# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Aug  1 06:42:02 2022
#   Inital geometry file: a 115 line input string
#   Ligand name: (3P)-N-[(1S)-3-amino-1-(3-chlorophenyl)-3-oxopropyl]-3-(2-fluorophenyl)-1H-pyrazole-4-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NC(=O)C[C@H](NC(=O)c1c[nH]nc1c2ccccc2F)c3cccc(Cl)c3
#
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
 N6O  N6O  "(3P)-N-[(1S)-3-amino-1-(3-chlorophenyl)-3-oxopropyl]-3-(2-fluorophenyl)-1H-pyrazole-4-carboxamide"
  ligand  43  27  .  2022-08-10  2022-08-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_N6O
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
 N6O  N1   N   NH1   0  -0.663  -0.5390  -11.4070  32.0580
 N6O  C7   C   CR6   0  -0.021  -1.6539   -7.3236  31.5600
 N6O  C8   C   CR16  0  -0.265  -1.2768   -8.6512  31.4458
 N6O  N2   N   NR15  0  -0.425  -4.0162  -13.3260  33.5061
 N6O  C9   C   C     0   0.495  -0.8696  -11.5669  33.3569
 N6O  O1   O   O     0  -0.480   2.3417  -12.5078  30.8308
 N6O  C1   C   CH2   0  -0.603   0.8495  -10.7475  30.1831
 N6O  C5   C   CR16  0  -0.243   0.5207   -6.7344  32.3389
 N6O  C6   C   CR16  0  -0.228  -0.7698   -6.3520  32.0037
 N6O  N3   N   N     0  -0.273  -3.5562  -13.6866  34.6965
 N6O  C4   C   CR16  0  -0.301   0.9124   -8.0611  32.2328
 N6O  C3   C   CR6   0   0.145   0.0184   -9.0266  31.7864
 N6O  C2   C   CH1   0  -0.134   0.4719  -10.4633  31.6334
 N6O  N    N   NH2   0  -0.802   1.1786  -12.7772  28.9178
 N6O  O    O   O     0  -0.472  -0.2569  -11.0226  34.2629
 N6O  C10  C   CR5   0  -0.309  -2.0434  -12.4199  33.6123
 N6O  C12  C   CR5   0   0.298  -2.3565  -13.1420  34.7893
 N6O  C11  C   CR15  0   0.037  -3.1589  -12.5732  32.8133
 N6O  C13  C   CR6   0  -0.142  -1.5694  -13.3410  36.0114
 N6O  C18  C   CR6   0   0.521  -0.2387  -13.7331  35.9738
 N6O  F    F   F     0  -0.304   0.3437  -13.9272  34.7818
 N6O  C17  C   CR16  0  -0.403   0.5069  -13.9625  37.1125
 N6O  C16  C   CR16  0  -0.243  -0.0980  -13.8018  38.3510
 N6O  C15  C   CR16  0  -0.258  -1.4307  -13.4203  38.4289
 N6O  C14  C   CR16  0  -0.270  -2.1550  -13.1954  37.2686
 N6O  H1   H   HNH1  0   0.409  -1.0599  -11.9033  31.3517
 N6O  H2   H   HCR6  0   0.270  -1.9906   -9.3895  31.1033
 N6O  H3   H   HNR5  0   0.430  -4.9344  -13.6236  33.2135
 N6O  H4   H   HCH2  0   0.303   1.5601   -9.9851  29.8536
 N6O  H5   H   HCH2  0   0.273  -0.0272  -10.6530  29.5369
 N6O  H6   H   HCR6  0   0.266   1.2214   -5.9892  32.6920
 N6O  H7   H   HCR6  0   0.277  -1.0805   -5.3197  32.0901
 N6O  H8   H   HCR6  0   0.257   1.9206   -8.3497  32.5050
 N6O  H9   H   HCH1  0   0.275   1.3617  -10.6034  32.2504
 N6O  H10  H   HNH2  0   0.400   1.6229  -13.6542  28.6969
 N6O  H11  H   HNH2  0   0.408   0.5110  -12.4181  28.2577
 N6O  H12  H   HCR5  0   0.308  -3.4040  -12.1824  31.8380
 N6O  H13  H   HCR6  0   0.278   1.5406  -14.2719  37.0281
 N6O  H14  H   HCR6  0   0.268   0.4750  -13.9784  39.2514
 N6O  H15  H   HCR6  0   0.261  -1.9063  -13.2951  39.3922
 N6O  H16  H   HCR6  0   0.263  -3.1918  -12.8913  37.3303
 N6O  C    C   C     0   0.529   1.5261  -12.0979  30.0193
 N6O  CL   CL  CL    0  -0.131  -3.2742   -6.8679  31.1369

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
 N6O  N    C    single    1.340  0.020  1.340
 N6O  C    C1   single    1.519  0.020  1.519
 N6O  C    O1   double    1.221  0.020  1.221
 N6O  C1   C2   single    1.525  0.020  1.525
 N6O  C2   C3   single    1.514  0.020  1.514
 N6O  C2   N1   single    1.447  0.020  1.447
 N6O  CL   C7   single    1.735  0.020  1.735
 N6O  C8   C3   aromatic  1.391  0.020  1.391
 N6O  C8   C7   aromatic  1.385  0.020  1.385
 N6O  C3   C4   aromatic  1.389  0.020  1.389
 N6O  C7   C6   aromatic  1.387  0.020  1.387
 N6O  N1   C9   single    1.350  0.020  1.350
 N6O  C6   C5   aromatic  1.387  0.020  1.387
 N6O  C4   C5   aromatic  1.387  0.020  1.387
 N6O  C11  N2   aromatic  1.335  0.020  1.335
 N6O  C11  C10  aromatic  1.381  0.020  1.381
 N6O  C9   C10  single    1.473  0.020  1.473
 N6O  C9   O    double    1.222  0.020  1.222
 N6O  N2   N3   aromatic  1.326  0.020  1.326
 N6O  C10  C12  aromatic  1.416  0.020  1.416
 N6O  N3   C12  aromatic  1.321  0.020  1.321
 N6O  C12  C13  single    1.467  0.020  1.467
 N6O  F    C18  single    1.341  0.020  1.341
 N6O  C13  C18  aromatic  1.388  0.020  1.388
 N6O  C13  C14  aromatic  1.395  0.020  1.395
 N6O  C18  C17  aromatic  1.380  0.020  1.380
 N6O  C14  C15  aromatic  1.386  0.020  1.386
 N6O  C17  C16  aromatic  1.388  0.020  1.388
 N6O  C15  C16  aromatic  1.388  0.020  1.388
 N6O  N1   H1   single    0.860  0.020  1.020
 N6O  C8   H2   single    0.930  0.020  1.080
 N6O  N2   H3   single    0.860  0.020  1.020
 N6O  C1   H4   single    0.970  0.020  1.090
 N6O  C1   H5   single    0.970  0.020  1.090
 N6O  C5   H6   single    0.930  0.020  1.080
 N6O  C6   H7   single    0.930  0.020  1.080
 N6O  C4   H8   single    0.930  0.020  1.080
 N6O  C2   H9   single    0.970  0.020  1.090
 N6O  N    H10  single    0.860  0.020  1.020
 N6O  N    H11  single    0.860  0.020  1.020
 N6O  C11  H12  single    0.930  0.020  1.080
 N6O  C17  H13  single    0.930  0.020  1.080
 N6O  C16  H14  single    0.930  0.020  1.080
 N6O  C15  H15  single    0.930  0.020  1.080
 N6O  C14  H16  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
 N6O  H1   N1   C2   118.46  3.000
 N6O  H1   N1   C9   119.29  3.000
 N6O  C2   N1   C9   122.06  3.000
 N6O  CL   C7   C6   119.30  3.000
 N6O  C6   C7   C8   121.63  3.000
 N6O  CL   C7   C8   119.07  3.000
 N6O  H2   C8   C3   120.49  3.000
 N6O  H2   C8   C7   120.02  3.000
 N6O  C3   C8   C7   119.48  3.000
 N6O  H3   N2   C11  126.91  3.000
 N6O  H3   N2   N3   119.73  3.000
 N6O  C11  N2   N3   113.36  3.000
 N6O  C10  C9   O    121.94  3.000
 N6O  O    C9   N1   122.55  3.000
 N6O  C10  C9   N1   115.50  3.000
 N6O  H5   C1   H4   106.43  3.000
 N6O  H5   C1   C    111.73  3.000
 N6O  H4   C1   C    107.34  3.000
 N6O  H5   C1   C2   110.33  3.000
 N6O  H4   C1   C2   108.51  3.000
 N6O  C    C1   C2   112.23  3.000
 N6O  H6   C5   C4   120.05  3.000
 N6O  H6   C5   C6   119.44  3.000
 N6O  C4   C5   C6   120.52  3.000
 N6O  H7   C6   C5   120.74  3.000
 N6O  H7   C6   C7   120.75  3.000
 N6O  C5   C6   C7   118.52  3.000
 N6O  C12  N3   N2   105.42  3.000
 N6O  H8   C4   C3   119.63  3.000
 N6O  H8   C4   C5   119.88  3.000
 N6O  C3   C4   C5   120.49  3.000
 N6O  C2   C3   C4   119.93  3.000
 N6O  C4   C3   C8   119.36  3.000
 N6O  C2   C3   C8   120.68  3.000
 N6O  H9   C2   C3   107.98  3.000
 N6O  H9   C2   C1   108.16  3.000
 N6O  C3   C2   C1   110.30  3.000
 N6O  H9   C2   N1   108.66  3.000
 N6O  C3   C2   N1   112.33  3.000
 N6O  C1   C2   N1   109.30  3.000
 N6O  H11  N    H10  117.38  3.000
 N6O  H11  N    C    122.06  3.000
 N6O  H10  N    C    120.47  3.000
 N6O  C11  C10  C12  104.23  3.000
 N6O  C12  C10  C9   127.99  3.000
 N6O  C11  C10  C9   127.42  3.000
 N6O  C13  C12  C10  130.01  3.000
 N6O  C13  C12  N3   119.33  3.000
 N6O  C10  C12  N3   110.66  3.000
 N6O  H12  C11  C10  131.80  3.000
 N6O  H12  C11  N2   121.84  3.000
 N6O  C10  C11  N2   106.33  3.000
 N6O  C14  C13  C18  117.17  3.000
 N6O  C14  C13  C12  120.76  3.000
 N6O  C18  C13  C12  122.02  3.000
 N6O  C17  C18  F    118.34  3.000
 N6O  C17  C18  C13  122.86  3.000
 N6O  F    C18  C13  118.78  3.000
 N6O  H13  C17  C16  121.27  3.000
 N6O  H13  C17  C18  119.94  3.000
 N6O  C16  C17  C18  118.79  3.000
 N6O  H14  C16  C15  120.43  3.000
 N6O  H14  C16  C17  119.55  3.000
 N6O  C15  C16  C17  120.02  3.000
 N6O  H15  C15  C14  119.80  3.000
 N6O  H15  C15  C16  120.25  3.000
 N6O  C14  C15  C16  119.94  3.000
 N6O  H16  C14  C15  119.90  3.000
 N6O  H16  C14  C13  118.88  3.000
 N6O  C15  C14  C13  121.22  3.000
 N6O  N    C    C1   115.07  3.000
 N6O  C1   C    O1   121.61  3.000
 N6O  N    C    O1   123.31  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
 N6O  CONST_01  C4   C3   C8   C7      0.00   0.0  0
 N6O  CONST_02  C4   C5   C6   C7      0.00   0.0  0
 N6O  CONST_03  C5   C4   C3   C8      0.00   0.0  0
 N6O  CONST_04  C5   C6   C7   C8      0.00   0.0  0
 N6O  CONST_05  C12  C10  C11  N2      0.00   0.0  0
 N6O  CONST_06  C10  C12  N3   N2      0.00   0.0  0
 N6O  CONST_07  C13  C12  N3   N2    180.00   0.0  0
 N6O  CONST_08  C3   C8   C7   C6      0.00   0.0  0
 N6O  CONST_09  C3   C4   C5   C6      0.00   0.0  0
 N6O  CONST_10  C10  C11  N2   N3      0.00   0.0  0
 N6O  CONST_11  C11  C10  C12  N3      0.00   0.0  0
 N6O  CONST_16  C11  N2   N3   C12     0.00   0.0  0
 N6O  CONST_17  C17  C18  C13  C12   180.00   0.0  0
 N6O  CONST_18  C15  C14  C13  C12   180.00   0.0  0
 N6O  CONST_19  C13  C12  C10  C11   180.00   0.0  0
 N6O  CONST_20  C16  C17  C18  C13     0.00   0.0  0
 N6O  CONST_21  C16  C15  C14  C13     0.00   0.0  0
 N6O  CONST_22  C15  C14  C13  C18     0.00   0.0  0
 N6O  CONST_23  C15  C16  C17  C18     0.00   0.0  0
 N6O  CONST_24  C14  C13  C18  C17     0.00   0.0  0
 N6O  CONST_25  C14  C15  C16  C17     0.00   0.0  0
 N6O  CONST_26  C2   C3   C8   C7    180.00   0.0  0
 N6O  CONST_27  C9   C10  C11  N2    180.00   0.0  0
 N6O  CONST_28  N3   C12  C10  C9    180.00   0.0  0
 N6O  CONST_29  C13  C12  C10  C9      0.00   0.0  0
 N6O  CONST_30  CL   C7   C6   C5    180.00   0.0  0
 N6O  CONST_31  C2   C3   C4   C5    180.00   0.0  0
 N6O  CONST_32  CL   C7   C8   C3    180.00   0.0  0
 N6O  CONST_33  F    C18  C13  C12     0.00   0.0  0
 N6O  CONST_34  C14  C13  C18  F     180.00   0.0  0
 N6O  CONST_35  C16  C17  C18  F     180.00   0.0  0
 N6O  CONST_36  H6   C5   C6   C7    180.00   0.0  0
 N6O  CONST_37  H8   C4   C3   C8    180.00   0.0  0
 N6O  CONST_38  H7   C6   C7   C8    180.00   0.0  0
 N6O  CONST_39  H2   C8   C7   C6    180.00   0.0  0
 N6O  CONST_40  H8   C4   C5   C6    180.00   0.0  0
 N6O  CONST_41  H12  C11  N2   N3    180.00   0.0  0
 N6O  CONST_42  H2   C8   C3   C4    180.00   0.0  0
 N6O  CONST_43  H7   C6   C5   C4    180.00   0.0  0
 N6O  CONST_44  H6   C5   C4   C3    180.00   0.0  0
 N6O  CONST_45  H3   N2   C11  C10   180.00   0.0  0
 N6O  CONST_46  H12  C11  C10  C12   180.00   0.0  0
 N6O  CONST_47  H3   N2   N3   C12   180.00   0.0  0
 N6O  CONST_48  H16  C14  C13  C12     0.00   0.0  0
 N6O  CONST_49  H13  C17  C18  C13   180.00   0.0  0
 N6O  CONST_50  H15  C15  C14  C13   180.00   0.0  0
 N6O  CONST_51  H16  C14  C13  C18   180.00   0.0  0
 N6O  CONST_52  H14  C16  C17  C18   180.00   0.0  0
 N6O  CONST_53  H15  C15  C16  C17   180.00   0.0  0
 N6O  CONST_54  H16  C14  C15  C16   180.00   0.0  0
 N6O  CONST_55  H13  C17  C16  C15   180.00   0.0  0
 N6O  CONST_56  H14  C16  C15  C14   180.00   0.0  0
 N6O  CONST_57  C10  C9   N1   C2    180.00   0.0  0
 N6O  CONST_58  H1   N1   C9   C10     0.00   0.0  0
 N6O  CONST_59  O    C9   N1   C2      0.00   0.0  0
 N6O  CONST_60  H10  N    C    O1      0.00   0.0  0
 N6O  CONST_61  H11  N    C    O1    180.00   0.0  0
 N6O  CONST_62  H10  N    C    C1    180.00   0.0  0
 N6O  CONST_63  H11  N    C    C1      0.00   0.0  0
 N6O  CONST_64  H1   N1   C9   O     180.00   0.0  0
 N6O  Var_01    C11  C10  C9   N1    -32.06  30.0  2
 N6O  Var_02    C12  C10  C9   N1    155.94  30.0  2
 N6O  Var_03    C11  C10  C9   O     146.55  30.0  2
 N6O  Var_04    C12  C10  C9   O     -25.45  30.0  2
 N6O  Var_05    C2   C1   C    O1    -40.20  30.0  3
 N6O  Var_06    N    C    C1   C2    140.99  30.0  2
 N6O  Var_07    H4   C1   C    O1     78.94  30.0  3
 N6O  Var_08    H5   C1   C    O1   -164.73  30.0  3
 N6O  Var_09    H4   C1   C    N     -99.86  30.0  3
 N6O  Var_10    H5   C1   C    N      16.46  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
 N6O  chir_01  C2  C1  C3  N1  negativ

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
 N6O  plan-1  N2   0.020
 N6O  plan-1  C9   0.020
 N6O  plan-1  N3   0.020
 N6O  plan-1  C10  0.020
 N6O  plan-1  C12  0.020
 N6O  plan-1  C11  0.020
 N6O  plan-1  C13  0.020
 N6O  plan-1  H3   0.020
 N6O  plan-1  H12  0.020
 N6O  plan-2  C7   0.020
 N6O  plan-2  C8   0.020
 N6O  plan-2  C5   0.020
 N6O  plan-2  C6   0.020
 N6O  plan-2  C4   0.020
 N6O  plan-2  C3   0.020
 N6O  plan-2  C2   0.020
 N6O  plan-2  H2   0.020
 N6O  plan-2  H6   0.020
 N6O  plan-2  H7   0.020
 N6O  plan-2  H8   0.020
 N6O  plan-2  CL   0.020
 N6O  plan-3  C12  0.020
 N6O  plan-3  C13  0.020
 N6O  plan-3  C18  0.020
 N6O  plan-3  F    0.020
 N6O  plan-3  C17  0.020
 N6O  plan-3  C16  0.020
 N6O  plan-3  C15  0.020
 N6O  plan-3  C14  0.020
 N6O  plan-3  H13  0.020
 N6O  plan-3  H14  0.020
 N6O  plan-3  H15  0.020
 N6O  plan-3  H16  0.020
 N6O  plan-4  N1   0.020
 N6O  plan-4  C9   0.020
 N6O  plan-4  C2   0.020
 N6O  plan-4  O    0.020
 N6O  plan-4  C10  0.020
 N6O  plan-4  H1   0.020
 N6O  plan-5  O1   0.020
 N6O  plan-5  C1   0.020
 N6O  plan-5  N    0.020
 N6O  plan-5  H10  0.020
 N6O  plan-5  H11  0.020
 N6O  plan-5  C    0.020

