# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 09:25:54 2020
#   Inital geometry file: a 109 line input string
#   Ligand name: N-{3-[5-chloro-2-(difluoromethoxy)phenyl]-1-methyl-1H-pyrazol-4-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cn1cc(NC(=O)c2cnn3cccnc23)c(n1)c4cc(Cl)ccc4OC(F)F
#
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
 KEP  KEP  N-{3-[5-chloro-2-(difluoromethoxy)phenyl]-1-methyl-1H-pyrazol-4-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide  ligand  42  29  .  2021-08-12  2021-08-12  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_KEP
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
 KEP  C4   C   CR6   0  -0.034  -2.1495  -0.0307  -0.6346
 KEP  C14  C   CR56  0   0.631   4.3060  -0.0586   0.4326
 KEP  C5   C   CR16  0  -0.287  -1.5501  -1.1320  -1.2456
 KEP  C6   C   CR6   0  -0.023  -2.0621  -2.4037  -1.0548
 KEP  C11  C   C     0   0.505   2.1241   1.0169  -0.3347
 KEP  C7   C   CR16  0  -0.218  -3.1927  -2.6118  -0.2828
 KEP  C8   C   CR16  0  -0.310  -3.8011  -1.5224   0.3199
 KEP  C9   C   CR6   0   0.323  -3.2801  -0.2498   0.1532
 KEP  C10  C   CH1   0   0.671  -3.5844   1.1459   2.0118
 KEP  C12  C   CR5   0  -0.387   2.9656  -0.1173   0.0500
 KEP  C13  C   CR15  0  -0.018   2.6637  -1.4884   0.0756
 KEP  N1   N   N     0  -0.276  -2.2771   2.3541  -1.1964
 KEP  N2   N   NH1   0  -0.750   0.7904   0.7831  -0.2444
 KEP  C3   C   CR5   0   0.221  -1.5652   1.3005  -0.8300
 KEP  N3   N   N     0  -0.290   3.6863  -2.2383   0.4362
 KEP  O1   O   O     0  -0.466   2.5803   2.0828  -0.7170
 KEP  N5   N   N     0  -0.412   5.1625   0.9515   0.6131
 KEP  C15  C   CR16  0  -0.042   6.3711   0.6441   1.0052
 KEP  C16  C   CR16  0  -0.389   6.8080  -0.6789   1.2424
 KEP  C17  C   CR16  0   0.090   5.9231  -1.6936   1.0597
 KEP  N4   N   N     0  -0.359   4.6762  -1.3691   0.6571
 KEP  C2   C   CR5   0   0.077  -0.2101   1.6539  -0.6601
 KEP  C1   C   CR15  0   0.007  -0.1587   2.9977  -0.9621
 KEP  N    N   NR5   0  -0.267  -1.4217   3.3549  -1.2740
 KEP  C    C   CH3   0  -0.507  -1.8682   4.6567  -1.7091
 KEP  O    O   O2    0  -0.498  -3.9179   0.8225   0.7381
 KEP  F1   F   F     0  -0.332  -3.9194   0.1544   2.8733
 KEP  F    F   F     0  -0.329  -2.2487   1.3037   2.1470
 KEP  CL   CL  CL    0  -0.116  -1.2807  -3.7489  -1.8129
 KEP  H1   H   HCR6  0   0.299  -0.6924  -0.9881  -1.8899
 KEP  H2   H   HCR6  0   0.291  -3.5976  -3.6047  -0.1462
 KEP  H3   H   HCR6  0   0.288  -4.6927  -1.6694   0.9140
 KEP  H4   H   HCH1  0   0.217  -4.1016   2.0617   2.2863
 KEP  H5   H   HCR5  0   0.266   1.7309  -1.9702  -0.1826
 KEP  H6   H   HNH1  0   0.414   0.4830  -0.0606   0.2137
 KEP  H7   H   HCR6  0   0.286   7.0611   1.4663   1.1518
 KEP  H8   H   HCR6  0   0.303   7.8172  -0.8834   1.5641
 KEP  H9   H   HCR6  0   0.333   6.1350  -2.7419   1.2111
 KEP  H10  H   HCR5  0   0.300   0.6508   3.7047  -0.9692
 KEP  H11  H   HCH3  0   0.264  -2.7115   4.9819  -1.1043
 KEP  H12  H   HCH3  0   0.261  -1.0552   5.3664  -1.5898
 KEP  H13  H   HCH3  0   0.261  -2.1657   4.6309  -2.7560

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
 KEP  F1   C10  single    1.356  0.020  1.356
 KEP  F    C10  single    1.352  0.020  1.352
 KEP  C10  O    single    1.356  0.020  1.356
 KEP  C8   C7   aromatic  1.386  0.020  1.386
 KEP  C8   C9   aromatic  1.385  0.020  1.385
 KEP  O    C9   single    1.378  0.020  1.378
 KEP  C7   C6   aromatic  1.385  0.020  1.385
 KEP  C9   C4   aromatic  1.395  0.020  1.395
 KEP  C16  C15  aromatic  1.413  0.020  1.413
 KEP  C16  C17  aromatic  1.359  0.020  1.359
 KEP  C15  N5   aromatic  1.307  0.020  1.307
 KEP  C17  N4   aromatic  1.350  0.020  1.350
 KEP  C6   C5   aromatic  1.384  0.020  1.384
 KEP  C6   CL   single    1.731  0.020  1.731
 KEP  N5   C14  aromatic  1.337  0.020  1.337
 KEP  C4   C5   aromatic  1.395  0.020  1.395
 KEP  C4   C3   single    1.467  0.020  1.467
 KEP  N4   C14  aromatic  1.380  0.020  1.380
 KEP  N4   N3   aromatic  1.336  0.020  1.336
 KEP  C14  C12  aromatic  1.395  0.020  1.395
 KEP  C3   N1   aromatic  1.323  0.020  1.323
 KEP  C3   C2   aromatic  1.411  0.020  1.411
 KEP  N1   N    aromatic  1.319  0.020  1.319
 KEP  N2   C2   single    1.390  0.020  1.390
 KEP  N2   C11  single    1.357  0.020  1.357
 KEP  C2   C1   aromatic  1.378  0.020  1.378
 KEP  N3   C13  aromatic  1.318  0.020  1.318
 KEP  C12  C11  single    1.464  0.020  1.464
 KEP  C12  C13  aromatic  1.404  0.020  1.404
 KEP  N    C1   aromatic  1.349  0.020  1.349
 KEP  N    C    single    1.443  0.020  1.443
 KEP  C11  O1   double    1.221  0.020  1.221
 KEP  C5   H1   single    0.930  0.020  1.080
 KEP  C7   H2   single    0.930  0.020  1.080
 KEP  C8   H3   single    0.930  0.020  1.080
 KEP  C10  H4   single    0.970  0.020  1.090
 KEP  C13  H5   single    0.930  0.020  1.080
 KEP  N2   H6   single    0.860  0.020  1.020
 KEP  C15  H7   single    0.930  0.020  1.080
 KEP  C16  H8   single    0.930  0.020  1.080
 KEP  C17  H9   single    0.930  0.020  1.080
 KEP  C1   H10  single    0.930  0.020  1.080
 KEP  C    H11  single    0.970  0.020  1.090
 KEP  C    H12  single    0.970  0.020  1.090
 KEP  C    H13  single    0.970  0.020  1.090

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
 KEP  C3   C4   C9   122.71  3.000
 KEP  C3   C4   C5   119.15  3.000
 KEP  C9   C4   C5   118.14  3.000
 KEP  N4   C14  N5   121.58  3.000
 KEP  N4   C14  C12  105.21  3.000
 KEP  N5   C14  C12  133.19  3.000
 KEP  H1   C5   C6   119.83  3.000
 KEP  H1   C5   C4   119.76  3.000
 KEP  C6   C5   C4   120.41  3.000
 KEP  CL   C6   C7   119.74  3.000
 KEP  CL   C6   C5   119.13  3.000
 KEP  C7   C6   C5   121.12  3.000
 KEP  O1   C11  N2   122.58  3.000
 KEP  O1   C11  C12  122.96  3.000
 KEP  N2   C11  C12  114.45  3.000
 KEP  H2   C7   C8   120.18  3.000
 KEP  H2   C7   C6   120.95  3.000
 KEP  C8   C7   C6   118.87  3.000
 KEP  H3   C8   C9   120.08  3.000
 KEP  H3   C8   C7   119.60  3.000
 KEP  C9   C8   C7   120.31  3.000
 KEP  O    C9   C8   119.32  3.000
 KEP  O    C9   C4   119.51  3.000
 KEP  C8   C9   C4   121.13  3.000
 KEP  H4   C10  F    110.27  3.000
 KEP  H4   C10  F1   109.77  3.000
 KEP  F    C10  F1   105.43  3.000
 KEP  H4   C10  O    108.73  3.000
 KEP  F    C10  O    111.40  3.000
 KEP  F1   C10  O    111.21  3.000
 KEP  C13  C12  C11  129.63  3.000
 KEP  C13  C12  C14  104.04  3.000
 KEP  C11  C12  C14  126.28  3.000
 KEP  H5   C13  N3   118.75  3.000
 KEP  H5   C13  C12  128.05  3.000
 KEP  N3   C13  C12  113.18  3.000
 KEP  N    N1   C3   105.76  3.000
 KEP  H6   N2   C2   116.15  3.000
 KEP  H6   N2   C11  118.30  3.000
 KEP  C2   N2   C11  125.42  3.000
 KEP  C2   C3   N1   110.53  3.000
 KEP  C2   C3   C4   126.43  3.000
 KEP  N1   C3   C4   123.04  3.000
 KEP  N4   N3   C13  104.47  3.000
 KEP  C15  N5   C14  117.08  3.000
 KEP  H7   C15  C16  119.40  3.000
 KEP  H7   C15  N5   116.80  3.000
 KEP  C16  C15  N5   123.80  3.000
 KEP  H8   C16  C17  120.52  3.000
 KEP  H8   C16  C15  121.11  3.000
 KEP  C17  C16  C15  118.37  3.000
 KEP  H9   C17  N4   117.15  3.000
 KEP  H9   C17  C16  125.32  3.000
 KEP  N4   C17  C16  117.53  3.000
 KEP  C17  N4   N3   125.27  3.000
 KEP  N3   N4   C14  113.09  3.000
 KEP  C17  N4   C14  121.64  3.000
 KEP  C1   C2   C3   104.69  3.000
 KEP  C1   C2   N2   130.50  3.000
 KEP  C3   C2   N2   124.79  3.000
 KEP  H10  C1   N    121.96  3.000
 KEP  H10  C1   C2   132.14  3.000
 KEP  N    C1   C2   105.90  3.000
 KEP  C    N    C1   126.74  3.000
 KEP  C    N    N1   120.10  3.000
 KEP  C1   N    N1   113.12  3.000
 KEP  H13  C    H12  109.01  3.000
 KEP  H13  C    H11  109.27  3.000
 KEP  H12  C    H11  108.91  3.000
 KEP  H13  C    N    110.67  3.000
 KEP  H12  C    N    108.95  3.000
 KEP  H11  C    N    110.00  3.000
 KEP  C10  O    C9   118.07  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
 KEP  CONST_01  C7   C8   C9   C4      0.00   0.0  0
 KEP  CONST_02  C7   C6   C5   C4      0.00   0.0  0
 KEP  CONST_03  N    N1   C3   C4    180.00   0.0  0
 KEP  CONST_04  C1   C2   C3   C4    180.00   0.0  0
 KEP  CONST_05  C16  C15  N5   C14     0.00   0.0  0
 KEP  CONST_06  C16  C17  N4   C14     0.00   0.0  0
 KEP  CONST_07  C13  N3   N4   C14     0.00   0.0  0
 KEP  CONST_08  N3   C13  C12  C14     0.00   0.0  0
 KEP  CONST_09  C8   C7   C6   C5      0.00   0.0  0
 KEP  CONST_10  C8   C9   C4   C5      0.00   0.0  0
 KEP  CONST_13  C9   C8   C7   C6      0.00   0.0  0
 KEP  CONST_14  C9   C4   C5   C6      0.00   0.0  0
 KEP  CONST_15  C3   C4   C5   C6    180.00   0.0  0
 KEP  CONST_16  C3   C4   C9   C8    180.00   0.0  0
 KEP  CONST_19  C15  N5   C14  C12   180.00   0.0  0
 KEP  CONST_20  C17  N4   C14  C12   180.00   0.0  0
 KEP  CONST_21  N3   N4   C14  C12     0.00   0.0  0
 KEP  CONST_22  N4   N3   C13  C12     0.00   0.0  0
 KEP  CONST_23  C17  N4   N3   C13   180.00   0.0  0
 KEP  CONST_24  N5   C14  C12  C13   180.00   0.0  0
 KEP  CONST_25  N4   C14  C12  C13     0.00   0.0  0
 KEP  CONST_26  C1   C2   C3   N1      0.00   0.0  0
 KEP  CONST_27  C2   C1   N    N1      0.00   0.0  0
 KEP  CONST_28  C1   N    N1   C3      0.00   0.0  0
 KEP  CONST_29  N    C1   C2   C3      0.00   0.0  0
 KEP  CONST_30  C16  C17  N4   N3    180.00   0.0  0
 KEP  CONST_31  N5   C14  N4   N3    180.00   0.0  0
 KEP  CONST_32  C17  C16  C15  N5      0.00   0.0  0
 KEP  CONST_33  C17  N4   C14  N5      0.00   0.0  0
 KEP  CONST_34  N4   C17  C16  C15     0.00   0.0  0
 KEP  CONST_35  N4   C14  N5   C15     0.00   0.0  0
 KEP  CONST_36  N    N1   C3   C2      0.00   0.0  0
 KEP  CONST_37  CL   C6   C5   C4    180.00   0.0  0
 KEP  CONST_38  N2   C2   C3   C4      0.00   0.0  0
 KEP  CONST_39  O    C9   C4   C5    180.00   0.0  0
 KEP  CONST_40  N5   C14  C12  C11     0.00   0.0  0
 KEP  CONST_41  N4   C14  C12  C11   180.00   0.0  0
 KEP  CONST_42  N3   C13  C12  C11   180.00   0.0  0
 KEP  CONST_43  O    C9   C8   C7    180.00   0.0  0
 KEP  CONST_44  CL   C6   C7   C8    180.00   0.0  0
 KEP  CONST_45  N2   C2   C3   N1    180.00   0.0  0
 KEP  CONST_46  N    C1   C2   N2    180.00   0.0  0
 KEP  CONST_47  O    C9   C4   C3      0.00   0.0  0
 KEP  CONST_48  C    N    N1   C3    180.00   0.0  0
 KEP  CONST_49  C    N    C1   C2    180.00   0.0  0
 KEP  CONST_50  H3   C8   C9   C4    180.00   0.0  0
 KEP  CONST_51  H7   C15  N5   C14   180.00   0.0  0
 KEP  CONST_52  H9   C17  N4   C14   180.00   0.0  0
 KEP  CONST_53  H5   C13  C12  C14   180.00   0.0  0
 KEP  CONST_54  H2   C7   C6   C5    180.00   0.0  0
 KEP  CONST_55  H1   C5   C6   C7    180.00   0.0  0
 KEP  CONST_56  H10  C1   N    N1    180.00   0.0  0
 KEP  CONST_57  H8   C16  C15  N5    180.00   0.0  0
 KEP  CONST_58  C2   N2   C11  C12   180.00   0.0  0
 KEP  CONST_59  C3   C2   N2   C11   180.00   0.0  0
 KEP  CONST_62  C2   N2   C11  O1      0.00   0.0  0
 KEP  Var_01    N2   C11  C12  C14  -159.71  30.0  2
 KEP  Var_02    H11  C    N    N1     53.80  30.0  2
 KEP  Var_03    F1   C10  O    C9    -64.42  30.0  2

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
 KEP  plan-1  C4   0.020
 KEP  plan-1  N1   0.020
 KEP  plan-1  N2   0.020
 KEP  plan-1  C3   0.020
 KEP  plan-1  C2   0.020
 KEP  plan-1  C1   0.020
 KEP  plan-1  N    0.020
 KEP  plan-1  C    0.020
 KEP  plan-1  H10  0.020
 KEP  plan-2  C4   0.020
 KEP  plan-2  C5   0.020
 KEP  plan-2  C6   0.020
 KEP  plan-2  C7   0.020
 KEP  plan-2  C8   0.020
 KEP  plan-2  C9   0.020
 KEP  plan-2  C3   0.020
 KEP  plan-2  O    0.020
 KEP  plan-2  CL   0.020
 KEP  plan-2  H1   0.020
 KEP  plan-2  H2   0.020
 KEP  plan-2  H3   0.020
 KEP  plan-3  C14  0.020
 KEP  plan-3  C11  0.020
 KEP  plan-3  C12  0.020
 KEP  plan-3  C13  0.020
 KEP  plan-3  N3   0.020
 KEP  plan-3  N5   0.020
 KEP  plan-3  C15  0.020
 KEP  plan-3  C16  0.020
 KEP  plan-3  C17  0.020
 KEP  plan-3  N4   0.020
 KEP  plan-3  H5   0.020
 KEP  plan-3  H7   0.020
 KEP  plan-3  H8   0.020
 KEP  plan-3  H9   0.020
 KEP  plan-4  C11  0.020
 KEP  plan-4  C12  0.020
 KEP  plan-4  N2   0.020
 KEP  plan-4  O1   0.020
 KEP  plan-4  C2   0.020
 KEP  plan-4  H6   0.020

