# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Mar 21 09:15:33 2022
#   Inital geometry file: a 141 line input string
#   Ligand name: 5-cyclopropyl-1-[3-[2-hydroxy-2-oxoethyl-(3-methoxyphenyl)sulfonyl-amino]phenyl]pyrazole-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cccc(c1)[S](=O)(=O)N(CC(O)=O)c2cccc(c2)n3ncc(C(O)=O)c3C4CC4
#
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
 QHQ  QHQ  '5-cyclopropyl-1-[3-[2-hydroxy-2-oxoethyl-(3-methoxyphenyl)sulfonyl-amino]phenyl]pyrazole-4-carboxylic acid'  ligand  52  33  .  2022-08-10  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_QHQ
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
 QHQ  C1   C  CH2    0  -0.466  -38.0113  -22.4165   5.1701
 QHQ  C10  C  CH1    0  -0.334  -41.0782  -18.3628   7.7936
 QHQ  C11  C  CH2    0  -0.488  -41.6675  -17.5530   6.6684
 QHQ  C12  C  CH2    0  -0.455  -42.3060  -17.5451   8.0182
 QHQ  C13  C  CR16   0  -0.272  -38.1743  -17.4082   5.2509
 QHQ  C14  C  CR16   0  -0.270  -38.0121  -17.8499   3.9453
 QHQ  C15  C  CR16   0  -0.245  -38.2002  -19.1846   3.6229
 QHQ  C16  C  CR6    0  -0.167  -41.3428  -21.8804   4.9216
 QHQ  C17  C  CR16   0  -0.335  -41.3524  -22.8961   5.8630
 QHQ  C18  C  CR6    0   0.406  -42.2620  -22.8398   6.9192
 QHQ  C19  C  CH3    0  -0.439  -43.1337  -23.8741   8.8657
 QHQ  C2   C  C      0   0.416  -36.4737  -22.2223   5.1793
 QHQ  C20  C  CR16   0  -0.366  -43.1634  -21.7781   6.9932
 QHQ  C21  C  CR16   0  -0.233  -43.1382  -20.7821   6.0272
 QHQ  C22  C  CR16   0  -0.266  -42.2262  -20.8111   4.9853
 QHQ  C3   C  CR6    0   0.310  -38.5695  -20.0897   4.6106
 QHQ  C4   C  CR16   0  -0.287  -38.7549  -19.6511   5.9162
 QHQ  C5   C  CR6    0   0.341  -38.5446  -18.3154   6.2314
 QHQ  C6   C  CR15   0  -0.069  -38.0257  -17.1679   9.4366
 QHQ  C7   C  CR5    0  -0.408  -39.3879  -17.4889   9.6071
 QHQ  C8   C  C      0   0.343  -40.1559  -17.3697  10.8967
 QHQ  C9   C  CR5    0   0.472  -39.7823  -17.9446   8.3601
 QHQ  N1   N  N      0  -0.656  -38.6989  -21.4718   4.2895
 QHQ  N2   N  NR5    0  -0.453  -38.6755  -17.8874   7.5734
 QHQ  N3   N  N      0  -0.292  -37.6014  -17.4142   8.2166
 QHQ  O1   O  OS     0  -0.638  -40.5113  -20.9431   2.6308
 QHQ  O2   O  OC    -1  -0.602  -35.9101  -22.7700   6.1436
 QHQ  O3   O  O      0  -0.579  -35.9627  -21.6043   4.2346
 QHQ  O4   O  OC    -1  -0.583  -41.2853  -17.8933  10.9494
 QHQ  O5   O  O      0  -0.600  -39.5656  -16.7631  11.8154
 QHQ  O6   O  O2     0  -0.463  -42.2007  -23.8470   7.8027
 QHQ  O7   O  OS     0  -0.645  -39.9861  -23.3281   3.2084
 QHQ  S1   S  S      0   1.351  -40.1412  -21.9421   3.6170
 QHQ  H1   H  HCH2   0   0.238  -38.3972  -22.3743   6.1927
 QHQ  H2   H  HCH2   0   0.276  -38.2012  -23.4267   4.8058
 QHQ  H6   H  HCH1   0   0.277  -41.2320  -19.4363   7.7307
 QHQ  H8   H  HCH2   0   0.250  -41.1324  -16.6639   6.3580
 QHQ  H7   H  HCH2   0   0.251  -42.1491  -18.0839   5.8587
 QHQ  H10  H  HCH2   0   0.245  -42.2162  -16.6529   8.6218
 QHQ  H9   H  HCH2   0   0.244  -43.2374  -18.0800   8.1521
 QHQ  H11  H  HCR6   0   0.270  -38.0121  -16.3695   5.5067
 QHQ  H12  H  HCR6   0   0.264  -37.7198  -17.1479   3.1759
 QHQ  H13  H  HCR6   0   0.263  -38.0362  -19.5316   2.6127
 QHQ  H14  H  HCR6   0   0.290  -40.6764  -23.7391   5.7957
 QHQ  H15  H  HCH3   0   0.262  -42.9180  -24.7707   9.4410
 QHQ  H16  H  HCH3   0   0.233  -43.0329  -23.0037   9.5188
 QHQ  H17  H  HCH3   0   0.232  -44.1632  -23.9270   8.5021
 QHQ  H18  H  HCR6   0   0.292  -43.8908  -21.7112   7.7904
 QHQ  H19  H  HCR6   0   0.277  -43.8466  -19.9667   6.0945
 QHQ  H20  H  HCR6   0   0.280  -42.2149  -20.0248   4.2446
 QHQ  H3   H  HCR6   0   0.281  -39.0348  -20.3471   6.6968
 QHQ  H4   H  HCR5   0   0.247  -37.3438  -16.7735  10.1751

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
 QHQ  O1   S1   double    1.452  0.020  1.452
 QHQ  O7   S1   double    1.453  0.020  1.453
 QHQ  C15  C14  aromatic  1.386  0.020  1.386
 QHQ  C15  C3   aromatic  1.390  0.020  1.390
 QHQ  S1   N1   single    1.659  0.020  1.659
 QHQ  S1   C16  single    1.775  0.020  1.775
 QHQ  C14  C13  aromatic  1.388  0.020  1.388
 QHQ  N1   C3   single    1.425  0.020  1.425
 QHQ  N1   C1   single    1.463  0.020  1.463
 QHQ  C3   C4   aromatic  1.390  0.020  1.390
 QHQ  C16  C22  aromatic  1.388  0.020  1.388
 QHQ  C16  C17  aromatic  1.385  0.020  1.385
 QHQ  C13  C5   aromatic  1.386  0.020  1.386
 QHQ  C22  C21  aromatic  1.385  0.020  1.385
 QHQ  O3   C2   deloc     1.239  0.020  1.239
 QHQ  C17  C18  aromatic  1.395  0.020  1.395
 QHQ  C1   C2   single    1.550  0.020  1.550
 QHQ  C4   C5   aromatic  1.388  0.020  1.388
 QHQ  C21  C20  aromatic  1.388  0.020  1.388
 QHQ  C5   N2   single    1.415  0.020  1.415
 QHQ  C2   O2   deloc     1.244  0.020  1.244
 QHQ  C18  C20  aromatic  1.395  0.020  1.395
 QHQ  C18  O6   single    1.341  0.020  1.341
 QHQ  O6   C19  single    1.415  0.020  1.415
 QHQ  C11  C10  single    1.506  0.020  1.506
 QHQ  C11  C12  single    1.493  0.020  1.493
 QHQ  N2   N3   aromatic  1.338  0.020  1.338
 QHQ  N2   C9   aromatic  1.359  0.020  1.359
 QHQ  N3   C6   aromatic  1.315  0.020  1.315
 QHQ  C10  C12  single    1.492  0.020  1.492
 QHQ  C10  C9   single    1.475  0.020  1.475
 QHQ  C9   C7   aromatic  1.385  0.020  1.385
 QHQ  C6   C7   aromatic  1.410  0.020  1.410
 QHQ  C7   C8   single    1.506  0.020  1.506
 QHQ  C8   O4   deloc     1.246  0.020  1.246
 QHQ  C8   O5   deloc     1.249  0.020  1.249
 QHQ  C1   H1   single    0.970  0.020  1.090
 QHQ  C1   H2   single    0.970  0.020  1.090
 QHQ  C10  H6   single    0.970  0.020  1.090
 QHQ  C11  H8   single    0.970  0.020  1.090
 QHQ  C11  H7   single    0.970  0.020  1.090
 QHQ  C12  H10  single    0.970  0.020  1.090
 QHQ  C12  H9   single    0.970  0.020  1.090
 QHQ  C13  H11  single    0.930  0.020  1.080
 QHQ  C14  H12  single    0.930  0.020  1.080
 QHQ  C15  H13  single    0.930  0.020  1.080
 QHQ  C17  H14  single    0.930  0.020  1.080
 QHQ  C19  H15  single    0.970  0.020  1.090
 QHQ  C19  H16  single    0.970  0.020  1.090
 QHQ  C19  H17  single    0.970  0.020  1.090
 QHQ  C20  H18  single    0.930  0.020  1.080
 QHQ  C21  H19  single    0.930  0.020  1.080
 QHQ  C22  H20  single    0.930  0.020  1.080
 QHQ  C4   H3   single    0.930  0.020  1.080
 QHQ  C6   H4   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
 QHQ  H2   C1   H1   106.66  3.000
 QHQ  H2   C1   N1   108.37  3.000
 QHQ  H1   C1   N1   111.84  3.000
 QHQ  H2   C1   C2   106.90  3.000
 QHQ  H1   C1   C2   109.86  3.000
 QHQ  N1   C1   C2   112.88  3.000
 QHQ  H6   C10  C9   115.27  3.000
 QHQ  H6   C10  C12  115.71  3.000
 QHQ  C9   C10  C12  120.65  3.000
 QHQ  H6   C10  C11  115.64  3.000
 QHQ  C9   C10  C11  118.57  3.000
 QHQ  C12  C10  C11   59.73  3.000
 QHQ  H7   C11  H8   114.11  3.000
 QHQ  H7   C11  C12  119.27  3.000
 QHQ  H8   C11  C12  117.77  3.000
 QHQ  H7   C11  C10  118.01  3.000
 QHQ  H8   C11  C10  117.52  3.000
 QHQ  C12  C11  C10   59.66  3.000
 QHQ  H9   C12  H10  114.22  3.000
 QHQ  H9   C12  C11  118.50  3.000
 QHQ  H10  C12  C11  118.27  3.000
 QHQ  H9   C12  C10  117.12  3.000
 QHQ  H10  C12  C10  117.90  3.000
 QHQ  C11  C12  C10   60.61  3.000
 QHQ  H11  C13  C5   120.08  3.000
 QHQ  H11  C13  C14  120.69  3.000
 QHQ  C5   C13  C14  119.23  3.000
 QHQ  H12  C14  C15  119.75  3.000
 QHQ  H12  C14  C13  119.61  3.000
 QHQ  C15  C14  C13  120.63  3.000
 QHQ  H13  C15  C3   119.71  3.000
 QHQ  H13  C15  C14  120.40  3.000
 QHQ  C3   C15  C14  119.87  3.000
 QHQ  S1   C16  C22  119.42  3.000
 QHQ  C22  C16  C17  121.95  3.000
 QHQ  S1   C16  C17  118.61  3.000
 QHQ  H14  C17  C18  119.06  3.000
 QHQ  H14  C17  C16  121.63  3.000
 QHQ  C18  C17  C16  119.31  3.000
 QHQ  O6   C18  C20  124.49  3.000
 QHQ  O6   C18  C17  116.01  3.000
 QHQ  C20  C18  C17  119.49  3.000
 QHQ  H17  C19  H16  108.92  3.000
 QHQ  H17  C19  H15  108.85  3.000
 QHQ  H16  C19  H15  108.81  3.000
 QHQ  H17  C19  O6   111.85  3.000
 QHQ  H16  C19  O6   111.90  3.000
 QHQ  H15  C19  O6   106.41  3.000
 QHQ  O3   C2   O2   128.59  3.000
 QHQ  O2   C2   C1   113.51  3.000
 QHQ  O3   C2   C1   117.85  3.000
 QHQ  H18  C20  C21  118.76  3.000
 QHQ  H18  C20  C18  121.40  3.000
 QHQ  C21  C20  C18  119.84  3.000
 QHQ  H19  C21  C22  119.58  3.000
 QHQ  H19  C21  C20  119.04  3.000
 QHQ  C22  C21  C20  121.38  3.000
 QHQ  H20  C22  C21  120.50  3.000
 QHQ  H20  C22  C16  121.49  3.000
 QHQ  C21  C22  C16  118.01  3.000
 QHQ  N1   C3   C4   120.38  3.000
 QHQ  C4   C3   C15  119.84  3.000
 QHQ  N1   C3   C15  119.72  3.000
 QHQ  H3   C4   C5   119.60  3.000
 QHQ  H3   C4   C3   120.60  3.000
 QHQ  C5   C4   C3   119.78  3.000
 QHQ  N2   C5   C4   119.50  3.000
 QHQ  N2   C5   C13  119.85  3.000
 QHQ  C4   C5   C13  120.63  3.000
 QHQ  H4   C6   N3   119.95  3.000
 QHQ  H4   C6   C7   127.64  3.000
 QHQ  N3   C6   C7   112.41  3.000
 QHQ  C9   C7   C8   130.69  3.000
 QHQ  C8   C7   C6   125.33  3.000
 QHQ  C9   C7   C6   103.96  3.000
 QHQ  O5   C8   O4   126.97  3.000
 QHQ  O5   C8   C7   115.29  3.000
 QHQ  O4   C8   C7   117.73  3.000
 QHQ  N2   C9   C7   105.99  3.000
 QHQ  C7   C9   C10  133.58  3.000
 QHQ  N2   C9   C10  120.34  3.000
 QHQ  S1   N1   C3   116.44  3.000
 QHQ  C3   N1   C1   116.62  3.000
 QHQ  S1   N1   C1   117.99  3.000
 QHQ  N3   N2   C9   112.97  3.000
 QHQ  C9   N2   C5   127.72  3.000
 QHQ  N3   N2   C5   119.25  3.000
 QHQ  N2   N3   C6   104.66  3.000
 QHQ  C19  O6   C18  118.63  3.000
 QHQ  O7   S1   O1   119.51  3.000
 QHQ  O7   S1   N1   106.95  3.000
 QHQ  O1   S1   N1   107.57  3.000
 QHQ  N1   S1   C16  106.31  3.000
 QHQ  O7   S1   C16  108.18  3.000
 QHQ  O1   S1   C16  107.63  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
 QHQ  CONST_01  C3   C15  C14  C13     0.00   0.0  0
 QHQ  CONST_02  C3   C4   C5   C13     0.00   0.0  0
 QHQ  CONST_05  C4   C3   C15  C14     0.00   0.0  0
 QHQ  CONST_06  C4   C5   C13  C14     0.00   0.0  0
 QHQ  CONST_07  N2   C5   C13  C14   180.00   0.0  0
 QHQ  CONST_08  C5   C13  C14  C15     0.00   0.0  0
 QHQ  CONST_09  C5   C4   C3   C15     0.00   0.0  0
 QHQ  CONST_10  C20  C21  C22  C16     0.00   0.0  0
 QHQ  CONST_11  C20  C18  C17  C16     0.00   0.0  0
 QHQ  CONST_12  C21  C22  C16  C17     0.00   0.0  0
 QHQ  CONST_13  C21  C20  C18  C17     0.00   0.0  0
 QHQ  CONST_14  C22  C16  C17  C18     0.00   0.0  0
 QHQ  CONST_15  C22  C21  C20  C18     0.00   0.0  0
 QHQ  CONST_16  N2   C5   C4   C3    180.00   0.0  0
 QHQ  CONST_19  C6   N3   N2   C5    180.00   0.0  0
 QHQ  CONST_20  C7   C9   N2   C5    180.00   0.0  0
 QHQ  CONST_21  C9   N2   N3   C6      0.00   0.0  0
 QHQ  CONST_22  N2   C9   C7   C6      0.00   0.0  0
 QHQ  CONST_23  N3   N2   C9   C7      0.00   0.0  0
 QHQ  CONST_24  N2   N3   C6   C7      0.00   0.0  0
 QHQ  CONST_25  N3   C6   C7   C9      0.00   0.0  0
 QHQ  CONST_26  C5   N2   C9   C10     0.00   0.0  0
 QHQ  CONST_27  N3   N2   C9   C10   180.00   0.0  0
 QHQ  CONST_28  C6   C7   C9   C10   180.00   0.0  0
 QHQ  CONST_29  C8   C7   C9   C10     0.00   0.0  0
 QHQ  CONST_30  N1   C3   C15  C14   180.00   0.0  0
 QHQ  CONST_31  O6   C18  C17  C16   180.00   0.0  0
 QHQ  CONST_32  S1   C16  C17  C18   180.00   0.0  0
 QHQ  CONST_33  S1   C16  C22  C21   180.00   0.0  0
 QHQ  CONST_34  O6   C18  C20  C21   180.00   0.0  0
 QHQ  CONST_35  N1   C3   C4   C5    180.00   0.0  0
 QHQ  CONST_36  N2   C9   C7   C8    180.00   0.0  0
 QHQ  CONST_37  N3   C6   C7   C8    180.00   0.0  0
 QHQ  CONST_38  H13  C15  C14  C13   180.00   0.0  0
 QHQ  CONST_39  H3   C4   C5   C13   180.00   0.0  0
 QHQ  CONST_40  H11  C13  C14  C15   180.00   0.0  0
 QHQ  CONST_41  H19  C21  C22  C16   180.00   0.0  0
 QHQ  CONST_42  H20  C22  C16  C17   180.00   0.0  0
 QHQ  CONST_43  H18  C20  C18  C17   180.00   0.0  0
 QHQ  CONST_44  H14  C17  C18  C20   180.00   0.0  0
 QHQ  CONST_45  H12  C14  C15  C3    180.00   0.0  0
 QHQ  CONST_46  H4   C6   C7   C9    180.00   0.0  0
 QHQ  Var_01    N2   C9   C10  C11   -60.09  30.0  2
 QHQ  Var_02    C9   C10  C12  C11   107.32  30.0  1
 QHQ  Var_03    H10  C12  C11  C10   107.88  30.0  1
 QHQ  Var_04    C3   N1   S1   C16   -72.19  30.0  3
 QHQ  Var_05    O1   S1   C16  C17   168.43  30.0  2
 QHQ  Var_06    C20  C18  O6   C19     2.11  30.0  2
 QHQ  Var_07    O4   C8   C7   C6   -168.45  30.0  2
 QHQ  Var_08    H15  C19  O6   C18   179.00  30.0  3
 QHQ  Var_09    O3   C2   C1   N1    -19.32  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
 QHQ  chir_01  C10  C11  C12  C9  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
 QHQ  plan-1  C10  0.020
 QHQ  plan-1  C5   0.020
 QHQ  plan-1  C6   0.020
 QHQ  plan-1  C7   0.020
 QHQ  plan-1  C8   0.020
 QHQ  plan-1  C9   0.020
 QHQ  plan-1  N2   0.020
 QHQ  plan-1  N3   0.020
 QHQ  plan-1  H4   0.020
 QHQ  plan-2  C13  0.020
 QHQ  plan-2  C14  0.020
 QHQ  plan-2  C15  0.020
 QHQ  plan-2  C3   0.020
 QHQ  plan-2  C4   0.020
 QHQ  plan-2  C5   0.020
 QHQ  plan-2  N1   0.020
 QHQ  plan-2  N2   0.020
 QHQ  plan-2  H11  0.020
 QHQ  plan-2  H12  0.020
 QHQ  plan-2  H13  0.020
 QHQ  plan-2  H3   0.020
 QHQ  plan-3  C16  0.020
 QHQ  plan-3  C17  0.020
 QHQ  plan-3  C18  0.020
 QHQ  plan-3  C20  0.020
 QHQ  plan-3  C21  0.020
 QHQ  plan-3  C22  0.020
 QHQ  plan-3  O6   0.020
 QHQ  plan-3  S1   0.020
 QHQ  plan-3  H14  0.020
 QHQ  plan-3  H18  0.020
 QHQ  plan-3  H19  0.020
 QHQ  plan-3  H20  0.020
 QHQ  plan-4  C1   0.020
 QHQ  plan-4  C3   0.020
 QHQ  plan-4  N1   0.020
 QHQ  plan-4  S1   0.020
 QHQ  plan-5  C1   0.020
 QHQ  plan-5  C2   0.020
 QHQ  plan-5  O2   0.020
 QHQ  plan-5  O3   0.020
 QHQ  plan-6  C7   0.020
 QHQ  plan-6  C8   0.020
 QHQ  plan-6  O4   0.020
 QHQ  plan-6  O5   0.020

