# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May  7 20:49:44 2020
#   Inital geometry file: a 96 line input string
#   Ligand name: 6-(5-bromo-2-hydroxyphenyl)-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(Br)cc1C2=CC(=C(C#N)C(=O)N2)c3ccccc3
#
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
 VRV  VRV  6-(5-bromo-2-hydroxyphenyl)-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile  ligand  34  23  .  2021-08-24  2021-08-24  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_VRV
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
 VRV  C1    C   CR16  0  -0.209   2.0853  -2.2519  -3.8838
 VRV  C2    C   CR16  0  -0.326   0.7465  -2.0275  -3.6317
 VRV  C3    C   CR6   0   0.343   0.2670  -1.9434  -2.3256
 VRV  C4    C   CR6   0  -0.077   1.1665  -2.0849  -1.2602
 VRV  C5    C   CR16  0  -0.247   2.5164  -2.3285  -1.5208
 VRV  C6    C   CR6   0  -0.125   2.9692  -2.4068  -2.8223
 VRV  C7    C   CR6   0   0.394   0.7151  -1.9878   0.1355
 VRV  N8    N   NR16  0  -0.710   1.0880  -2.9779   0.9745
 VRV  C9    C   CR6   0   0.564   0.7885  -3.0419   2.3218
 VRV  C10   C   CR6   0  -0.282  -0.0042  -1.9287   2.7994
 VRV  C11   C   CR6   0   0.316  -0.3957  -0.8969   1.9713
 VRV  C12   C   CR16  0  -0.510  -0.0253  -0.9396   0.6098
 VRV  C13   C   CR6   0   0.029  -1.1840   0.2481   2.4552
 VRV  C14   C   CR16  0  -0.287  -2.3062   0.6613   1.7370
 VRV  C15   C   CR16  0  -0.239  -3.0580   1.7399   2.1757
 VRV  C16   C   CR16  0  -0.250  -2.6840   2.4281   3.3228
 VRV  C17   C   CR16  0  -0.241  -1.5563   2.0336   4.0306
 VRV  C18   C   CR16  0  -0.284  -0.8104   0.9458   3.6032
 VRV  C19   C   CSP   0   0.021  -0.4019  -2.0151   4.1588
 VRV  N20   N   NS    0  -0.244  -0.7229  -2.1185   5.2615
 VRV  O21   O   OC    0  -0.455   1.1586  -3.9794   3.0074
 VRV  O22   O   OH1   0  -0.602  -1.0499  -1.7461  -2.1764
 VRV  BR23  BR  BR    0  -0.035   4.7979  -2.7156  -3.1608
 VRV  H1    H   HCR6  0   0.291   2.4279  -2.3110  -4.9080
 VRV  H2    H   HCR6  0   0.289   0.0537  -1.9219  -4.4563
 VRV  H5    H   HCR6  0   0.301   3.2053  -2.4273  -0.6915
 VRV  HN8   H   HNR6  0   0.439   1.5973  -3.7689   0.5967
 VRV  H12   H   HCR6  0   0.320  -0.2507  -0.1027  -0.0355
 VRV  H14   H   HCR6  0   0.266  -2.6064   0.1254   0.8449
 VRV  H15   H   HCR6  0   0.267  -3.9353   2.0445   1.6205
 VRV  H16   H   HCR6  0   0.267  -3.2671   3.2742   3.6619
 VRV  H17   H   HCR6  0   0.267  -1.2508   2.5762   4.9152
 VRV  H18   H   HCR6  0   0.270   0.0802   0.6607   4.1480
 VRV  HO22  H   HOH1  0   0.481  -1.3281  -1.8186  -1.2544

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
 VRV  C1   C6    aromatic  1.390  0.020  1.390
 VRV  C1   C2    aromatic  1.381  0.020  1.381
 VRV  C1   H1    single    0.930  0.020  1.080
 VRV  C2   C3    aromatic  1.394  0.020  1.394
 VRV  C2   H2    single    0.930  0.020  1.080
 VRV  C3   C4    aromatic  1.401  0.020  1.401
 VRV  C3   O22   single    1.340  0.020  1.340
 VRV  C4   C5    aromatic  1.396  0.020  1.396
 VRV  C4   C7    single    1.470  0.020  1.470
 VRV  C5   C6    aromatic  1.380  0.020  1.380
 VRV  C5   H5    single    0.930  0.020  1.080
 VRV  C6   BR23  single    1.885  0.020  1.885
 VRV  C7   C12   aromatic  1.368  0.020  1.368
 VRV  C7   N8    aromatic  1.350  0.020  1.350
 VRV  N8   C9    aromatic  1.382  0.020  1.382
 VRV  N8   HN8   single    0.860  0.020  1.020
 VRV  C9   C10   aromatic  1.448  0.020  1.448
 VRV  C9   O21   double    1.219  0.020  1.219
 VRV  C10  C11   aromatic  1.380  0.020  1.380
 VRV  C10  C19   single    1.419  0.020  1.419
 VRV  C11  C13   single    1.472  0.020  1.472
 VRV  C11  C12   aromatic  1.412  0.020  1.412
 VRV  C12  H12   single    0.930  0.020  1.080
 VRV  C13  C18   aromatic  1.394  0.020  1.394
 VRV  C13  C14   aromatic  1.395  0.020  1.395
 VRV  C14  C15   aromatic  1.386  0.020  1.386
 VRV  C14  H14   single    0.930  0.020  1.080
 VRV  C15  C16   aromatic  1.389  0.020  1.389
 VRV  C15  H15   single    0.930  0.020  1.080
 VRV  C16  C17   aromatic  1.389  0.020  1.389
 VRV  C16  H16   single    0.930  0.020  1.080
 VRV  C17  C18   aromatic  1.386  0.020  1.386
 VRV  C17  H17   single    0.930  0.020  1.080
 VRV  C18  H18   single    0.930  0.020  1.080
 VRV  C19  N20   triple    1.153  0.020  1.153
 VRV  O22  HO22  single    0.850  0.020  0.980

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
 VRV  H1    C1   C6   121.04  3.000
 VRV  H1    C1   C2   119.27  3.000
 VRV  C6    C1   C2   119.69  3.000
 VRV  H2    C2   C3   119.20  3.000
 VRV  H2    C2   C1   119.83  3.000
 VRV  C3    C2   C1   120.96  3.000
 VRV  O22   C3   C4   124.12  3.000
 VRV  O22   C3   C2   116.83  3.000
 VRV  C4    C3   C2   119.05  3.000
 VRV  C7    C4   C5   119.05  3.000
 VRV  C7    C4   C3   121.20  3.000
 VRV  C5    C4   C3   119.75  3.000
 VRV  H5    C5   C6   120.55  3.000
 VRV  H5    C5   C4   119.22  3.000
 VRV  C6    C5   C4   120.21  3.000
 VRV  BR23  C6   C5   119.79  3.000
 VRV  BR23  C6   C1   119.86  3.000
 VRV  C5    C6   C1   120.34  3.000
 VRV  C12   C7   N8   119.73  3.000
 VRV  N8    C7   C4   117.17  3.000
 VRV  C12   C7   C4   123.08  3.000
 VRV  HN8   N8   C9   115.86  3.000
 VRV  HN8   N8   C7   118.64  3.000
 VRV  C9    N8   C7   125.45  3.000
 VRV  O21   C9   C10  124.90  3.000
 VRV  O21   C9   N8   121.21  3.000
 VRV  C10   C9   N8   113.88  3.000
 VRV  C19   C10  C11  122.75  3.000
 VRV  C19   C10  C9   115.00  3.000
 VRV  C11   C10  C9   122.17  3.000
 VRV  C13   C11  C12  118.76  3.000
 VRV  C12   C11  C10  118.81  3.000
 VRV  C13   C11  C10  122.43  3.000
 VRV  H12   C12  C11  119.86  3.000
 VRV  H12   C12  C7   119.95  3.000
 VRV  C11   C12  C7   119.97  3.000
 VRV  C18   C13  C14  119.42  3.000
 VRV  C14   C13  C11  119.47  3.000
 VRV  C18   C13  C11  121.09  3.000
 VRV  H14   C14  C15  119.70  3.000
 VRV  H14   C14  C13  120.03  3.000
 VRV  C15   C14  C13  120.26  3.000
 VRV  H15   C15  C16  120.17  3.000
 VRV  H15   C15  C14  119.76  3.000
 VRV  C16   C15  C14  120.06  3.000
 VRV  H16   C16  C17  120.01  3.000
 VRV  H16   C16  C15  120.07  3.000
 VRV  C17   C16  C15  119.92  3.000
 VRV  H17   C17  C18  119.58  3.000
 VRV  H17   C17  C16  120.24  3.000
 VRV  C18   C17  C16  120.18  3.000
 VRV  H18   C18  C17  119.62  3.000
 VRV  H18   C18  C13  120.21  3.000
 VRV  C17   C18  C13  120.15  3.000
 VRV  N20   C19  C10  180.00  3.000
 VRV  HO22  O22  C3   112.23  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
 VRV  CONST_01  C4    C5   C6   C1     0.00  0.0  0
 VRV  CONST_02  C4    C3   C2   C1     0.00  0.0  0
 VRV  CONST_03  C5    C6   C1   C2     0.00  0.0  0
 VRV  CONST_04  C5    C4   C3   C2     0.00  0.0  0
 VRV  CONST_05  C7    C4   C3   C2   180.00  0.0  0
 VRV  CONST_06  C6    C1   C2   C3     0.00  0.0  0
 VRV  CONST_07  C6    C5   C4   C3     0.00  0.0  0
 VRV  CONST_10  C11   C12  C7   C4   180.00  0.0  0
 VRV  CONST_11  C9    N8   C7   C4   180.00  0.0  0
 VRV  CONST_14  C7    C4   C5   C6   180.00  0.0  0
 VRV  CONST_15  C10   C11  C12  C7     0.00  0.0  0
 VRV  CONST_16  C13   C11  C12  C7   180.00  0.0  0
 VRV  CONST_17  C10   C9   N8   C7     0.00  0.0  0
 VRV  CONST_18  C11   C12  C7   N8     0.00  0.0  0
 VRV  CONST_19  C11   C10  C9   N8     0.00  0.0  0
 VRV  CONST_20  C12   C7   N8   C9     0.00  0.0  0
 VRV  CONST_21  C13   C11  C10  C9   180.00  0.0  0
 VRV  CONST_22  C12   C11  C10  C9     0.00  0.0  0
 VRV  CONST_25  C17   C18  C13  C11  180.00  0.0  0
 VRV  CONST_26  C15   C14  C13  C11  180.00  0.0  0
 VRV  CONST_29  C16   C17  C18  C13    0.00  0.0  0
 VRV  CONST_30  C16   C15  C14  C13    0.00  0.0  0
 VRV  CONST_31  C17   C18  C13  C14    0.00  0.0  0
 VRV  CONST_32  C17   C16  C15  C14    0.00  0.0  0
 VRV  CONST_33  C18   C13  C14  C15    0.00  0.0  0
 VRV  CONST_34  C18   C17  C16  C15    0.00  0.0  0
 VRV  CONST_35  O22   C3   C2   C1   180.00  0.0  0
 VRV  CONST_36  BR23  C6   C1   C2   180.00  0.0  0
 VRV  CONST_37  BR23  C6   C5   C4   180.00  0.0  0
 VRV  CONST_38  O22   C3   C4   C5   180.00  0.0  0
 VRV  CONST_39  O22   C3   C4   C7     0.00  0.0  0
 VRV  CONST_40  O21   C9   N8   C7   180.00  0.0  0
 VRV  CONST_41  C19   C10  C9   N8   180.00  0.0  0
 VRV  CONST_42  O21   C9   C10  C11  180.00  0.0  0
 VRV  CONST_43  C19   C10  C11  C12  180.00  0.0  0
 VRV  CONST_44  C19   C10  C11  C13    0.00  0.0  0
 VRV  CONST_45  H5    C5   C6   C1   180.00  0.0  0
 VRV  CONST_46  H1    C1   C2   C3   180.00  0.0  0
 VRV  CONST_47  H2    C2   C3   C4   180.00  0.0  0
 VRV  CONST_48  H12   C12  C7   C4     0.00  0.0  0
 VRV  CONST_49  HN8   N8   C7   C4     0.00  0.0  0
 VRV  CONST_50  H18   C18  C13  C11    0.00  0.0  0
 VRV  CONST_51  H14   C14  C13  C11    0.00  0.0  0
 VRV  CONST_52  H17   C17  C18  C13  180.00  0.0  0
 VRV  CONST_53  H15   C15  C14  C13  180.00  0.0  0
 VRV  CONST_54  H16   C16  C15  C14  180.00  0.0  0

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
 VRV  plan-1  C1    0.020
 VRV  plan-1  C2    0.020
 VRV  plan-1  C3    0.020
 VRV  plan-1  C4    0.020
 VRV  plan-1  C5    0.020
 VRV  plan-1  C6    0.020
 VRV  plan-1  C7    0.020
 VRV  plan-1  O22   0.020
 VRV  plan-1  BR23  0.020
 VRV  plan-1  H1    0.020
 VRV  plan-1  H2    0.020
 VRV  plan-1  H5    0.020
 VRV  plan-2  C4    0.020
 VRV  plan-2  C7    0.020
 VRV  plan-2  N8    0.020
 VRV  plan-2  C9    0.020
 VRV  plan-2  C10   0.020
 VRV  plan-2  C11   0.020
 VRV  plan-2  C12   0.020
 VRV  plan-2  C13   0.020
 VRV  plan-2  C19   0.020
 VRV  plan-2  N20   0.020
 VRV  plan-2  O21   0.020
 VRV  plan-2  HN8   0.020
 VRV  plan-2  H12   0.020
 VRV  plan-3  C11   0.020
 VRV  plan-3  C13   0.020
 VRV  plan-3  C14   0.020
 VRV  plan-3  C15   0.020
 VRV  plan-3  C16   0.020
 VRV  plan-3  C17   0.020
 VRV  plan-3  C18   0.020
 VRV  plan-3  H14   0.020
 VRV  plan-3  H15   0.020
 VRV  plan-3  H16   0.020
 VRV  plan-3  H17   0.020
 VRV  plan-3  H18   0.020

