# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar  8 14:16:15 2022
#   Inital geometry file: a 114 line input string
#   Ligand name: 5-(5-chloro-2,4-dihydroxyphenyl)-N-(4-sulfamoylbenzyl)-1H-pyrazole-4-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: N[S](=O)(=O)c1ccc(CNC(=O)c2cn[nH]c2c3cc(Cl)c(O)cc3O)cc1
#
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
 2DD  2DD  5-(5-chloro-2,4-dihydroxyphenyl)-N-(4-sulfamoylbenzyl)-1H-pyrazole-4-carboxamide  ligand  43  28  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_2DD
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
 2DD  CL1   CL  CL    0  -0.116   7.5424  -0.1525  -0.8361
 2DD  C1    C   CR6   0  -0.186   6.0873   0.0264   0.0917
 2DD  C2    C   CR6   0   0.441   6.1076   0.8160   1.2445
 2DD  C3    C   CR16  0  -0.441   4.9292   0.9670   1.9629
 2DD  C4    C   CR6   0   0.349   3.7505   0.3419   1.5703
 2DD  O4    O   OH1   0  -0.664   2.6680   0.5107   2.3332
 2DD  O2    O   OH1   0  -0.606   7.2001   1.4454   1.6858
 2DD  C6    C   CR16  0  -0.242   4.9285  -0.6068  -0.3035
 2DD  C5    C   CR6   0  -0.139   3.7457  -0.4745   0.4236
 2DD  C7    C   CR5   0   0.483   2.5978  -1.2940   0.0244
 2DD  N2    N   NR15  0  -0.483   2.7784  -2.5985  -0.2421
 2DD  N1    N   N     0  -0.242   1.6869  -3.2300  -0.6573
 2DD  C9    C   CR15  0  -0.073   0.7527  -2.3086  -0.6787
 2DD  C8    C   CR5   0  -0.356   1.2541  -1.0589  -0.2570
 2DD  C10   C   C     0   0.564   0.5221   0.2035  -0.1610
 2DD  O5    O   O     0  -0.535   0.8418   1.0841   0.6486
 2DD  N3    N   NH1   0  -0.630  -0.5180   0.3389  -0.9882
 2DD  C17   C   CH2   0  -0.375  -1.4232   1.4656  -0.9990
 2DD  C11   C   CR6   0   0.129  -2.8336   1.0505  -0.6674
 2DD  C12   C   CR16  0  -0.280  -3.1076   0.3689   0.5189
 2DD  C13   C   CR16  0  -0.200  -4.3981  -0.0139   0.8293
 2DD  C16   C   CR16  0  -0.296  -3.8745   1.3426  -1.5376
 2DD  C15   C   CR16  0  -0.219  -5.1775   0.9645  -1.2407
 2DD  C14   C   CR6   0  -0.220  -5.4258   0.2894  -0.0582
 2DD  S1    S   S     0   1.361  -7.0712  -0.2325   0.3297
 2DD  O6    O   OS    0  -0.651  -7.8939  -0.0273  -0.8550
 2DD  O7    O   OS    0  -0.666  -7.0324  -1.5632   0.9189
 2DD  N4    N   NC2   0  -0.886  -7.4506   0.7966   1.5641
 2DD  H3    H   HCR6  0   0.282   4.9270   1.5891   2.8497
 2DD  H4    H   HOH1  0   0.488   1.8741   0.6696   1.7474
 2DD  H2    H   HOH1  0   0.472   7.9564   1.2819   1.1071
 2DD  H6    H   HCR6  0   0.292   4.9436  -1.2168  -1.1977
 2DD  HA    H   HNR5  0   0.430   3.6375  -3.1156  -0.1238
 2DD  H9    H   HCR5  0   0.278  -0.2564  -2.5605  -0.9704
 2DD  HB    H   HNH1  0   0.420  -0.6646  -0.3662  -1.6934
 2DD  H171  H   HCH2  0   0.282  -1.3960   1.9404  -1.9808
 2DD  H172  H   HCH2  0   0.287  -1.0691   2.2023  -0.2789
 2DD  H12   H   HCR6  0   0.268  -2.3071   0.1346   1.2097
 2DD  H13   H   HCR6  0   0.286  -4.5980  -0.5409   1.7528
 2DD  H16   H   HCR6  0   0.272  -3.6725   1.8672  -2.4631
 2DD  H15   H   HCR6  0   0.285  -5.9760   1.1928  -1.9329
 2DD  H4N1  H   HNC2  0   0.416  -7.6430   1.7401   1.2431
 2DD  H4N2  H   HNC2  0   0.420  -8.2313   0.4466   2.1119

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
 2DD  CL1  C1    single    1.735  0.020  1.735
 2DD  C1   C2    aromatic  1.397  0.020  1.397
 2DD  C1   C6    aromatic  1.378  0.020  1.378
 2DD  C2   C3    aromatic  1.388  0.020  1.388
 2DD  C2   O2    single    1.336  0.020  1.336
 2DD  C3   C4    aromatic  1.391  0.020  1.391
 2DD  C3   H3    single    0.930  0.020  1.080
 2DD  C4   O4    single    1.335  0.020  1.335
 2DD  C4   C5    aromatic  1.408  0.020  1.408
 2DD  O4   H4    single    0.850  0.020  0.980
 2DD  O2   H2    single    0.850  0.020  0.980
 2DD  C6   C5    aromatic  1.395  0.020  1.395
 2DD  C6   H6    single    0.930  0.020  1.080
 2DD  C5   C7    single    1.466  0.020  1.466
 2DD  C7   N2    aromatic  1.344  0.020  1.344
 2DD  C7   C8    aromatic  1.393  0.020  1.393
 2DD  N2   N1    aromatic  1.328  0.020  1.328
 2DD  N2   HA    single    0.860  0.020  1.020
 2DD  N1   C9    aromatic  1.312  0.020  1.312
 2DD  C9   C8    aromatic  1.411  0.020  1.411
 2DD  C9   H9    single    0.930  0.020  1.080
 2DD  C8   C10   single    1.462  0.020  1.462
 2DD  C10  O5    double    1.238  0.020  1.238
 2DD  C10  N3    single    1.336  0.020  1.336
 2DD  N3   C17   single    1.445  0.020  1.445
 2DD  N3   HB    single    0.860  0.020  1.020
 2DD  C17  C11   single    1.507  0.020  1.507
 2DD  C17  H171  single    0.970  0.020  1.090
 2DD  C17  H172  single    0.970  0.020  1.090
 2DD  C11  C12   aromatic  1.395  0.020  1.395
 2DD  C11  C16   aromatic  1.388  0.020  1.388
 2DD  C12  C13   aromatic  1.381  0.020  1.381
 2DD  C12  H12   single    0.930  0.020  1.080
 2DD  C13  C14   aromatic  1.391  0.020  1.391
 2DD  C13  H13   single    0.930  0.020  1.080
 2DD  C16  C15   aromatic  1.389  0.020  1.389
 2DD  C16  H16   single    0.930  0.020  1.080
 2DD  C15  C14   aromatic  1.384  0.020  1.384
 2DD  C15  H15   single    0.930  0.020  1.080
 2DD  C14  S1    single    1.769  0.020  1.769
 2DD  S1   O6    double    1.457  0.020  1.457
 2DD  S1   O7    double    1.456  0.020  1.456
 2DD  S1   N4    single    1.651  0.020  1.651
 2DD  N4   H4N1  single    0.890  0.020  1.040
 2DD  N4   H4N2  single    0.890  0.020  1.040

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
 2DD  C6    C1   C2    120.55  3.000
 2DD  C6    C1   CL1   120.29  3.000
 2DD  C2    C1   CL1   119.16  3.000
 2DD  O2    C2   C3    118.17  3.000
 2DD  O2    C2   C1    123.41  3.000
 2DD  C3    C2   C1    118.42  3.000
 2DD  H3    C3   C4    119.18  3.000
 2DD  H3    C3   C2    119.20  3.000
 2DD  C4    C3   C2    121.63  3.000
 2DD  C5    C4   O4    122.42  3.000
 2DD  C5    C4   C3    119.57  3.000
 2DD  O4    C4   C3    117.97  3.000
 2DD  H4    O4   C4    109.22  3.000
 2DD  H2    O2   C2    111.26  3.000
 2DD  H6    C6   C5    119.73  3.000
 2DD  H6    C6   C1    118.94  3.000
 2DD  C5    C6   C1    121.33  3.000
 2DD  C7    C5   C6    117.97  3.000
 2DD  C7    C5   C4    123.28  3.000
 2DD  C6    C5   C4    118.48  3.000
 2DD  C8    C7   N2    104.68  3.000
 2DD  C8    C7   C5    135.73  3.000
 2DD  N2    C7   C5    119.45  3.000
 2DD  HA    N2   N1    119.51  3.000
 2DD  HA    N2   C7    126.04  3.000
 2DD  N1    N2   C7    114.42  3.000
 2DD  C9    N1   N2    104.85  3.000
 2DD  H9    C9   C8    128.26  3.000
 2DD  H9    C9   N1    120.37  3.000
 2DD  C8    C9   N1    111.35  3.000
 2DD  C10   C8   C9    127.32  3.000
 2DD  C10   C8   C7    127.98  3.000
 2DD  C9    C8   C7    104.70  3.000
 2DD  N3    C10  O5    122.26  3.000
 2DD  N3    C10  C8    115.89  3.000
 2DD  O5    C10  C8    121.85  3.000
 2DD  HB    N3   C17   116.68  3.000
 2DD  HB    N3   C10   118.40  3.000
 2DD  C17   N3   C10   124.85  3.000
 2DD  H172  C17  H171  107.01  3.000
 2DD  H172  C17  C11   110.18  3.000
 2DD  H171  C17  C11   109.95  3.000
 2DD  H172  C17  N3    108.58  3.000
 2DD  H171  C17  N3    109.30  3.000
 2DD  C11   C17  N3    111.70  3.000
 2DD  C16   C11  C12   119.26  3.000
 2DD  C16   C11  C17   120.39  3.000
 2DD  C12   C11  C17   120.35  3.000
 2DD  H12   C12  C13   119.15  3.000
 2DD  H12   C12  C11   120.19  3.000
 2DD  C13   C12  C11   120.65  3.000
 2DD  H13   C13  C14   120.95  3.000
 2DD  H13   C13  C12   119.96  3.000
 2DD  C14   C13  C12   119.10  3.000
 2DD  H16   C16  C15   119.31  3.000
 2DD  H16   C16  C11   119.87  3.000
 2DD  C15   C16  C11   120.82  3.000
 2DD  H15   C15  C14   121.16  3.000
 2DD  H15   C15  C16   119.91  3.000
 2DD  C14   C15  C16   118.93  3.000
 2DD  S1    C14  C15   119.87  3.000
 2DD  S1    C14  C13   118.87  3.000
 2DD  C15   C14  C13   121.25  3.000
 2DD  N4    S1   O7    105.85  3.000
 2DD  N4    S1   O6    112.97  3.000
 2DD  O7    S1   O6    118.23  3.000
 2DD  N4    S1   C14   101.17  3.000
 2DD  O7    S1   C14   109.49  3.000
 2DD  O6    S1   C14   107.78  3.000
 2DD  H4N2  N4   H4N1  110.19  3.000
 2DD  H4N2  N4   S1    111.41  3.000
 2DD  H4N1  N4   S1    112.73  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
 2DD  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 2DD  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 2DD  CONST_03  C7    C5   C6   C1    180.00   0.0  0
 2DD  CONST_04  C5    C6   C1   C2      0.00   0.0  0
 2DD  CONST_05  C5    C4   C3   C2      0.00   0.0  0
 2DD  CONST_06  C6    C1   C2   C3      0.00   0.0  0
 2DD  CONST_07  C6    C5   C4   C3      0.00   0.0  0
 2DD  CONST_08  C7    C5   C4   C3    180.00   0.0  0
 2DD  CONST_13  N1    N2   C7   C5    180.00   0.0  0
 2DD  CONST_14  C9    C8   C7   C5    180.00   0.0  0
 2DD  CONST_15  C9    N1   N2   C7      0.00   0.0  0
 2DD  CONST_16  N1    C9   C8   C7      0.00   0.0  0
 2DD  CONST_17  C9    C8   C7   N2      0.00   0.0  0
 2DD  CONST_18  C8    C9   N1   N2      0.00   0.0  0
 2DD  CONST_19  C8    C7   N2   N1      0.00   0.0  0
 2DD  CONST_20  C14   C13  C12  C11     0.00   0.0  0
 2DD  CONST_21  C14   C15  C16  C11     0.00   0.0  0
 2DD  CONST_22  C15   C16  C11  C12     0.00   0.0  0
 2DD  CONST_23  C15   C14  C13  C12     0.00   0.0  0
 2DD  CONST_24  C16   C11  C12  C13     0.00   0.0  0
 2DD  CONST_25  C16   C15  C14  C13     0.00   0.0  0
 2DD  CONST_26  C3    C2   C1   CL1   180.00   0.0  0
 2DD  CONST_27  C5    C6   C1   CL1   180.00   0.0  0
 2DD  CONST_28  O4    C4   C3   C2    180.00   0.0  0
 2DD  CONST_29  O2    C2   C3   C4    180.00   0.0  0
 2DD  CONST_30  C6    C5   C4   O4    180.00   0.0  0
 2DD  CONST_31  C7    C5   C4   O4      0.00   0.0  0
 2DD  CONST_32  C6    C1   C2   O2    180.00   0.0  0
 2DD  CONST_33  C10   C8   C7   C5      0.00   0.0  0
 2DD  CONST_34  C10   C8   C7   N2    180.00   0.0  0
 2DD  CONST_35  C10   C8   C9   N1    180.00   0.0  0
 2DD  CONST_36  C13   C12  C11  C17   180.00   0.0  0
 2DD  CONST_37  C15   C16  C11  C17   180.00   0.0  0
 2DD  CONST_38  S1    C14  C13  C12   180.00   0.0  0
 2DD  CONST_39  S1    C14  C15  C16   180.00   0.0  0
 2DD  CONST_40  H3    C3   C2   C1    180.00   0.0  0
 2DD  CONST_41  H6    C6   C1   C2    180.00   0.0  0
 2DD  CONST_42  HA    N2   C7   C5      0.00   0.0  0
 2DD  CONST_43  H9    C9   C8   C7    180.00   0.0  0
 2DD  CONST_44  H13   C13  C12  C11   180.00   0.0  0
 2DD  CONST_45  H15   C15  C16  C11   180.00   0.0  0
 2DD  CONST_46  H16   C16  C11  C12   180.00   0.0  0
 2DD  CONST_47  H12   C12  C11  C16   180.00   0.0  0
 2DD  CONST_48  C17   N3   C10  C8    180.00   0.0  0
 2DD  CONST_49  HB    N3   C10  C8      0.00   0.0  0
 2DD  CONST_50  C17   N3   C10  O5      0.00   0.0  0
 2DD  Var_01    O5    C10  C8   C7    -28.98  30.0  2
 2DD  Var_02    C12   C11  C17  N3     55.77  30.0  2
 2DD  Var_03    O6    S1   C14  C13  -169.19  30.0  2
 2DD  Var_04    C11   C17  N3   C10  -117.60  30.0  3
 2DD  Var_05    H4N1  N4   S1   C14    74.48  30.0  3

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
 2DD  plan-1  C5   0.020
 2DD  plan-1  C7   0.020
 2DD  plan-1  N2   0.020
 2DD  plan-1  N1   0.020
 2DD  plan-1  C9   0.020
 2DD  plan-1  C8   0.020
 2DD  plan-1  C10  0.020
 2DD  plan-1  HA   0.020
 2DD  plan-1  H9   0.020
 2DD  plan-2  CL1  0.020
 2DD  plan-2  C1   0.020
 2DD  plan-2  C2   0.020
 2DD  plan-2  C3   0.020
 2DD  plan-2  C4   0.020
 2DD  plan-2  O4   0.020
 2DD  plan-2  O2   0.020
 2DD  plan-2  C6   0.020
 2DD  plan-2  C5   0.020
 2DD  plan-2  C7   0.020
 2DD  plan-2  H3   0.020
 2DD  plan-2  H6   0.020
 2DD  plan-3  C17  0.020
 2DD  plan-3  C11  0.020
 2DD  plan-3  C12  0.020
 2DD  plan-3  C13  0.020
 2DD  plan-3  C16  0.020
 2DD  plan-3  C15  0.020
 2DD  plan-3  C14  0.020
 2DD  plan-3  S1   0.020
 2DD  plan-3  H12  0.020
 2DD  plan-3  H13  0.020
 2DD  plan-3  H16  0.020
 2DD  plan-3  H15  0.020
 2DD  plan-4  C8   0.020
 2DD  plan-4  C10  0.020
 2DD  plan-4  O5   0.020
 2DD  plan-4  N3   0.020
 2DD  plan-4  C17  0.020
 2DD  plan-4  HB   0.020

