# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 17:57:03 2022
#   Inital geometry file: a 82 line input string
#   Ligand name: (2S,4R)-6-fluoro-2',5'-dioxo-2,3-dihydrospiro[chromene-4,4'-imidazolidine]-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NC(=O)[C@@H]1C[C@@]2(NC(=O)NC2=O)c3cc(F)ccc3O1
#
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
 FIS  FIS  (2S,4R)-6-fluoro-2',5'-dioxo-2,3-dihydrospiro[chromene-4,4'-imidazolidine]-2-carboxamide  ligand  30  20  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_FIS
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
 FIS  O3I   O  O     0  -0.464  -1.2097   3.7736  -1.4332
 FIS  O6I   O  O     0  -0.404  -0.7866   1.4005   2.4394
 FIS  N1I   N  NR15  0  -0.644  -0.2176   1.7440  -0.9721
 FIS  C2I   C  CR5   0   0.671  -0.8859   2.8805  -0.6859
 FIS  N4    N  NR15  0  -0.695  -1.1490   2.8416   0.6844
 FIS  F17   F  F     0  -0.316  -4.0373  -1.8314  -0.2889
 FIS  C16   C  CR16  0  -0.342  -0.5827  -2.8538  -0.2691
 FIS  C11   C  CR6   0   0.344   0.0519  -1.6201  -0.1244
 FIS  C12   C  CR6   0   0.139  -0.7033  -0.4565  -0.0052
 FIS  C13   C  CR16  0  -0.461  -2.0938  -0.5373  -0.0751
 FIS  C14   C  CR6   0   0.530  -2.6973  -1.7628  -0.2253
 FIS  C15   C  CR16  0  -0.403  -1.9602  -2.9316  -0.3150
 FIS  O10   O  O2    0  -0.474   1.4027  -1.6338  -0.1097
 FIS  C5    C  CR5   0   0.572  -0.6986   1.7091   1.2784
 FIS  O20   O  O     0  -0.466   3.8603  -1.3650   0.8909
 FIS  C19   C  C     0   0.481   3.5176  -0.6014   0.0071
 FIS  C7I   C  CR5   0  -0.136  -0.0265   0.8834   0.1723
 FIS  C8I   C  CH2   0  -0.458   1.4476   0.6858   0.5326
 FIS  C9    C  CH1   0  -0.071   2.0464  -0.4020  -0.3432
 FIS  H1I   H  HNR5  0   0.419  -0.0037   1.4744  -1.9192
 FIS  HN4   H  HNR5  0   0.433  -1.6286   3.5878   1.1685
 FIS  H16   H  HCR6  0   0.283   0.0156  -3.7515  -0.3550
 FIS  H13   H  HCR6  0   0.287  -2.7073   0.3541  -0.0103
 FIS  H15   H  HCR6  0   0.289  -2.4536  -3.8873  -0.4321
 FIS  H211  H  HNH2  0   0.411   5.3390   0.1696  -0.4983
 FIS  H212  H  HNH2  0   0.415   4.0347   0.7463  -1.4578
 FIS  H8I1  H  HCH2  0   0.289   1.5350   0.3894   1.5808
 FIS  H8I2  H  HCH2  0   0.295   1.9877   1.6242   0.4034
 FIS  H9    H  HCH1  0   0.273   1.9450  -0.1302  -1.4034
 FIS  N21   N  NH2   0  -0.798   4.3512   0.1704  -0.6965

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
 FIS  O3I  C2I   double    1.209  0.020  1.209
 FIS  O6I  C5    double    1.205  0.020  1.205
 FIS  N1I  C2I   single    1.349  0.020  1.349
 FIS  N1I  C7I   single    1.445  0.020  1.445
 FIS  N1I  H1I   single    0.860  0.020  1.020
 FIS  C2I  N4    single    1.396  0.020  1.396
 FIS  N4   C5    single    1.356  0.020  1.356
 FIS  N4   HN4   single    0.860  0.020  1.020
 FIS  F17  C14   single    1.343  0.020  1.343
 FIS  C16  C11   aromatic  1.395  0.020  1.395
 FIS  C16  C15   aromatic  1.380  0.020  1.380
 FIS  C16  H16   single    0.930  0.020  1.080
 FIS  C11  C12   aromatic  1.392  0.020  1.392
 FIS  C11  O10   single    1.351  0.020  1.351
 FIS  C12  C13   aromatic  1.395  0.020  1.395
 FIS  C12  C7I   single    1.512  0.020  1.512
 FIS  C13  C14   aromatic  1.374  0.020  1.374
 FIS  C13  H13   single    0.930  0.020  1.080
 FIS  C14  C15   aromatic  1.385  0.020  1.385
 FIS  C15  H15   single    0.930  0.020  1.080
 FIS  O10  C9    single    1.409  0.020  1.409
 FIS  C5   C7I   single    1.535  0.020  1.535
 FIS  N21  C19   single    1.336  0.020  1.336
 FIS  N21  H211  single    0.860  0.020  1.020
 FIS  N21  H212  single    0.860  0.020  1.020
 FIS  O20  C19   double    1.217  0.020  1.217
 FIS  C19  C9    single    1.525  0.020  1.525
 FIS  C7I  C8I   single    1.530  0.020  1.530
 FIS  C8I  C9    single    1.520  0.020  1.520
 FIS  C8I  H8I1  single    0.970  0.020  1.090
 FIS  C8I  H8I2  single    0.970  0.020  1.090
 FIS  C9   H9    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
 FIS  H1I   N1I  C7I   123.85  3.000
 FIS  H1I   N1I  C2I   122.00  3.000
 FIS  C7I   N1I  C2I   113.54  3.000
 FIS  N4    C2I  N1I   106.15  3.000
 FIS  N4    C2I  O3I   125.24  3.000
 FIS  N1I   C2I  O3I   128.61  3.000
 FIS  HN4   N4   C5    124.37  3.000
 FIS  HN4   N4   C2I   122.62  3.000
 FIS  C5    N4   C2I   113.00  3.000
 FIS  H16   C16  C15   120.15  3.000
 FIS  H16   C16  C11   119.36  3.000
 FIS  C15   C16  C11   120.48  3.000
 FIS  O10   C11  C12   123.37  3.000
 FIS  O10   C11  C16   116.55  3.000
 FIS  C12   C11  C16   120.08  3.000
 FIS  C7I   C12  C13   120.24  3.000
 FIS  C7I   C12  C11   120.53  3.000
 FIS  C13   C12  C11   119.22  3.000
 FIS  H13   C13  C14   119.43  3.000
 FIS  H13   C13  C12   120.90  3.000
 FIS  C14   C13  C12   119.67  3.000
 FIS  C15   C14  C13   121.74  3.000
 FIS  C15   C14  F17   119.00  3.000
 FIS  C13   C14  F17   119.26  3.000
 FIS  H15   C15  C14   120.65  3.000
 FIS  H15   C15  C16   120.56  3.000
 FIS  C14   C15  C16   118.78  3.000
 FIS  C9    O10  C11   116.48  3.000
 FIS  C7I   C5   N4    106.20  3.000
 FIS  C7I   C5   O6I   126.06  3.000
 FIS  N4    C5   O6I   127.74  3.000
 FIS  C9    C19  O20   121.35  3.000
 FIS  C9    C19  N21   113.91  3.000
 FIS  O20   C19  N21   124.68  3.000
 FIS  C8I   C7I  C5    108.76  3.000
 FIS  C8I   C7I  C12   110.15  3.000
 FIS  C5    C7I  C12   111.43  3.000
 FIS  C8I   C7I  N1I   113.01  3.000
 FIS  C5    C7I  N1I   101.09  3.000
 FIS  C12   C7I  N1I   112.08  3.000
 FIS  H8I2  C8I  H8I1  107.91  3.000
 FIS  H8I2  C8I  C9    110.65  3.000
 FIS  H8I1  C8I  C9    109.09  3.000
 FIS  H8I2  C8I  C7I   109.77  3.000
 FIS  H8I1  C8I  C7I   109.75  3.000
 FIS  C9    C8I  C7I   109.65  3.000
 FIS  H9    C9   C8I   110.03  3.000
 FIS  H9    C9   C19   110.05  3.000
 FIS  C8I   C9   C19   109.95  3.000
 FIS  H9    C9   O10   109.50  3.000
 FIS  C8I   C9   O10   110.50  3.000
 FIS  C19   C9   O10   106.75  3.000
 FIS  H212  N21  H211  117.25  3.000
 FIS  H212  N21  C19   122.21  3.000
 FIS  H211  N21  C19   120.51  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
 FIS  CONST_01  C13   C12  C11  C16    0.00  0.0  0
 FIS  CONST_02  C13   C14  C15  C16    0.00  0.0  0
 FIS  CONST_03  C14   C15  C16  C11    0.00  0.0  0
 FIS  CONST_04  C14   C13  C12  C11    0.00  0.0  0
 FIS  CONST_05  C15   C16  C11  C12    0.00  0.0  0
 FIS  CONST_06  C15   C14  C13  C12    0.00  0.0  0
 FIS  CONST_07  C5    N4   C2I  N1I    0.00  0.0  0
 FIS  CONST_08  C7I   C5   N4   C2I    0.00  0.0  0
 FIS  CONST_09  C7I   N1I  C2I  N4     0.00  0.0  0
 FIS  CONST_10  C12   C13  C14  F17  180.00  0.0  0
 FIS  CONST_11  C16   C15  C14  F17  180.00  0.0  0
 FIS  CONST_12  C7I   N1I  C2I  O3I  180.00  0.0  0
 FIS  CONST_13  C5    N4   C2I  O3I  180.00  0.0  0
 FIS  CONST_14  C2I   N4   C5   O6I  180.00  0.0  0
 FIS  CONST_15  H15   C15  C16  C11  180.00  0.0  0
 FIS  CONST_16  H13   C13  C12  C11  180.00  0.0  0
 FIS  CONST_17  H16   C16  C11  C12  180.00  0.0  0
 FIS  CONST_18  HN4   N4   C2I  N1I  180.00  0.0  0
 FIS  CONST_19  H1I   N1I  C2I  N4   180.00  0.0  0
 FIS  CONST_20  H211  N21  C19  C9   180.00  0.0  0
 FIS  CONST_21  H212  N21  C19  C9     0.00  0.0  0

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
 FIS  chir_01  C7I  C12  C5   C8I  negativ
 FIS  chir_02  C9   O10  C8I  C19  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
 FIS  plan-1  O20   0.020
 FIS  plan-1  C19   0.020
 FIS  plan-1  C9    0.020
 FIS  plan-1  H211  0.020
 FIS  plan-1  H212  0.020
 FIS  plan-1  N21   0.020
 FIS  plan-2  F17   0.020
 FIS  plan-2  C16   0.020
 FIS  plan-2  C11   0.020
 FIS  plan-2  C12   0.020
 FIS  plan-2  C13   0.020
 FIS  plan-2  C14   0.020
 FIS  plan-2  C15   0.020
 FIS  plan-2  O10   0.020
 FIS  plan-2  C7I   0.020
 FIS  plan-2  H16   0.020
 FIS  plan-2  H13   0.020
 FIS  plan-2  H15   0.020
 FIS  plan-3  O3I   0.020
 FIS  plan-3  O6I   0.020
 FIS  plan-3  N1I   0.020
 FIS  plan-3  C2I   0.020
 FIS  plan-3  N4    0.020
 FIS  plan-3  C5    0.020
 FIS  plan-3  C7I   0.020
 FIS  plan-3  H1I   0.020
 FIS  plan-3  HN4   0.020

