# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Mar 21 08:06:30 2022
#   Inital geometry file: a 92 line input string
#   Ligand name: 1-[1-(3-fluorophenyl)-6,7-dihydro-4~{H}-pyrazolo[4,3-c]pyridin-5-yl]propan-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC(=O)N1CCc2n(ncc2C1)c3cccc(F)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
 QPN  QPN  1-[1-(3-fluorophenyl)-6,7-dihydro-4~{H}-pyrazolo[4,3-c]pyridin-5-yl]propan-1-one  ligand  36  20  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_QPN
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
 QPN  C6   C  CH2   0  -0.352  23.2836   3.2673   9.0529
 QPN  C7   C  CH2   0  -0.510  21.9049   3.3054   9.7138
 QPN  C8   C  CR5   0   0.435  21.1552   2.1170   9.2208
 QPN  C10  C  CH2   0  -0.352  23.2005   0.9499   8.3260
 QPN  N12  N  N     0  -0.274  19.5050   0.7270   8.6328
 QPN  C15  C  CR16  0  -0.298  17.5714   2.7583   9.1015
 QPN  C17  C  CR16  0  -0.413  16.7605   4.3191  10.7593
 QPN  C20  C  CR16  0  -0.458  18.9996   3.4083  10.9360
 QPN  C1   C  CH3   0  -0.661  26.4935   3.3624  10.4666
 QPN  C2   C  CH2   0  -0.576  25.2894   2.6195  11.0463
 QPN  O4   O  O     0  -0.492  25.1870   0.4141  10.1605
 QPN  N5   N  NT    0  -0.454  23.8711   1.9429   9.1507
 QPN  C9   C  CR5   0  -0.202  21.7274   1.0581   8.5630
 QPN  C11  C  CR15  0  -0.072  20.6479   0.2262   8.2165
 QPN  N13  N  NR5   0  -0.470  19.8177   1.8748   9.2493
 QPN  C14  C  CR6   0   0.358  18.7918   2.6863   9.7668
 QPN  C16  C  CR16  0  -0.235  16.5658   3.5643   9.6101
 QPN  C18  C  CR6   0   0.540  17.9830   4.2246  11.3924
 QPN  F19  F  F     0  -0.311  18.1990   4.9374  12.5066
 QPN  H1   H  HCH2  0   0.284  23.9362   4.0188   9.4861
 QPN  H2   H  HCH2  0   0.273  23.1894   3.5148   7.9926
 QPN  H3   H  HCH2  0   0.276  21.3967   4.2393   9.4635
 QPN  H4   H  HCH2  0   0.271  22.0224   3.2838  10.8009
 QPN  H5   H  HCH2  0   0.275  23.5732  -0.0398   8.5793
 QPN  H6   H  HCH2  0   0.260  23.4415   1.1239   7.2721
 QPN  H7   H  HCR6  0   0.276  17.4130   2.1928   8.1946
 QPN  H8   H  HCR6  0   0.283  15.9824   4.9605  11.1507
 QPN  H9   H  HCR6  0   0.297  19.9152   3.3311  11.5057
 QPN  H10  H  HCH3  0   0.244  26.8887   4.0672  11.1969
 QPN  H11  H  HCH3  0   0.235  27.2916   2.6669  10.2079
 QPN  H12  H  HCH3  0   0.232  26.2353   3.9236   9.5682
 QPN  H13  H  HCH2  0   0.267  25.5917   2.0964  11.9534
 QPN  H14  H  HCH2  0   0.255  24.5128   3.3266  11.3388
 QPN  H15  H  HCR5  0   0.264  20.6669  -0.7171   7.6905
 QPN  H16  H  HCR6  0   0.275  15.6171   3.6179   9.0936
 QPN  C3   C  C     0   0.534  24.7691   1.5622  10.0933

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
 QPN  C11  N12  aromatic  1.315  0.020  1.315
 QPN  C11  C9   aromatic  1.406  0.020  1.406
 QPN  N12  N13  aromatic  1.340  0.020  1.340
 QPN  C15  C16  aromatic  1.386  0.020  1.386
 QPN  C15  C14  aromatic  1.392  0.020  1.392
 QPN  C9   C10  single    1.496  0.020  1.496
 QPN  C9   C8   aromatic  1.372  0.020  1.372
 QPN  C10  N5   single    1.454  0.020  1.454
 QPN  C16  C17  aromatic  1.389  0.020  1.389
 QPN  N13  C8   aromatic  1.360  0.020  1.360
 QPN  N13  C14  single    1.407  0.020  1.407
 QPN  C8   C7   single    1.489  0.020  1.489
 QPN  N5   C6   single    1.452  0.020  1.452
 QPN  N5   C3   single    1.356  0.020  1.356
 QPN  C14  C20  aromatic  1.390  0.020  1.390
 QPN  C1   C2   single    1.529  0.020  1.529
 QPN  C6   C7   single    1.529  0.020  1.529
 QPN  O4   C3   double    1.224  0.020  1.224
 QPN  C3   C2   single    1.516  0.020  1.516
 QPN  C17  C18  aromatic  1.380  0.020  1.380
 QPN  C20  C18  aromatic  1.381  0.020  1.381
 QPN  C18  F19  single    1.340  0.020  1.340
 QPN  C6   H1   single    0.970  0.020  1.090
 QPN  C6   H2   single    0.970  0.020  1.090
 QPN  C7   H3   single    0.970  0.020  1.090
 QPN  C7   H4   single    0.970  0.020  1.090
 QPN  C10  H5   single    0.970  0.020  1.090
 QPN  C10  H6   single    0.970  0.020  1.090
 QPN  C15  H7   single    0.930  0.020  1.080
 QPN  C17  H8   single    0.930  0.020  1.080
 QPN  C20  H9   single    0.930  0.020  1.080
 QPN  C1   H10  single    0.970  0.020  1.090
 QPN  C1   H11  single    0.970  0.020  1.090
 QPN  C1   H12  single    0.970  0.020  1.090
 QPN  C2   H13  single    0.970  0.020  1.090
 QPN  C2   H14  single    0.970  0.020  1.090
 QPN  C11  H15  single    0.930  0.020  1.080
 QPN  C16  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
 QPN  H2   C6   H1   106.39  3.000
 QPN  H2   C6   N5   107.87  3.000
 QPN  H1   C6   N5   111.18  3.000
 QPN  H2   C6   C7   109.63  3.000
 QPN  H1   C6   C7   110.62  3.000
 QPN  N5   C6   C7   111.00  3.000
 QPN  H4   C7   H3   107.13  3.000
 QPN  H4   C7   C8   111.56  3.000
 QPN  H3   C7   C8   111.85  3.000
 QPN  H4   C7   C6   109.41  3.000
 QPN  H3   C7   C6   109.98  3.000
 QPN  C8   C7   C6   106.91  3.000
 QPN  N13  C8   C9   106.44  3.000
 QPN  N13  C8   C7   129.09  3.000
 QPN  C9   C8   C7   124.39  3.000
 QPN  H6   C10  H5   107.06  3.000
 QPN  H6   C10  C9   110.96  3.000
 QPN  H5   C10  C9   111.49  3.000
 QPN  H6   C10  N5   109.62  3.000
 QPN  H5   C10  N5   109.35  3.000
 QPN  C9   C10  N5   108.35  3.000
 QPN  N13  N12  C11  105.60  3.000
 QPN  H7   C15  C16  120.41  3.000
 QPN  H7   C15  C14  120.18  3.000
 QPN  C16  C15  C14  119.41  3.000
 QPN  H8   C17  C18  120.79  3.000
 QPN  H8   C17  C16  121.39  3.000
 QPN  C18  C17  C16  117.82  3.000
 QPN  H9   C20  C18  119.43  3.000
 QPN  H9   C20  C14  122.20  3.000
 QPN  C18  C20  C14  118.35  3.000
 QPN  H12  C1   H11  107.84  3.000
 QPN  H12  C1   H10  107.77  3.000
 QPN  H11  C1   H10  107.85  3.000
 QPN  H12  C1   C2   112.08  3.000
 QPN  H11  C1   C2   110.90  3.000
 QPN  H10  C1   C2   110.24  3.000
 QPN  H14  C2   H13  106.59  3.000
 QPN  H14  C2   C3   112.12  3.000
 QPN  H13  C2   C3   106.48  3.000
 QPN  H14  C2   C1   110.34  3.000
 QPN  H13  C2   C1   109.29  3.000
 QPN  C3   C2   C1   111.78  3.000
 QPN  C3   N5   C10  120.51  3.000
 QPN  C3   N5   C6   124.79  3.000
 QPN  C10  N5   C6   113.45  3.000
 QPN  C11  C9   C10  132.39  3.000
 QPN  C10  C9   C8   122.86  3.000
 QPN  C11  C9   C8   104.75  3.000
 QPN  H15  C11  C9   128.54  3.000
 QPN  H15  C11  N12  120.12  3.000
 QPN  C9   C11  N12  111.33  3.000
 QPN  C14  N13  N12  119.55  3.000
 QPN  C14  N13  C8   128.50  3.000
 QPN  N12  N13  C8   111.87  3.000
 QPN  N13  C14  C20  120.01  3.000
 QPN  C20  C14  C15  120.42  3.000
 QPN  N13  C14  C15  119.57  3.000
 QPN  H16  C16  C17  119.43  3.000
 QPN  H16  C16  C15  119.35  3.000
 QPN  C17  C16  C15  121.21  3.000
 QPN  F19  C18  C20  118.06  3.000
 QPN  F19  C18  C17  119.19  3.000
 QPN  C20  C18  C17  122.75  3.000
 QPN  N5   C3   O4   121.84  3.000
 QPN  O4   C3   C2   120.18  3.000
 QPN  N5   C3   C2   117.94  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
 QPN  CONST_01  N12  C11  C9   C8      0.00   0.0  0
 QPN  CONST_02  C11  N12  N13  C8      0.00   0.0  0
 QPN  CONST_05  C9   C8   N13  N12     0.00   0.0  0
 QPN  CONST_08  C18  C17  C16  C15     0.00   0.0  0
 QPN  CONST_09  C18  C20  C14  C15     0.00   0.0  0
 QPN  CONST_10  C14  C15  C16  C17     0.00   0.0  0
 QPN  CONST_11  C14  C20  C18  C17     0.00   0.0  0
 QPN  CONST_12  C16  C15  C14  C20     0.00   0.0  0
 QPN  CONST_13  C16  C17  C18  C20     0.00   0.0  0
 QPN  CONST_14  N13  N12  C11  C9      0.00   0.0  0
 QPN  CONST_15  C14  N13  C8   C9    180.00   0.0  0
 QPN  CONST_16  C14  N13  N12  C11   180.00   0.0  0
 QPN  CONST_17  N13  C8   C9   C11     0.00   0.0  0
 QPN  CONST_18  C16  C15  C14  N13   180.00   0.0  0
 QPN  CONST_19  C18  C20  C14  N13   180.00   0.0  0
 QPN  CONST_20  C14  N13  C8   C7      0.00   0.0  0
 QPN  CONST_21  F19  C18  C20  C14   180.00   0.0  0
 QPN  CONST_22  F19  C18  C17  C16   180.00   0.0  0
 QPN  CONST_23  H15  C11  C9   C8    180.00   0.0  0
 QPN  CONST_24  H8   C17  C16  C15   180.00   0.0  0
 QPN  CONST_25  H9   C20  C14  C15   180.00   0.0  0
 QPN  CONST_26  H7   C15  C16  C17   180.00   0.0  0
 QPN  CONST_27  H16  C16  C15  C14   180.00   0.0  0
 QPN  CONST_28  O4   C3   N5   C6    180.00   0.0  0
 QPN  CONST_29  C2   C3   N5   C6      0.00   0.0  0
 QPN  CONST_30  O4   C3   N5   C10     0.00   0.0  0
 QPN  CONST_31  C2   C3   N5   C10   180.00   0.0  0
 QPN  Var_01    C9   C10  N5   C6    -48.33  30.0  1
 QPN  Var_02    C9   C8   C7   C6     13.76  30.0  1
 QPN  Var_03    C10  N5   C6   C7     69.77  30.0  1
 QPN  Var_04    N5   C10  C9   C8     12.83  30.0  1
 QPN  Var_05    N5   C6   C7   C8    -47.27  30.0  1
 QPN  Var_06    N5   C3   C2   C1    -86.35  30.0  1
 QPN  Var_07    H10  C1   C2   C3   -176.14  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
 QPN  plan-1  C15  0.020
 QPN  plan-1  C17  0.020
 QPN  plan-1  C20  0.020
 QPN  plan-1  N13  0.020
 QPN  plan-1  C14  0.020
 QPN  plan-1  C16  0.020
 QPN  plan-1  C18  0.020
 QPN  plan-1  F19  0.020
 QPN  plan-1  H7   0.020
 QPN  plan-1  H8   0.020
 QPN  plan-1  H9   0.020
 QPN  plan-1  H16  0.020
 QPN  plan-2  C7   0.020
 QPN  plan-2  C8   0.020
 QPN  plan-2  C10  0.020
 QPN  plan-2  N12  0.020
 QPN  plan-2  C9   0.020
 QPN  plan-2  C11  0.020
 QPN  plan-2  N13  0.020
 QPN  plan-2  C14  0.020
 QPN  plan-2  H15  0.020
 QPN  plan-3  C6   0.020
 QPN  plan-3  C10  0.020
 QPN  plan-3  C2   0.020
 QPN  plan-3  O4   0.020
 QPN  plan-3  N5   0.020
 QPN  plan-3  C3   0.020

