# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Mar 21 08:48:32 2022
#   Inital geometry file: a 133 line input string
#   Ligand name: 5-cyclopropyl-1-[3-[2-hydroxy-2-oxoethyl(phenylsulfonyl)amino]phenyl]pyrazole-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)CN(c1cccc(c1)n2ncc(C(O)=O)c2C3CC3)[S](=O)(=O)c4ccccc4
#
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
 QHK  QHK  '5-cyclopropyl-1-[3-[2-hydroxy-2-oxoethyl(phenylsulfonyl)amino]phenyl]pyrazole-4-carboxylic acid'  ligand  48  31  .  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_QHK
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
 QHK  C1   C  CH2    0  -0.468  -37.9385  -22.3285   5.7050
 QHK  C11  C  CR5    0   0.469  -39.6464  -17.7895   8.7957
 QHK  C12  C  CH1    0  -0.334  -40.9584  -18.2985   8.3534
 QHK  C13  C  CH2    0  -0.489  -41.6729  -17.5764   7.2415
 QHK  C14  C  CH2    0  -0.458  -42.1998  -17.5201   8.6378
 QHK  C15  C  CR16   0  -0.293  -38.7173  -19.5559   6.3545
 QHK  C16  C  CR6    0  -0.178  -41.2267  -22.0801   5.5657
 QHK  C17  C  CR16   0  -0.237  -41.2163  -23.1956   6.3962
 QHK  C18  C  CR16   0  -0.244  -42.0479  -23.2168   7.5050
 QHK  C19  C  CR16   0  -0.236  -42.8819  -22.1388   7.7733
 QHK  C2   C  C      0   0.417  -36.4137  -22.0465   5.7240
 QHK  C20  C  CR16   0  -0.248  -42.8901  -21.0359   6.9305
 QHK  C21  C  CR16   0  -0.238  -42.0582  -20.9983   5.8213
 QHK  C3   C  CR6    0   0.315  -38.5888  -20.0460   5.0601
 QHK  C4   C  CR16   0  -0.247  -38.3097  -19.1725   4.0153
 QHK  C5   C  CR16   0  -0.270  -38.1558  -17.8193   4.2692
 QHK  C6   C  CR16   0  -0.274  -38.2617  -17.3249   5.5619
 QHK  C7   C  CR6    0   0.343  -38.5396  -18.2002   6.6003
 QHK  C8   C  CR15   0  -0.070  -37.8729  -16.8470   9.6966
 QHK  C9   C  CR5    0  -0.403  -39.1964  -17.2376   9.9831
 QHK  N1   N  N      0  -0.656  -38.6741  -21.4438   4.8013
 QHK  N2   N  NR5    0  -0.453  -38.6032  -17.7146   7.9275
 QHK  N3   N  N      0  -0.291  -37.5190  -17.1425   8.4652
 QHK  O1   O  OS     0  -0.639  -40.6111  -21.0153   3.2554
 QHK  O2   O  OC    -1  -0.601  -35.8281  -22.5595   6.6941
 QHK  O3   O  O      0  -0.578  -35.9318  -21.4011   4.7825
 QHK  O4   O  OC    -1  -0.585  -40.9246  -17.7400  11.5075
 QHK  O5   O  O      0  -0.600  -39.3102  -16.3282  12.1272
 QHK  O6   O  OS     0  -0.645  -39.8771  -23.3673   3.7314
 QHK  S1   S  S      0   1.347  -40.1136  -22.0088   4.1906
 QHK  H1   H  HCH2   0   0.240  -38.3343  -22.2916   6.7244
 QHK  H2   H  HCH2   0   0.276  -38.0651  -23.3549   5.3578
 QHK  H8   H  HCH1   0   0.278  -41.0662  -19.3791   8.3589
 QHK  H10  H  HCH2   0   0.251  -41.2047  -16.6856   6.8417
 QHK  H9   H  HCH2   0   0.252  -42.1974  -18.1678   6.5033
 QHK  H12  H  HCH2   0   0.246  -42.1013  -16.5923   9.1837
 QHK  H11  H  HCH2   0   0.246  -43.0939  -18.0818   8.8767
 QHK  H13  H  HCR6   0   0.282  -38.9217  -20.2254   7.1803
 QHK  H14  H  HCR6   0   0.285  -40.5783  -24.0429   6.1838
 QHK  H15  H  HCR6   0   0.271  -42.0462  -24.0803   8.1565
 QHK  H16  H  HCR6   0   0.271  -43.5307  -22.1614   8.6388
 QHK  H17  H  HCR6   0   0.277  -43.5490  -20.2020   7.1348
 QHK  H18  H  HCR6   0   0.284  -42.0702  -20.1405   5.1630
 QHK  H3   H  HCR6   0   0.263  -38.1858  -19.5575   3.0131
 QHK  H4   H  HCR6   0   0.264  -37.9334  -17.1426   3.4550
 QHK  H5   H  HCR6   0   0.269  -38.1252  -16.2705   5.7625
 QHK  H6   H  HCR5   0   0.248  -37.1676  -16.3708  10.3613
 QHK  C10  C  C      0   0.342  -39.8800  -17.0884  11.3165

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
 QHK  O1   S1   double    1.452  0.020  1.452
 QHK  O6   S1   double    1.453  0.020  1.453
 QHK  C4   C5   aromatic  1.385  0.020  1.385
 QHK  C4   C3   aromatic  1.390  0.020  1.390
 QHK  S1   N1   single    1.663  0.020  1.663
 QHK  S1   C16  single    1.771  0.020  1.771
 QHK  C5   C6   aromatic  1.388  0.020  1.388
 QHK  N1   C3   single    1.424  0.020  1.424
 QHK  N1   C1   single    1.463  0.020  1.463
 QHK  C16  C17  aromatic  1.391  0.020  1.391
 QHK  C16  C21  aromatic  1.388  0.020  1.388
 QHK  C3   C15  aromatic  1.390  0.020  1.390
 QHK  C6   C7   aromatic  1.386  0.020  1.386
 QHK  C17  C18  aromatic  1.386  0.020  1.386
 QHK  C21  C20  aromatic  1.387  0.020  1.387
 QHK  O3   C2   deloc     1.239  0.020  1.239
 QHK  C1   C2   single    1.551  0.020  1.551
 QHK  C15  C7   aromatic  1.389  0.020  1.389
 QHK  C18  C19  aromatic  1.389  0.020  1.389
 QHK  C7   N2   single    1.415  0.020  1.415
 QHK  C20  C19  aromatic  1.388  0.020  1.388
 QHK  C2   O2   deloc     1.244  0.020  1.244
 QHK  C13  C12  single    1.506  0.020  1.506
 QHK  C13  C14  single    1.493  0.020  1.493
 QHK  N2   N3   aromatic  1.339  0.020  1.339
 QHK  N2   C11  aromatic  1.359  0.020  1.359
 QHK  N3   C8   aromatic  1.315  0.020  1.315
 QHK  C12  C11  single    1.475  0.020  1.475
 QHK  C12  C14  single    1.493  0.020  1.493
 QHK  C11  C9   aromatic  1.385  0.020  1.385
 QHK  C8   C9   aromatic  1.409  0.020  1.409
 QHK  C9   C10  single    1.506  0.020  1.506
 QHK  C10  O4   deloc     1.246  0.020  1.246
 QHK  C10  O5   deloc     1.249  0.020  1.249
 QHK  C1   H1   single    0.970  0.020  1.090
 QHK  C1   H2   single    0.970  0.020  1.090
 QHK  C12  H8   single    0.970  0.020  1.090
 QHK  C13  H10  single    0.970  0.020  1.090
 QHK  C13  H9   single    0.970  0.020  1.090
 QHK  C14  H12  single    0.970  0.020  1.090
 QHK  C14  H11  single    0.970  0.020  1.090
 QHK  C15  H13  single    0.930  0.020  1.080
 QHK  C17  H14  single    0.930  0.020  1.080
 QHK  C18  H15  single    0.930  0.020  1.080
 QHK  C19  H16  single    0.930  0.020  1.080
 QHK  C20  H17  single    0.930  0.020  1.080
 QHK  C21  H18  single    0.930  0.020  1.080
 QHK  C4   H3   single    0.930  0.020  1.080
 QHK  C5   H4   single    0.930  0.020  1.080
 QHK  C6   H5   single    0.930  0.020  1.080
 QHK  C8   H6   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
 QHK  H2   C1   H1   106.63  3.000
 QHK  H2   C1   N1   108.30  3.000
 QHK  H1   C1   N1   111.92  3.000
 QHK  H2   C1   C2   106.81  3.000
 QHK  H1   C1   C2   109.76  3.000
 QHK  N1   C1   C2   113.08  3.000
 QHK  N2   C11  C9   106.04  3.000
 QHK  C9   C11  C12  133.14  3.000
 QHK  N2   C11  C12  120.67  3.000
 QHK  H8   C12  C14  115.81  3.000
 QHK  H8   C12  C13  115.70  3.000
 QHK  C14  C12  C13   59.73  3.000
 QHK  H8   C12  C11  115.48  3.000
 QHK  C14  C12  C11  120.18  3.000
 QHK  C13  C12  C11  118.55  3.000
 QHK  H9   C13  H10  114.04  3.000
 QHK  H9   C13  C14  119.19  3.000
 QHK  H10  C13  C14  117.83  3.000
 QHK  H9   C13  C12  118.15  3.000
 QHK  H10  C13  C12  117.51  3.000
 QHK  C14  C13  C12   59.69  3.000
 QHK  H11  C14  H12  114.15  3.000
 QHK  H11  C14  C13  118.57  3.000
 QHK  H12  C14  C13  118.19  3.000
 QHK  H11  C14  C12  117.28  3.000
 QHK  H12  C14  C12  117.90  3.000
 QHK  C13  C14  C12   60.58  3.000
 QHK  H13  C15  C7   119.52  3.000
 QHK  H13  C15  C3   120.65  3.000
 QHK  C7   C15  C3   119.80  3.000
 QHK  S1   C16  C21  119.22  3.000
 QHK  C21  C16  C17  121.30  3.000
 QHK  S1   C16  C17  119.43  3.000
 QHK  H14  C17  C18  119.93  3.000
 QHK  H14  C17  C16  121.02  3.000
 QHK  C18  C17  C16  119.04  3.000
 QHK  H15  C18  C19  120.27  3.000
 QHK  H15  C18  C17  119.54  3.000
 QHK  C19  C18  C17  120.19  3.000
 QHK  H16  C19  C20  119.91  3.000
 QHK  H16  C19  C18  119.89  3.000
 QHK  C20  C19  C18  120.20  3.000
 QHK  O3   C2   O2   128.64  3.000
 QHK  O2   C2   C1   113.42  3.000
 QHK  O3   C2   C1   117.89  3.000
 QHK  H17  C20  C21  119.69  3.000
 QHK  H17  C20  C19  120.08  3.000
 QHK  C21  C20  C19  120.23  3.000
 QHK  H18  C21  C20  120.11  3.000
 QHK  H18  C21  C16  120.85  3.000
 QHK  C20  C21  C16  119.04  3.000
 QHK  N1   C3   C4   119.48  3.000
 QHK  N1   C3   C15  120.65  3.000
 QHK  C4   C3   C15  119.79  3.000
 QHK  H3   C4   C5   120.34  3.000
 QHK  H3   C4   C3   119.75  3.000
 QHK  C5   C4   C3   119.89  3.000
 QHK  H4   C5   C6   119.59  3.000
 QHK  H4   C5   C4   119.73  3.000
 QHK  C6   C5   C4   120.67  3.000
 QHK  H5   C6   C7   120.11  3.000
 QHK  H5   C6   C5   120.67  3.000
 QHK  C7   C6   C5   119.22  3.000
 QHK  N2   C7   C6   119.67  3.000
 QHK  N2   C7   C15  119.69  3.000
 QHK  C6   C7   C15  120.61  3.000
 QHK  H6   C8   N3   119.99  3.000
 QHK  H6   C8   C9   127.62  3.000
 QHK  N3   C8   C9   112.39  3.000
 QHK  C8   C9   C11  103.97  3.000
 QHK  C8   C9   C10  125.37  3.000
 QHK  C11  C9   C10  130.64  3.000
 QHK  S1   N1   C3   116.88  3.000
 QHK  C3   N1   C1   116.82  3.000
 QHK  S1   N1   C1   117.17  3.000
 QHK  N3   N2   C7   119.15  3.000
 QHK  N3   N2   C11  112.87  3.000
 QHK  C7   N2   C11  127.93  3.000
 QHK  N2   N3   C8   104.73  3.000
 QHK  O6   S1   O1   119.46  3.000
 QHK  O6   S1   N1   107.03  3.000
 QHK  O1   S1   N1   107.50  3.000
 QHK  N1   S1   C16  105.83  3.000
 QHK  O6   S1   C16  108.06  3.000
 QHK  O1   S1   C16  108.20  3.000
 QHK  O5   C10  O4   126.97  3.000
 QHK  O5   C10  C9   115.34  3.000
 QHK  O4   C10  C9   117.68  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
 QHK  CONST_03  C8   N3   N2   C11     0.00   0.0  0
 QHK  CONST_04  N3   C8   C9   C11     0.00   0.0  0
 QHK  CONST_05  C5   C4   C3   C15     0.00   0.0  0
 QHK  CONST_06  C5   C6   C7   C15     0.00   0.0  0
 QHK  CONST_08  C19  C18  C17  C16     0.00   0.0  0
 QHK  CONST_09  C19  C20  C21  C16     0.00   0.0  0
 QHK  CONST_10  C20  C21  C16  C17     0.00   0.0  0
 QHK  CONST_11  C20  C19  C18  C17     0.00   0.0  0
 QHK  CONST_12  C21  C16  C17  C18     0.00   0.0  0
 QHK  CONST_13  C21  C20  C19  C18     0.00   0.0  0
 QHK  CONST_14  C6   C5   C4   C3      0.00   0.0  0
 QHK  CONST_15  C6   C7   C15  C3      0.00   0.0  0
 QHK  CONST_16  N2   C7   C15  C3    180.00   0.0  0
 QHK  CONST_17  C7   C6   C5   C4      0.00   0.0  0
 QHK  CONST_18  C7   C15  C3   C4      0.00   0.0  0
 QHK  CONST_19  N2   C7   C6   C5    180.00   0.0  0
 QHK  CONST_21  C8   N3   N2   C7    180.00   0.0  0
 QHK  CONST_22  C9   C11  N2   C7    180.00   0.0  0
 QHK  CONST_23  N2   C11  C9   C8      0.00   0.0  0
 QHK  CONST_24  N3   N2   C11  C9      0.00   0.0  0
 QHK  CONST_25  N2   N3   C8   C9      0.00   0.0  0
 QHK  CONST_26  C7   N2   C11  C12     0.00   0.0  0
 QHK  CONST_27  N3   N2   C11  C12   180.00   0.0  0
 QHK  CONST_28  C8   C9   C11  C12   180.00   0.0  0
 QHK  CONST_29  N2   C11  C9   C10   180.00   0.0  0
 QHK  CONST_30  C12  C11  C9   C10     0.00   0.0  0
 QHK  CONST_31  N3   C8   C9   C10   180.00   0.0  0
 QHK  CONST_32  S1   C16  C17  C18   180.00   0.0  0
 QHK  CONST_33  S1   C16  C21  C20   180.00   0.0  0
 QHK  CONST_34  N1   C3   C4   C5    180.00   0.0  0
 QHK  CONST_35  N1   C3   C15  C7    180.00   0.0  0
 QHK  CONST_36  H6   C8   C9   C11   180.00   0.0  0
 QHK  CONST_37  H3   C4   C3   C15   180.00   0.0  0
 QHK  CONST_38  H5   C6   C7   C15   180.00   0.0  0
 QHK  CONST_39  H15  C18  C17  C16   180.00   0.0  0
 QHK  CONST_40  H17  C20  C21  C16   180.00   0.0  0
 QHK  CONST_41  H18  C21  C16  C17   180.00   0.0  0
 QHK  CONST_42  H16  C19  C18  C17   180.00   0.0  0
 QHK  CONST_43  H14  C17  C18  C19   180.00   0.0  0
 QHK  CONST_44  H4   C5   C4   C3    180.00   0.0  0
 QHK  CONST_45  H13  C15  C3   C4    180.00   0.0  0
 QHK  Var_01    C14  C13  C12  C11  -110.19  30.0  1
 QHK  Var_02    N2   C11  C12  C13   -60.01  30.0  2
 QHK  Var_03    O4   C10  C9   C11    13.96  30.0  2
 QHK  Var_04    C3   N1   S1   C16   -77.39  30.0  3
 QHK  Var_05    O1   S1   C16  C17   161.01  30.0  2
 QHK  Var_06    O3   C2   C1   N1    -18.26  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
 QHK  chir_01  C12  C13  C11  C14  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
 QHK  plan-1  C11  0.020
 QHK  plan-1  C12  0.020
 QHK  plan-1  C7   0.020
 QHK  plan-1  C8   0.020
 QHK  plan-1  C9   0.020
 QHK  plan-1  N2   0.020
 QHK  plan-1  N3   0.020
 QHK  plan-1  H6   0.020
 QHK  plan-1  C10  0.020
 QHK  plan-2  C16  0.020
 QHK  plan-2  C17  0.020
 QHK  plan-2  C18  0.020
 QHK  plan-2  C19  0.020
 QHK  plan-2  C20  0.020
 QHK  plan-2  C21  0.020
 QHK  plan-2  S1   0.020
 QHK  plan-2  H14  0.020
 QHK  plan-2  H15  0.020
 QHK  plan-2  H16  0.020
 QHK  plan-2  H17  0.020
 QHK  plan-2  H18  0.020
 QHK  plan-3  C15  0.020
 QHK  plan-3  C3   0.020
 QHK  plan-3  C4   0.020
 QHK  plan-3  C5   0.020
 QHK  plan-3  C6   0.020
 QHK  plan-3  C7   0.020
 QHK  plan-3  N1   0.020
 QHK  plan-3  N2   0.020
 QHK  plan-3  H13  0.020
 QHK  plan-3  H3   0.020
 QHK  plan-3  H4   0.020
 QHK  plan-3  H5   0.020
 QHK  plan-4  C1   0.020
 QHK  plan-4  C3   0.020
 QHK  plan-4  N1   0.020
 QHK  plan-4  S1   0.020
 QHK  plan-5  C1   0.020
 QHK  plan-5  C2   0.020
 QHK  plan-5  O2   0.020
 QHK  plan-5  O3   0.020
 QHK  plan-6  C9   0.020
 QHK  plan-6  O4   0.020
 QHK  plan-6  O5   0.020
 QHK  plan-6  C10  0.020

