# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 12 09:29:57 2020
#   Inital geometry file: a 90 line input string
#   Ligand name: 2-(4-fluoranyl-3-oxidanyl-phenyl)carbonylquinoline-7-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(ccc1F)C(=O)c2ccc3ccc(cc3n2)C#N
#
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
 9N2  9N2  2-(4-fluoranyl-3-oxidanyl-phenyl)carbonylquinoline-7-carbonitrile  ligand  31  22  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_9N2
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
 9N2  F    F  F     0  -0.304   4.7956   2.4983  -0.6414
 9N2  C12  C  CR6   0   0.483   3.9158   1.5094  -0.4538
 9N2  C11  C  CR16  0  -0.400   2.7218   1.5153  -1.1378
 9N2  C10  C  CR16  0  -0.269   1.8070   0.4945  -0.9225
 9N2  C13  C  CR6   0   0.231   4.2522   0.4959   0.4451
 9N2  O1   O  OH1   0  -0.618   5.4378   0.5827   1.0668
 9N2  C14  C  CR16  0  -0.394   3.3437  -0.5314   0.6309
 9N2  C9   C  CR6   0  -0.010   2.1154  -0.5325  -0.0355
 9N2  C8   C  C     0   0.346   1.2190  -1.6928   0.1727
 9N2  O    O  O     0  -0.373   1.6491  -2.7733   0.5171
 9N2  C7   C  CR6   0   0.102  -0.2611  -1.5377  -0.0199
 9N2  C6   C  CR16  0  -0.279  -1.0203  -2.6628  -0.4212
 9N2  C5   C  CR16  0  -0.185  -2.3734  -2.5330  -0.5287
 9N2  N1   N  N     0  -0.431  -0.7861  -0.3773   0.2669
 9N2  C15  C  CR66  0   0.222  -2.1263  -0.2364   0.1842
 9N2  C4   C  CR66  0   0.108  -2.9768  -1.2956  -0.2163
 9N2  C3   C  CR16  0  -0.300  -4.3708  -1.0806  -0.2886
 9N2  C2   C  CR16  0  -0.236  -4.9004   0.1374   0.0247
 9N2  C16  C  CR16  0  -0.285  -2.6845   1.0181   0.5052
 9N2  C1   C  CR6   0   0.001  -4.0442   1.1935   0.4238
 9N2  C    C  CSP   0   0.065  -4.6100   2.4649   0.7451
 9N2  N    N  NS    0  -0.242  -5.0731   3.4879   1.0014
 9N2  H1   H  HCR6  0   0.292   2.5077   2.3162  -1.8332
 9N2  H2   H  HCR6  0   0.270   0.8749   0.5043  -1.4670
 9N2  H3   H  HOH1  0   0.483   5.5579  -0.1632   1.6661
 9N2  H4   H  HCR6  0   0.289   3.5877  -1.3357   1.3152
 9N2  H5   H  HCR6  0   0.286  -0.5312  -3.5991  -0.6493
 9N2  H6   H  HCR6  0   0.284  -2.9872  -3.3662  -0.8464
 9N2  H7   H  HCR6  0   0.281  -5.0174  -1.8934  -0.5932
 9N2  H8   H  HCR6  0   0.289  -5.9672   0.3042  -0.0284
 9N2  H9   H  HCR6  0   0.293  -2.0290   1.8235   0.8083

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
 9N2  O    C8   double    1.213  0.020  1.213
 9N2  N    C    triple    1.152  0.020  1.152
 9N2  C2   C3   aromatic  1.365  0.020  1.365
 9N2  C2   C1   aromatic  1.417  0.020  1.417
 9N2  C8   C7   single    1.501  0.020  1.501
 9N2  C8   C9   single    1.481  0.020  1.481
 9N2  C3   C4   aromatic  1.412  0.020  1.412
 9N2  C    C1   single    1.428  0.020  1.428
 9N2  C5   C6   aromatic  1.364  0.020  1.364
 9N2  C5   C4   aromatic  1.412  0.020  1.412
 9N2  C1   C16  aromatic  1.373  0.020  1.373
 9N2  C6   C7   aromatic  1.415  0.020  1.415
 9N2  C4   C15  aromatic  1.416  0.020  1.416
 9N2  C7   N1   aromatic  1.306  0.020  1.306
 9N2  C16  C15  aromatic  1.410  0.020  1.410
 9N2  C15  N1   aromatic  1.350  0.020  1.350
 9N2  C14  C9   aromatic  1.397  0.020  1.397
 9N2  C14  C13  aromatic  1.384  0.020  1.384
 9N2  C9   C10  aromatic  1.392  0.020  1.392
 9N2  O1   C13  single    1.342  0.020  1.342
 9N2  C13  C12  aromatic  1.396  0.020  1.396
 9N2  C10  C11  aromatic  1.388  0.020  1.388
 9N2  C12  C11  aromatic  1.376  0.020  1.376
 9N2  C12  F    single    1.337  0.020  1.337
 9N2  C11  H1   single    0.930  0.020  1.080
 9N2  C10  H2   single    0.930  0.020  1.080
 9N2  O1   H3   single    0.850  0.020  0.980
 9N2  C14  H4   single    0.930  0.020  1.080
 9N2  C6   H5   single    0.930  0.020  1.080
 9N2  C5   H6   single    0.930  0.020  1.080
 9N2  C3   H7   single    0.930  0.020  1.080
 9N2  C2   H8   single    0.930  0.020  1.080
 9N2  C16  H9   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
 9N2  C13  C12  C11  122.16  3.000
 9N2  C11  C12  F    119.87  3.000
 9N2  C13  C12  F    117.97  3.000
 9N2  H1   C11  C10  120.92  3.000
 9N2  H1   C11  C12  119.62  3.000
 9N2  C10  C11  C12  119.46  3.000
 9N2  H2   C10  C9   121.31  3.000
 9N2  H2   C10  C11  118.97  3.000
 9N2  C9   C10  C11  119.71  3.000
 9N2  C14  C13  O1   124.47  3.000
 9N2  O1   C13  C12  117.67  3.000
 9N2  C14  C13  C12  117.86  3.000
 9N2  H3   O1   C13  110.37  3.000
 9N2  H4   C14  C9   119.90  3.000
 9N2  H4   C14  C13  119.19  3.000
 9N2  C9   C14  C13  120.90  3.000
 9N2  C8   C9   C14  117.75  3.000
 9N2  C14  C9   C10  119.88  3.000
 9N2  C8   C9   C10  122.25  3.000
 9N2  C7   C8   O    118.57  3.000
 9N2  C7   C8   C9   119.87  3.000
 9N2  O    C8   C9   121.55  3.000
 9N2  N1   C7   C6   123.59  3.000
 9N2  N1   C7   C8   117.40  3.000
 9N2  C6   C7   C8   118.90  3.000
 9N2  H5   C6   C5   121.00  3.000
 9N2  H5   C6   C7   120.38  3.000
 9N2  C5   C6   C7   118.62  3.000
 9N2  H6   C5   C4   119.81  3.000
 9N2  H6   C5   C6   120.83  3.000
 9N2  C4   C5   C6   119.35  3.000
 9N2  C15  N1   C7   118.58  3.000
 9N2  C16  C15  C4   119.47  3.000
 9N2  C16  C15  N1   118.15  3.000
 9N2  C4   C15  N1   122.38  3.000
 9N2  C3   C4   C15  119.57  3.000
 9N2  C15  C4   C5   117.48  3.000
 9N2  C3   C4   C5   122.95  3.000
 9N2  H7   C3   C2   120.20  3.000
 9N2  H7   C3   C4   119.32  3.000
 9N2  C2   C3   C4   120.47  3.000
 9N2  H8   C2   C1   119.67  3.000
 9N2  H8   C2   C3   120.63  3.000
 9N2  C1   C2   C3   119.70  3.000
 9N2  H9   C16  C1   121.43  3.000
 9N2  H9   C16  C15  119.10  3.000
 9N2  C1   C16  C15  119.48  3.000
 9N2  C    C1   C16  119.51  3.000
 9N2  C16  C1   C2   121.31  3.000
 9N2  C    C1   C2   119.18  3.000
 9N2  N    C    C1   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
 9N2  CONST_01  C9   C14  C13  C12    0.00   0.0  0
 9N2  CONST_02  C9   C10  C11  C12    0.00   0.0  0
 9N2  CONST_03  C14  C9   C10  C11    0.00   0.0  0
 9N2  CONST_04  C14  C13  C12  C11    0.00   0.0  0
 9N2  CONST_05  C13  C14  C9   C10    0.00   0.0  0
 9N2  CONST_06  C13  C12  C11  C10    0.00   0.0  0
 9N2  CONST_07  C4   C5   C6   C7     0.00   0.0  0
 9N2  CONST_08  C4   C15  N1   C7     0.00   0.0  0
 9N2  CONST_09  C16  C15  N1   C7   180.00   0.0  0
 9N2  CONST_10  C3   C4   C5   C6   180.00   0.0  0
 9N2  CONST_11  C15  C4   C5   C6     0.00   0.0  0
 9N2  CONST_12  C15  N1   C7   C6     0.00   0.0  0
 9N2  CONST_13  N1   C7   C6   C5     0.00   0.0  0
 9N2  CONST_14  C2   C3   C4   C5   180.00   0.0  0
 9N2  CONST_15  C16  C15  C4   C5   180.00   0.0  0
 9N2  CONST_16  N1   C15  C4   C5     0.00   0.0  0
 9N2  CONST_17  C3   C4   C15  N1   180.00   0.0  0
 9N2  CONST_18  C1   C16  C15  N1   180.00   0.0  0
 9N2  CONST_19  C2   C3   C4   C15    0.00   0.0  0
 9N2  CONST_20  C2   C1   C16  C15    0.00   0.0  0
 9N2  CONST_21  C1   C2   C3   C4     0.00   0.0  0
 9N2  CONST_22  C1   C16  C15  C4     0.00   0.0  0
 9N2  CONST_23  C16  C1   C2   C3     0.00   0.0  0
 9N2  CONST_24  C16  C15  C4   C3     0.00   0.0  0
 9N2  CONST_25  C14  C13  C12  F    180.00   0.0  0
 9N2  CONST_26  C10  C11  C12  F    180.00   0.0  0
 9N2  CONST_27  C8   C9   C10  C11  180.00   0.0  0
 9N2  CONST_28  O1   C13  C12  C11  180.00   0.0  0
 9N2  CONST_29  C8   C9   C14  C13  180.00   0.0  0
 9N2  CONST_30  C9   C14  C13  O1   180.00   0.0  0
 9N2  CONST_31  C5   C6   C7   C8   180.00   0.0  0
 9N2  CONST_32  C15  N1   C7   C8   180.00   0.0  0
 9N2  CONST_33  C    C1   C16  C15  180.00   0.0  0
 9N2  CONST_34  C    C1   C2   C3   180.00   0.0  0
 9N2  CONST_35  H4   C14  C13  C12  180.00   0.0  0
 9N2  CONST_36  H2   C10  C11  C12  180.00   0.0  0
 9N2  CONST_37  H1   C11  C12  C13  180.00   0.0  0
 9N2  CONST_38  H6   C5   C6   C7   180.00   0.0  0
 9N2  CONST_39  H7   C3   C4   C5     0.00   0.0  0
 9N2  CONST_40  H5   C6   C7   N1   180.00   0.0  0
 9N2  CONST_41  H9   C16  C15  N1     0.00   0.0  0
 9N2  CONST_42  H8   C2   C3   C4   180.00   0.0  0
 9N2  Var_01    C7   C8   C9   C10  -28.84  30.0  2
 9N2  Var_02    C6   C7   C8   C9   151.47  30.0  2

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
 9N2  plan-1  F    0.020
 9N2  plan-1  C12  0.020
 9N2  plan-1  C11  0.020
 9N2  plan-1  C10  0.020
 9N2  plan-1  C13  0.020
 9N2  plan-1  O1   0.020
 9N2  plan-1  C14  0.020
 9N2  plan-1  C9   0.020
 9N2  plan-1  C8   0.020
 9N2  plan-1  H1   0.020
 9N2  plan-1  H2   0.020
 9N2  plan-1  H4   0.020
 9N2  plan-2  C8   0.020
 9N2  plan-2  C7   0.020
 9N2  plan-2  C6   0.020
 9N2  plan-2  C5   0.020
 9N2  plan-2  N1   0.020
 9N2  plan-2  C15  0.020
 9N2  plan-2  C4   0.020
 9N2  plan-2  C3   0.020
 9N2  plan-2  C2   0.020
 9N2  plan-2  C16  0.020
 9N2  plan-2  C1   0.020
 9N2  plan-2  C    0.020
 9N2  plan-2  N    0.020
 9N2  plan-2  H5   0.020
 9N2  plan-2  H6   0.020
 9N2  plan-2  H7   0.020
 9N2  plan-2  H8   0.020
 9N2  plan-2  H9   0.020
 9N2  plan-3  C9   0.020
 9N2  plan-3  C8   0.020
 9N2  plan-3  O    0.020
 9N2  plan-3  C7   0.020

