# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 09:51:09 2020
#   Inital geometry file: a 103 line input string
#   Ligand name: N-{5-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: FC(F)Oc1ccc(Cl)cc1c2[nH]ncc2NC(=O)c3cnn4cccnc34
#
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
 KES  KES  N-{5-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide  ligand  39  28  .  2021-08-12  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_KES
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
 KES  C4   C   CR15  0  -0.033   2.3732   0.8093   1.4164
 KES  C14  C   CR16  0  -0.324  -3.0690   1.6858  -0.3411
 KES  C5   C   CR16  0   0.091   5.6255   1.7174   0.9473
 KES  C6   C   C     0   0.506   1.8583  -1.1230  -0.2511
 KES  C11  C   CR16  0  -0.239  -3.6305  -0.7868   0.7952
 KES  C7   C   CR5   0   0.068  -0.3800  -2.0706  -0.3199
 KES  C8   C   CR15  0  -0.097  -0.2183  -3.4044  -0.7396
 KES  C9   C   CR5   0   0.383  -1.7395  -1.8344  -0.4050
 KES  C10  C   CR6   0  -0.068  -2.5505  -0.6613  -0.0764
 KES  C12  C   CR6   0  -0.038  -4.4073   0.3166   1.0972
 KES  C13  C   CR16  0  -0.206  -4.1309   1.5534   0.5388
 KES  N1   N   N     0  -0.289   3.3853   1.5831   1.7495
 KES  N2   N   N     0  -0.361   4.3836   1.1903   0.9520
 KES  C3   C   CR5   0  -0.386   2.6860  -0.1065   0.3974
 KES  N3   N   NH1   0  -0.762   0.5651  -1.1723   0.1664
 KES  CL   CL  CL    0  -0.116  -5.7356   0.1480   2.1920
 KES  C15  C   CR6   0   0.337  -2.2828   0.5847  -0.6479
 KES  O1   O   O2    0  -0.490  -1.2634   0.6137  -1.5654
 KES  C16  C   CH1   0   0.664  -0.3708   1.6356  -1.6038
 KES  F1   F   F     0  -0.332  -0.9015   2.7283  -2.2031
 KES  F    F   F     0  -0.329  -0.0210   2.0250  -0.3593
 KES  N5   N   NR15  0  -0.484  -2.2791  -2.9956  -0.8316
 KES  N4   N   N     0  -0.249  -1.3836  -3.9403  -1.0537
 KES  O    O   O     0  -0.466   2.2939  -1.8775  -1.1062
 KES  C    C   CR16  0  -0.388   6.5263   1.1954   0.0740
 KES  C2   C   CR56  0   0.634   4.0261   0.1615   0.1046
 KES  N    N   N     0  -0.411   4.9004  -0.3615  -0.7605
 KES  C1   C   CR16  0  -0.043   6.1069   0.1427  -0.7692
 KES  H1   H   HCR5  0   0.281   1.4379   0.9332   1.9422
 KES  H3   H   HCR6  0   0.333   5.8204   2.5229   1.6400
 KES  H4   H   HCR6  0   0.292  -3.8433  -1.7452   1.2499
 KES  H5   H   HCR5  0   0.271   0.6890  -3.9791  -0.8229
 KES  H6   H   HCR6  0   0.295  -4.7404   2.4147   0.7746
 KES  H7   H   HNH1  0   0.409   0.2487  -0.5222   0.8675
 KES  H8   H   HCH1  0   0.237   0.5059   1.3122  -2.1616
 KES  H9   H   HNR5  0   0.424  -3.2532  -3.1705  -1.0244
 KES  H10  H   HCR6  0   0.303   7.5337   1.5782   0.0290
 KES  H11  H   HCR6  0   0.286   6.8100  -0.2879  -1.4722
 KES  H2   H   HCR6  0   0.296  -2.8927   2.6511  -0.7925

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
 KES  C    C5   aromatic  1.359  0.020  1.359
 KES  C    C1   aromatic  1.412  0.020  1.412
 KES  C5   N2   aromatic  1.349  0.020  1.349
 KES  C1   N    aromatic  1.308  0.020  1.308
 KES  CL   C12  single    1.730  0.020  1.730
 KES  C13  C14  aromatic  1.386  0.020  1.386
 KES  C13  C12  aromatic  1.385  0.020  1.385
 KES  N    C2   aromatic  1.336  0.020  1.336
 KES  N2   C2   aromatic  1.380  0.020  1.380
 KES  N2   N1   aromatic  1.337  0.020  1.337
 KES  C14  C15  aromatic  1.387  0.020  1.387
 KES  C12  C11  aromatic  1.383  0.020  1.383
 KES  C2   C3   aromatic  1.398  0.020  1.398
 KES  N1   C4   aromatic  1.317  0.020  1.317
 KES  C15  O1   single    1.372  0.020  1.372
 KES  C15  C10  aromatic  1.397  0.020  1.397
 KES  C11  C10  aromatic  1.394  0.020  1.394
 KES  F    C16  single    1.350  0.020  1.350
 KES  C3   C4   aromatic  1.405  0.020  1.405
 KES  C3   C6   single    1.463  0.020  1.463
 KES  O1   C16  single    1.357  0.020  1.357
 KES  C10  C9   single    1.463  0.020  1.463
 KES  C16  F1   single    1.355  0.020  1.355
 KES  N3   C6   single    1.360  0.020  1.360
 KES  N3   C7   single    1.392  0.020  1.392
 KES  C6   O    double    1.221  0.020  1.221
 KES  C9   C7   aromatic  1.382  0.020  1.382
 KES  C9   N5   aromatic  1.350  0.020  1.350
 KES  C7   C8   aromatic  1.408  0.020  1.408
 KES  N5   N4   aromatic  1.321  0.020  1.321
 KES  C8   N4   aromatic  1.321  0.020  1.321
 KES  C4   H1   single    0.930  0.020  1.080
 KES  C14  H2   single    0.930  0.020  1.080
 KES  C5   H3   single    0.930  0.020  1.080
 KES  C11  H4   single    0.930  0.020  1.080
 KES  C8   H5   single    0.930  0.020  1.080
 KES  C13  H6   single    0.930  0.020  1.080
 KES  N3   H7   single    0.860  0.020  1.020
 KES  C16  H8   single    0.970  0.020  1.090
 KES  N5   H9   single    0.860  0.020  1.020
 KES  C    H10  single    0.930  0.020  1.080
 KES  C1   H11  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
 KES  H1   C4   C3   128.35  3.000
 KES  H1   C4   N1   118.36  3.000
 KES  C3   C4   N1   113.28  3.000
 KES  H2   C14  C15  121.63  3.000
 KES  H2   C14  C13  118.42  3.000
 KES  C15  C14  C13  119.93  3.000
 KES  H3   C5   C    125.38  3.000
 KES  H3   C5   N2   117.08  3.000
 KES  C    C5   N2   117.54  3.000
 KES  O    C6   N3   122.14  3.000
 KES  O    C6   C3   122.56  3.000
 KES  N3   C6   C3   115.29  3.000
 KES  H4   C11  C12  120.30  3.000
 KES  H4   C11  C10  119.68  3.000
 KES  C12  C11  C10  120.01  3.000
 KES  N3   C7   C9   125.38  3.000
 KES  C9   C7   C8   104.87  3.000
 KES  N3   C7   C8   129.63  3.000
 KES  H5   C8   N4   120.56  3.000
 KES  H5   C8   C7   128.71  3.000
 KES  N4   C8   C7   110.74  3.000
 KES  N5   C9   C10  122.62  3.000
 KES  N5   C9   C7   105.40  3.000
 KES  C10  C9   C7   131.92  3.000
 KES  C15  C10  C9   121.13  3.000
 KES  C9   C10  C11  119.85  3.000
 KES  C15  C10  C11  119.00  3.000
 KES  CL   C12  C13  119.70  3.000
 KES  C13  C12  C11  120.83  3.000
 KES  CL   C12  C11  119.47  3.000
 KES  H6   C13  C12  120.73  3.000
 KES  H6   C13  C14  119.63  3.000
 KES  C12  C13  C14  119.63  3.000
 KES  N2   N1   C4   104.50  3.000
 KES  C2   N2   N1   113.08  3.000
 KES  N1   N2   C5   125.08  3.000
 KES  C2   N2   C5   121.84  3.000
 KES  C2   C3   C6   125.66  3.000
 KES  C6   C3   C4   130.43  3.000
 KES  C2   C3   C4   103.91  3.000
 KES  H7   N3   C7   116.52  3.000
 KES  H7   N3   C6   119.29  3.000
 KES  C7   N3   C6   124.19  3.000
 KES  O1   C15  C10  115.78  3.000
 KES  C10  C15  C14  120.59  3.000
 KES  O1   C15  C14  123.52  3.000
 KES  C16  O1   C15  121.57  3.000
 KES  H8   C16  F    110.45  3.000
 KES  H8   C16  F1   109.18  3.000
 KES  F    C16  F1   106.06  3.000
 KES  H8   C16  O1   108.69  3.000
 KES  F1   C16  O1   111.24  3.000
 KES  F    C16  O1   111.19  3.000
 KES  H9   N5   N4   119.92  3.000
 KES  H9   N5   C9   126.58  3.000
 KES  N4   N5   C9   113.43  3.000
 KES  N5   N4   C8   105.55  3.000
 KES  H10  C    C1   121.13  3.000
 KES  H10  C    C5   120.64  3.000
 KES  C1   C    C5   118.23  3.000
 KES  N    C2   C3   133.45  3.000
 KES  C3   C2   N2   105.23  3.000
 KES  N    C2   N2   121.32  3.000
 KES  C1   N    C2   117.19  3.000
 KES  H11  C1   N    116.73  3.000
 KES  H11  C1   C    119.39  3.000
 KES  N    C1   C    123.87  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
 KES  CONST_01  C5   N2   N1   C4   180.00   0.0  0
 KES  CONST_02  C2   N2   N1   C4     0.00   0.0  0
 KES  CONST_03  N    C2   C3   C4   180.00   0.0  0
 KES  CONST_04  N2   C2   C3   C4     0.00   0.0  0
 KES  CONST_05  C11  C12  C13  C14    0.00   0.0  0
 KES  CONST_06  C11  C10  C15  C14    0.00   0.0  0
 KES  CONST_07  C9   C10  C15  C14  180.00   0.0  0
 KES  CONST_08  N    C1   C    C5     0.00   0.0  0
 KES  CONST_09  N    C2   N2   C5     0.00   0.0  0
 KES  CONST_10  C3   C2   N2   C5   180.00   0.0  0
 KES  CONST_14  N4   N5   C9   C7     0.00   0.0  0
 KES  CONST_15  N5   N4   C8   C7     0.00   0.0  0
 KES  CONST_16  C10  C9   C7   C8   180.00   0.0  0
 KES  CONST_17  N5   C9   C7   C8     0.00   0.0  0
 KES  CONST_18  C9   N5   N4   C8     0.00   0.0  0
 KES  CONST_19  C12  C11  C10  C9   180.00   0.0  0
 KES  CONST_20  N4   C8   C7   C9     0.00   0.0  0
 KES  CONST_21  C13  C14  C15  C10    0.00   0.0  0
 KES  CONST_22  C13  C12  C11  C10    0.00   0.0  0
 KES  CONST_23  N4   N5   C9   C10  180.00   0.0  0
 KES  CONST_24  C15  C14  C13  C12    0.00   0.0  0
 KES  CONST_25  C15  C10  C11  C12    0.00   0.0  0
 KES  CONST_26  C    C5   N2   N1   180.00   0.0  0
 KES  CONST_27  N    C2   N2   N1   180.00   0.0  0
 KES  CONST_28  C3   C2   N2   N1     0.00   0.0  0
 KES  CONST_29  C2   C3   C4   N1     0.00   0.0  0
 KES  CONST_30  C1   C    C5   N2     0.00   0.0  0
 KES  CONST_31  C1   N    C2   N2     0.00   0.0  0
 KES  CONST_32  C3   C4   N1   N2     0.00   0.0  0
 KES  CONST_33  C1   N    C2   C3   180.00   0.0  0
 KES  CONST_35  C2   N2   C5   C      0.00   0.0  0
 KES  CONST_36  C2   N    C1   C      0.00   0.0  0
 KES  CONST_37  CL   C12  C13  C14  180.00   0.0  0
 KES  CONST_38  N    C2   C3   C6     0.00   0.0  0
 KES  CONST_39  N2   C2   C3   C6   180.00   0.0  0
 KES  CONST_40  N1   C4   C3   C6   180.00   0.0  0
 KES  CONST_41  O1   C15  C10  C11  180.00   0.0  0
 KES  CONST_42  O1   C15  C10  C9     0.00   0.0  0
 KES  CONST_43  CL   C12  C11  C10  180.00   0.0  0
 KES  CONST_44  N3   C7   C9   C10    0.00   0.0  0
 KES  CONST_45  O1   C15  C14  C13  180.00   0.0  0
 KES  CONST_46  N5   C9   C7   N3   180.00   0.0  0
 KES  CONST_47  N4   C8   C7   N3   180.00   0.0  0
 KES  CONST_48  H11  C1   C    C5   180.00   0.0  0
 KES  CONST_49  H6   C13  C12  C11  180.00   0.0  0
 KES  CONST_50  H9   N5   C9   C7   180.00   0.0  0
 KES  CONST_51  H4   C11  C10  C9     0.00   0.0  0
 KES  CONST_52  H5   C8   C7   C9   180.00   0.0  0
 KES  CONST_53  H2   C14  C15  C10  180.00   0.0  0
 KES  CONST_54  H3   C5   N2   N1     0.00   0.0  0
 KES  CONST_55  H10  C    C5   N2   180.00   0.0  0
 KES  CONST_56  H1   C4   N1   N2   180.00   0.0  0
 KES  CONST_57  C3   C6   N3   C7   180.00   0.0  0
 KES  CONST_61  O    C6   N3   C7     0.00   0.0  0
 KES  Var_01    N3   C6   C3   C4     2.11  30.0  2
 KES  Var_02    F    C16  O1   C15   40.17  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
 KES  plan-1  C7   0.020
 KES  plan-1  C8   0.020
 KES  plan-1  C9   0.020
 KES  plan-1  C10  0.020
 KES  plan-1  N3   0.020
 KES  plan-1  N5   0.020
 KES  plan-1  N4   0.020
 KES  plan-1  H5   0.020
 KES  plan-1  H9   0.020
 KES  plan-2  C14  0.020
 KES  plan-2  C11  0.020
 KES  plan-2  C9   0.020
 KES  plan-2  C10  0.020
 KES  plan-2  C12  0.020
 KES  plan-2  C13  0.020
 KES  plan-2  CL   0.020
 KES  plan-2  C15  0.020
 KES  plan-2  O1   0.020
 KES  plan-2  H4   0.020
 KES  plan-2  H6   0.020
 KES  plan-2  H2   0.020
 KES  plan-3  C4   0.020
 KES  plan-3  C5   0.020
 KES  plan-3  C6   0.020
 KES  plan-3  N1   0.020
 KES  plan-3  N2   0.020
 KES  plan-3  C3   0.020
 KES  plan-3  C    0.020
 KES  plan-3  C2   0.020
 KES  plan-3  N    0.020
 KES  plan-3  C1   0.020
 KES  plan-3  H1   0.020
 KES  plan-3  H3   0.020
 KES  plan-3  H10  0.020
 KES  plan-3  H11  0.020
 KES  plan-4  C6   0.020
 KES  plan-4  C7   0.020
 KES  plan-4  C3   0.020
 KES  plan-4  N3   0.020
 KES  plan-4  O    0.020
 KES  plan-4  H7   0.020

