8239
 OB5  C24  C  CR16  0  -0.389   5.3955  -1.0003   0.7510
 OB5  C25  C  CR16  0  -0.232   4.7823   0.0672   0.1115
 OB5  C26  C  CH3   0  -0.666   2.9420   3.3142   1.7350
 OB5  O06  O  O2    0  -0.467   5.2657  -2.6632   2.5054
 OB5  C27  C  CH3   0  -0.438   6.5377  -3.1617   2.1377
 OB5  H1   H  HCR6  0   0.274  -6.1687   2.8331   1.5463
 OB5  H2   H  HCR6  0   0.267  -4.4459  -0.6907   3.2823
 OB5  H3   H  HCR6  0   0.257  -2.7232  -0.7000   1.5398
 OB5  H4   H  HCR6  0   0.260  -4.4509   2.8196  -0.1868
 OB5  H5   H  HOH1  0   0.476  -6.9725   1.7565   3.4179
 OB5  H6   H  HCH1  0   0.286  -0.2899   0.2755  -2.8012
 OB5  H7   H  HCH1  0   0.264  -2.1092   3.2667  -0.7497
 OB5  H8   H  HCR6  0   0.258  -4.1885  -1.2753  -0.8775
 OB5  H9   H  HCR6  0   0.266  -4.5520  -3.6847  -1.0424
 OB5  H10  H  HCR6  0   0.274  -0.3946  -4.2475  -1.9353
 OB5  H11  H  HCR6  0   0.245  -0.0325  -1.8508  -1.7805
 OB5  H12  H  HOH1  0   0.476  -1.9538  -5.9425  -1.7766
 OB5  H13  H  HCH2  0   0.277   0.2772   3.1029  -0.0815
 OB5  H14  H  HCH2  0   0.275  -0.4666   1.9641   1.0379
 OB5  H15  H  HCH1  0   0.325   0.5104   0.1207  -0.1263
 OB5  H16  H  HCH2  0   0.251   4.4238   3.0933   0.1865
 OB5  H17  H  HCH2  0   0.261   2.8914   3.7202  -0.3737
 OB5  H18  H  HCR6  0   0.263   1.9536   0.2725   1.9479
 OB5  H19  H  HCR6  0   0.269   3.0143  -1.6378   3.0796
 OB5  H20  H  HCR6  0   0.285   6.3627  -1.3304   0.3982
 OB5  H21  H  HCR6  0   0.267   5.2828   0.5436  -0.7219
 OB5  H22  H  HCH3  0   0.232   1.8644   3.2280   1.8745
 OB5  H23  H  HCH3  0   0.234   3.4346   2.6563   2.4505
 OB5  H24  H  HCH3  0   0.244   3.2325   4.3372   1.9745
 OB5  H25  H  HCH3  0   0.262   6.7522  -3.9865   2.8125
 OB5  H26  H  HCH3  0   0.231   6.5484  -3.5365   1.1114
 OB5  H27  H  HCH3  0   0.231   7.3193  -2.4058   2.2479

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
 OB5  O02  C14  single    1.346  0.020  1.346
 OB5  C14  C13  aromatic  1.396  0.020  1.396
 OB5  C14  C15  aromatic  1.391  0.020  1.391
 OB5  C13  C12  aromatic  1.381  0.020  1.381
 OB5  C12  C10  aromatic  1.400  0.020  1.400
 OB5  C15  C16  aromatic  1.386  0.020  1.386
 OB5  C16  C10  aromatic  1.396  0.020  1.396
 OB5  C10  C08  single    1.456  0.020  1.456
 OB5  O01  C02  single    1.345  0.020  1.345
 OB5  C01  C02  aromatic  1.393  0.020  1.393
 OB5  C01  C06  aromatic  1.385  0.020  1.385
 OB5  C02  C03  aromatic  1.395  0.020  1.395
 OB5  C08  C07  double    1.345  0.020  1.345
 OB5  C08  C09  single    1.520  0.020  1.520
 OB5  C06  C05  aromatic  1.395  0.020  1.395
 OB5  C03  C04  aromatic  1.382  0.020  1.382
 OB5  C05  C04  aromatic  1.398  0.020  1.398
 OB5  C05  C07  single    1.461  0.020  1.461
 OB5  C07  C11  single    1.521  0.020  1.521
 OB5  C09  O03  single    1.407  0.020  1.407
 OB5  C09  C18  single    1.561  0.020  1.561
 OB5  O03  C11  single    1.416  0.020  1.416
 OB5  C11  C17  single    1.551  0.020  1.551
 OB5  C20  C26  single    1.517  0.020  1.517
 OB5  C20  N01  single    1.467  0.020  1.467
 OB5  C18  C17  single    1.538  0.020  1.538
 OB5  C18  S01  single    1.792  0.020  1.792
 OB5  O05  S01  double    1.456  0.020  1.456
 OB5  N01  S01  single    1.646  0.020  1.646
 OB5  N01  C19  single    1.421  0.020  1.421
 OB5  S01  O04  double    1.457  0.020  1.457
 OB5  C21  C19  aromatic  1.392  0.020  1.392
 OB5  C21  C22  aromatic  1.382  0.020  1.382
 OB5  C19  C25  aromatic  1.387  0.020  1.387
 OB5  C22  C23  aromatic  1.397  0.020  1.397
 OB5  C25  C24  aromatic  1.387  0.020  1.387
 OB5  C23  C24  aromatic  1.395  0.020  1.395
 OB5  C23  O06  single    1.343  0.020  1.343
 OB5  O06  C27  single    1.415  0.020  1.415
 OB5  C01  H1   single    0.930  0.020  1.080
 OB5  C03  H2   single    0.930  0.020  1.080
 OB5  C04  H3   single    0.930  0.020  1.080
 OB5  C06  H4   single    0.930  0.020  1.080
 OB5  O01  H5   single    0.850  0.020  0.980
 OB5  C09  H6   single    0.970  0.020  1.090
 OB5  C11  H7   single    0.970  0.020  1.090
 OB5  C12  H8   single    0.930  0.020  1.080
 OB5  C13  H9   single    0.930  0.020  1.080
 OB5  C15  H10  single    0.930  0.020  1.080
 OB5  C16  H11  single    0.930  0.020  1.080
 OB5  O02  H12  single    0.850  0.020  0.980
 OB5  C17  H13  single    0.970  0.020  1.090
 OB5  C17  H14  single    0.970  0.020  1.090
 OB5  C18  H15  single    0.970  0.020  1.090
 OB5  C20  H16  single    0.970  0.020  1.090
 OB5  C20  H17  single    0.970  0.020  1.090
 OB5  C21  H18  single    0.930  0.020  1.080
 OB5  C22  H19  single    0.930  0.020  1.080
 OB5  C24  H20  single    0.930  0.020  1.080
 OB5  C25  H21  single    0.930  0.020  1.080
 OB5  C26  H22  single    0.970  0.020  1.090
 OB5  C26  H23  single    0.970  0.020  1.090
 OB5  C26  H24  single    0.970  0.020  1.090
 OB5  C27  H25  single    0.970  0.020  1.090
 OB5  C27  H26  single    0.970  0.020  1.090
 OB5  C27  H27  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
 OB5  H1   C01  C06  119.69  3.000
 OB5  H1   C01  C02  120.32  3.000
 OB5  C06  C01  C02  119.99  3.000
 OB5  O01  C02  C03  117.89  3.000
 OB5  C03  C02  C01  119.39  3.000
 OB5  O01  C02  C01  122.72  3.000
 OB5  H2   C03  C04  120.26  3.000
 OB5  H2   C03  C02  119.76  3.000
 OB5  C04  C03  C02  119.98  3.000
 OB5  H3   C04  C05  119.69  3.000
 OB5  H3   C04  C03  118.86  3.000
 OB5  C05  C04  C03  121.44  3.000
 OB5  C07  C05  C06  120.59  3.000
 OB5  C07  C05  C04  121.60  3.000
 OB5  C06  C05  C04  117.78  3.000
 OB5  H4   C06  C05  120.00  3.000
 OB5  H4   C06  C01  118.58  3.000
 OB5  C05  C06  C01  121.41  3.000
 OB5  H5   O01  C02  110.54  3.000
 OB5  C11  C07  C08  104.74  3.000
 OB5  C11  C07  C05  122.50  3.000
 OB5  C08  C07  C05  131.98  3.000
 OB5  C10  C08  C09  122.62  3.000
 OB5  C09  C08  C07  104.30  3.000
 OB5  C10  C08  C07  132.91  3.000
 OB5  H6   C09  O03  112.02  3.000
 OB5  H6   C09  C18  116.64  3.000
 OB5  O03  C09  C18  102.16  3.000
 OB5  H6   C09  C08  116.86  3.000
 OB5  C18  C09  C08  104.42  3.000
 OB5  O03  C09  C08  102.86  3.000
 OB5  C16  C10  C12  117.50  3.000
 OB5  C16  C10  C08  120.31  3.000
 OB5  C12  C10  C08  122.15  3.000
 OB5  H7   C11  O03  112.02  3.000
 OB5  H7   C11  C17  114.95  3.000
 OB5  O03  C11  C17  101.56  3.000
 OB5  H7   C11  C07  117.52  3.000
 OB5  C17  C11  C07  106.25  3.000
 OB5  O03  C11  C07  102.71  3.000
 OB5  H8   C12  C13  118.61  3.000
 OB5  H8   C12  C10  119.87  3.000
 OB5  C13  C12  C10  121.51  3.000
 OB5  H9   C13  C14  119.73  3.000
 OB5  H9   C13  C12  120.12  3.000
 OB5  C14  C13  C12  120.15  3.000
 OB5  O02  C14  C15  122.90  3.000
 OB5  C15  C14  C13  119.24  3.000
 OB5  O02  C14  C13  117.87  3.000
 OB5  H10  C15  C16  119.54  3.000
 OB5  H10  C15  C14  120.43  3.000
 OB5  C16  C15  C14  120.04  3.000
 OB5  H11  C16  C15  117.97  3.000
 OB5  H11  C16  C10  120.48  3.000
 OB5  C15  C16  C10  121.55  3.000
 OB5  H12  O02  C14  110.44  3.000
 OB5  H14  C17  H13  107.87  3.000
 OB5  H14  C17  C18  112.54  3.000
 OB5  H13  C17  C18  113.14  3.000
 OB5  H14  C17  C11  112.94  3.000
 OB5  H13  C17  C11  110.20  3.000
 OB5  C18  C17  C11  100.10  3.000
 OB5  H15  C18  S01  105.21  3.000
 OB5  H15  C18  C17  113.37  3.000
 OB5  S01  C18  C17  114.30  3.000
 OB5  H15  C18  C09  112.16  3.000
 OB5  S01  C18  C09  111.12  3.000
 OB5  C17  C18  C09  100.91  3.000
 OB5  O05  S01  O04  119.05  3.000
 OB5  O04  S01  N01  108.32  3.000
 OB5  O05  S01  N01  108.41  3.000
 OB5  O04  S01  C18  105.89  3.000
 OB5  N01  S01  C18  105.38  3.000
 OB5  O05  S01  C18  108.97  3.000
 OB5  C11  O03  C09   96.59  3.000
 OB5  C20  N01  C19  118.74  3.000
 OB5  C19  N01  S01  118.07  3.000
 OB5  C20  N01  S01  122.72  3.000
 OB5  C25  C19  C21  119.05  3.000
 OB5  C25  C19  N01  120.26  3.000
 OB5  C21  C19  N01  120.67  3.000
 OB5  H17  C20  H16  106.58  3.000
 OB5  H17  C20  C26  110.03  3.000
 OB5  H16  C20  C26  110.23  3.000
 OB5  H17  C20  N01  108.59  3.000
 OB5  H16  C20  N01  108.30  3.000
 OB5  C26  C20  N01  112.90  3.000
 OB5  H18  C21  C22  119.50  3.000
 OB5  H18  C21  C19  119.87  3.000
 OB5  C22  C21  C19  120.63  3.000
 OB5  H19  C22  C23  119.59  3.000
 OB5  H19  C22  C21  120.25  3.000
 OB5  C23  C22  C21  120.16  3.000
 OB5  O06  C23  C24  124.28  3.000
 OB5  O06  C23  C22  116.27  3.000
 OB5  C24  C23  C22  119.44  3.000
 OB5  H20  C24  C25  118.68  3.000
 OB5  H20  C24  C23  121.57  3.000
 OB5  C25  C24  C23  119.75  3.000
 OB5  H21  C25  C24  119.28  3.000
 OB5  H21  C25  C19  119.75  3.000
 OB5  C24  C25  C19  120.97  3.000
 OB5  H24  C26  H23  107.57  3.000
 OB5  H24  C26  H22  108.04  3.000
 OB5  H23  C26  H22  108.37  3.000
 OB5  H24  C26  C20  109.34  3.000
 OB5  H23  C26  C20  112.00  3.000
 OB5  H22  C26  C20  111.38  3.000
 OB5  C27  O06  C23  118.74  3.000
 OB5  H27  C27  H26  108.96  3.000
 OB5  H27  C27  H25  108.72  3.000
 OB5  H26  C27  H25  108.72  3.000
 OB5  H27  C27  O06  111.91  3.000
 OB5  H26  C27  O06  111.96  3.000
 OB5  H25  C27  O06  106.47  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
 OB5  CONST_01  C04  C03  C02  C01    0.00   0.0  0
 OB5  CONST_02  C04  C05  C06  C01    0.00   0.0  0
 OB5  CONST_03  C05  C06  C01  C02    0.00   0.0  0
 OB5  CONST_04  C05  C04  C03  C02    0.00   0.0  0
 OB5  CONST_05  C06  C01  C02  C03    0.00   0.0  0
 OB5  CONST_06  C06  C05  C04  C03    0.00   0.0  0
 OB5  CONST_07  C14  C13  C12  C10    0.00   0.0  0
 OB5  CONST_08  C14  C15  C16  C10    0.00   0.0  0
 OB5  CONST_09  C15  C14  C13  C12    0.00   0.0  0
 OB5  CONST_10  C15  C16  C10  C12    0.00   0.0  0
 OB5  CONST_11  C16  C15  C14  C13    0.00   0.0  0
 OB5  CONST_12  C16  C10  C12  C13    0.00   0.0  0
 OB5  CONST_13  C23  C22  C21  C19    0.00   0.0  0
 OB5  CONST_14  C23  C24  C25  C19    0.00   0.0  0
 OB5  CONST_15  C24  C25  C19  C21    0.00   0.0  0
 OB5  CONST_16  C24  C23  C22  C21    0.00   0.0  0
 OB5  CONST_17  C25  C19  C21  C22    0.00   0.0  0
 OB5  CONST_18  C25  C24  C23  C22    0.00   0.0  0
 OB5  CONST_19  C07  C05  C06  C01  180.00   0.0  0
 OB5  CONST_20  C07  C05  C04  C03  180.00   0.0  0
 OB5  CONST_21  C13  C12  C10  C08  180.00   0.0  0
 OB5  CONST_22  C15  C16  C10  C08  180.00   0.0  0
 OB5  CONST_23  O01  C02  C03  C04  180.00   0.0  0
 OB5  CONST_24  O01  C02  C01  C06  180.00   0.0  0
 OB5  CONST_25  O02  C14  C13  C12  180.00   0.0  0
 OB5  CONST_26  O02  C14  C15  C16  180.00   0.0  0
 OB5  CONST_27  C22  C21  C19  N01  180.00   0.0  0
 OB5  CONST_28  C24  C25  C19  N01  180.00   0.0  0
 OB5  CONST_29  O06  C23  C22  C21  180.00   0.0  0
 OB5  CONST_30  O06  C23  C24  C25  180.00   0.0  0
 OB5  CONST_31  H2   C03  C02  C01  180.00   0.0  0
 OB5  CONST_32  H4   C06  C01  C02  180.00   0.0  0
 OB5  CONST_33  H3   C04  C03  C02  180.00   0.0  0
 OB5  CONST_34  H1   C01  C02  C03  180.00   0.0  0
 OB5  CONST_35  H8   C12  C10  C08    0.00   0.0  0
 OB5  CONST_36  H11  C16  C10  C08    0.00   0.0  0
 OB5  CONST_37  H9   C13  C12  C10  180.00   0.0  0
 OB5  CONST_38  H10  C15  C16  C10  180.00   0.0  0
 OB5  CONST_39  H19  C22  C21  C19  180.00   0.0  0
 OB5  CONST_40  H20  C24  C25  C19  180.00   0.0  0
 OB5  CONST_41  H21  C25  C19  C21  180.00   0.0  0
 OB5  CONST_42  H18  C21  C22  C23  180.00   0.0  0
 OB5  Var_01    C08  C07  C05  C04   39.75  30.0  2
 OB5  Var_02    C10  C08  C07  C05    6.44  30.0  1
 OB5  Var_03    C12  C10  C08  C07   29.45  30.0  2
 OB5  Var_04    C19  N01  S01  C18   84.95  30.0  2
 OB5  Var_05    C26  C20  N01  C19  -65.17  30.0  2
 OB5  Var_06    H25  C27  O06  C23  179.74  30.0  3
 OB5  Var_07    H22  C26  C20  N01  -58.82  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
 OB5  chir_01  C09  C08  O03  C18  negativ
 OB5  chir_02  C11  O03  C17  C07  positiv
 OB5  chir_03  C18  S01  C09  C17  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
 OB5  plan-1  C01  0.020
 OB5  plan-1  C02  0.020
 OB5  plan-1  C03  0.020
 OB5  plan-1  C04  0.020
 OB5  plan-1  C05  0.020
 OB5  plan-1  C06  0.020
 OB5  plan-1  O01  0.020
 OB5  plan-1  C07  0.020
 OB5  plan-1  H1   0.020
 OB5  plan-1  H2   0.020
 OB5  plan-1  H3   0.020
 OB5  plan-1  H4   0.020
 OB5  plan-2  C08  0.020
 OB5  plan-2  C10  0.020
 OB5  plan-2  C12  0.020
 OB5  plan-2  C13  0.020
 OB5  plan-2  C14  0.020
 OB5  plan-2  C15  0.020
 OB5  plan-2  C16  0.020
 OB5  plan-2  O02  0.020
 OB5  plan-2  H8   0.020
 OB5  plan-2  H9   0.020
 OB5  plan-2  H10  0.020
 OB5  plan-2  H11  0.020
 OB5  plan-3  N01  0.020
 OB5  plan-3  C19  0.020
 OB5  plan-3  C21  0.020
 OB5  plan-3  C22  0.020
 OB5  plan-3  C23  0.020
 OB5  plan-3  C24  0.020
 OB5  plan-3  C25  0.020
 OB5  plan-3  O06  0.020
 OB5  plan-3  H18  0.020
 OB5  plan-3  H19  0.020
 OB5  plan-3  H20  0.020
 OB5  plan-3  H21  0.020
 OB5  plan-4  S01  0.020
 OB5  plan-4  N01  0.020
 OB5  plan-4  C19  0.020
 OB5  plan-4  C20  0.020

