# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 08:02:12 2020
#   Inital geometry file: a 105 line input string
#   Ligand name: 6-fluoranyl-~{N}-[(1-oxidanylcyclohexyl)methyl]-4-oxidanylidene-chromene-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC1(CCCCC1)CNC(=O)C2=CC(=O)c3cc(F)ccc3O2
#
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
 FYE  FYE  6-fluoranyl-~{N}-[(1-oxidanylcyclohexyl)methyl]-4-oxidanylidene-chromene-2-carboxamide  ligand  41  23  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FYE
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
 FYE  C4   C  CH2   0  -0.432  -6.1928   0.3144  -0.2763
 FYE  C14  C  CR16  0  -0.403   3.8703   2.2142   0.8633
 FYE  C5   C  CH2   0  -0.430  -5.1812  -0.5465   0.4736
 FYE  C6   C  CH2   0  -0.288  -2.8082  -1.0076   1.0503
 FYE  C11  C  CR66  0  -0.111   3.3542  -0.2534  -0.3279
 FYE  C7   C  C     0   0.534  -0.6518  -1.6232   0.0506
 FYE  C8   C  CR6   0   0.257   0.7853  -1.2098  -0.1249
 FYE  C9   C  CR16  0  -0.466   1.6701  -1.9726  -0.7863
 FYE  C10  C  CR6   0   0.464   3.0494  -1.5523  -0.9451
 FYE  C12  C  CR16  0  -0.460   4.6388   0.2942  -0.3915
 FYE  C13  C  CR6   0   0.558   4.8705   1.5074   0.2014
 FYE  C3   C  CH2   0  -0.433  -5.9517   1.7993  -0.0256
 FYE  F    F  F     0  -0.307   6.0978   2.0397   0.1497
 FYE  C15  C  CR16  0  -0.307   2.6013   1.6830   0.9309
 FYE  C16  C  CR66  0   0.377   2.3532   0.4504   0.3340
 FYE  O2   O  O     0  -0.421   3.8873  -2.2124  -1.5377
 FYE  O3   O  O     0  -0.470   1.0925  -0.0335   0.4250
 FYE  O1   O  O     0  -0.457  -1.0351  -2.6666  -0.4485
 FYE  N    N  NH1   0  -0.660  -1.4056  -0.7877   0.7728
 FYE  C    C  CT    0   0.207  -3.7345  -0.1718   0.1523
 FYE  O    O  OH1   0  -0.675  -3.5137  -0.4983  -1.2069
 FYE  C2   C  CH2   0  -0.424  -4.5193   2.1885  -0.3716
 FYE  C1   C  CH2   0  -0.473  -3.5182   1.3274   0.3918
 FYE  H1   H  HCH2  0   0.216  -6.1313   0.1091  -1.3484
 FYE  H2   H  HCH2  0   0.229  -7.2028   0.0371   0.0338
 FYE  H4   H  HCH2  0   0.223  -5.3335  -0.4296   1.5515
 FYE  H5   H  HCH2  0   0.236  -5.3394  -1.6064   0.2524
 FYE  H6   H  HCH2  0   0.261  -3.0285  -2.0676   0.9228
 FYE  H7   H  HCH2  0   0.259  -2.9867  -0.7579   2.0976
 FYE  H8   H  HCR6  0   0.295   1.3501  -2.9151  -1.2063
 FYE  H9   H  HCR6  0   0.296   5.4312  -0.2363  -0.9028
 FYE  H10  H  HCH2  0   0.228  -6.6589   2.3996  -0.6028
 FYE  H11  H  HCH2  0   0.209  -6.1420   2.0249   1.0294
 FYE  H12  H  HCR6  0   0.301   1.8079   2.2127   1.4407
 FYE  H13  H  HNH1  0   0.415  -0.9766   0.0252   1.1849
 FYE  H14  H  HOH1  0   0.445  -2.6909  -0.0897  -1.4960
 FYE  H15  H  HCH2  0   0.214  -4.3581   2.0806  -1.4481
 FYE  H16  H  HCH2  0   0.230  -4.3447   3.2414  -0.1389
 FYE  H17  H  HCH2  0   0.226  -3.6104   1.5298   1.4642
 FYE  H18  H  HCH2  0   0.232  -2.4968   1.6097   0.1137
 FYE  H3   H  HCR6  0   0.303   4.0898   3.1703   1.3192

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
 FYE  C2   C1   single    1.525  0.020  1.525
 FYE  C2   C3   single    1.524  0.020  1.524
 FYE  O    C    single    1.415  0.020  1.415
 FYE  C1   C    single    1.534  0.020  1.534
 FYE  C    C6   single    1.537  0.020  1.537
 FYE  C    C5   single    1.529  0.020  1.529
 FYE  C3   C4   single    1.525  0.020  1.525
 FYE  C6   N    single    1.447  0.020  1.447
 FYE  C4   C5   single    1.525  0.020  1.525
 FYE  N    C7   single    1.337  0.020  1.337
 FYE  C7   O1   double    1.218  0.020  1.218
 FYE  C7   C8   single    1.506  0.020  1.506
 FYE  O3   C8   single    1.334  0.020  1.334
 FYE  O3   C16  single    1.353  0.020  1.353
 FYE  C15  C16  aromatic  1.392  0.020  1.392
 FYE  C15  C14  aromatic  1.377  0.020  1.377
 FYE  C8   C9   double    1.343  0.020  1.343
 FYE  C16  C11  aromatic  1.391  0.020  1.391
 FYE  C14  C13  aromatic  1.392  0.020  1.392
 FYE  C9   C10  single    1.451  0.020  1.451
 FYE  C11  C12  aromatic  1.398  0.020  1.398
 FYE  C11  C10  single    1.470  0.020  1.470
 FYE  C13  F    single    1.339  0.020  1.339
 FYE  C13  C12  aromatic  1.370  0.020  1.370
 FYE  C10  O2   double    1.220  0.020  1.220
 FYE  C4   H1   single    0.970  0.020  1.090
 FYE  C4   H2   single    0.970  0.020  1.090
 FYE  C14  H3   single    0.930  0.020  1.080
 FYE  C5   H4   single    0.970  0.020  1.090
 FYE  C5   H5   single    0.970  0.020  1.090
 FYE  C6   H6   single    0.970  0.020  1.090
 FYE  C6   H7   single    0.970  0.020  1.090
 FYE  C9   H8   single    0.930  0.020  1.080
 FYE  C12  H9   single    0.930  0.020  1.080
 FYE  C3   H10  single    0.970  0.020  1.090
 FYE  C3   H11  single    0.970  0.020  1.090
 FYE  C15  H12  single    0.930  0.020  1.080
 FYE  N    H13  single    0.860  0.020  1.020
 FYE  O    H14  single    0.850  0.020  0.980
 FYE  C2   H15  single    0.970  0.020  1.090
 FYE  C2   H16  single    0.970  0.020  1.090
 FYE  C1   H17  single    0.970  0.020  1.090
 FYE  C1   H18  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
 FYE  H2   C4   H1   106.43  3.000
 FYE  H2   C4   C3   110.29  3.000
 FYE  H1   C4   C3   109.58  3.000
 FYE  H2   C4   C5   109.29  3.000
 FYE  H1   C4   C5   109.80  3.000
 FYE  C3   C4   C5   111.33  3.000
 FYE  H3   C14  C15  120.47  3.000
 FYE  H3   C14  C13  120.22  3.000
 FYE  C15  C14  C13  119.31  3.000
 FYE  H5   C5   H4   106.40  3.000
 FYE  H5   C5   C    109.37  3.000
 FYE  H4   C5   C    108.20  3.000
 FYE  H5   C5   C4   110.58  3.000
 FYE  H4   C5   C4   109.36  3.000
 FYE  C    C5   C4   112.71  3.000
 FYE  H7   C6   H6   107.56  3.000
 FYE  H7   C6   C    109.74  3.000
 FYE  H6   C6   C    109.79  3.000
 FYE  H7   C6   N    107.93  3.000
 FYE  H6   C6   N    108.74  3.000
 FYE  C    C6   N    112.93  3.000
 FYE  C16  C11  C12  118.99  3.000
 FYE  C12  C11  C10  121.17  3.000
 FYE  C16  C11  C10  119.84  3.000
 FYE  N    C7   O1   125.38  3.000
 FYE  O1   C7   C8   119.19  3.000
 FYE  N    C7   C8   115.43  3.000
 FYE  O3   C8   C9   123.52  3.000
 FYE  C9   C8   C7   122.04  3.000
 FYE  O3   C8   C7   114.44  3.000
 FYE  H8   C9   C10  119.47  3.000
 FYE  H8   C9   C8   119.47  3.000
 FYE  C10  C9   C8   121.06  3.000
 FYE  O2   C10  C9   123.32  3.000
 FYE  O2   C10  C11  122.65  3.000
 FYE  C9   C10  C11  114.03  3.000
 FYE  H9   C12  C13  120.98  3.000
 FYE  H9   C12  C11  120.16  3.000
 FYE  C13  C12  C11  118.85  3.000
 FYE  F    C13  C12  119.37  3.000
 FYE  C12  C13  C14  122.26  3.000
 FYE  F    C13  C14  118.37  3.000
 FYE  H11  C3   H10  106.45  3.000
 FYE  H11  C3   C2   109.23  3.000
 FYE  H10  C3   C2   110.37  3.000
 FYE  H11  C3   C4   109.35  3.000
 FYE  H10  C3   C4   110.22  3.000
 FYE  C2   C3   C4   111.09  3.000
 FYE  H12  C15  C16  120.33  3.000
 FYE  H12  C15  C14  120.68  3.000
 FYE  C16  C15  C14  118.99  3.000
 FYE  O3   C16  C15  116.99  3.000
 FYE  C15  C16  C11  121.59  3.000
 FYE  O3   C16  C11  121.42  3.000
 FYE  C16  O3   C8   120.13  3.000
 FYE  H13  N    C7   119.03  3.000
 FYE  H13  N    C6   117.20  3.000
 FYE  C7   N    C6   123.73  3.000
 FYE  C1   C    O    110.70  3.000
 FYE  C1   C    C6   110.81  3.000
 FYE  O    C    C6   109.98  3.000
 FYE  C6   C    C5   108.32  3.000
 FYE  C1   C    C5   109.89  3.000
 FYE  O    C    C5   107.04  3.000
 FYE  H14  O    C    108.89  3.000
 FYE  H16  C2   H15  106.33  3.000
 FYE  H16  C2   C1   109.43  3.000
 FYE  H15  C2   C1   109.89  3.000
 FYE  H16  C2   C3   110.36  3.000
 FYE  H15  C2   C3   109.68  3.000
 FYE  C1   C2   C3   111.04  3.000
 FYE  H18  C1   H17  106.23  3.000
 FYE  H18  C1   C2   109.84  3.000
 FYE  H17  C1   C2   109.30  3.000
 FYE  H18  C1   C    110.10  3.000
 FYE  H17  C1   C    108.77  3.000
 FYE  C2   C1   C    112.41  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
 FYE  CONST_01  C11  C16  C15  C14     0.00   0.0  0
 FYE  CONST_02  C11  C12  C13  C14     0.00   0.0  0
 FYE  CONST_03  C15  C16  C11  C12     0.00   0.0  0
 FYE  CONST_04  C15  C14  C13  C12     0.00   0.0  0
 FYE  CONST_05  C16  C15  C14  C13     0.00   0.0  0
 FYE  CONST_06  C16  C11  C12  C13     0.00   0.0  0
 FYE  CONST_07  F    C13  C12  C11   180.00   0.0  0
 FYE  CONST_08  C15  C14  C13  F     180.00   0.0  0
 FYE  CONST_09  H9   C12  C13  C14   180.00   0.0  0
 FYE  CONST_10  H12  C15  C16  C11   180.00   0.0  0
 FYE  CONST_11  H3   C14  C13  C12   180.00   0.0  0
 FYE  CONST_12  C8   C7   N    C6    180.00   0.0  0
 FYE  CONST_13  H13  N    C7   C8      0.00   0.0  0
 FYE  CONST_14  O1   C7   N    C6      0.00   0.0  0
 FYE  Var_01    C1   C2   C3   C4    -55.53  30.0  1
 FYE  Var_02    C2   C3   C4   C5     55.00  30.0  1
 FYE  Var_03    C8   C9   C10  C11    -0.04  30.0  1
 FYE  Var_04    C15  C16  O3   C8    180.00  30.0  1
 FYE  Var_05    C16  C11  C10  C9      0.04  30.0  1
 FYE  Var_06    O3   C8   C9   C10     0.06  30.0  1
 FYE  Var_07    C    C1   C2   C3     55.91  30.0  1
 FYE  Var_08    C    C5   C4   C3    -54.89  30.0  1
 FYE  Var_09    N    C7   C8   C9    177.66  30.0  2
 FYE  Var_10    C    C6   N    C7   -101.12  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
 FYE  chir_01  C  C1  C6  C5  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
 FYE  plan-1  C6   0.020
 FYE  plan-1  C7   0.020
 FYE  plan-1  C8   0.020
 FYE  plan-1  O1   0.020
 FYE  plan-1  N    0.020
 FYE  plan-1  H13  0.020
 FYE  plan-2  C14  0.020
 FYE  plan-2  C11  0.020
 FYE  plan-2  C10  0.020
 FYE  plan-2  C12  0.020
 FYE  plan-2  C13  0.020
 FYE  plan-2  F    0.020
 FYE  plan-2  C15  0.020
 FYE  plan-2  C16  0.020
 FYE  plan-2  O3   0.020
 FYE  plan-2  H9   0.020
 FYE  plan-2  H12  0.020
 FYE  plan-2  H3   0.020
 FYE  plan-3  C11  0.020
 FYE  plan-3  C9   0.020
 FYE  plan-3  C10  0.020
 FYE  plan-3  O2   0.020

