# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr  4 19:24:55 2020
#   Inital geometry file: a 96 line input string
#   Ligand name: 3-(4-fluorophenyl)-5-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Fc1ccc(cc1)c2[nH]nc3CCN(Cc23)c4ccccn4
#
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
 4V9  4V9  3-(4-fluorophenyl)-5-(pyridin-2-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine  ligand  37  22  .  2021-08-04  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_4V9
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
 4V9  C1   C  CR6   0   0.542  -3.1411  -0.5853  -0.0927
 4V9  C2   C  CR16  0  -0.060  -3.5982  -2.8048   0.2979
 4V9  C3   C  CR16  0  -0.370  -4.9603  -2.6025   0.3871
 4V9  C11  C  CR5   0   0.426   1.4391   1.2956   0.1761
 4V9  C12  C  CR6   0   0.050   2.5400   0.3416   0.0700
 4V9  C13  C  CR16  0  -0.286   3.8182   0.7617  -0.3083
 4V9  C14  C  CR16  0  -0.397   4.8675  -0.1365  -0.4108
 4V9  C15  C  CR6   0   0.521   4.6278  -1.4700  -0.1404
 4V9  C16  C  CR16  0  -0.393   3.3783  -1.9260   0.2309
 4V9  C17  C  CR16  0  -0.310   2.3409  -1.0137   0.3373
 4V9  F    F  F     0  -0.311   5.6367  -2.3472  -0.2437
 4V9  C7   C  CR56  0  -0.216   0.0693   1.1610   0.0223
 4V9  C6   C  C     0  -0.331  -0.7822  -0.0279  -0.2890
 4V9  N4   N  NR15  0  -0.521   1.6415   2.6086   0.4252
 4V9  N3   N  N     0  -0.288   0.5266   3.3291   0.4360
 4V9  C8   C  CR56  0   0.228  -0.4350   2.4599   0.1860
 4V9  C9   C  C     0  -0.499  -1.8783   2.7775   0.0137
 4V9  C10  C  C     0  -0.329  -2.4761   1.6759  -0.8557
 4V9  N1   N  NR6   0  -0.520  -2.1813   0.3656  -0.3053
 4V9  C5   C  CR16  0  -0.404  -4.5166  -0.2749  -0.0063
 4V9  C4   C  CR16  0  -0.150  -5.4120  -1.2936   0.2296
 4V9  N2   N  N     0  -0.485  -2.7158  -1.8405   0.0601
 4V9  H1   H  HCR6  0   0.253  -3.1851  -3.8012   0.4185
 4V9  H2   H  HCR6  0   0.257  -5.6373  -3.4239   0.5728
 4V9  H3   H  HCR6  0   0.266   4.0090   1.8002  -0.5462
 4V9  H4   H  HCR6  0   0.286   5.8532   0.1974  -0.7069
 4V9  H5   H  HCR6  0   0.286   3.2142  -2.9743   0.4416
 4V9  H6   H  HCR6  0   0.267   1.3712  -1.3730   0.6513
 4V9  H7   H  H     0   0.241  -0.4812  -0.4849  -1.2423
 4V9  H8   H  H     0   0.266  -0.6616  -0.7997   0.4694
 4V9  H9   H  HNR5  0   0.419   2.5196   3.0565   0.6355
 4V9  H10  H  H     0   0.254  -2.3983   2.8106   0.9752
 4V9  H11  H  H     0   0.254  -2.0166   3.7495  -0.4629
 4V9  H12  H  H     0   0.270  -3.5474   1.8181  -0.9500
 4V9  H13  H  H     0   0.248  -2.0654   1.7493  -1.8698
 4V9  H14  H  HCR6  0   0.269  -4.8824   0.7370  -0.0971
 4V9  H15  H  HCR6  0   0.266  -6.4679  -1.0659   0.3013

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
 4V9  C9   C10  single    1.525  0.020  1.525
 4V9  C9   C8   single    1.488  0.020  1.488
 4V9  C10  N1   single    1.452  0.020  1.452
 4V9  N3   C8   aromatic  1.320  0.020  1.320
 4V9  N3   N4   aromatic  1.327  0.020  1.327
 4V9  C8   C7   aromatic  1.403  0.020  1.403
 4V9  N4   C11  aromatic  1.352  0.020  1.352
 4V9  N2   C2   aromatic  1.329  0.020  1.329
 4V9  N2   C1   aromatic  1.334  0.020  1.334
 4V9  N1   C6   single    1.454  0.020  1.454
 4V9  N1   C1   single    1.368  0.020  1.368
 4V9  C7   C11  aromatic  1.385  0.020  1.385
 4V9  C7   C6   single    1.495  0.020  1.495
 4V9  C11  C12  single    1.461  0.020  1.461
 4V9  C2   C3   aromatic  1.380  0.020  1.380
 4V9  C1   C5   aromatic  1.413  0.020  1.413
 4V9  C17  C12  aromatic  1.396  0.020  1.396
 4V9  C17  C16  aromatic  1.386  0.020  1.386
 4V9  C12  C13  aromatic  1.398  0.020  1.398
 4V9  C3   C4   aromatic  1.394  0.020  1.394
 4V9  C5   C4   aromatic  1.377  0.020  1.377
 4V9  C16  C15  aromatic  1.381  0.020  1.381
 4V9  C13  C14  aromatic  1.385  0.020  1.385
 4V9  C15  C14  aromatic  1.382  0.020  1.382
 4V9  C15  F    single    1.341  0.020  1.341
 4V9  C2   H1   single    0.930  0.020  1.080
 4V9  C3   H2   single    0.930  0.020  1.080
 4V9  C13  H3   single    0.930  0.020  1.080
 4V9  C14  H4   single    0.930  0.020  1.080
 4V9  C16  H5   single    0.930  0.020  1.080
 4V9  C17  H6   single    0.930  0.020  1.080
 4V9  C6   H7   single    0.970  0.020  1.090
 4V9  C6   H8   single    0.970  0.020  1.090
 4V9  N4   H9   single    0.860  0.020  1.020
 4V9  C9   H10  single    0.970  0.020  1.090
 4V9  C9   H11  single    0.970  0.020  1.090
 4V9  C10  H12  single    0.970  0.020  1.090
 4V9  C10  H13  single    0.970  0.020  1.090
 4V9  C5   H14  single    0.930  0.020  1.080
 4V9  C4   H15  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
 4V9  N2   C1   C5   120.67  3.000
 4V9  C5   C1   N1   122.68  3.000
 4V9  N2   C1   N1   116.63  3.000
 4V9  H1   C2   N2   115.68  3.000
 4V9  H1   C2   C3   120.20  3.000
 4V9  N2   C2   C3   124.11  3.000
 4V9  H2   C3   C4   122.03  3.000
 4V9  H2   C3   C2   121.21  3.000
 4V9  C4   C3   C2   116.76  3.000
 4V9  N4   C11  C7   105.25  3.000
 4V9  C7   C11  C12  132.37  3.000
 4V9  N4   C11  C12  122.34  3.000
 4V9  C17  C12  C13  118.31  3.000
 4V9  C13  C12  C11  120.84  3.000
 4V9  C17  C12  C11  120.85  3.000
 4V9  H3   C13  C14  118.19  3.000
 4V9  H3   C13  C12  120.61  3.000
 4V9  C14  C13  C12  121.19  3.000
 4V9  H4   C14  C15  120.63  3.000
 4V9  H4   C14  C13  120.68  3.000
 4V9  C15  C14  C13  118.68  3.000
 4V9  F    C15  C16  119.04  3.000
 4V9  F    C15  C14  119.06  3.000
 4V9  C16  C15  C14  121.90  3.000
 4V9  H5   C16  C17  120.64  3.000
 4V9  H5   C16  C15  120.64  3.000
 4V9  C17  C16  C15  118.73  3.000
 4V9  H6   C17  C16  118.37  3.000
 4V9  H6   C17  C12  120.43  3.000
 4V9  C16  C17  C12  121.19  3.000
 4V9  C8   C7   C6   123.77  3.000
 4V9  C6   C7   C11  131.58  3.000
 4V9  C8   C7   C11  104.63  3.000
 4V9  H8   C6   H7   106.20  3.000
 4V9  H8   C6   N1   107.83  3.000
 4V9  H7   C6   N1   111.49  3.000
 4V9  H8   C6   C7   110.83  3.000
 4V9  H7   C6   C7   110.81  3.000
 4V9  N1   C6   C7   109.59  3.000
 4V9  H9   N4   N3   119.26  3.000
 4V9  H9   N4   C11  126.92  3.000
 4V9  N3   N4   C11  113.76  3.000
 4V9  C8   N3   N4   104.65  3.000
 4V9  C9   C8   N3   126.02  3.000
 4V9  N3   C8   C7   111.70  3.000
 4V9  C9   C8   C7   122.20  3.000
 4V9  H11  C9   H10  107.26  3.000
 4V9  H11  C9   C10  110.16  3.000
 4V9  H10  C9   C10  109.67  3.000
 4V9  H11  C9   C8   111.32  3.000
 4V9  H10  C9   C8   111.47  3.000
 4V9  C10  C9   C8   106.98  3.000
 4V9  H13  C10  H12  106.30  3.000
 4V9  H13  C10  N1   109.57  3.000
 4V9  H12  C10  N1   110.59  3.000
 4V9  H13  C10  C9   109.40  3.000
 4V9  H12  C10  C9   110.00  3.000
 4V9  N1   C10  C9   110.87  3.000
 4V9  C10  N1   C6   116.36  3.000
 4V9  C6   N1   C1   119.05  3.000
 4V9  C10  N1   C1   122.96  3.000
 4V9  H14  C5   C4   119.18  3.000
 4V9  H14  C5   C1   122.04  3.000
 4V9  C4   C5   C1   118.76  3.000
 4V9  H15  C4   C5   119.35  3.000
 4V9  H15  C4   C3   120.41  3.000
 4V9  C5   C4   C3   120.24  3.000
 4V9  C2   N2   C1   119.45  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
 4V9  CONST_01  C3   C2   N2   C1      0.00   0.0  0
 4V9  CONST_02  C3   C4   C5   C1      0.00   0.0  0
 4V9  CONST_03  C5   C1   N2   C2      0.00   0.0  0
 4V9  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 4V9  CONST_05  C8   N3   N4   C11     0.00   0.0  0
 4V9  CONST_06  N3   C8   C7   C11     0.00   0.0  0
 4V9  CONST_07  C16  C17  C12  C11   180.00   0.0  0
 4V9  CONST_08  C14  C13  C12  C11   180.00   0.0  0
 4V9  CONST_09  N3   N4   C11  C12   180.00   0.0  0
 4V9  CONST_10  C8   C7   C11  C12   180.00   0.0  0
 4V9  CONST_11  C15  C16  C17  C12     0.00   0.0  0
 4V9  CONST_12  C15  C14  C13  C12     0.00   0.0  0
 4V9  CONST_15  C16  C17  C12  C13     0.00   0.0  0
 4V9  CONST_16  C16  C15  C14  C13     0.00   0.0  0
 4V9  CONST_17  C17  C12  C13  C14     0.00   0.0  0
 4V9  CONST_18  C17  C16  C15  C14     0.00   0.0  0
 4V9  CONST_21  N4   N3   C8   C7      0.00   0.0  0
 4V9  CONST_22  N3   N4   C11  C7      0.00   0.0  0
 4V9  CONST_23  C8   C7   C11  N4      0.00   0.0  0
 4V9  CONST_24  N2   C2   C3   C4      0.00   0.0  0
 4V9  CONST_25  N2   C1   C5   C4      0.00   0.0  0
 4V9  CONST_26  N1   C1   N2   C2    180.00   0.0  0
 4V9  CONST_27  C6   C7   C11  C12     0.00   0.0  0
 4V9  CONST_28  C4   C5   C1   N1    180.00   0.0  0
 4V9  CONST_29  F    C15  C14  C13   180.00   0.0  0
 4V9  CONST_30  F    C15  C16  C17   180.00   0.0  0
 4V9  CONST_31  H1   C2   N2   C1    180.00   0.0  0
 4V9  CONST_32  H15  C4   C5   C1    180.00   0.0  0
 4V9  CONST_33  H14  C5   C4   C3    180.00   0.0  0
 4V9  CONST_34  H6   C17  C12  C11     0.00   0.0  0
 4V9  CONST_35  H3   C13  C12  C11     0.00   0.0  0
 4V9  CONST_36  H9   N4   C11  C12     0.00   0.0  0
 4V9  CONST_37  H5   C16  C17  C12   180.00   0.0  0
 4V9  CONST_38  H4   C14  C13  C12   180.00   0.0  0
 4V9  CONST_39  H2   C3   C4   C5    180.00   0.0  0
 4V9  Var_01    C9   C10  N1   C1    129.12  30.0  1
 4V9  Var_02    C7   C6   N1   C1   -156.86  30.0  1
 4V9  Var_03    N1   C6   C7   C11   178.48  30.0  1
 4V9  Var_04    C10  C9   C8   C7    -22.11  30.0  1
 4V9  Var_05    N2   C1   N1   C6     -2.85  30.0  2
 4V9  Var_06    N1   C10  C9   C8     53.02  30.0  1

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
 4V9  plan-1  C11  0.020
 4V9  plan-1  C12  0.020
 4V9  plan-1  C13  0.020
 4V9  plan-1  C14  0.020
 4V9  plan-1  C15  0.020
 4V9  plan-1  C16  0.020
 4V9  plan-1  C17  0.020
 4V9  plan-1  F    0.020
 4V9  plan-1  H3   0.020
 4V9  plan-1  H4   0.020
 4V9  plan-1  H5   0.020
 4V9  plan-1  H6   0.020
 4V9  plan-2  C1   0.020
 4V9  plan-2  C2   0.020
 4V9  plan-2  C3   0.020
 4V9  plan-2  N1   0.020
 4V9  plan-2  C5   0.020
 4V9  plan-2  C4   0.020
 4V9  plan-2  N2   0.020
 4V9  plan-2  H1   0.020
 4V9  plan-2  H2   0.020
 4V9  plan-2  H14  0.020
 4V9  plan-2  H15  0.020
 4V9  plan-3  C11  0.020
 4V9  plan-3  C12  0.020
 4V9  plan-3  C7   0.020
 4V9  plan-3  C6   0.020
 4V9  plan-3  N4   0.020
 4V9  plan-3  N3   0.020
 4V9  plan-3  C8   0.020
 4V9  plan-3  C9   0.020
 4V9  plan-3  H9   0.020

