# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Sun Jun 14 16:41:29 2020
#   Inital geometry file: a 149 line input string
#   Ligand name: (1S,2R,4S)-N-(4-chlorophenyl)-N-ethyl-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN(c1ccc(Cl)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
 OB6  OB6  (1S,2R,4S)-N-(4-chlorophenyl)-N-ethyl-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonamide  ligand  58  34  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_OB6
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
 OB6  C01  C   CR6   0   0.346   5.2428  -1.0406  -3.0973
 OB6  C02  C   CR16  0  -0.367   5.4420  -0.4545  -1.8475
 OB6  C03  C   CR16  0  -0.302   4.4778  -0.5706  -0.8634
 OB6  C04  C   CR6   0   0.028   3.2883  -1.2692  -1.0883
 OB6  C05  C   CR16  0  -0.319   3.1156  -1.8661  -2.3407
 OB6  C06  C   CR16  0  -0.322   4.0696  -1.7512  -3.3370
 OB6  C07  C   C     0   0.114   2.2774  -1.4209  -0.0514
 OB6  O01  O   OH1   0  -0.628   6.1475  -0.9598  -4.0904
 OB6  C08  C   C     0   0.089   1.9161  -0.6304   0.9744
 OB6  C09  C   CH1   0  -0.099   0.7628  -1.3659   1.6361
 OB6  C10  C   CH1   0  -0.444  -0.4376  -1.1173   0.6707
 OB6  C11  C   CH2   0  -0.447  -0.0742  -2.0534  -0.4938
 OB6  C12  C   CH1   0  -0.103   1.2973  -2.5832  -0.0009
 OB6  C13  C   CR6   0   0.006   2.2864   0.7349   1.3390
 OB6  C14  C   CR16  0  -0.296   2.4504   1.7281   0.3720
 OB6  C15  C   CR16  0  -0.366   2.7756   3.0267   0.7217
 OB6  C16  C   CR6   0   0.349   2.9444   3.3670   2.0632
 OB6  C17  C   CR16  0  -0.324   2.7737   2.3912   3.0434
 OB6  C18  C   CR16  0  -0.297   2.4437   1.0982   2.6789
 OB6  O02  O   OH1   0  -0.627   3.2628   4.6114   2.4624
 OB6  O03  O   O2    0  -0.452   1.0627  -2.7183   1.3900
 OB6  S01  S   S     0   1.359  -1.9991  -1.5107   1.4618
 OB6  N01  N   N     0  -0.687  -3.1427  -1.3192   0.2940
 OB6  C19  C   CR6   0   0.304  -3.5249  -0.0033  -0.0753
 OB6  C20  C   CH2   0  -0.311  -3.7176  -2.4564  -0.4345
 OB6  C21  C   CH3   0  -0.647  -5.0841  -2.8486   0.0925
 OB6  C22  C   CR16  0  -0.261  -2.9835   0.5770  -1.2173
 OB6  C23  C   CR16  0  -0.212  -3.3693   1.8480  -1.6124
 OB6  C24  C   CR6   0  -0.034  -4.3014   2.5339  -0.8486
 OB6  C25  C   CR16  0  -0.217  -4.8525   1.9712   0.2927
 OB6  C26  C   CR16  0  -0.249  -4.4612   0.6978   0.6755
 OB6  CL1  CL  CL    0  -0.119  -4.7894   4.1234  -1.3309
 OB6  O04  O   OS    0  -0.652  -2.0095  -2.9116   1.8533
 OB6  O05  O   OS    0  -0.657  -2.2028  -0.4880   2.4773
 OB6  H1   H   HCR6  0   0.273   6.3574   0.0873  -1.6375
 OB6  H2   H   HCR6  0   0.260   4.6671  -0.1232   0.1037
 OB6  H3   H   HCR6  0   0.253   2.2148  -2.4281  -2.5564
 OB6  H4   H   HCR6  0   0.266   3.9090  -2.2176  -4.3010
 OB6  H5   H   HOH1  0   0.476   6.9209  -0.4621  -3.8022
 OB6  H6   H   HCH1  0   0.284   0.5826  -1.1639   2.6912
 OB6  H7   H   HCH1  0   0.329  -0.5216  -0.0665   0.3864
 OB6  H8   H   HCH2  0   0.279  -0.7743  -2.8816  -0.6073
 OB6  H9   H   HCH2  0   0.276  -0.0197  -1.5307  -1.4470
 OB6  H10  H   HCH1  0   0.267   1.6174  -3.5237  -0.4461
 OB6  H11  H   HCR6  0   0.258   2.3101   1.4867  -0.6740
 OB6  H12  H   HCR6  0   0.275   2.8880   3.7788  -0.0509
 OB6  H13  H   HCR6  0   0.267   2.8994   2.6491   4.0875
 OB6  H14  H   HCR6  0   0.258   2.3224   0.3545   3.4571
 OB6  H15  H   HOH1  0   0.476   3.3421   5.1999   1.7033
 OB6  H16  H   HCH2  0   0.259  -3.7767  -2.1724  -1.4860
 OB6  H17  H   HCH2  0   0.259  -3.0346  -3.3021  -0.3849
 OB6  H18  H   HCH3  0   0.231  -5.0226  -3.1717   1.1313
 OB6  H19  H   HCH3  0   0.230  -5.7879  -2.0180   0.0312
 OB6  H20  H   HCH3  0   0.238  -5.4876  -3.6713  -0.4981
 OB6  H21  H   HCR6  0   0.280  -2.2561   0.0320  -1.8067
 OB6  H22  H   HCR6  0   0.287  -2.9451   2.2957  -2.5004
 OB6  H23  H   HCR6  0   0.287  -5.5804   2.5160   0.8778
 OB6  H24  H   HCR6  0   0.276  -4.8916   0.2475   1.5592

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
 OB6  O02  C16  single    1.345  0.020  1.345
 OB6  C17  C16  aromatic  1.394  0.020  1.394
 OB6  C17  C18  aromatic  1.383  0.020  1.383
 OB6  C16  C15  aromatic  1.394  0.020  1.394
 OB6  C02  C03  aromatic  1.383  0.020  1.383
 OB6  C02  C01  aromatic  1.395  0.020  1.395
 OB6  C18  C13  aromatic  1.397  0.020  1.397
 OB6  O01  C01  single    1.346  0.020  1.346
 OB6  C03  C04  aromatic  1.398  0.020  1.398
 OB6  C15  C14  aromatic  1.384  0.020  1.384
 OB6  C01  C06  aromatic  1.392  0.020  1.392
 OB6  C13  C14  aromatic  1.396  0.020  1.396
 OB6  C13  C08  single    1.461  0.020  1.461
 OB6  C04  C07  single    1.456  0.020  1.456
 OB6  C04  C05  aromatic  1.398  0.020  1.398
 OB6  C08  C07  double    1.345  0.020  1.345
 OB6  C08  C09  single    1.520  0.020  1.520
 OB6  C06  C05  aromatic  1.384  0.020  1.384
 OB6  C07  C12  single    1.521  0.020  1.521
 OB6  C25  C26  aromatic  1.386  0.020  1.386
 OB6  C25  C24  aromatic  1.387  0.020  1.387
 OB6  C09  O03  single    1.407  0.020  1.407
 OB6  C09  C10  single    1.560  0.020  1.560
 OB6  O03  C12  single    1.417  0.020  1.417
 OB6  C26  C19  aromatic  1.390  0.020  1.390
 OB6  CL1  C24  single    1.731  0.020  1.731
 OB6  C12  C11  single    1.551  0.020  1.551
 OB6  C24  C23  aromatic  1.387  0.020  1.387
 OB6  C21  C20  single    1.516  0.020  1.516
 OB6  C10  C11  single    1.538  0.020  1.538
 OB6  C10  S01  single    1.794  0.020  1.794
 OB6  C19  N01  single    1.419  0.020  1.419
 OB6  C19  C22  aromatic  1.391  0.020  1.391
 OB6  C20  N01  single    1.468  0.020  1.468
 OB6  N01  S01  single    1.646  0.020  1.646
 OB6  C23  C22  aromatic  1.386  0.020  1.386
 OB6  O04  S01  double    1.455  0.020  1.455
 OB6  S01  O05  double    1.456  0.020  1.456
 OB6  C02  H1   single    0.930  0.020  1.080
 OB6  C03  H2   single    0.930  0.020  1.080
 OB6  C05  H3   single    0.930  0.020  1.080
 OB6  C06  H4   single    0.930  0.020  1.080
 OB6  O01  H5   single    0.850  0.020  0.980
 OB6  C09  H6   single    0.970  0.020  1.090
 OB6  C10  H7   single    0.970  0.020  1.090
 OB6  C11  H8   single    0.970  0.020  1.090
 OB6  C11  H9   single    0.970  0.020  1.090
 OB6  C12  H10  single    0.970  0.020  1.090
 OB6  C14  H11  single    0.930  0.020  1.080
 OB6  C15  H12  single    0.930  0.020  1.080
 OB6  C17  H13  single    0.930  0.020  1.080
 OB6  C18  H14  single    0.930  0.020  1.080
 OB6  O02  H15  single    0.850  0.020  0.980
 OB6  C20  H16  single    0.970  0.020  1.090
 OB6  C20  H17  single    0.970  0.020  1.090
 OB6  C21  H18  single    0.970  0.020  1.090
 OB6  C21  H19  single    0.970  0.020  1.090
 OB6  C21  H20  single    0.970  0.020  1.090
 OB6  C22  H21  single    0.930  0.020  1.080
 OB6  C23  H22  single    0.930  0.020  1.080
 OB6  C25  H23  single    0.930  0.020  1.080
 OB6  C26  H24  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
 OB6  O01  C01  C06  118.03  3.000
 OB6  C06  C01  C02  119.28  3.000
 OB6  O01  C01  C02  122.69  3.000
 OB6  H1   C02  C03  119.53  3.000
 OB6  H1   C02  C01  120.27  3.000
 OB6  C03  C02  C01  120.19  3.000
 OB6  H2   C03  C04  119.95  3.000
 OB6  H2   C03  C02  118.64  3.000
 OB6  C04  C03  C02  121.39  3.000
 OB6  C07  C04  C05  120.51  3.000
 OB6  C05  C04  C03  117.56  3.000
 OB6  C07  C04  C03  121.89  3.000
 OB6  H3   C05  C06  118.22  3.000
 OB6  H3   C05  C04  120.17  3.000
 OB6  C06  C05  C04  121.62  3.000
 OB6  H4   C06  C05  120.19  3.000
 OB6  H4   C06  C01  119.86  3.000
 OB6  C05  C06  C01  119.95  3.000
 OB6  C12  C07  C08  104.52  3.000
 OB6  C12  C07  C04  123.40  3.000
 OB6  C08  C07  C04  131.96  3.000
 OB6  H5   O01  C01  110.47  3.000
 OB6  C13  C08  C09  122.42  3.000
 OB6  C09  C08  C07  104.57  3.000
 OB6  C13  C08  C07  132.21  3.000
 OB6  H6   C09  O03  112.52  3.000
 OB6  H6   C09  C10  116.26  3.000
 OB6  O03  C09  C10  102.06  3.000
 OB6  H6   C09  C08  117.24  3.000
 OB6  C10  C09  C08  103.73  3.000
 OB6  O03  C09  C08  103.14  3.000
 OB6  H7   C10  S01  105.01  3.000
 OB6  H7   C10  C11  114.01  3.000
 OB6  S01  C10  C11  113.96  3.000
 OB6  H7   C10  C09  111.94  3.000
 OB6  S01  C10  C09  111.21  3.000
 OB6  C11  C10  C09  100.94  3.000
 OB6  H9   C11  H8   107.80  3.000
 OB6  H9   C11  C12  113.47  3.000
 OB6  H8   C11  C12  109.96  3.000
 OB6  H9   C11  C10  112.50  3.000
 OB6  H8   C11  C10  112.92  3.000
 OB6  C12  C11  C10  100.15  3.000
 OB6  H10  C12  O03  111.57  3.000
 OB6  H10  C12  C11  115.17  3.000
 OB6  O03  C12  C11  101.43  3.000
 OB6  H10  C12  C07  117.20  3.000
 OB6  C11  C12  C07  107.35  3.000
 OB6  O03  C12  C07  102.25  3.000
 OB6  C18  C13  C14  117.79  3.000
 OB6  C14  C13  C08  121.46  3.000
 OB6  C18  C13  C08  120.72  3.000
 OB6  H11  C14  C15  118.94  3.000
 OB6  H11  C14  C13  119.70  3.000
 OB6  C15  C14  C13  121.35  3.000
 OB6  H12  C15  C16  120.26  3.000
 OB6  H12  C15  C14  119.69  3.000
 OB6  C16  C15  C14  120.05  3.000
 OB6  O02  C16  C17  117.91  3.000
 OB6  C17  C16  C15  119.41  3.000
 OB6  O02  C16  C15  122.69  3.000
 OB6  H13  C17  C18  120.29  3.000
 OB6  H13  C17  C16  119.82  3.000
 OB6  C18  C17  C16  119.89  3.000
 OB6  H14  C18  C17  118.63  3.000
 OB6  H14  C18  C13  119.86  3.000
 OB6  C17  C18  C13  121.50  3.000
 OB6  H15  O02  C16  110.52  3.000
 OB6  C12  O03  C09   96.62  3.000
 OB6  O05  S01  O04  119.20  3.000
 OB6  O05  S01  N01  108.42  3.000
 OB6  O04  S01  N01  107.35  3.000
 OB6  O05  S01  C10  105.98  3.000
 OB6  O04  S01  C10  109.64  3.000
 OB6  N01  S01  C10  105.45  3.000
 OB6  C20  N01  C19  118.93  3.000
 OB6  C20  N01  S01  122.29  3.000
 OB6  C19  N01  S01  118.67  3.000
 OB6  C26  C19  C22  119.70  3.000
 OB6  C22  C19  N01  119.72  3.000
 OB6  C26  C19  N01  120.56  3.000
 OB6  H17  C20  H16  106.28  3.000
 OB6  H17  C20  C21  110.42  3.000
 OB6  H16  C20  C21  110.71  3.000
 OB6  H17  C20  N01  109.49  3.000
 OB6  H16  C20  N01  107.33  3.000
 OB6  C21  C20  N01  112.39  3.000
 OB6  H20  C21  H19  107.79  3.000
 OB6  H20  C21  H18  108.27  3.000
 OB6  H19  C21  H18  108.41  3.000
 OB6  H20  C21  C20  109.91  3.000
 OB6  H19  C21  C20  111.42  3.000
 OB6  H18  C21  C20  110.93  3.000
 OB6  H21  C22  C23  119.55  3.000
 OB6  H21  C22  C19  119.89  3.000
 OB6  C23  C22  C19  120.55  3.000
 OB6  H22  C23  C24  120.75  3.000
 OB6  H22  C23  C22  120.31  3.000
 OB6  C24  C23  C22  118.94  3.000
 OB6  CL1  C24  C25  119.33  3.000
 OB6  CL1  C24  C23  119.36  3.000
 OB6  C25  C24  C23  121.31  3.000
 OB6  H23  C25  C26  120.24  3.000
 OB6  H23  C25  C24  120.56  3.000
 OB6  C26  C25  C24  119.20  3.000
 OB6  H24  C26  C25  119.73  3.000
 OB6  H24  C26  C19  119.98  3.000
 OB6  C25  C26  C19  120.29  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
 OB6  CONST_01  C04  C03  C02  C01     0.00   0.0  0
 OB6  CONST_02  C04  C05  C06  C01     0.00   0.0  0
 OB6  CONST_03  C05  C04  C03  C02     0.00   0.0  0
 OB6  CONST_04  C05  C06  C01  C02     0.00   0.0  0
 OB6  CONST_05  C06  C01  C02  C03     0.00   0.0  0
 OB6  CONST_06  C06  C05  C04  C03     0.00   0.0  0
 OB6  CONST_07  C16  C17  C18  C13     0.00   0.0  0
 OB6  CONST_08  C16  C15  C14  C13     0.00   0.0  0
 OB6  CONST_09  C17  C16  C15  C14     0.00   0.0  0
 OB6  CONST_10  C17  C18  C13  C14     0.00   0.0  0
 OB6  CONST_11  C18  C17  C16  C15     0.00   0.0  0
 OB6  CONST_12  C18  C13  C14  C15     0.00   0.0  0
 OB6  CONST_13  C24  C25  C26  C19     0.00   0.0  0
 OB6  CONST_14  C24  C23  C22  C19     0.00   0.0  0
 OB6  CONST_15  C25  C26  C19  C22     0.00   0.0  0
 OB6  CONST_16  C25  C24  C23  C22     0.00   0.0  0
 OB6  CONST_17  C26  C25  C24  C23     0.00   0.0  0
 OB6  CONST_18  C26  C19  C22  C23     0.00   0.0  0
 OB6  CONST_19  C07  C04  C03  C02   180.00   0.0  0
 OB6  CONST_20  C07  C04  C05  C06   180.00   0.0  0
 OB6  CONST_21  C17  C18  C13  C08   180.00   0.0  0
 OB6  CONST_22  C15  C14  C13  C08   180.00   0.0  0
 OB6  CONST_23  O01  C01  C02  C03   180.00   0.0  0
 OB6  CONST_24  O01  C01  C06  C05   180.00   0.0  0
 OB6  CONST_25  O02  C16  C15  C14   180.00   0.0  0
 OB6  CONST_26  O02  C16  C17  C18   180.00   0.0  0
 OB6  CONST_27  C25  C26  C19  N01   180.00   0.0  0
 OB6  CONST_28  C23  C22  C19  N01   180.00   0.0  0
 OB6  CONST_29  CL1  C24  C23  C22   180.00   0.0  0
 OB6  CONST_30  CL1  C24  C25  C26   180.00   0.0  0
 OB6  CONST_31  H2   C03  C02  C01   180.00   0.0  0
 OB6  CONST_32  H3   C05  C06  C01   180.00   0.0  0
 OB6  CONST_33  H4   C06  C01  C02   180.00   0.0  0
 OB6  CONST_34  H1   C02  C03  C04   180.00   0.0  0
 OB6  CONST_35  H14  C18  C13  C08     0.00   0.0  0
 OB6  CONST_36  H11  C14  C13  C08     0.00   0.0  0
 OB6  CONST_37  H13  C17  C18  C13   180.00   0.0  0
 OB6  CONST_38  H12  C15  C14  C13   180.00   0.0  0
 OB6  CONST_39  H23  C25  C26  C19   180.00   0.0  0
 OB6  CONST_40  H22  C23  C22  C19   180.00   0.0  0
 OB6  CONST_41  H24  C26  C19  C22   180.00   0.0  0
 OB6  CONST_42  H21  C22  C23  C24   180.00   0.0  0
 OB6  Var_01    C08  C07  C04  C03    30.99  30.0  2
 OB6  Var_02    C13  C08  C07  C04     8.47  30.0  1
 OB6  Var_03    C18  C13  C08  C07  -143.39  30.0  2
 OB6  Var_04    C19  N01  S01  C10   -75.52  30.0  1
 OB6  Var_05    C21  C20  N01  C19   -83.14  30.0  2
 OB6  Var_06    H18  C21  C20  N01   -62.29  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
 OB6  chir_01  C09  C08  O03  C10  positiv
 OB6  chir_02  C10  S01  C09  C11  negativ
 OB6  chir_03  C12  O03  C11  C07  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
 OB6  plan-1  C01  0.020
 OB6  plan-1  C02  0.020
 OB6  plan-1  C03  0.020
 OB6  plan-1  C04  0.020
 OB6  plan-1  C05  0.020
 OB6  plan-1  C06  0.020
 OB6  plan-1  C07  0.020
 OB6  plan-1  O01  0.020
 OB6  plan-1  H1   0.020
 OB6  plan-1  H2   0.020
 OB6  plan-1  H3   0.020
 OB6  plan-1  H4   0.020
 OB6  plan-2  C08  0.020
 OB6  plan-2  C13  0.020
 OB6  plan-2  C14  0.020
 OB6  plan-2  C15  0.020
 OB6  plan-2  C16  0.020
 OB6  plan-2  C17  0.020
 OB6  plan-2  C18  0.020
 OB6  plan-2  O02  0.020
 OB6  plan-2  H11  0.020
 OB6  plan-2  H12  0.020
 OB6  plan-2  H13  0.020
 OB6  plan-2  H14  0.020
 OB6  plan-3  N01  0.020
 OB6  plan-3  C19  0.020
 OB6  plan-3  C22  0.020
 OB6  plan-3  C23  0.020
 OB6  plan-3  C24  0.020
 OB6  plan-3  C25  0.020
 OB6  plan-3  C26  0.020
 OB6  plan-3  CL1  0.020
 OB6  plan-3  H21  0.020
 OB6  plan-3  H22  0.020
 OB6  plan-3  H23  0.020
 OB6  plan-3  H24  0.020
 OB6  plan-4  S01  0.020
 OB6  plan-4  N01  0.020
 OB6  plan-4  C19  0.020
 OB6  plan-4  C20  0.020

