# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 03:33:19 2020
#   Inital geometry file: a 125 line input string
#   Ligand name: 8-[4-(1-cyclopentylpiperidin-4-yl)pyrazol-1-yl]-3~{H}-pyrido[3,4-d]pyrimidin-4-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O=C1NC=Nc2c1ccnc2n3cc(cn3)C4CCN(CC4)C5CCCC5
#
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
 FQN  FQN  8-[4-(1-cyclopentylpiperidin-4-yl)pyrazol-1-yl]-3~{H}-pyrido[3,4-d]pyrimidin-4-one  ligand  51  27  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_FQN
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
 FQN  C5   C  CR6   0   0.580  -6.5900   0.4782   0.2182
 FQN  C7   C  CR15  0  -0.082  -0.1048   0.8761  -0.8611
 FQN  C8   C  CR5   0  -0.079   0.4265  -0.1605  -0.0563
 FQN  C3   C  CR66  0   0.156  -4.1496   0.1602   0.0347
 FQN  N1   N  NR16  0  -0.659  -6.2299   1.7806   0.4678
 FQN  C6   C  CR16  0   0.152  -4.9446   2.2129   0.5241
 FQN  C11  C  CH2   0  -0.413   2.6599  -0.9036  -0.9141
 FQN  C10  C  CH1   0  -0.361   1.8544  -0.4241   0.2939
 FQN  C9   C  CR15  0   0.006  -0.6769  -0.8859   0.3063
 FQN  C14  C  CH2   0  -0.414   2.5514   0.7972   0.8895
 FQN  O    O  O     0  -0.434  -7.7490   0.1190   0.1865
 FQN  C4   C  CR66  0  -0.017  -5.4328  -0.3965   0.0047
 FQN  C    C  CR16  0  -0.356  -5.6002  -1.7652  -0.1949
 FQN  N2   N  N     0  -0.430  -3.9147   1.4789   0.3188
 FQN  C2   C  CR6   0   0.439  -3.0791  -0.7321  -0.2029
 FQN  N    N  N     0  -0.399  -3.2406  -2.0199  -0.3657
 FQN  C1   C  CR16  0  -0.064  -4.4719  -2.5366  -0.3471
 FQN  N3   N  NR5   0  -0.370  -1.7546  -0.2729  -0.2478
 FQN  N4   N  N     0  -0.268  -1.4122   0.7983  -0.9689
 FQN  C13  C  CH2   0  -0.287   4.0134   0.5046   1.1906
 FQN  N5   N  NT    0  -0.429   4.7306   0.0675   0.0030
 FQN  C12  C  CH2   0  -0.290   4.1156  -1.1328  -0.5413
 FQN  H1   H  HCR5  0   0.259   0.4291   1.6681  -1.3657
 FQN  H2   H  HNR6  0   0.440  -6.9701   2.4500   0.6390
 FQN  H3   H  HCR6  0   0.307  -4.8236   3.2616   0.7640
 FQN  H5   H  HCH2  0   0.218   2.6012  -0.1598  -1.7154
 FQN  H6   H  HCH1  0   0.234   1.8754  -1.2223   1.0462
 FQN  H7   H  HCR5  0   0.291  -0.7770  -1.7664   0.9202
 FQN  H8   H  HCH2  0   0.217   2.4929   1.6367   0.1893
 FQN  H9   H  HCH2  0   0.236   2.0494   1.1100   1.8080
 FQN  H10  H  HCR6  0   0.286  -6.5846  -2.2108  -0.2166
 FQN  H11  H  HCR6  0   0.282  -4.5448  -3.6088  -0.4756
 FQN  H12  H  HCH2  0   0.244   4.4770   1.4131   1.5761
 FQN  H13  H  HCH2  0   0.182   4.0745  -0.2496   1.9977
 FQN  H16  H  HCH2  0   0.183   4.1753  -1.9711   0.1786
 FQN  H17  H  HCH2  0   0.246   4.6636  -1.4470  -1.4306
 FQN  C15  C  CH1   0  -0.018   6.1456  -0.1460   0.2643
 FQN  C16  C  CH2   0  -0.468   6.9496  -0.4475  -1.0199
 FQN  C17  C  CH2   0  -0.443   8.3246   0.2307  -0.8459
 FQN  C18  C  CH2   0  -0.446   8.3357   0.7535   0.5930
 FQN  C19  C  CH2   0  -0.470   6.8699   1.0579   0.8730
 FQN  H14  H  HCH1  0   0.185   6.2743  -0.9922   0.9662
 FQN  H15  H  HCH2  0   0.232   7.0465  -1.5200  -1.1911
 FQN  H18  H  HCH2  0   0.227   6.4208  -0.0343  -1.8818
 FQN  H19  H  HCH2  0   0.229   9.1541  -0.4479  -1.0479
 FQN  H20  H  HCH2  0   0.224   8.4221   1.0652  -1.5429
 FQN  H21  H  HCH2  0   0.218   8.6852  -0.0258   1.2763
 FQN  H22  H  HCH2  0   0.231   8.9881   1.6170   0.7299
 FQN  H23  H  HCH2  0   0.217   6.5638   1.9706   0.3503
 FQN  H24  H  HCH2  0   0.236   6.6647   1.1977   1.9353
 FQN  H4   H  HCH2  0   0.235   2.2372  -1.8313  -1.3068

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
 FQN  C13  C14  single    1.521  0.020  1.521
 FQN  C13  N5   single    1.455  0.020  1.455
 FQN  C14  C10  single    1.527  0.020  1.527
 FQN  N5   C12  single    1.454  0.020  1.454
 FQN  C7   N4   aromatic  1.314  0.020  1.314
 FQN  C7   C8   aromatic  1.416  0.020  1.416
 FQN  C10  C8   single    1.494  0.020  1.494
 FQN  C10  C11  single    1.529  0.020  1.529
 FQN  N4   N3   aromatic  1.336  0.020  1.336
 FQN  C8   C9   aromatic  1.369  0.020  1.369
 FQN  N3   C9   aromatic  1.358  0.020  1.358
 FQN  N3   C2   single    1.403  0.020  1.403
 FQN  N    C2   aromatic  1.308  0.020  1.308
 FQN  N    C1   aromatic  1.335  0.020  1.335
 FQN  C2   C3   aromatic  1.414  0.020  1.414
 FQN  C12  C11  single    1.520  0.020  1.520
 FQN  N2   C3   single    1.369  0.020  1.369
 FQN  N2   C6   double    1.281  0.020  1.281
 FQN  C1   C    aromatic  1.375  0.020  1.375
 FQN  C3   C4   aromatic  1.399  0.020  1.399
 FQN  C6   N1   single    1.357  0.020  1.357
 FQN  C    C4   aromatic  1.393  0.020  1.393
 FQN  C4   C5   single    1.466  0.020  1.466
 FQN  N1   C5   single    1.374  0.020  1.374
 FQN  C5   O    double    1.214  0.020  1.214
 FQN  C7   H1   single    0.930  0.020  1.080
 FQN  N1   H2   single    0.860  0.020  1.020
 FQN  C6   H3   single    0.930  0.020  1.080
 FQN  C11  H4   single    0.970  0.020  1.090
 FQN  C11  H5   single    0.970  0.020  1.090
 FQN  C10  H6   single    0.970  0.020  1.090
 FQN  C9   H7   single    0.930  0.020  1.080
 FQN  C14  H8   single    0.970  0.020  1.090
 FQN  C14  H9   single    0.970  0.020  1.090
 FQN  C    H10  single    0.930  0.020  1.080
 FQN  C1   H11  single    0.930  0.020  1.080
 FQN  C13  H12  single    0.970  0.020  1.090
 FQN  C13  H13  single    0.970  0.020  1.090
 FQN  C12  H16  single    0.970  0.020  1.090
 FQN  C12  H17  single    0.970  0.020  1.090
 FQN  N5   C15  single    1.455  0.020  1.455
 FQN  C15  C16  single    1.545  0.020  1.545
 FQN  C16  C17  single    1.543  0.020  1.543
 FQN  C17  C18  single    1.531  0.020  1.531
 FQN  C18  C19  single    1.523  0.020  1.523
 FQN  C19  C15  single    1.531  0.020  1.531
 FQN  C15  H14  single    0.970  0.020  1.090
 FQN  C16  H15  single    0.970  0.020  1.090
 FQN  C16  H18  single    0.970  0.020  1.090
 FQN  C17  H19  single    0.970  0.020  1.090
 FQN  C17  H20  single    0.970  0.020  1.090
 FQN  C18  H21  single    0.970  0.020  1.090
 FQN  C18  H22  single    0.970  0.020  1.090
 FQN  C19  H23  single    0.970  0.020  1.090
 FQN  C19  H24  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
 FQN  C4   C5   O    124.98  3.000
 FQN  O    C5   N1   122.38  3.000
 FQN  C4   C5   N1   112.64  3.000
 FQN  H1   C7   N4   119.79  3.000
 FQN  H1   C7   C8   128.09  3.000
 FQN  N4   C7   C8   112.12  3.000
 FQN  C9   C8   C10  127.93  3.000
 FQN  C9   C8   C7   103.65  3.000
 FQN  C10  C8   C7   128.41  3.000
 FQN  C2   C3   N2   120.85  3.000
 FQN  N2   C3   C4   123.02  3.000
 FQN  C2   C3   C4   116.09  3.000
 FQN  H2   N1   C6   118.34  3.000
 FQN  H2   N1   C5   117.75  3.000
 FQN  C6   N1   C5   123.89  3.000
 FQN  H3   C6   N2   120.04  3.000
 FQN  H3   C6   N1   115.06  3.000
 FQN  N2   C6   N1   124.90  3.000
 FQN  H5   C11  H4   107.04  3.000
 FQN  H5   C11  C12  109.47  3.000
 FQN  H4   C11  C12  109.31  3.000
 FQN  H5   C11  C10  109.69  3.000
 FQN  H4   C11  C10  110.27  3.000
 FQN  C12  C11  C10  110.98  3.000
 FQN  H6   C10  C14  107.80  3.000
 FQN  H6   C10  C11  107.67  3.000
 FQN  C14  C10  C11  108.57  3.000
 FQN  H6   C10  C8   107.91  3.000
 FQN  C11  C10  C8   111.95  3.000
 FQN  C14  C10  C8   112.74  3.000
 FQN  H7   C9   N3   121.83  3.000
 FQN  H7   C9   C8   131.17  3.000
 FQN  N3   C9   C8   106.99  3.000
 FQN  H9   C14  H8   107.08  3.000
 FQN  H9   C14  C13  109.29  3.000
 FQN  H8   C14  C13  108.99  3.000
 FQN  H9   C14  C10  110.32  3.000
 FQN  H8   C14  C10  109.84  3.000
 FQN  C13  C14  C10  111.22  3.000
 FQN  C    C4   C3   120.27  3.000
 FQN  C    C4   C5   120.80  3.000
 FQN  C3   C4   C5   118.91  3.000
 FQN  H10  C    C1   120.92  3.000
 FQN  H10  C    C4   121.15  3.000
 FQN  C1   C    C4   117.93  3.000
 FQN  C6   N2   C3   116.55  3.000
 FQN  N3   C2   N    115.78  3.000
 FQN  N    C2   C3   123.28  3.000
 FQN  N3   C2   C3   120.92  3.000
 FQN  C1   N    C2   119.54  3.000
 FQN  H11  C1   N    116.34  3.000
 FQN  H11  C1   C    120.90  3.000
 FQN  N    C1   C    122.75  3.000
 FQN  N4   N3   C2   121.46  3.000
 FQN  C2   N3   C9   126.05  3.000
 FQN  N4   N3   C9   112.26  3.000
 FQN  N3   N4   C7   104.96  3.000
 FQN  H13  C13  H12  106.65  3.000
 FQN  H13  C13  N5   111.32  3.000
 FQN  H12  C13  N5   109.23  3.000
 FQN  H13  C13  C14  109.19  3.000
 FQN  H12  C13  C14  108.57  3.000
 FQN  N5   C13  C14  111.73  3.000
 FQN  C15  N5   C12  110.94  3.000
 FQN  C15  N5   C13  112.15  3.000
 FQN  C12  N5   C13  110.18  3.000
 FQN  H17  C12  H16  106.56  3.000
 FQN  H17  C12  N5   109.29  3.000
 FQN  H16  C12  N5   111.03  3.000
 FQN  H17  C12  C11  108.94  3.000
 FQN  H16  C12  C11  108.99  3.000
 FQN  N5   C12  C11  111.86  3.000
 FQN  H14  C15  C19  107.10  3.000
 FQN  H14  C15  C16  108.51  3.000
 FQN  C19  C15  C16  103.75  3.000
 FQN  H14  C15  N5   109.83  3.000
 FQN  C19  C15  N5   114.59  3.000
 FQN  C16  C15  N5   112.68  3.000
 FQN  H18  C16  H15  106.93  3.000
 FQN  H18  C16  C17  110.74  3.000
 FQN  H15  C16  C17  111.77  3.000
 FQN  H18  C16  C15  109.28  3.000
 FQN  H15  C16  C15  111.63  3.000
 FQN  C17  C16  C15  106.51  3.000
 FQN  H20  C17  H19  106.83  3.000
 FQN  H20  C17  C18  109.79  3.000
 FQN  H19  C17  C18  112.40  3.000
 FQN  H20  C17  C16  110.09  3.000
 FQN  H19  C17  C16  112.54  3.000
 FQN  C18  C17  C16  105.22  3.000
 FQN  H22  C18  H21  107.13  3.000
 FQN  H22  C18  C19  113.22  3.000
 FQN  H21  C18  C19  109.58  3.000
 FQN  H22  C18  C17  113.11  3.000
 FQN  H21  C18  C17  110.25  3.000
 FQN  C19  C18  C17  103.54  3.000
 FQN  H24  C19  H23  107.78  3.000
 FQN  H24  C19  C18  112.68  3.000
 FQN  H23  C19  C18  110.35  3.000
 FQN  H24  C19  C15  113.51  3.000
 FQN  H23  C19  C15  109.46  3.000
 FQN  C18  C19  C15  103.00  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
 FQN  CONST_01  C9   N3   N4   C7     0.00   0.0  0
 FQN  CONST_02  C2   N3   N4   C7   180.00   0.0  0
 FQN  CONST_03  N3   C9   C8   C7     0.00   0.0  0
 FQN  CONST_04  N3   N4   C7   C8     0.00   0.0  0
 FQN  CONST_05  N4   N3   C9   C8     0.00   0.0  0
 FQN  CONST_06  C2   N3   C9   C8   180.00   0.0  0
 FQN  CONST_09  C1   N    C2   C3     0.00   0.0  0
 FQN  CONST_10  C1   C    C4   C3     0.00   0.0  0
 FQN  CONST_11  N4   C7   C8   C9     0.00   0.0  0
 FQN  CONST_13  N3   C2   C3   C4   180.00   0.0  0
 FQN  CONST_14  N    C2   C3   C4     0.00   0.0  0
 FQN  CONST_15  N    C1   C    C4     0.00   0.0  0
 FQN  CONST_16  C2   N    C1   C      0.00   0.0  0
 FQN  CONST_17  C2   C3   C4   C      0.00   0.0  0
 FQN  CONST_19  N3   C2   N    C1   180.00   0.0  0
 FQN  CONST_20  N4   C7   C8   C10  180.00   0.0  0
 FQN  CONST_21  N3   C9   C8   C10  180.00   0.0  0
 FQN  CONST_22  N3   C2   C3   N2     0.00   0.0  0
 FQN  CONST_23  N2   C6   N1   C5     0.00   0.0  0
 FQN  CONST_24  N1   C6   N2   C3     0.00   0.0  0
 FQN  CONST_25  C4   C5   N1   C6     0.00   0.0  0
 FQN  CONST_26  O    C5   N1   C6   180.00   0.0  0
 FQN  CONST_27  H10  C    C4   C5     0.00   0.0  0
 FQN  CONST_28  H7   C9   C8   C7   180.00   0.0  0
 FQN  CONST_29  H1   C7   C8   C10    0.00   0.0  0
 FQN  CONST_30  H11  C1   C    C4   180.00   0.0  0
 FQN  CONST_31  H3   C6   N1   C5   180.00   0.0  0
 FQN  CONST_32  H2   N1   C5   C4   180.00   0.0  0
 FQN  Var_01    C13  N5   C12  C11   59.22  30.0  1
 FQN  Var_02    N5   C13  C14  C10   57.31  30.0  1
 FQN  Var_03    N5   C12  C11  C10  -57.55  30.0  1
 FQN  Var_04    C12  N5   C13  C14  -58.97  30.0  1
 FQN  Var_05    C18  C17  C16  C15    6.70  30.0  1
 FQN  Var_06    C17  C18  C19  C15   42.52  30.0  1
 FQN  Var_07    C19  C18  C17  C16  -30.24  30.0  1

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
 FQN  chir_01  C10  C14  C8   C11  negativ
 FQN  chir_02  C15  N5   C16  C19  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
 FQN  plan-1  C7   0.020
 FQN  plan-1  C8   0.020
 FQN  plan-1  C10  0.020
 FQN  plan-1  C9   0.020
 FQN  plan-1  C2   0.020
 FQN  plan-1  N3   0.020
 FQN  plan-1  N4   0.020
 FQN  plan-1  H1   0.020
 FQN  plan-1  H7   0.020
 FQN  plan-2  C5   0.020
 FQN  plan-2  C3   0.020
 FQN  plan-2  N1   0.020
 FQN  plan-2  C6   0.020
 FQN  plan-2  O    0.020
 FQN  plan-2  C4   0.020
 FQN  plan-2  C    0.020
 FQN  plan-2  N2   0.020
 FQN  plan-2  C2   0.020
 FQN  plan-2  N    0.020
 FQN  plan-2  C1   0.020
 FQN  plan-2  N3   0.020
 FQN  plan-2  H2   0.020
 FQN  plan-2  H3   0.020
 FQN  plan-2  H10  0.020
 FQN  plan-2  H11  0.020

