# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  1 06:28:55 2020
#   Inital geometry file: a 118 line input string
#   Ligand name: 4-[3-cyano-6-(3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-yl]benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cccc(c1)C2=CC(=C(C#N)C(=O)N2)c3ccc(cc3)C(O)=O
#
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
 QZZ  QZZ  '4-[3-cyano-6-(3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-yl]benzoic acid'  ligand  39  26  .  2021-08-20  2021-08-20  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_QZZ
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
 QZZ  C5    C  CR16   0  -0.225   3.9416  -2.6241  -0.9124
 QZZ  C6    C  CR16   0  -0.316   2.8163  -1.8212  -0.9244
 QZZ  C19   C  CR16   0  -0.274  -3.0780   0.5144  -0.8442
 QZZ  C23   C  CR16   0  -0.280  -2.2742  -0.7929   1.0042
 QZZ  C20   C  CR16   0  -0.276  -4.3366  -0.0410  -0.6810
 QZZ  C22   C  CR16   0  -0.274  -3.5401  -1.3293   1.1703
 QZZ  C4    C  CR16   0  -0.377   5.1282  -2.1944  -0.3304
 QZZ  C8    C  CR16   0  -0.396   4.0604  -0.1104   0.2379
 QZZ  C18   C  CR6    0   0.021  -2.0321   0.1452   0.0007
 QZZ  C7    C  CR6    0   0.074   2.8785  -0.5528  -0.3439
 QZZ  C21   C  CR6    0  -0.098  -4.5893  -0.9642   0.3302
 QZZ  C3    C  CR6    0   0.410   5.1899  -0.9295   0.2500
 QZZ  C10   C  C1     0  -0.485   0.4199  -0.1778  -0.1747
 QZZ  C12   C  C      0  -0.287  -0.4501   2.0578  -0.3113
 QZZ  C11   C  C      0   0.317  -0.6796   0.7009  -0.1708
 QZZ  C9    C  C      0   0.437   1.6880   0.3089  -0.3431
 QZZ  C13   C  C      0   0.553   0.8783   2.5953  -0.4964
 QZZ  C24   C  C      0   0.401  -5.9801  -1.5661   0.5106
 QZZ  N17   N  NS     0  -0.251  -2.3003   3.8352  -0.1419
 QZZ  N15   N  NH1    0  -0.726   1.8730   1.6373  -0.5048
 QZZ  O14   O  O      0  -0.464   1.1427   3.7791  -0.6373
 QZZ  O25   O  O      0  -0.588  -6.8542  -1.1915  -0.2928
 QZZ  O26   O  OC    -1  -0.588  -6.1151  -2.3776   1.4449
 QZZ  O2    O  O2     0  -0.469   6.2799  -0.4179   0.8436
 QZZ  H5    H  HCR6   0   0.272   3.9056  -3.6033  -1.3709
 QZZ  H6    H  HCR6   0   0.268   1.9088  -2.1646  -1.4020
 QZZ  H4    H  HCR6   0   0.290   5.9860  -2.8521  -0.3401
 QZZ  H19   H  HCR6   0   0.260  -2.9056   1.2141  -1.6521
 QZZ  H20   H  HCR6   0   0.251  -5.1343   0.2437  -1.3539
 QZZ  H23   H  HCR6   0   0.260  -1.4742  -1.0881   1.6719
 QZZ  H22   H  HCR6   0   0.252  -3.7159  -2.0437   1.9631
 QZZ  H8    H  HCR6   0   0.277   4.1201   0.8579   0.7216
 QZZ  H10   H  H      0   0.293   0.2667  -1.2380  -0.0417
 QZZ  H15   H  HNH1   0   0.435   2.8098   1.9810  -0.6809
 QZZ  H11C  H  HCH3   0   0.232   7.8284  -1.4776  -0.0692
 QZZ  H12C  H  HCH3   0   0.263   8.1947  -0.6137   1.4338
 QZZ  H13C  H  HCH3   0   0.233   7.2790  -2.1300   1.4913
 QZZ  C1    C  CH3    0  -0.439   7.4478  -1.2137   0.9205
 QZZ  C16   C  CSP    0   0.018  -1.4836   3.0249  -0.2255

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
 QZZ  C16  C12   single    1.418  0.020  1.418
 QZZ  C16  N17   triple    1.154  0.020  1.154
 QZZ  C5   C6    aromatic  1.382  0.020  1.382
 QZZ  C5   C4    aromatic  1.390  0.020  1.390
 QZZ  C6   C7    aromatic  1.396  0.020  1.396
 QZZ  C19  C20   aromatic  1.385  0.020  1.385
 QZZ  C19  C18   aromatic  1.394  0.020  1.394
 QZZ  C23  C22   aromatic  1.385  0.020  1.385
 QZZ  C23  C18   aromatic  1.395  0.020  1.395
 QZZ  C20  C21   aromatic  1.392  0.020  1.392
 QZZ  C22  C21   aromatic  1.393  0.020  1.393
 QZZ  C4   C3    aromatic  1.393  0.020  1.393
 QZZ  C8   C7    aromatic  1.390  0.020  1.390
 QZZ  C8   C3    aromatic  1.395  0.020  1.395
 QZZ  C18  C11   single    1.472  0.020  1.472
 QZZ  C7   C9    single    1.470  0.020  1.470
 QZZ  C21  C24   single    1.526  0.020  1.526
 QZZ  C3   O2    single    1.342  0.020  1.342
 QZZ  C10  C11   single    1.408  0.020  1.408
 QZZ  C10  C9    double    1.369  0.020  1.369
 QZZ  C12  C11   double    1.383  0.020  1.383
 QZZ  C12  C13   single    1.445  0.020  1.445
 QZZ  C9   N15   single    1.351  0.020  1.351
 QZZ  C13  N15   single    1.381  0.020  1.381
 QZZ  C13  O14   double    1.221  0.020  1.221
 QZZ  C24  O25   deloc     1.245  0.020  1.245
 QZZ  C24  O26   deloc     1.245  0.020  1.245
 QZZ  C1   O2    single    1.415  0.020  1.415
 QZZ  C5   H5    single    0.930  0.020  1.080
 QZZ  C6   H6    single    0.930  0.020  1.080
 QZZ  C4   H4    single    0.930  0.020  1.080
 QZZ  C19  H19   single    0.930  0.020  1.080
 QZZ  C20  H20   single    0.930  0.020  1.080
 QZZ  C23  H23   single    0.930  0.020  1.080
 QZZ  C22  H22   single    0.930  0.020  1.080
 QZZ  C8   H8    single    0.930  0.020  1.080
 QZZ  C10  H10   single    0.930  0.020  1.080
 QZZ  N15  H15   single    0.860  0.020  1.020
 QZZ  C1   H11C  single    0.970  0.020  1.090
 QZZ  C1   H12C  single    0.970  0.020  1.090
 QZZ  C1   H13C  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
 QZZ  H5    C5   C4    119.06  3.000
 QZZ  H5    C5   C6    119.66  3.000
 QZZ  C4    C5   C6    121.27  3.000
 QZZ  H6    C6   C7    120.62  3.000
 QZZ  H6    C6   C5    120.17  3.000
 QZZ  C7    C6   C5    119.19  3.000
 QZZ  H19   C19  C18   120.26  3.000
 QZZ  H19   C19  C20   119.45  3.000
 QZZ  C18   C19  C20   120.26  3.000
 QZZ  H23   C23  C18   119.91  3.000
 QZZ  H23   C23  C22   119.72  3.000
 QZZ  C18   C23  C22   120.36  3.000
 QZZ  H20   C20  C21   119.51  3.000
 QZZ  H20   C20  C19   119.41  3.000
 QZZ  C21   C20  C19   121.08  3.000
 QZZ  H22   C22  C21   119.53  3.000
 QZZ  H22   C22  C23   119.49  3.000
 QZZ  C21   C22  C23   120.98  3.000
 QZZ  H4    C4   C3    121.40  3.000
 QZZ  H4    C4   C5    119.06  3.000
 QZZ  C3    C4   C5    119.54  3.000
 QZZ  H8    C8   C3    118.42  3.000
 QZZ  H8    C8   C7    121.19  3.000
 QZZ  C3    C8   C7    120.35  3.000
 QZZ  C11   C18  C23   119.81  3.000
 QZZ  C11   C18  C19   121.24  3.000
 QZZ  C23   C18  C19   118.93  3.000
 QZZ  C9    C7   C8    120.14  3.000
 QZZ  C9    C7   C6    119.78  3.000
 QZZ  C8    C7   C6    120.07  3.000
 QZZ  C24   C21  C22   120.79  3.000
 QZZ  C24   C21  C20   120.84  3.000
 QZZ  C22   C21  C20   118.37  3.000
 QZZ  O2    C3   C8    115.94  3.000
 QZZ  O2    C3   C4    124.48  3.000
 QZZ  C8    C3   C4    119.58  3.000
 QZZ  H10   C10  C9    119.73  3.000
 QZZ  H10   C10  C11   120.13  3.000
 QZZ  C9    C10  C11   120.14  3.000
 QZZ  C13   C12  C11   122.03  3.000
 QZZ  C13   C12  C16   115.10  3.000
 QZZ  C11   C12  C16   122.81  3.000
 QZZ  C12   C11  C10   118.85  3.000
 QZZ  C12   C11  C18   122.31  3.000
 QZZ  C10   C11  C18   118.84  3.000
 QZZ  N15   C9   C10   119.43  3.000
 QZZ  N15   C9   C7    117.74  3.000
 QZZ  C10   C9   C7    122.83  3.000
 QZZ  O14   C13  N15   121.05  3.000
 QZZ  O14   C13  C12   125.06  3.000
 QZZ  N15   C13  C12   113.89  3.000
 QZZ  O26   C24  O25   127.18  3.000
 QZZ  O26   C24  C21   116.40  3.000
 QZZ  O25   C24  C21   116.42  3.000
 QZZ  H15   N15  C13   115.57  3.000
 QZZ  H15   N15  C9    118.75  3.000
 QZZ  C13   N15  C9    125.64  3.000
 QZZ  C1    O2   C3    118.67  3.000
 QZZ  H13C  C1   H12C  108.80  3.000
 QZZ  H13C  C1   H11C  108.94  3.000
 QZZ  H12C  C1   H11C  108.77  3.000
 QZZ  H13C  C1   O2    111.86  3.000
 QZZ  H12C  C1   O2    106.40  3.000
 QZZ  H11C  C1   O2    111.96  3.000
 QZZ  N17   C16  C12   180.00  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
 QZZ  CONST_01  C8    C7   C6   C5      0.00   0.0  0
 QZZ  CONST_02  C8    C3   C4   C5      0.00   0.0  0
 QZZ  CONST_03  C3    C4   C5   C6      0.00   0.0  0
 QZZ  CONST_04  C3    C8   C7   C6      0.00   0.0  0
 QZZ  CONST_05  C22   C21  C20  C19     0.00   0.0  0
 QZZ  CONST_06  C22   C23  C18  C19     0.00   0.0  0
 QZZ  CONST_07  C20   C21  C22  C23     0.00   0.0  0
 QZZ  CONST_08  C20   C19  C18  C23     0.00   0.0  0
 QZZ  CONST_09  C7    C6   C5   C4      0.00   0.0  0
 QZZ  CONST_10  C7    C8   C3   C4      0.00   0.0  0
 QZZ  CONST_11  C21   C20  C19  C18     0.00   0.0  0
 QZZ  CONST_12  C21   C22  C23  C18     0.00   0.0  0
 QZZ  CONST_13  C9    C7   C6   C5    180.00   0.0  0
 QZZ  CONST_14  C11   C18  C19  C20   180.00   0.0  0
 QZZ  CONST_15  C11   C18  C23  C22   180.00   0.0  0
 QZZ  CONST_16  C9    C7   C8   C3    180.00   0.0  0
 QZZ  CONST_17  C9    N15  C13  C12     0.00   0.0  0
 QZZ  CONST_18  O2    C3   C4   C5    180.00   0.0  0
 QZZ  CONST_19  C24   C21  C20  C19   180.00   0.0  0
 QZZ  CONST_20  C24   C21  C22  C23   180.00   0.0  0
 QZZ  CONST_21  O2    C3   C8   C7    180.00   0.0  0
 QZZ  CONST_22  O14   C13  N15  C9    180.00   0.0  0
 QZZ  CONST_23  H4    C4   C5   C6    180.00   0.0  0
 QZZ  CONST_24  H8    C8   C7   C6    180.00   0.0  0
 QZZ  CONST_25  H23   C23  C18  C19   180.00   0.0  0
 QZZ  CONST_26  H19   C19  C18  C23   180.00   0.0  0
 QZZ  CONST_27  H22   C22  C21  C20   180.00   0.0  0
 QZZ  CONST_28  H20   C20  C21  C22   180.00   0.0  0
 QZZ  CONST_29  H6    C6   C5   C4    180.00   0.0  0
 QZZ  CONST_30  H5    C5   C6   C7    180.00   0.0  0
 QZZ  CONST_31  H15   N15  C13  C12   180.00   0.0  0
 QZZ  Var_01    C10   C9   C7   C6     37.00  30.0  2
 QZZ  Var_02    C10   C11  C18  C19  -131.83  30.0  2
 QZZ  Var_03    O25   C24  C21  C20     0.37  30.0  2
 QZZ  Var_04    H11C  C1   O2   C3     61.43  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
 QZZ  plan-1  C5   0.020
 QZZ  plan-1  C6   0.020
 QZZ  plan-1  C4   0.020
 QZZ  plan-1  C8   0.020
 QZZ  plan-1  C7   0.020
 QZZ  plan-1  C3   0.020
 QZZ  plan-1  C9   0.020
 QZZ  plan-1  O2   0.020
 QZZ  plan-1  H5   0.020
 QZZ  plan-1  H6   0.020
 QZZ  plan-1  H4   0.020
 QZZ  plan-1  H8   0.020
 QZZ  plan-2  C19  0.020
 QZZ  plan-2  C23  0.020
 QZZ  plan-2  C20  0.020
 QZZ  plan-2  C22  0.020
 QZZ  plan-2  C18  0.020
 QZZ  plan-2  C21  0.020
 QZZ  plan-2  C11  0.020
 QZZ  plan-2  C24  0.020
 QZZ  plan-2  H19  0.020
 QZZ  plan-2  H20  0.020
 QZZ  plan-2  H23  0.020
 QZZ  plan-2  H22  0.020
 QZZ  plan-3  C18  0.020
 QZZ  plan-3  C7   0.020
 QZZ  plan-3  C10  0.020
 QZZ  plan-3  C12  0.020
 QZZ  plan-3  C11  0.020
 QZZ  plan-3  C9   0.020
 QZZ  plan-3  C13  0.020
 QZZ  plan-3  N17  0.020
 QZZ  plan-3  N15  0.020
 QZZ  plan-3  O14  0.020
 QZZ  plan-3  H10  0.020
 QZZ  plan-3  H15  0.020
 QZZ  plan-3  C16  0.020
 QZZ  plan-4  C21  0.020
 QZZ  plan-4  C24  0.020
 QZZ  plan-4  O25  0.020
 QZZ  plan-4  O26  0.020

