# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 12 16:32:00 2020
#   Inital geometry file: a 150 line input string
#   Ligand name: 2-[4-[4-cyclopentyl-3-[(1~{R},2~{S})-2-pyridin-2-ylcyclopropyl]phenyl]phenyl]sulfonylethanol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCC[S](=O)(=O)c1ccc(cc1)c2ccc(C3CCCC3)c(c2)[C@@H]4C[C@@H]4c5ccccn5
#
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
 9M6  9M6  2-[4-[4-cyclopentyl-3-[(1~{R},2~{S})-2-pyridin-2-ylcyclopropyl]phenyl]phenyl]sulfonylethanol  ligand  61  32  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_9M6
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
 9M6  C2   C  CH2   0  -0.414  -4.9328   2.4482   0.2375
 9M6  C12  C  CR16  0  -0.215   3.4830   1.8931  -0.7806
 9M6  C13  C  CH2   0  -0.136   7.9188   1.2974   1.3642
 9M6  C14  C  CH2   0  -0.625   6.4034   1.2979   1.2165
 9M6  C15  C  CR6   0  -0.196   4.1544   0.7559  -0.3539
 9M6  C17  C  CR6   0   0.100  -0.0959   0.8628  -0.1862
 9M6  C18  C  CR16  0  -0.368  -0.7828   0.2355   0.8490
 9M6  C19  C  CH1   0  -0.301  -2.8269  -0.4098   2.1022
 9M6  C20  C  CR6   0   0.059  -2.1720   0.2500   0.9356
 9M6  N1   N  N     0  -0.439  -5.0943  -2.7404   0.4284
 9M6  C5   C  CH2   0  -0.452  -6.4068   2.3366  -0.1295
 9M6  C6   C  CR6   0   0.170  -2.9161   0.9208  -0.0434
 9M6  C7   C  CR16  0  -0.303  -2.2231   1.5494  -1.0781
 9M6  C9   C  CR6   0   0.105   1.3763   0.8255  -0.2467
 9M6  O3   O  OS    0  -0.666   6.3817   1.6856  -1.3992
 9M6  O2   O  OS    0  -0.667   6.3520  -0.6760  -0.5353
 9M6  O1   O  OH1   0  -0.663   8.1916   1.7622   2.6633
 9M6  C16  C  CR16  0  -0.212   3.4613  -0.3494   0.1208
 9M6  C10  C  CR16  0  -0.301   2.0795  -0.3074   0.1708
 9M6  C11  C  CR16  0  -0.301   2.1006   1.9205  -0.7237
 9M6  C8   C  CR16  0  -0.307  -0.8436   1.5274  -1.1575
 9M6  C1   C  CH1   0  -0.369  -4.4159   1.0207   0.0059
 9M6  C3   C  CH2   0  -0.435  -5.1501   0.5661  -1.2763
 9M6  C4   C  CH2   0  -0.447  -6.4012   1.4646  -1.3923
 9M6  C27  C  CH1   0  -0.321  -3.6199  -1.6995   1.9734
 9M6  C21  C  CH2   0  -0.491  -2.2923  -1.6778   2.6736
 9M6  C22  C  CR6   0   0.304  -3.8363  -2.3714   0.6721
 9M6  C23  C  CR16  0  -0.334  -2.8165  -2.6009  -0.2524
 9M6  C24  C  CR16  0  -0.159  -3.1237  -3.2077  -1.4572
 9M6  C25  C  CR16  0  -0.322  -4.4358  -3.5811  -1.7106
 9M6  C26  C  CR16  0  -0.092  -5.3782  -3.3286  -0.7278
 9M6  H1   H  HCH2  0   0.221  -4.4275   3.1487  -0.4351
 9M6  H2   H  HCH2  0   0.236  -4.7582   2.7941   1.2582
 9M6  H3   H  HCR6  0   0.286   4.0216   2.7546  -1.1513
 9M6  H4   H  HCH2  0   0.221   8.3027   0.2843   1.2049
 9M6  H5   H  HCH2  0   0.219   8.3627   1.9438   0.5994
 9M6  H6   H  HCH2  0   0.306   5.9344   0.6354   1.9464
 9M6  H7   H  HCH2  0   0.307   5.9929   2.3024   1.3351
 9M6  H8   H  HCR6  0   0.253  -0.2227  -0.2584   1.6345
 9M6  H9   H  HCH1  0   0.287  -3.2606   0.2837   2.8172
 9M6  H10  H  HCH2  0   0.220  -6.9490   1.8352   0.6769
 9M6  H11  H  HCH2  0   0.230  -6.8854   3.3044  -0.2879
 9M6  H12  H  HCR6  0   0.246  -2.7777   2.0688  -1.8509
 9M6  H13  H  HOH1  0   0.462   9.1437   1.7313   2.7959
 9M6  H14  H  HCR6  0   0.286   3.9826  -1.2414   0.4409
 9M6  H15  H  HCR6  0   0.266   1.5446  -1.1813   0.5185
 9M6  H16  H  HCR6  0   0.270   1.5836   2.8162  -1.0415
 9M6  H17  H  HCR6  0   0.253  -0.3511   2.0124  -1.9912
 9M6  H18  H  HCH1  0   0.259  -4.7886   0.4132   0.8330
 9M6  H19  H  HCH2  0   0.228  -4.5134   0.6798  -2.1547
 9M6  H20  H  HCH2  0   0.247  -5.4007  -0.4926  -1.2163
 9M6  H21  H  HCH2  0   0.229  -7.3208   0.8874  -1.4959
 9M6  H22  H  HCH2  0   0.225  -6.3249   2.0976  -2.2785
 9M6  H23  H  HCH1  0   0.270  -4.4949  -1.7504   2.6102
 9M6  H24  H  HCH2  0   0.254  -1.4549  -2.1494   2.1730
 9M6  H25  H  HCH2  0   0.271  -2.2909  -1.8059   3.7479
 9M6  H26  H  HCR6  0   0.255  -1.7962  -2.3167  -0.0365
 9M6  H27  H  HCR6  0   0.269  -2.3462  -3.3907  -2.1876
 9M6  H28  H  HCR6  0   0.265  -4.7219  -4.0587  -2.6374
 9M6  H29  H  HCR6  0   0.258  -6.4140  -3.6134  -0.8788
 9M6  S1   S  S     0   1.199   5.9220   0.7158  -0.4063

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
 9M6  C4   C5   single    1.535  0.020  1.535
 9M6  C4   C3   single    1.545  0.020  1.545
 9M6  C5   C2   single    1.523  0.020  1.523
 9M6  C3   C1   single    1.546  0.020  1.546
 9M6  C7   C8   aromatic  1.382  0.020  1.382
 9M6  C7   C6   aromatic  1.395  0.020  1.395
 9M6  C2   C1   single    1.536  0.020  1.536
 9M6  O1   C13  single    1.406  0.020  1.406
 9M6  C8   C17  aromatic  1.394  0.020  1.394
 9M6  C1   C6   single    1.504  0.020  1.504
 9M6  C13  C14  single    1.523  0.020  1.523
 9M6  C10  C16  aromatic  1.383  0.020  1.383
 9M6  C10  C9   aromatic  1.397  0.020  1.397
 9M6  C6   C20  aromatic  1.401  0.020  1.401
 9M6  C16  C15  aromatic  1.388  0.020  1.388
 9M6  C17  C9   single    1.474  0.020  1.474
 9M6  C17  C18  aromatic  1.392  0.020  1.392
 9M6  C9   C11  aromatic  1.397  0.020  1.397
 9M6  O2   S1   double    1.462  0.020  1.462
 9M6  C20  C18  aromatic  1.392  0.020  1.392
 9M6  C20  C19  single    1.492  0.020  1.492
 9M6  C14  S1   single    1.790  0.020  1.790
 9M6  C15  S1   single    1.769  0.020  1.769
 9M6  C15  C12  aromatic  1.388  0.020  1.388
 9M6  S1   O3   double    1.462  0.020  1.462
 9M6  C11  C12  aromatic  1.384  0.020  1.384
 9M6  N1   C26  aromatic  1.328  0.020  1.328
 9M6  N1   C22  aromatic  1.333  0.020  1.333
 9M6  C19  C27  single    1.519  0.020  1.519
 9M6  C19  C21  single    1.490  0.020  1.490
 9M6  C26  C25  aromatic  1.385  0.020  1.385
 9M6  C27  C22  single    1.480  0.020  1.480
 9M6  C27  C21  single    1.501  0.020  1.501
 9M6  C22  C23  aromatic  1.395  0.020  1.395
 9M6  C25  C24  aromatic  1.387  0.020  1.387
 9M6  C23  C24  aromatic  1.384  0.020  1.384
 9M6  C2   H1   single    0.970  0.020  1.090
 9M6  C2   H2   single    0.970  0.020  1.090
 9M6  C12  H3   single    0.930  0.020  1.080
 9M6  C13  H4   single    0.970  0.020  1.090
 9M6  C13  H5   single    0.970  0.020  1.090
 9M6  C14  H6   single    0.970  0.020  1.090
 9M6  C14  H7   single    0.970  0.020  1.090
 9M6  C18  H8   single    0.930  0.020  1.080
 9M6  C19  H9   single    0.970  0.020  1.090
 9M6  C5   H10  single    0.970  0.020  1.090
 9M6  C5   H11  single    0.970  0.020  1.090
 9M6  C7   H12  single    0.930  0.020  1.080
 9M6  O1   H13  single    0.850  0.020  0.980
 9M6  C16  H14  single    0.930  0.020  1.080
 9M6  C10  H15  single    0.930  0.020  1.080
 9M6  C11  H16  single    0.930  0.020  1.080
 9M6  C8   H17  single    0.930  0.020  1.080
 9M6  C1   H18  single    0.970  0.020  1.090
 9M6  C3   H19  single    0.970  0.020  1.090
 9M6  C3   H20  single    0.970  0.020  1.090
 9M6  C4   H21  single    0.970  0.020  1.090
 9M6  C4   H22  single    0.970  0.020  1.090
 9M6  C27  H23  single    0.970  0.020  1.090
 9M6  C21  H24  single    0.970  0.020  1.090
 9M6  C21  H25  single    0.970  0.020  1.090
 9M6  C23  H26  single    0.930  0.020  1.080
 9M6  C24  H27  single    0.930  0.020  1.080
 9M6  C25  H28  single    0.930  0.020  1.080
 9M6  C26  H29  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
 9M6  H2   C2   H1   107.33  3.000
 9M6  H2   C2   C1   112.44  3.000
 9M6  H1   C2   C1   110.29  3.000
 9M6  H2   C2   C5   113.79  3.000
 9M6  H1   C2   C5   110.21  3.000
 9M6  C1   C2   C5   102.78  3.000
 9M6  H3   C12  C11  119.72  3.000
 9M6  H3   C12  C15  121.14  3.000
 9M6  C11  C12  C15  119.14  3.000
 9M6  H5   C13  H4   107.60  3.000
 9M6  H5   C13  O1   111.80  3.000
 9M6  H4   C13  O1   111.84  3.000
 9M6  H5   C13  C14  109.60  3.000
 9M6  H4   C13  C14  109.58  3.000
 9M6  O1   C13  C14  106.41  3.000
 9M6  H7   C14  H6   108.92  3.000
 9M6  H7   C14  S1   107.26  3.000
 9M6  H6   C14  S1   107.06  3.000
 9M6  H7   C14  C13  111.34  3.000
 9M6  H6   C14  C13  111.26  3.000
 9M6  S1   C14  C13  110.83  3.000
 9M6  C16  C15  S1   119.40  3.000
 9M6  S1   C15  C12  119.53  3.000
 9M6  C16  C15  C12  121.06  3.000
 9M6  C8   C17  C9   121.27  3.000
 9M6  C9   C17  C18  120.80  3.000
 9M6  C8   C17  C18  117.93  3.000
 9M6  H8   C18  C20  118.39  3.000
 9M6  H8   C18  C17  119.31  3.000
 9M6  C20  C18  C17  122.28  3.000
 9M6  H9   C19  C21  115.72  3.000
 9M6  H9   C19  C27  112.91  3.000
 9M6  C21  C19  C27   59.83  3.000
 9M6  H9   C19  C20  114.06  3.000
 9M6  C21  C19  C20  121.25  3.000
 9M6  C27  C19  C20  122.56  3.000
 9M6  C6   C20  C19  121.68  3.000
 9M6  C19  C20  C18  118.83  3.000
 9M6  C6   C20  C18  119.45  3.000
 9M6  C26  N1   C22  118.91  3.000
 9M6  H11  C5   H10  107.23  3.000
 9M6  H11  C5   C4   112.72  3.000
 9M6  H10  C5   C4   110.37  3.000
 9M6  H11  C5   C2   113.23  3.000
 9M6  H10  C5   C2   109.62  3.000
 9M6  C4   C5   C2   103.68  3.000
 9M6  C1   C6   C7   119.33  3.000
 9M6  C1   C6   C20  122.59  3.000
 9M6  C7   C6   C20  118.06  3.000
 9M6  H12  C7   C8   118.52  3.000
 9M6  H12  C7   C6   119.39  3.000
 9M6  C8   C7   C6   122.09  3.000
 9M6  C11  C9   C10  118.47  3.000
 9M6  C11  C9   C17  120.80  3.000
 9M6  C10  C9   C17  120.72  3.000
 9M6  H13  O1   C13  107.98  3.000
 9M6  H14  C16  C10  119.72  3.000
 9M6  H14  C16  C15  121.14  3.000
 9M6  C10  C16  C15  119.13  3.000
 9M6  H15  C10  C16  118.75  3.000
 9M6  H15  C10  C9   120.13  3.000
 9M6  C16  C10  C9   121.10  3.000
 9M6  H16  C11  C9   120.10  3.000
 9M6  H16  C11  C12  118.79  3.000
 9M6  C9   C11  C12  121.10  3.000
 9M6  H17  C8   C7   119.41  3.000
 9M6  H17  C8   C17  120.39  3.000
 9M6  C7   C8   C17  120.19  3.000
 9M6  H18  C1   C3   107.62  3.000
 9M6  H18  C1   C6   109.17  3.000
 9M6  C3   C1   C6   115.27  3.000
 9M6  H18  C1   C2   106.74  3.000
 9M6  C6   C1   C2   113.72  3.000
 9M6  C3   C1   C2   103.80  3.000
 9M6  H20  C3   H19  106.25  3.000
 9M6  H20  C3   C4   112.52  3.000
 9M6  H19  C3   C4   110.59  3.000
 9M6  H20  C3   C1   110.44  3.000
 9M6  H19  C3   C1   111.11  3.000
 9M6  C4   C3   C1   106.02  3.000
 9M6  H22  C4   H21  106.78  3.000
 9M6  H22  C4   C3   109.97  3.000
 9M6  H21  C4   C3   112.48  3.000
 9M6  H22  C4   C5   109.79  3.000
 9M6  H21  C4   C5   112.08  3.000
 9M6  C3   C4   C5   105.76  3.000
 9M6  H23  C27  C22  112.17  3.000
 9M6  H23  C27  C21  116.16  3.000
 9M6  C22  C27  C21  123.09  3.000
 9M6  H23  C27  C19  114.30  3.000
 9M6  C21  C27  C19   59.11  3.000
 9M6  C22  C27  C19  122.41  3.000
 9M6  H25  C21  H24  113.96  3.000
 9M6  H25  C21  C27  117.56  3.000
 9M6  H24  C21  C27  117.50  3.000
 9M6  H25  C21  C19  118.82  3.000
 9M6  H24  C21  C19  118.07  3.000
 9M6  C27  C21  C19   61.06  3.000
 9M6  C23  C22  C27  123.38  3.000
 9M6  C23  C22  N1   121.52  3.000
 9M6  C27  C22  N1   115.10  3.000
 9M6  H26  C23  C24  119.92  3.000
 9M6  H26  C23  C22  120.94  3.000
 9M6  C24  C23  C22  119.13  3.000
 9M6  H27  C24  C25  120.70  3.000
 9M6  H27  C24  C23  120.15  3.000
 9M6  C25  C24  C23  119.14  3.000
 9M6  H28  C25  C26  120.58  3.000
 9M6  H28  C25  C24  121.71  3.000
 9M6  C26  C25  C24  117.70  3.000
 9M6  H29  C26  C25  120.21  3.000
 9M6  H29  C26  N1   116.21  3.000
 9M6  C25  C26  N1   123.58  3.000
 9M6  O2   S1   O3   118.61  3.000
 9M6  O3   S1   C15  108.62  3.000
 9M6  O2   S1   C15  108.54  3.000
 9M6  O3   S1   C14  108.39  3.000
 9M6  C15  S1   C14  103.56  3.000
 9M6  O2   S1   C14  108.08  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
 9M6  CONST_01  C10  C16  C15  C12     0.00   0.0  0
 9M6  CONST_02  C10  C9   C11  C12     0.00   0.0  0
 9M6  CONST_03  C17  C9   C11  C12   180.00   0.0  0
 9M6  CONST_04  C9   C10  C16  C15     0.00   0.0  0
 9M6  CONST_05  C9   C11  C12  C15     0.00   0.0  0
 9M6  CONST_06  C6   C7   C8   C17     0.00   0.0  0
 9M6  CONST_07  C16  C10  C9   C17   180.00   0.0  0
 9M6  CONST_08  C6   C20  C18  C17     0.00   0.0  0
 9M6  CONST_09  C7   C8   C17  C18     0.00   0.0  0
 9M6  CONST_12  C7   C6   C20  C18     0.00   0.0  0
 9M6  CONST_13  C8   C7   C6   C20     0.00   0.0  0
 9M6  CONST_14  C8   C17  C18  C20     0.00   0.0  0
 9M6  CONST_15  C9   C17  C18  C20   180.00   0.0  0
 9M6  CONST_16  C24  C25  C26  N1      0.00   0.0  0
 9M6  CONST_17  C24  C23  C22  N1      0.00   0.0  0
 9M6  CONST_18  C9   C17  C8   C7    180.00   0.0  0
 9M6  CONST_19  C11  C9   C10  C16     0.00   0.0  0
 9M6  CONST_20  C11  C12  C15  C16     0.00   0.0  0
 9M6  CONST_23  C25  C26  N1   C22     0.00   0.0  0
 9M6  CONST_24  C25  C24  C23  C22     0.00   0.0  0
 9M6  CONST_25  C26  N1   C22  C23     0.00   0.0  0
 9M6  CONST_26  C26  C25  C24  C23     0.00   0.0  0
 9M6  CONST_27  C19  C20  C18  C17   180.00   0.0  0
 9M6  CONST_28  C1   C6   C20  C18   180.00   0.0  0
 9M6  CONST_29  C7   C6   C20  C19   180.00   0.0  0
 9M6  CONST_30  C1   C6   C20  C19     0.00   0.0  0
 9M6  CONST_31  C1   C6   C7   C8    180.00   0.0  0
 9M6  CONST_32  C26  N1   C22  C27   180.00   0.0  0
 9M6  CONST_33  C24  C23  C22  C27   180.00   0.0  0
 9M6  CONST_34  C10  C16  C15  S1    180.00   0.0  0
 9M6  CONST_35  C11  C12  C15  S1    180.00   0.0  0
 9M6  CONST_36  H14  C16  C15  C12   180.00   0.0  0
 9M6  CONST_37  H15  C10  C16  C15   180.00   0.0  0
 9M6  CONST_38  H16  C11  C12  C15   180.00   0.0  0
 9M6  CONST_39  H12  C7   C8   C17   180.00   0.0  0
 9M6  CONST_40  H17  C8   C17  C18   180.00   0.0  0
 9M6  CONST_41  H8   C18  C20  C19     0.00   0.0  0
 9M6  CONST_42  H28  C25  C26  N1    180.00   0.0  0
 9M6  CONST_43  H26  C23  C22  N1    180.00   0.0  0
 9M6  CONST_44  H3   C12  C11  C9    180.00   0.0  0
 9M6  CONST_45  H29  C26  N1   C22   180.00   0.0  0
 9M6  CONST_46  H27  C24  C23  C22   180.00   0.0  0
 9M6  Var_01    C3   C4   C5   C2     28.27  30.0  1
 9M6  Var_02    C27  C19  C20  C18  -109.56  30.0  2
 9M6  Var_03    N1   C22  C27  C19  -132.38  30.0  2
 9M6  Var_04    C22  C27  C21  C19   110.84  30.0  1
 9M6  Var_05    C1   C3   C4   C5     -3.94  30.0  1
 9M6  Var_06    C4   C5   C2   C1    -41.85  30.0  1
 9M6  Var_07    O2   S1   C15  C12  -153.49  30.0  2
 9M6  Var_08    C15  S1   C14  C13   178.64  30.0  3
 9M6  Var_09    O1   C13  C14  S1   -179.79  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
 9M6  chir_02  C1   C3   C2   C6   positiv
 9M6  chir_03  C19  C20  C27  C21  both
 9M6  chir_04  C27  C19  C22  C21  both

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
 9M6  plan-1  N1   0.020
 9M6  plan-1  C27  0.020
 9M6  plan-1  C22  0.020
 9M6  plan-1  C23  0.020
 9M6  plan-1  C24  0.020
 9M6  plan-1  C25  0.020
 9M6  plan-1  C26  0.020
 9M6  plan-1  H26  0.020
 9M6  plan-1  H27  0.020
 9M6  plan-1  H28  0.020
 9M6  plan-1  H29  0.020
 9M6  plan-2  C17  0.020
 9M6  plan-2  C18  0.020
 9M6  plan-2  C19  0.020
 9M6  plan-2  C20  0.020
 9M6  plan-2  C6   0.020
 9M6  plan-2  C7   0.020
 9M6  plan-2  C9   0.020
 9M6  plan-2  C8   0.020
 9M6  plan-2  C1   0.020
 9M6  plan-2  H8   0.020
 9M6  plan-2  H12  0.020
 9M6  plan-2  H17  0.020
 9M6  plan-3  C12  0.020
 9M6  plan-3  C15  0.020
 9M6  plan-3  C17  0.020
 9M6  plan-3  C9   0.020
 9M6  plan-3  C16  0.020
 9M6  plan-3  C10  0.020
 9M6  plan-3  C11  0.020
 9M6  plan-3  H3   0.020
 9M6  plan-3  H14  0.020
 9M6  plan-3  H15  0.020
 9M6  plan-3  H16  0.020
 9M6  plan-3  S1   0.020

