# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 01:00:18 2020
#   Inital geometry file: a 137 line input string
#   Ligand name: 8-[4-[2-[4-(3-chlorophenyl)piperidin-1-yl]ethyl]pyrazol-1-yl]-3~{H}-pyrido[3,4-d]pyrimidin-4-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1cccc(c1)C2CCN(CC2)CCc3cnn(c3)c4nccc5C(=O)NC=Nc45
#
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
 FQ5  FQ5  8-[4-[2-[4-(3-chlorophenyl)piperidin-1-yl]ethyl]pyrazol-1-yl]-3~{H}-pyrido[3,4-d]pyrimidin-4-one  ligand  54  31  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FQ5
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
 FQ5  C1   C   CR16  0  -0.238   9.0434  -0.6383   0.4321
 FQ5  N2   N   N     0  -0.268  -3.4713   1.5627  -0.7983
 FQ5  C3   C   CR16  0  -0.330   7.0672  -1.6168   1.4050
 FQ5  C4   C   CR6   0   0.193   6.2523  -0.6999   0.7470
 FQ5  C6   C   CH1   0  -0.351   4.7548  -0.7495   0.9045
 FQ5  C13  C   CR15  0  -0.064  -2.1700   1.7091  -0.8990
 FQ5  C14  C   CR6   0   0.442  -4.9674  -0.2992  -0.8575
 FQ5  C15  C   CR16  0  -0.063  -6.3893  -1.8182  -1.8001
 FQ5  C22  C   CH2   0  -0.416   4.1629   0.5675   1.4089
 FQ5  C20  C   CR6   0   0.580  -8.2925   0.0288   0.8192
 FQ5  C17  C   CR66  0  -0.017  -7.2187  -0.4192  -0.0736
 FQ5  C16  C   CR16  0  -0.355  -7.4468  -1.4187  -1.0169
 FQ5  N3   N   N     0  -0.401  -5.1819  -1.2524  -1.7272
 FQ5  N5   N   NR16  0  -0.659  -7.8684   0.9703   1.7256
 FQ5  C19  C   CR16  0   0.151  -6.5923   1.4258   1.8026
 FQ5  N4   N   N     0  -0.430  -5.6392   1.0705   1.0237
 FQ5  C18  C   CR66  0   0.155  -5.9491   0.1546   0.0540
 FQ5  N1   N   NR5   0  -0.371  -3.6738   0.2430  -0.8529
 FQ5  C12  C   CR15  0   0.029  -2.5160  -0.4504  -1.0062
 FQ5  C11  C   CR5   0  -0.145  -1.5014   0.4695  -1.0309
 FQ5  C10  C   CH2   0  -0.546  -0.0308   0.2311  -1.1155
 FQ5  N    N   NT    0  -0.423   2.0576   0.1271   0.2284
 FQ5  C8   C   CH2   0  -0.289   2.5462  -1.1648  -0.2203
 FQ5  C7   C   CH2   0  -0.412   4.0564  -1.1469  -0.3980
 FQ5  C21  C   CH2   0  -0.281   2.6481   0.4749   1.5090
 FQ5  C5   C   CR16  0  -0.284   6.8507   0.2532  -0.0762
 FQ5  C    C   CR6   0  -0.019   8.2275   0.2732  -0.2208
 FQ5  CL   CL  CL    0  -0.135   8.9500   1.4728  -1.2485
 FQ5  C2   C   CR16  0  -0.242   8.4464  -1.5868   1.2487
 FQ5  H1   H   HCR6  0   0.277  10.1172  -0.6102   0.3063
 FQ5  H2   H   HCR6  0   0.253   6.6167  -2.3651   2.0459
 FQ5  H3   H   HCH1  0   0.241   4.5274  -1.5214   1.6496
 FQ5  H4   H   HCR5  0   0.262  -1.7322   2.6972  -0.8892
 FQ5  H5   H   HCR6  0   0.282  -6.5043  -2.6095  -2.5295
 FQ5  H6   H   HCH2  0   0.239   4.5782   0.8197   2.3873
 FQ5  H7   H   HCH2  0   0.222   4.4229   1.3823   0.7270
 FQ5  H8   H   HCR6  0   0.286  -8.4203  -1.8766  -1.1216
 FQ5  H9   H   HNR6  0   0.440  -8.5472   1.3280   2.3858
 FQ5  H10  H   HCR6  0   0.307  -6.4072   2.1388   2.5960
 FQ5  H11  H   HCR5  0   0.292  -2.5026  -1.5260  -1.0718
 FQ5  H12  H   HCH2  0   0.249   0.1554  -0.7010  -1.6516
 FQ5  H13  H   HCH2  0   0.241   0.4411   1.0274  -1.6964
 FQ5  H17  H   HCH2  0   0.188   2.2714  -1.9634   0.4933
 FQ5  H18  H   HCH2  0   0.242   2.0797  -1.4224  -1.1721
 FQ5  H19  H   HCH2  0   0.222   4.3154  -0.4374  -1.1900
 FQ5  H20  H   HCH2  0   0.238   4.3951  -2.1328  -0.7244
 FQ5  H21  H   HCH2  0   0.186   2.3820  -0.2598   2.2907
 FQ5  H22  H   HCH2  0   0.238   2.2458   1.4381   1.8311
 FQ5  H23  H   HCR6  0   0.269   6.2461   0.9795  -0.6050
 FQ5  H24  H   HCR6  0   0.265   9.0655  -2.3078   1.7661
 FQ5  C9   C   CH2   0  -0.247   0.6103   0.1951   0.2734
 FQ5  O    O   O     0  -0.433  -9.4382  -0.3702   0.7846
 FQ5  H14  H   HCH2  0   0.233   0.3355   1.1153   0.7955
 FQ5  H15  H   HCH2  0   0.194   0.1713  -0.6339   0.8546

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
 FQ5  C13  N2   aromatic  1.313  0.020  1.313
 FQ5  C13  C11  aromatic  1.415  0.020  1.415
 FQ5  C10  C11  single    1.492  0.020  1.492
 FQ5  C10  C9   single    1.530  0.020  1.530
 FQ5  N2   N1   aromatic  1.336  0.020  1.336
 FQ5  C11  C12  aromatic  1.370  0.020  1.370
 FQ5  N1   C12  aromatic  1.358  0.020  1.358
 FQ5  N1   C14  single    1.403  0.020  1.403
 FQ5  CL   C    single    1.737  0.020  1.737
 FQ5  C7   C8   single    1.521  0.020  1.521
 FQ5  C7   C6   single    1.531  0.020  1.531
 FQ5  N3   C14  aromatic  1.308  0.020  1.308
 FQ5  N3   C15  aromatic  1.335  0.020  1.335
 FQ5  C14  C18  aromatic  1.414  0.020  1.414
 FQ5  C8   N    single    1.452  0.020  1.452
 FQ5  N4   C18  single    1.369  0.020  1.369
 FQ5  N4   C19  double    1.281  0.020  1.281
 FQ5  C18  C17  aromatic  1.399  0.020  1.399
 FQ5  C    C5   aromatic  1.384  0.020  1.384
 FQ5  C    C1   aromatic  1.387  0.020  1.387
 FQ5  C15  C16  aromatic  1.375  0.020  1.375
 FQ5  C9   N    single    1.450  0.020  1.450
 FQ5  N    C21  single    1.452  0.020  1.452
 FQ5  C5   C4   aromatic  1.394  0.020  1.394
 FQ5  C19  N5   single    1.357  0.020  1.357
 FQ5  C1   C2   aromatic  1.387  0.020  1.387
 FQ5  C17  C16  aromatic  1.393  0.020  1.393
 FQ5  C17  C20  single    1.467  0.020  1.467
 FQ5  C4   C6   single    1.507  0.020  1.507
 FQ5  C4   C3   aromatic  1.392  0.020  1.392
 FQ5  C6   C22  single    1.529  0.020  1.529
 FQ5  N5   C20  single    1.374  0.020  1.374
 FQ5  C2   C3   aromatic  1.388  0.020  1.388
 FQ5  C20  O    double    1.214  0.020  1.214
 FQ5  C22  C21  single    1.521  0.020  1.521
 FQ5  C1   H1   single    0.930  0.020  1.080
 FQ5  C3   H2   single    0.930  0.020  1.080
 FQ5  C6   H3   single    0.970  0.020  1.090
 FQ5  C13  H4   single    0.930  0.020  1.080
 FQ5  C15  H5   single    0.930  0.020  1.080
 FQ5  C22  H6   single    0.970  0.020  1.090
 FQ5  C22  H7   single    0.970  0.020  1.090
 FQ5  C16  H8   single    0.930  0.020  1.080
 FQ5  N5   H9   single    0.860  0.020  1.020
 FQ5  C19  H10  single    0.930  0.020  1.080
 FQ5  C12  H11  single    0.930  0.020  1.080
 FQ5  C10  H12  single    0.970  0.020  1.090
 FQ5  C10  H13  single    0.970  0.020  1.090
 FQ5  C9   H14  single    0.970  0.020  1.090
 FQ5  C9   H15  single    0.970  0.020  1.090
 FQ5  C8   H17  single    0.970  0.020  1.090
 FQ5  C8   H18  single    0.970  0.020  1.090
 FQ5  C7   H19  single    0.970  0.020  1.090
 FQ5  C7   H20  single    0.970  0.020  1.090
 FQ5  C21  H21  single    0.970  0.020  1.090
 FQ5  C21  H22  single    0.970  0.020  1.090
 FQ5  C5   H23  single    0.930  0.020  1.080
 FQ5  C2   H24  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
 FQ5  H1   C1   C2   120.91  3.000
 FQ5  H1   C1   C    120.82  3.000
 FQ5  C2   C1   C    118.27  3.000
 FQ5  N1   N2   C13  104.91  3.000
 FQ5  H2   C3   C2   119.65  3.000
 FQ5  H2   C3   C4   119.42  3.000
 FQ5  C2   C3   C4   120.94  3.000
 FQ5  C5   C4   C6   120.72  3.000
 FQ5  C6   C4   C3   120.72  3.000
 FQ5  C5   C4   C3   118.56  3.000
 FQ5  H3   C6   C7   107.50  3.000
 FQ5  H3   C6   C22  107.57  3.000
 FQ5  C7   C6   C22  109.13  3.000
 FQ5  H3   C6   C4   107.48  3.000
 FQ5  C22  C6   C4   113.01  3.000
 FQ5  C7   C6   C4   111.91  3.000
 FQ5  H4   C13  C11  127.63  3.000
 FQ5  H4   C13  N2   120.17  3.000
 FQ5  C11  C13  N2   112.19  3.000
 FQ5  N1   C14  C18  120.93  3.000
 FQ5  C18  C14  N3   123.26  3.000
 FQ5  N1   C14  N3   115.80  3.000
 FQ5  H5   C15  N3   116.27  3.000
 FQ5  H5   C15  C16  120.96  3.000
 FQ5  N3   C15  C16  122.76  3.000
 FQ5  H7   C22  H6   107.22  3.000
 FQ5  H7   C22  C21  108.85  3.000
 FQ5  H6   C22  C21  109.50  3.000
 FQ5  H7   C22  C6   110.11  3.000
 FQ5  H6   C22  C6   110.31  3.000
 FQ5  C21  C22  C6   110.78  3.000
 FQ5  N5   C20  C17  112.64  3.000
 FQ5  N5   C20  O    122.37  3.000
 FQ5  C17  C20  O    124.99  3.000
 FQ5  C18  C17  C16  120.30  3.000
 FQ5  C16  C17  C20  120.76  3.000
 FQ5  C18  C17  C20  118.92  3.000
 FQ5  H8   C16  C17  121.13  3.000
 FQ5  H8   C16  C15  120.95  3.000
 FQ5  C17  C16  C15  117.91  3.000
 FQ5  C15  N3   C14  119.56  3.000
 FQ5  H9   N5   C19  118.36  3.000
 FQ5  H9   N5   C20  117.74  3.000
 FQ5  C19  N5   C20  123.89  3.000
 FQ5  H10  C19  N4   120.06  3.000
 FQ5  H10  C19  N5   115.05  3.000
 FQ5  N4   C19  N5   124.89  3.000
 FQ5  C18  N4   C19  116.60  3.000
 FQ5  N4   C18  C17  122.97  3.000
 FQ5  C17  C18  C14  116.07  3.000
 FQ5  N4   C18  C14  120.93  3.000
 FQ5  C12  N1   C14  126.05  3.000
 FQ5  C14  N1   N2   121.45  3.000
 FQ5  C12  N1   N2   112.30  3.000
 FQ5  H11  C12  C11  131.29  3.000
 FQ5  H11  C12  N1   121.80  3.000
 FQ5  C11  C12  N1   106.90  3.000
 FQ5  C10  C11  C12  128.59  3.000
 FQ5  C12  C11  C13  103.69  3.000
 FQ5  C10  C11  C13  127.67  3.000
 FQ5  H13  C10  H12  106.71  3.000
 FQ5  H13  C10  C9   108.58  3.000
 FQ5  H12  C10  C9   110.75  3.000
 FQ5  H13  C10  C11  109.83  3.000
 FQ5  H12  C10  C11  109.42  3.000
 FQ5  C9   C10  C11  111.42  3.000
 FQ5  C21  N    C8   110.41  3.000
 FQ5  C21  N    C9   111.55  3.000
 FQ5  C8   N    C9   112.78  3.000
 FQ5  H18  C8   H17  106.64  3.000
 FQ5  H18  C8   C7   109.00  3.000
 FQ5  H17  C8   C7   109.32  3.000
 FQ5  H18  C8   N    109.62  3.000
 FQ5  H17  C8   N    111.07  3.000
 FQ5  C7   C8   N    111.09  3.000
 FQ5  H20  C7   H19  107.19  3.000
 FQ5  H20  C7   C8   109.40  3.000
 FQ5  H19  C7   C8   109.10  3.000
 FQ5  H20  C7   C6   110.31  3.000
 FQ5  H19  C7   C6   109.85  3.000
 FQ5  C8   C7   C6   110.90  3.000
 FQ5  H22  C21  H21  106.80  3.000
 FQ5  H22  C21  N    108.75  3.000
 FQ5  H21  C21  N    111.50  3.000
 FQ5  H22  C21  C22  109.42  3.000
 FQ5  H21  C21  C22  109.07  3.000
 FQ5  N    C21  C22  111.19  3.000
 FQ5  H23  C5   C    119.64  3.000
 FQ5  H23  C5   C4   120.47  3.000
 FQ5  C    C5   C4   119.89  3.000
 FQ5  CL   C    C5   119.04  3.000
 FQ5  C5   C    C1   121.76  3.000
 FQ5  CL   C    C1   119.19  3.000
 FQ5  H24  C2   C3   120.01  3.000
 FQ5  H24  C2   C1   119.41  3.000
 FQ5  C3   C2   C1   120.58  3.000
 FQ5  H15  C9   H14  106.31  3.000
 FQ5  H15  C9   N    112.23  3.000
 FQ5  H14  C9   N    107.78  3.000
 FQ5  H15  C9   C10  109.21  3.000
 FQ5  H14  C9   C10  107.96  3.000
 FQ5  N    C9   C10  113.03  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
 FQ5  CONST_01  C4   C5   C    C1      0.00   0.0  0
 FQ5  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 FQ5  CONST_03  C12  C11  C13  N2      0.00   0.0  0
 FQ5  CONST_04  C11  C12  N1   N2      0.00   0.0  0
 FQ5  CONST_07  C    C5   C4   C3      0.00   0.0  0
 FQ5  CONST_08  C    C1   C2   C3      0.00   0.0  0
 FQ5  CONST_09  C12  N1   N2   C13     0.00   0.0  0
 FQ5  CONST_10  C14  N1   N2   C13   180.00   0.0  0
 FQ5  CONST_11  N1   C12  C11  C13     0.00   0.0  0
 FQ5  CONST_12  C11  C12  N1   C14   180.00   0.0  0
 FQ5  CONST_13  C16  C15  N3   C14     0.00   0.0  0
 FQ5  CONST_14  C16  C17  C18  C14     0.00   0.0  0
 FQ5  CONST_15  N1   C14  N3   C15   180.00   0.0  0
 FQ5  CONST_16  C18  C14  N3   C15     0.00   0.0  0
 FQ5  CONST_17  C18  C17  C16  C15     0.00   0.0  0
 FQ5  CONST_18  N1   C14  C18  C17   180.00   0.0  0
 FQ5  CONST_19  N3   C14  C18  C17     0.00   0.0  0
 FQ5  CONST_20  N3   C15  C16  C17     0.00   0.0  0
 FQ5  CONST_23  C11  C13  N2   N1      0.00   0.0  0
 FQ5  CONST_24  C2   C1   C    C5      0.00   0.0  0
 FQ5  CONST_25  C2   C3   C4   C5      0.00   0.0  0
 FQ5  CONST_26  C    C5   C4   C6    180.00   0.0  0
 FQ5  CONST_27  C2   C3   C4   C6    180.00   0.0  0
 FQ5  CONST_28  N1   C14  C18  N4      0.00   0.0  0
 FQ5  CONST_29  N4   C19  N5   C20     0.00   0.0  0
 FQ5  CONST_30  C19  N5   C20  C17     0.00   0.0  0
 FQ5  CONST_31  C18  N4   C19  N5      0.00   0.0  0
 FQ5  CONST_32  C10  C11  C13  N2    180.00   0.0  0
 FQ5  CONST_33  CL   C    C5   C4    180.00   0.0  0
 FQ5  CONST_34  C10  C11  C12  N1    180.00   0.0  0
 FQ5  CONST_35  C2   C1   C    CL    180.00   0.0  0
 FQ5  CONST_36  C19  N5   C20  O     180.00   0.0  0
 FQ5  CONST_37  H23  C5   C    C1    180.00   0.0  0
 FQ5  CONST_38  H2   C3   C2   C1    180.00   0.0  0
 FQ5  CONST_39  H11  C12  N1   N2    180.00   0.0  0
 FQ5  CONST_40  H1   C1   C2   C3    180.00   0.0  0
 FQ5  CONST_41  H24  C2   C3   C4    180.00   0.0  0
 FQ5  CONST_42  H5   C15  N3   C14   180.00   0.0  0
 FQ5  CONST_43  H8   C16  C17  C20     0.00   0.0  0
 FQ5  CONST_44  H4   C13  N2   N1    180.00   0.0  0
 FQ5  CONST_45  H10  C19  N5   C20   180.00   0.0  0
 FQ5  CONST_46  H9   N5   C20  C17   180.00   0.0  0
 FQ5  Var_01    N    C8   C7   C6     57.47  30.0  1
 FQ5  Var_02    N    C21  C22  C6    -57.54  30.0  1
 FQ5  Var_03    C8   N    C21  C22    60.72  30.0  1
 FQ5  Var_04    C21  N    C8   C7    -60.63  30.0  1
 FQ5  Var_05    C9   C10  C11  C13    83.05  30.0  3
 FQ5  Var_06    N    C9   C10  C11  -173.00  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
 FQ5  chir_01  C6  C7  C4  C22  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
 FQ5  plan-1  N2   0.020
 FQ5  plan-1  C13  0.020
 FQ5  plan-1  C14  0.020
 FQ5  plan-1  N1   0.020
 FQ5  plan-1  C12  0.020
 FQ5  plan-1  C11  0.020
 FQ5  plan-1  C10  0.020
 FQ5  plan-1  H4   0.020
 FQ5  plan-1  H11  0.020
 FQ5  plan-2  C1   0.020
 FQ5  plan-2  C3   0.020
 FQ5  plan-2  C4   0.020
 FQ5  plan-2  C6   0.020
 FQ5  plan-2  C5   0.020
 FQ5  plan-2  C    0.020
 FQ5  plan-2  CL   0.020
 FQ5  plan-2  C2   0.020
 FQ5  plan-2  H1   0.020
 FQ5  plan-2  H2   0.020
 FQ5  plan-2  H23  0.020
 FQ5  plan-2  H24  0.020
 FQ5  plan-3  C14  0.020
 FQ5  plan-3  C15  0.020
 FQ5  plan-3  C20  0.020
 FQ5  plan-3  C17  0.020
 FQ5  plan-3  C16  0.020
 FQ5  plan-3  N3   0.020
 FQ5  plan-3  N5   0.020
 FQ5  plan-3  C19  0.020
 FQ5  plan-3  N4   0.020
 FQ5  plan-3  C18  0.020
 FQ5  plan-3  N1   0.020
 FQ5  plan-3  H5   0.020
 FQ5  plan-3  H8   0.020
 FQ5  plan-3  H9   0.020
 FQ5  plan-3  H10  0.020
 FQ5  plan-3  O    0.020

