# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 17:02:30 2020
#   Inital geometry file: a 85 line input string
#   Ligand name: 7-hydroxy-N-methyl-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CNC(=O)c1cnn2c(O)cc(nc12)c3ccccc3
#
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
 KKP  KKP  7-hydroxy-N-methyl-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide  ligand  32  20  .  2021-08-12  2021-08-12  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_KKP
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
 KKP  C10   C  CR16  0  -0.277  -2.5262   1.7539  -0.1574
 KKP  C13   C  CR5   0  -0.378   2.2855   0.0065   0.0970
 KKP  O01   O  OH1   0  -0.564   0.0325  -3.7990  -0.1201
 KKP  C02   C  CR6   0   0.663  -0.1478  -2.5018  -0.0621
 KKP  C03   C  CR16  0  -0.517  -1.3379  -1.8241  -0.0675
 KKP  C04   C  CR6   0   0.274  -1.3222  -0.4132  -0.0038
 KKP  C05   C  CR6   0   0.048  -2.5791   0.3657  -0.0072
 KKP  C06   C  CR16  0  -0.326  -3.8262  -0.2429   0.1406
 KKP  C07   C  CR16  0  -0.234  -4.9886   0.5135   0.1350
 KKP  C08   C  CR16  0  -0.257  -4.9246   1.8909  -0.0227
 KKP  C09   C  CR16  0  -0.237  -3.6879   2.5076  -0.1680
 KKP  N11   N  N     0  -0.465  -0.2026   0.2775   0.0523
 KKP  C12   C  CR56  0   0.648   0.9459  -0.3897   0.0561
 KKP  N15   N  NH1   0  -0.650   4.1014   1.5510  -0.0189
 KKP  C16   C  CH3   0  -0.511   4.7233   2.8525   0.0213
 KKP  O17   O  O     0  -0.491   2.0279   2.3389   0.3530
 KKP  C18   C  CR15  0  -0.025   3.0012  -1.2023   0.0691
 KKP  N20   N  N     0  -0.427   0.9876  -1.7701   0.0043
 KKP  N19   N  N     0  -0.288   2.2315  -2.2691   0.0161
 KKP  H101  H  HCR6  0   0.265  -1.5667   2.2397  -0.2696
 KKP  H011  H  HOH1  0   0.508  -0.8148  -4.2623  -0.1678
 KKP  H031  H  HCR6  0   0.303  -2.2544  -2.3906  -0.1364
 KKP  H061  H  HCR6  0   0.257  -3.9128  -1.3131   0.2719
 KKP  H071  H  HCR6  0   0.264  -5.9452   0.0225   0.2552
 KKP  H081  H  HCR6  0   0.264  -5.8313   2.4816  -0.0316
 KKP  H091  H  HCR6  0   0.262  -3.6281   3.5811  -0.2896
 KKP  H151  H  HNH1  0   0.403   4.6823   0.7621  -0.2432
 KKP  H163  H  HCH3  0   0.235   4.3311   3.5153  -0.7513
 KKP  H161  H  HCH3  0   0.236   4.5833   3.3366   0.9880
 KKP  H162  H  HCH3  0   0.248   5.7893   2.7268  -0.1449
 KKP  H181  H  HCR5  0   0.278   4.0722  -1.3414   0.1009
 KKP  C14   C  C     0   0.493   2.7763   1.3891   0.1541

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
 KKP  C16  N15   single    1.443  0.020  1.443
 KKP  O17  C14   double    1.225  0.020  1.225
 KKP  N15  C14   single    1.346  0.020  1.346
 KKP  C14  C13   single    1.468  0.020  1.468
 KKP  C13  C18   aromatic  1.405  0.020  1.405
 KKP  C13  C12   aromatic  1.398  0.020  1.398
 KKP  C18  N19   aromatic  1.316  0.020  1.316
 KKP  C09  C10   aromatic  1.385  0.020  1.385
 KKP  C09  C08   aromatic  1.390  0.020  1.390
 KKP  C10  C05   aromatic  1.397  0.020  1.397
 KKP  C12  N11   aromatic  1.328  0.020  1.328
 KKP  C12  N20   aromatic  1.382  0.020  1.382
 KKP  N11  C04   aromatic  1.317  0.020  1.317
 KKP  N19  N20   aromatic  1.340  0.020  1.340
 KKP  C08  C07   aromatic  1.388  0.020  1.388
 KKP  C05  C04   single    1.479  0.020  1.479
 KKP  C05  C06   aromatic  1.396  0.020  1.396
 KKP  N20  C02   aromatic  1.352  0.020  1.352
 KKP  C04  C03   aromatic  1.412  0.020  1.412
 KKP  C07  C06   aromatic  1.387  0.020  1.387
 KKP  C02  C03   aromatic  1.370  0.020  1.370
 KKP  C02  O01   single    1.311  0.020  1.311
 KKP  C10  H101  single    0.930  0.020  1.080
 KKP  O01  H011  single    0.850  0.020  0.980
 KKP  C03  H031  single    0.930  0.020  1.080
 KKP  C06  H061  single    0.930  0.020  1.080
 KKP  C07  H071  single    0.930  0.020  1.080
 KKP  C08  H081  single    0.930  0.020  1.080
 KKP  C09  H091  single    0.930  0.020  1.080
 KKP  N15  H151  single    0.860  0.020  1.020
 KKP  C16  H163  single    0.970  0.020  1.090
 KKP  C16  H161  single    0.970  0.020  1.090
 KKP  C16  H162  single    0.970  0.020  1.090
 KKP  C18  H181  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
 KKP  H101  C10  C09   119.94  3.000
 KKP  H101  C10  C05   119.41  3.000
 KKP  C09   C10  C05   120.65  3.000
 KKP  C18   C13  C14   129.84  3.000
 KKP  C18   C13  C12   104.11  3.000
 KKP  C14   C13  C12   126.05  3.000
 KKP  H011  O01  C02   110.84  3.000
 KKP  N20   C02  C03   117.51  3.000
 KKP  C03   C02  O01   127.52  3.000
 KKP  N20   C02  O01   114.96  3.000
 KKP  H031  C03  C04   122.44  3.000
 KKP  H031  C03  C02   118.57  3.000
 KKP  C04   C03  C02   118.98  3.000
 KKP  N11   C04  C05   116.53  3.000
 KKP  C05   C04  C03   121.11  3.000
 KKP  N11   C04  C03   122.37  3.000
 KKP  C06   C05  C04   121.98  3.000
 KKP  C06   C05  C10   118.58  3.000
 KKP  C04   C05  C10   119.43  3.000
 KKP  H061  C06  C07   118.23  3.000
 KKP  H061  C06  C05   121.06  3.000
 KKP  C07   C06  C05   120.72  3.000
 KKP  H071  C07  C08   120.25  3.000
 KKP  H071  C07  C06   119.54  3.000
 KKP  C08   C07  C06   120.21  3.000
 KKP  H081  C08  C09   120.17  3.000
 KKP  H081  C08  C07   120.27  3.000
 KKP  C09   C08  C07   119.56  3.000
 KKP  H091  C09  C08   120.08  3.000
 KKP  H091  C09  C10   119.63  3.000
 KKP  C08   C09  C10   120.29  3.000
 KKP  C12   N11  C04   118.16  3.000
 KKP  N20   C12  N11   121.85  3.000
 KKP  N20   C12  C13   104.79  3.000
 KKP  N11   C12  C13   133.36  3.000
 KKP  H151  N15  C16   117.71  3.000
 KKP  H151  N15  C14   120.22  3.000
 KKP  C16   N15  C14   121.95  3.000
 KKP  H162  C16  H161  108.25  3.000
 KKP  H162  C16  H163  108.34  3.000
 KKP  H161  C16  H163  108.18  3.000
 KKP  H162  C16  N15   108.32  3.000
 KKP  H161  C16  N15   111.71  3.000
 KKP  H163  C16  N15   111.92  3.000
 KKP  H181  C18  N19   118.45  3.000
 KKP  H181  C18  C13   127.96  3.000
 KKP  N19   C18  C13   113.59  3.000
 KKP  N19   N20  C12   113.55  3.000
 KKP  N19   N20  C02   125.33  3.000
 KKP  C12   N20  C02   121.12  3.000
 KKP  N20   N19  C18   103.96  3.000
 KKP  O17   C14  N15   121.93  3.000
 KKP  N15   C14  C13   115.93  3.000
 KKP  O17   C14  C13   122.14  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
 KKP  CONST_01  C07   C08  C09  C10    0.00   0.0  0
 KKP  CONST_02  N11   C04  C05  C10    0.00   0.0  0
 KKP  CONST_03  C03   C04  C05  C10  180.00   0.0  0
 KKP  CONST_04  C07   C06  C05  C10    0.00   0.0  0
 KKP  CONST_05  N20   N19  C18  C13    0.00   0.0  0
 KKP  CONST_06  C04   N11  C12  C13  180.00   0.0  0
 KKP  CONST_07  N19   N20  C12  C13    0.00   0.0  0
 KKP  CONST_08  C02   N20  C12  C13  180.00   0.0  0
 KKP  CONST_09  N11   C12  N20  C02    0.00   0.0  0
 KKP  CONST_10  C18   N19  N20  C02  180.00   0.0  0
 KKP  CONST_11  N11   C04  C03  C02    0.00   0.0  0
 KKP  CONST_12  C05   C04  C03  C02  180.00   0.0  0
 KKP  CONST_13  C12   N11  C04  C03    0.00   0.0  0
 KKP  CONST_14  C06   C05  C04  C03    0.00   0.0  0
 KKP  CONST_15  C12   N20  C02  C03    0.00   0.0  0
 KKP  CONST_16  N19   N20  C02  C03  180.00   0.0  0
 KKP  CONST_17  N20   C12  N11  C04    0.00   0.0  0
 KKP  CONST_18  C09   C10  C05  C04  180.00   0.0  0
 KKP  CONST_19  C07   C06  C05  C04  180.00   0.0  0
 KKP  CONST_20  N20   C02  C03  C04    0.00   0.0  0
 KKP  CONST_21  C08   C09  C10  C05    0.00   0.0  0
 KKP  CONST_22  C12   N11  C04  C05  180.00   0.0  0
 KKP  CONST_23  C08   C07  C06  C05    0.00   0.0  0
 KKP  CONST_24  C09   C10  C05  C06    0.00   0.0  0
 KKP  CONST_25  N11   C04  C05  C06  180.00   0.0  0
 KKP  CONST_26  C09   C08  C07  C06    0.00   0.0  0
 KKP  CONST_27  C18   C13  C12  N11  180.00   0.0  0
 KKP  CONST_28  N19   N20  C12  N11  180.00   0.0  0
 KKP  CONST_29  N19   C18  C13  C12    0.00   0.0  0
 KKP  CONST_30  C18   N19  N20  C12    0.00   0.0  0
 KKP  CONST_31  N20   C12  C13  C18    0.00   0.0  0
 KKP  CONST_32  C12   N20  C02  O01  180.00   0.0  0
 KKP  CONST_33  N19   N20  C02  O01    0.00   0.0  0
 KKP  CONST_34  C04   C03  C02  O01  180.00   0.0  0
 KKP  CONST_35  C14   C13  C12  N11    0.00   0.0  0
 KKP  CONST_36  N19   C18  C13  C14  180.00   0.0  0
 KKP  CONST_37  N20   C12  C13  C14  180.00   0.0  0
 KKP  CONST_38  H081  C08  C09  C10  180.00   0.0  0
 KKP  CONST_39  H061  C06  C05  C10  180.00   0.0  0
 KKP  CONST_40  H101  C10  C05  C04    0.00   0.0  0
 KKP  CONST_41  H091  C09  C10  C05  180.00   0.0  0
 KKP  CONST_42  H031  C03  C04  C05    0.00   0.0  0
 KKP  CONST_43  H071  C07  C06  C05  180.00   0.0  0
 KKP  CONST_44  H181  C18  C13  C12  180.00   0.0  0
 KKP  CONST_45  C16   N15  C14  C13  180.00   0.0  0
 KKP  CONST_46  H151  N15  C14  C13    0.00   0.0  0
 KKP  CONST_47  O17   C14  N15  C16    0.00   0.0  0
 KKP  Var_01    O17   C14  C13  C12   10.08  30.0  2
 KKP  Var_02    H163  C16  N15  C14  -60.52  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
 KKP  plan-1  C10   0.020
 KKP  plan-1  C04   0.020
 KKP  plan-1  C05   0.020
 KKP  plan-1  C06   0.020
 KKP  plan-1  C07   0.020
 KKP  plan-1  C08   0.020
 KKP  plan-1  C09   0.020
 KKP  plan-1  H101  0.020
 KKP  plan-1  H061  0.020
 KKP  plan-1  H071  0.020
 KKP  plan-1  H081  0.020
 KKP  plan-1  H091  0.020
 KKP  plan-2  C13   0.020
 KKP  plan-2  O01   0.020
 KKP  plan-2  C02   0.020
 KKP  plan-2  C03   0.020
 KKP  plan-2  C04   0.020
 KKP  plan-2  C05   0.020
 KKP  plan-2  N11   0.020
 KKP  plan-2  C12   0.020
 KKP  plan-2  C18   0.020
 KKP  plan-2  N20   0.020
 KKP  plan-2  N19   0.020
 KKP  plan-2  H031  0.020
 KKP  plan-2  H181  0.020
 KKP  plan-2  C14   0.020
 KKP  plan-3  C13   0.020
 KKP  plan-3  N15   0.020
 KKP  plan-3  C16   0.020
 KKP  plan-3  O17   0.020
 KKP  plan-3  H151  0.020
 KKP  plan-3  C14   0.020

