# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 10 17:57:05 2022
#   Inital geometry file: a 82 line input string
#   Ligand name: (2R,4S)-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
 FIR  FIR  (2R,4S)-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_FIR
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
 FIR  O3I   O  O     0  -0.464   3.7399   1.4609  -1.2420
 FIR  O6I   O  O     0  -0.404   1.4144  -2.4392  -0.8082
 FIR  N1I   N  NR15  0  -0.644   1.7308   0.9720  -0.2216
 FIR  C2I   C  CR5   0   0.671   2.8597   0.7023  -0.9096
 FIR  N4    N  NR15  0  -0.694   2.8306  -0.6665  -1.1818
 FIR  O10   O  O2    0  -0.474  -1.6223   0.0630   1.4282
 FIR  C16   C  CR16  0  -0.341  -2.8636   0.2287  -0.5433
 FIR  C11   C  CR6   0   0.344  -1.6223   0.0897   0.0777
 FIR  C12   C  CR6   0   0.138  -0.4655  -0.0126  -0.6900
 FIR  C13   C  CR16  0  -0.461  -0.5610   0.0680  -2.0790
 FIR  C14   C  CR6   0   0.530  -1.7936   0.2127  -2.6689
 FIR  C15   C  CR16  0  -0.404  -2.9558   0.2857  -1.9194
 FIR  C9    C  CH1   0  -0.070  -0.3867   0.3025   2.0628
 FIR  C5    C  CR5   0   0.571   1.7114  -1.2753  -0.7182
 FIR  F17   F  F     0  -0.316  -1.8761   0.2873  -4.0076
 FIR  N21   N  NH2   0  -0.799   0.1681   0.6597   4.3730
 FIR  C19   C  C     0   0.482  -0.5697  -0.0695   3.5310
 FIR  C7I   C  CR5   0  -0.136   0.8832  -0.1820  -0.0283
 FIR  C8I   C  CH2   0  -0.458   0.7049  -0.5550   1.4449
 FIR  H1I   H  HNR5  0   0.419   1.4539   1.9151   0.0007
 FIR  HN4   H  HNR5  0   0.433   3.5760  -1.1406  -1.6727
 FIR  H16   H  HCR6  0   0.283  -3.7559   0.3011   0.0647
 FIR  H13   H  HCR6  0   0.287   0.3246   0.0153  -2.7019
 FIR  H15   H  HCR6  0   0.289  -3.9175   0.3987  -2.4022
 FIR  H9    H  HCH1  0   0.273  -0.1278   1.3663   1.9704
 FIR  H211  H  HNH2  0   0.411   0.1741   0.4512   5.3587
 FIR  H212  H  HNH2  0   0.415   0.7026   1.4553   4.0678
 FIR  H8I1  H  HCH2  0   0.294   1.6472  -0.4178   1.9763
 FIR  H8I2  H  HCH2  0   0.288   0.4223  -1.6073   1.5278
 FIR  O20   O  O     0  -0.466  -1.2914  -0.9918   3.8630

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
 FIR  O3I  C2I   double    1.209  0.020  1.209
 FIR  O6I  C5    double    1.205  0.020  1.205
 FIR  N1I  C2I   single    1.349  0.020  1.349
 FIR  N1I  C7I   single    1.445  0.020  1.445
 FIR  N1I  H1I   single    0.860  0.020  1.020
 FIR  C2I  N4    single    1.396  0.020  1.396
 FIR  N4   C5    single    1.356  0.020  1.356
 FIR  N4   HN4   single    0.860  0.020  1.020
 FIR  O10  C11   single    1.351  0.020  1.351
 FIR  O10  C9    single    1.410  0.020  1.410
 FIR  C16  C11   aromatic  1.395  0.020  1.395
 FIR  C16  C15   aromatic  1.380  0.020  1.380
 FIR  C16  H16   single    0.930  0.020  1.080
 FIR  C11  C12   aromatic  1.392  0.020  1.392
 FIR  C12  C13   aromatic  1.395  0.020  1.395
 FIR  C12  C7I   single    1.512  0.020  1.512
 FIR  C13  C14   aromatic  1.374  0.020  1.374
 FIR  C13  H13   single    0.930  0.020  1.080
 FIR  C14  C15   aromatic  1.385  0.020  1.385
 FIR  C14  F17   single    1.343  0.020  1.343
 FIR  C15  H15   single    0.930  0.020  1.080
 FIR  C9   C19   single    1.526  0.020  1.526
 FIR  C9   C8I   single    1.519  0.020  1.519
 FIR  C9   H9    single    0.970  0.020  1.090
 FIR  C5   C7I   single    1.535  0.020  1.535
 FIR  O20  C19   double    1.217  0.020  1.217
 FIR  N21  C19   single    1.336  0.020  1.336
 FIR  N21  H211  single    0.860  0.020  1.020
 FIR  N21  H212  single    0.860  0.020  1.020
 FIR  C7I  C8I   single    1.530  0.020  1.530
 FIR  C8I  H8I1  single    0.970  0.020  1.090
 FIR  C8I  H8I2  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
 FIR  H1I   N1I  C7I   123.84  3.000
 FIR  H1I   N1I  C2I   121.97  3.000
 FIR  C7I   N1I  C2I   113.54  3.000
 FIR  N4    C2I  N1I   106.14  3.000
 FIR  N4    C2I  O3I   125.24  3.000
 FIR  N1I   C2I  O3I   128.62  3.000
 FIR  HN4   N4   C5    124.35  3.000
 FIR  HN4   N4   C2I   122.64  3.000
 FIR  C5    N4   C2I   113.01  3.000
 FIR  C9    O10  C11   116.54  3.000
 FIR  H16   C16  C15   120.15  3.000
 FIR  H16   C16  C11   119.35  3.000
 FIR  C15   C16  C11   120.49  3.000
 FIR  C12   C11  C16   120.08  3.000
 FIR  C12   C11  O10   123.36  3.000
 FIR  C16   C11  O10   116.56  3.000
 FIR  C7I   C12  C13   120.23  3.000
 FIR  C7I   C12  C11   120.55  3.000
 FIR  C13   C12  C11   119.22  3.000
 FIR  H13   C13  C14   119.42  3.000
 FIR  H13   C13  C12   120.91  3.000
 FIR  C14   C13  C12   119.67  3.000
 FIR  F17   C14  C15   119.01  3.000
 FIR  F17   C14  C13   119.26  3.000
 FIR  C15   C14  C13   121.74  3.000
 FIR  H15   C15  C14   120.66  3.000
 FIR  H15   C15  C16   120.56  3.000
 FIR  C14   C15  C16   118.77  3.000
 FIR  H9    C9   C8I   110.05  3.000
 FIR  H9    C9   C19   110.20  3.000
 FIR  C8I   C9   C19   109.87  3.000
 FIR  H9    C9   O10   109.47  3.000
 FIR  C8I   C9   O10   110.54  3.000
 FIR  C19   C9   O10   106.66  3.000
 FIR  C7I   C5   N4    106.21  3.000
 FIR  C7I   C5   O6I   126.06  3.000
 FIR  N4    C5   O6I   127.73  3.000
 FIR  H212  N21  H211  117.22  3.000
 FIR  H212  N21  C19   122.27  3.000
 FIR  H211  N21  C19   120.45  3.000
 FIR  N21   C19  O20   124.68  3.000
 FIR  N21   C19  C9    114.03  3.000
 FIR  O20   C19  C9    121.22  3.000
 FIR  C8I   C7I  C5    108.78  3.000
 FIR  C8I   C7I  C12   110.17  3.000
 FIR  C5    C7I  C12   111.37  3.000
 FIR  C8I   C7I  N1I   113.07  3.000
 FIR  C5    C7I  N1I   101.08  3.000
 FIR  C12   C7I  N1I   112.05  3.000
 FIR  H8I2  C8I  H8I1  107.92  3.000
 FIR  H8I2  C8I  C7I   109.75  3.000
 FIR  H8I1  C8I  C7I   109.74  3.000
 FIR  H8I2  C8I  C9    109.07  3.000
 FIR  H8I1  C8I  C9    110.59  3.000
 FIR  C7I   C8I  C9    109.73  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
 FIR  CONST_01  C13   C12  C11  C16    0.00  0.0  0
 FIR  CONST_02  C13   C14  C15  C16    0.00  0.0  0
 FIR  CONST_03  C14   C15  C16  C11    0.00  0.0  0
 FIR  CONST_04  C14   C13  C12  C11    0.00  0.0  0
 FIR  CONST_05  C15   C16  C11  C12    0.00  0.0  0
 FIR  CONST_06  C15   C14  C13  C12    0.00  0.0  0
 FIR  CONST_07  C5    N4   C2I  N1I    0.00  0.0  0
 FIR  CONST_08  C7I   C5   N4   C2I    0.00  0.0  0
 FIR  CONST_09  C7I   N1I  C2I  N4     0.00  0.0  0
 FIR  CONST_10  F17   C14  C15  C16  180.00  0.0  0
 FIR  CONST_11  F17   C14  C13  C12  180.00  0.0  0
 FIR  CONST_12  C7I   N1I  C2I  O3I  180.00  0.0  0
 FIR  CONST_13  C5    N4   C2I  O3I  180.00  0.0  0
 FIR  CONST_14  C2I   N4   C5   O6I  180.00  0.0  0
 FIR  CONST_15  H16   C16  C11  O10    0.00  0.0  0
 FIR  CONST_16  H15   C15  C16  C11  180.00  0.0  0
 FIR  CONST_17  H13   C13  C12  C11  180.00  0.0  0
 FIR  CONST_18  HN4   N4   C2I  N1I  180.00  0.0  0
 FIR  CONST_19  H1I   N1I  C2I  N4   180.00  0.0  0
 FIR  CONST_20  H211  N21  C19  C9   180.00  0.0  0
 FIR  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
 FIR  chir_01  C9   O10  C19  C8I  negativ
 FIR  chir_02  C7I  C12  C5   C8I  positiv

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

