# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 01:17:30 2020
#   Inital geometry file: a 143 line input string
#   Ligand name: (1S,2R,4S)-N-(2-chlorophenyl)-5,6-bis(4-hydroxyphenyl)-N-methyl-7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN(c1ccccc1Cl)[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
 OB3  OB3  (1S,2R,4S)-N-(2-chlorophenyl)-5,6-bis(4-hydroxyphenyl)-N-methyl-7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonamide  ligand  55  33  .  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_OB3
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
 OB3  C01  C   CR16  0  -0.370  -2.2485   3.7116  -1.2958
 OB3  C02  C   CR6   0   0.347  -2.6290   3.9675   0.0191
 OB3  C03  C   CR16  0  -0.319  -2.6458   2.9223   0.9429
 OB3  C04  C   CR16  0  -0.299  -2.2957   1.6453   0.5478
 OB3  C05  C   CR6   0   0.008  -1.9237   1.3664  -0.7708
 OB3  C06  C   CR16  0  -0.297  -1.8954   2.4274  -1.6763
 OB3  O01  O   OH1   0  -0.627  -2.9785   5.1927   0.4506
 OB3  C07  C   C     0   0.087  -1.5221   0.0244  -1.1852
 OB3  C08  C   C     0   0.112  -1.9689  -1.1995  -0.8525
 OB3  C09  C   CH1   0  -0.103  -0.9127  -2.1515  -1.3941
 OB3  C10  C   CR6   0   0.030  -3.1231  -1.6348  -0.0793
 OB3  C11  C   CH1   0  -0.099  -0.2410  -0.2353  -1.9594
 OB3  C12  C   CR16  0  -0.305  -4.3127  -0.8975  -0.0511
 OB3  C13  C   CR16  0  -0.320  -5.4085  -1.3242   0.6721
 OB3  C14  C   CR6   0   0.345  -5.3481  -2.5145   1.3987
 OB3  C15  C   CR16  0  -0.368  -4.1807  -3.2710   1.3694
 OB3  C16  C   CR16  0  -0.320  -3.0905  -2.8350   0.6323
 OB3  O02  O   OH1   0  -0.628  -6.4400  -2.8801   2.0953
 OB3  C17  C   CH1   0  -0.433   0.7918  -0.6007  -0.8477
 OB3  C18  C   CH2   0  -0.439   0.3326  -2.0214  -0.4792
 OB3  S01  S   S     0   1.355   2.4691  -0.5086  -1.4788
 OB3  O03  O   O2    0  -0.452  -0.4781  -1.4825  -2.5648
 OB3  N01  N   N     0  -0.680   3.4483  -0.8990  -0.2072
 OB3  O04  O   OS    0  -0.651   2.6475  -1.5209  -2.5081
 OB3  O05  O   OS    0  -0.654   2.7068   0.8902  -1.8022
 OB3  C19  C   CR6   0   0.385   3.9498   0.1296   0.6235
 OB3  C20  C   CH3   0  -0.520   3.9751  -2.2456  -0.0147
 OB3  C21  C   CR6   0  -0.072   3.4267   0.3379   1.8988
 OB3  C22  C   CR16  0  -0.222   3.9485   1.3100   2.7384
 OB3  C23  C   CR16  0  -0.253   5.0070   2.0905   2.2996
 OB3  C24  C   CR16  0  -0.255   5.5439   1.8949   1.0343
 OB3  C25  C   CR16  0  -0.248   5.0182   0.9169   0.2063
 OB3  CL1  CL  CL    0  -0.091   2.1112  -0.6340   2.4574
 OB3  H1   H   HCR6  0   0.274  -2.2254   4.5134  -2.0247
 OB3  H2   H   HCR6  0   0.267  -2.9217   3.1191   1.9714
 OB3  H3   H   HCR6  0   0.256  -2.2962   0.8519   1.2840
 OB3  H4   H   HCR6  0   0.261  -1.6059   2.2518  -2.7053
 OB3  H5   H   HOH1  0   0.476  -2.9132   5.8353  -0.2649
 OB3  H6   H   HCH1  0   0.266  -1.2271  -3.1714  -1.6096
 OB3  H7   H   HCH1  0   0.283   0.0671   0.5247  -2.6757
 OB3  H8   H   HCR6  0   0.258  -4.3890   0.0202  -0.6190
 OB3  H9   H   HCR6  0   0.266  -6.3210  -0.7412   0.6709
 OB3  H10  H   HCR6  0   0.274  -4.1164  -4.2023   1.9204
 OB3  H11  H   HCR6  0   0.256  -2.1969  -3.4468   0.6293
 OB3  H12  H   HOH1  0   0.476  -6.2871  -3.7170   2.5481
 OB3  H13  H   HCH1  0   0.321   0.7632   0.1024  -0.0142
 OB3  H14  H   HCH2  0   0.272   0.1021  -2.1229   0.5793
 OB3  H15  H   HCH2  0   0.276   1.0647  -2.7888  -0.7313
 OB3  H16  H   HCH3  0   0.255   5.0412  -2.2776  -0.2399
 OB3  H17  H   HCH3  0   0.250   3.8174  -2.5631   1.0151
 OB3  H18  H   HCH3  0   0.262   3.4697  -2.9546  -0.6630
 OB3  H19  H   HCR6  0   0.286   3.5307   1.4562   3.7249
 OB3  H20  H   HCR6  0   0.275   5.4142   2.8496   2.9536
 OB3  H21  H   HCR6  0   0.270   6.3732   2.4998   0.6936
 OB3  H22  H   HCR6  0   0.274   5.4380   0.7496  -0.7764

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
 OB3  O01  C02  single    1.345  0.020  1.345
 OB3  C03  C02  aromatic  1.395  0.020  1.395
 OB3  C03  C04  aromatic  1.382  0.020  1.382
 OB3  C02  C01  aromatic  1.393  0.020  1.393
 OB3  C15  C16  aromatic  1.386  0.020  1.386
 OB3  C15  C14  aromatic  1.391  0.020  1.391
 OB3  C04  C05  aromatic  1.398  0.020  1.398
 OB3  C16  C10  aromatic  1.396  0.020  1.396
 OB3  O02  C14  single    1.346  0.020  1.346
 OB3  C01  C06  aromatic  1.385  0.020  1.385
 OB3  C14  C13  aromatic  1.396  0.020  1.396
 OB3  C05  C06  aromatic  1.395  0.020  1.395
 OB3  C05  C07  single    1.461  0.020  1.461
 OB3  C24  C23  aromatic  1.388  0.020  1.388
 OB3  C24  C25  aromatic  1.385  0.020  1.385
 OB3  C10  C08  single    1.456  0.020  1.456
 OB3  C10  C12  aromatic  1.400  0.020  1.400
 OB3  C07  C08  double    1.345  0.020  1.345
 OB3  C07  C11  single    1.519  0.020  1.519
 OB3  C23  C22  aromatic  1.386  0.020  1.386
 OB3  C08  C09  single    1.522  0.020  1.522
 OB3  C13  C12  aromatic  1.381  0.020  1.381
 OB3  O03  C11  single    1.406  0.020  1.406
 OB3  O03  C09  single    1.417  0.020  1.417
 OB3  C25  C19  aromatic  1.391  0.020  1.391
 OB3  C11  C17  single    1.561  0.020  1.561
 OB3  C09  C18  single    1.551  0.020  1.551
 OB3  C22  C21  aromatic  1.386  0.020  1.386
 OB3  C19  C21  aromatic  1.394  0.020  1.394
 OB3  C19  N01  single    1.414  0.020  1.414
 OB3  C17  C18  single    1.538  0.020  1.538
 OB3  C17  S01  single    1.794  0.020  1.794
 OB3  C21  CL1  single    1.728  0.020  1.728
 OB3  N01  C20  single    1.459  0.020  1.459
 OB3  N01  S01  single    1.652  0.020  1.652
 OB3  O04  S01  double    1.455  0.020  1.455
 OB3  S01  O05  double    1.455  0.020  1.455
 OB3  C01  H1   single    0.930  0.020  1.080
 OB3  C03  H2   single    0.930  0.020  1.080
 OB3  C04  H3   single    0.930  0.020  1.080
 OB3  C06  H4   single    0.930  0.020  1.080
 OB3  O01  H5   single    0.850  0.020  0.980
 OB3  C09  H6   single    0.970  0.020  1.090
 OB3  C11  H7   single    0.970  0.020  1.090
 OB3  C12  H8   single    0.930  0.020  1.080
 OB3  C13  H9   single    0.930  0.020  1.080
 OB3  C15  H10  single    0.930  0.020  1.080
 OB3  C16  H11  single    0.930  0.020  1.080
 OB3  O02  H12  single    0.850  0.020  0.980
 OB3  C17  H13  single    0.970  0.020  1.090
 OB3  C18  H14  single    0.970  0.020  1.090
 OB3  C18  H15  single    0.970  0.020  1.090
 OB3  C20  H16  single    0.970  0.020  1.090
 OB3  C20  H17  single    0.970  0.020  1.090
 OB3  C20  H18  single    0.970  0.020  1.090
 OB3  C22  H19  single    0.930  0.020  1.080
 OB3  C23  H20  single    0.930  0.020  1.080
 OB3  C24  H21  single    0.930  0.020  1.080
 OB3  C25  H22  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
 OB3  H1   C01  C06  119.71  3.000
 OB3  H1   C01  C02  120.32  3.000
 OB3  C06  C01  C02  119.96  3.000
 OB3  O01  C02  C03  117.83  3.000
 OB3  C03  C02  C01  119.40  3.000
 OB3  O01  C02  C01  122.77  3.000
 OB3  H2   C03  C04  120.27  3.000
 OB3  H2   C03  C02  119.73  3.000
 OB3  C04  C03  C02  120.00  3.000
 OB3  H3   C04  C05  119.69  3.000
 OB3  H3   C04  C03  118.87  3.000
 OB3  C05  C04  C03  121.43  3.000
 OB3  C07  C05  C06  120.60  3.000
 OB3  C07  C05  C04  121.60  3.000
 OB3  C06  C05  C04  117.76  3.000
 OB3  H4   C06  C05  119.91  3.000
 OB3  H4   C06  C01  118.64  3.000
 OB3  C05  C06  C01  121.44  3.000
 OB3  H5   O01  C02  110.58  3.000
 OB3  C11  C07  C08  104.52  3.000
 OB3  C11  C07  C05  122.24  3.000
 OB3  C08  C07  C05  132.42  3.000
 OB3  C10  C08  C09  123.52  3.000
 OB3  C09  C08  C07  104.52  3.000
 OB3  C10  C08  C07  131.83  3.000
 OB3  H6   C09  O03  111.55  3.000
 OB3  H6   C09  C18  115.30  3.000
 OB3  O03  C09  C18  101.63  3.000
 OB3  H6   C09  C08  117.14  3.000
 OB3  C18  C09  C08  107.15  3.000
 OB3  O03  C09  C08  102.21  3.000
 OB3  C16  C10  C12  117.55  3.000
 OB3  C12  C10  C08  121.80  3.000
 OB3  C16  C10  C08  120.62  3.000
 OB3  H7   C11  O03  112.54  3.000
 OB3  H7   C11  C17  116.40  3.000
 OB3  O03  C11  C17  102.16  3.000
 OB3  H7   C11  C07  117.03  3.000
 OB3  C17  C11  C07  103.60  3.000
 OB3  O03  C11  C07  103.23  3.000
 OB3  H8   C12  C13  118.76  3.000
 OB3  H8   C12  C10  119.75  3.000
 OB3  C13  C12  C10  121.49  3.000
 OB3  H9   C13  C14  119.75  3.000
 OB3  H9   C13  C12  120.12  3.000
 OB3  C14  C13  C12  120.13  3.000
 OB3  O02  C14  C15  122.95  3.000
 OB3  O02  C14  C13  117.78  3.000
 OB3  C15  C14  C13  119.28  3.000
 OB3  H10  C15  C16  119.59  3.000
 OB3  H10  C15  C14  120.41  3.000
 OB3  C16  C15  C14  120.00  3.000
 OB3  H11  C16  C15  118.21  3.000
 OB3  H11  C16  C10  120.24  3.000
 OB3  C15  C16  C10  121.54  3.000
 OB3  H12  O02  C14  110.51  3.000
 OB3  H13  C17  S01  105.08  3.000
 OB3  H13  C17  C18  113.86  3.000
 OB3  S01  C17  C18  114.25  3.000
 OB3  H13  C17  C11  112.09  3.000
 OB3  S01  C17  C11  110.86  3.000
 OB3  C18  C17  C11  100.91  3.000
 OB3  H15  C18  H14  107.55  3.000
 OB3  H15  C18  C17  113.23  3.000
 OB3  H14  C18  C17  112.49  3.000
 OB3  H15  C18  C09  110.11  3.000
 OB3  H14  C18  C09  113.33  3.000
 OB3  C17  C18  C09  100.13  3.000
 OB3  O05  S01  O04  119.45  3.000
 OB3  O05  S01  N01  107.55  3.000
 OB3  O04  S01  N01  107.91  3.000
 OB3  O05  S01  C17  106.27  3.000
 OB3  O04  S01  C17  109.13  3.000
 OB3  N01  S01  C17  105.74  3.000
 OB3  C11  O03  C09   96.59  3.000
 OB3  C20  N01  C19  117.76  3.000
 OB3  C20  N01  S01  122.27  3.000
 OB3  C19  N01  S01  119.38  3.000
 OB3  C25  C19  C21  118.55  3.000
 OB3  C21  C19  N01  120.86  3.000
 OB3  C25  C19  N01  120.52  3.000
 OB3  H18  C20  H17  107.87  3.000
 OB3  H18  C20  H16  108.22  3.000
 OB3  H17  C20  H16  109.18  3.000
 OB3  H18  C20  N01  110.85  3.000
 OB3  H17  C20  N01  109.98  3.000
 OB3  H16  C20  N01  110.67  3.000
 OB3  CL1  C21  C22  119.02  3.000
 OB3  CL1  C21  C19  119.82  3.000
 OB3  C22  C21  C19  121.16  3.000
 OB3  H19  C22  C23  120.51  3.000
 OB3  H19  C22  C21  120.12  3.000
 OB3  C23  C22  C21  119.37  3.000
 OB3  H20  C23  C24  120.29  3.000
 OB3  H20  C23  C22  119.42  3.000
 OB3  C24  C23  C22  120.30  3.000
 OB3  H21  C24  C25  119.85  3.000
 OB3  H21  C24  C23  120.32  3.000
 OB3  C25  C24  C23  119.83  3.000
 OB3  H22  C25  C24  120.33  3.000
 OB3  H22  C25  C19  118.88  3.000
 OB3  C24  C25  C19  120.79  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
 OB3  CONST_01  C04  C03  C02  C01     0.00   0.0  0
 OB3  CONST_02  C04  C05  C06  C01     0.00   0.0  0
 OB3  CONST_03  C05  C04  C03  C02     0.00   0.0  0
 OB3  CONST_04  C05  C06  C01  C02     0.00   0.0  0
 OB3  CONST_05  C06  C01  C02  C03     0.00   0.0  0
 OB3  CONST_06  C06  C05  C04  C03     0.00   0.0  0
 OB3  CONST_07  C14  C15  C16  C10     0.00   0.0  0
 OB3  CONST_08  C14  C13  C12  C10     0.00   0.0  0
 OB3  CONST_09  C15  C16  C10  C12     0.00   0.0  0
 OB3  CONST_10  C15  C14  C13  C12     0.00   0.0  0
 OB3  CONST_11  C16  C15  C14  C13     0.00   0.0  0
 OB3  CONST_12  C16  C10  C12  C13     0.00   0.0  0
 OB3  CONST_13  C23  C24  C25  C19     0.00   0.0  0
 OB3  CONST_14  C23  C22  C21  C19     0.00   0.0  0
 OB3  CONST_15  C24  C23  C22  C21     0.00   0.0  0
 OB3  CONST_16  C24  C25  C19  C21     0.00   0.0  0
 OB3  CONST_17  C25  C24  C23  C22     0.00   0.0  0
 OB3  CONST_18  C25  C19  C21  C22     0.00   0.0  0
 OB3  CONST_19  C07  C05  C06  C01   180.00   0.0  0
 OB3  CONST_20  C07  C05  C04  C03   180.00   0.0  0
 OB3  CONST_21  C15  C16  C10  C08   180.00   0.0  0
 OB3  CONST_22  C13  C12  C10  C08   180.00   0.0  0
 OB3  CONST_23  O01  C02  C03  C04   180.00   0.0  0
 OB3  CONST_24  O01  C02  C01  C06   180.00   0.0  0
 OB3  CONST_25  O02  C14  C13  C12   180.00   0.0  0
 OB3  CONST_26  O02  C14  C15  C16   180.00   0.0  0
 OB3  CONST_27  C24  C25  C19  N01   180.00   0.0  0
 OB3  CONST_28  C22  C21  C19  N01   180.00   0.0  0
 OB3  CONST_29  CL1  C21  C22  C23   180.00   0.0  0
 OB3  CONST_30  CL1  C21  C19  C25   180.00   0.0  0
 OB3  CONST_31  H2   C03  C02  C01   180.00   0.0  0
 OB3  CONST_32  H3   C04  C03  C02   180.00   0.0  0
 OB3  CONST_33  H4   C06  C01  C02   180.00   0.0  0
 OB3  CONST_34  H1   C01  C02  C03   180.00   0.0  0
 OB3  CONST_35  H11  C16  C10  C08     0.00   0.0  0
 OB3  CONST_36  H8   C12  C10  C08     0.00   0.0  0
 OB3  CONST_37  H10  C15  C16  C10   180.00   0.0  0
 OB3  CONST_38  H9   C13  C12  C10   180.00   0.0  0
 OB3  CONST_39  H21  C24  C25  C19   180.00   0.0  0
 OB3  CONST_40  H19  C22  C21  C19   180.00   0.0  0
 OB3  CONST_41  H20  C23  C22  C21   180.00   0.0  0
 OB3  CONST_42  H22  C25  C19  C21   180.00   0.0  0
 OB3  Var_01    C08  C07  C05  C04    38.27  30.0  2
 OB3  Var_02    C10  C08  C07  C05     8.58  30.0  1
 OB3  Var_03    C16  C10  C08  C07  -151.10  30.0  2
 OB3  Var_04    C19  N01  S01  C17   -92.00  30.0  2
 OB3  Var_05    H16  C20  N01  C19   -63.57  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
 OB3  chir_01  C09  C08  O03  C18  negativ
 OB3  chir_02  C11  O03  C17  C07  positiv
 OB3  chir_03  C17  S01  C11  C18  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
 OB3  plan-1  C01  0.020
 OB3  plan-1  C02  0.020
 OB3  plan-1  C03  0.020
 OB3  plan-1  C04  0.020
 OB3  plan-1  C05  0.020
 OB3  plan-1  C06  0.020
 OB3  plan-1  O01  0.020
 OB3  plan-1  C07  0.020
 OB3  plan-1  H1   0.020
 OB3  plan-1  H2   0.020
 OB3  plan-1  H3   0.020
 OB3  plan-1  H4   0.020
 OB3  plan-2  C08  0.020
 OB3  plan-2  C10  0.020
 OB3  plan-2  C12  0.020
 OB3  plan-2  C13  0.020
 OB3  plan-2  C14  0.020
 OB3  plan-2  C15  0.020
 OB3  plan-2  C16  0.020
 OB3  plan-2  O02  0.020
 OB3  plan-2  H8   0.020
 OB3  plan-2  H9   0.020
 OB3  plan-2  H10  0.020
 OB3  plan-2  H11  0.020
 OB3  plan-3  N01  0.020
 OB3  plan-3  C19  0.020
 OB3  plan-3  C21  0.020
 OB3  plan-3  C22  0.020
 OB3  plan-3  C23  0.020
 OB3  plan-3  C24  0.020
 OB3  plan-3  C25  0.020
 OB3  plan-3  CL1  0.020
 OB3  plan-3  H19  0.020
 OB3  plan-3  H20  0.020
 OB3  plan-3  H21  0.020
 OB3  plan-3  H22  0.020
 OB3  plan-4  S01  0.020
 OB3  plan-4  N01  0.020
 OB3  plan-4  C19  0.020
 OB3  plan-4  C20  0.020

