# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 00:38:32 2020
#   Inital geometry file: a 137 line input string
#   Ligand name: amino{4-[(3aS,4R,8aS,8bR)-2-(4-fluorobenzyl)-1,3-dioxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]phenyl}methaniminium
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: NC(=[NH2+])c1ccc(cc1)[C@H]2[C@@H]3[C@H]([C@@H]4CCCN24)C(=O)N(Cc5ccc(F)cc5)C3=O
#
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
 FSN  FSN  amino{4-[(3aS,4R,8aS,8bR)-2-(4-fluorobenzyl)-1,3-dioxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]phenyl}methaniminium  ligand  54  30  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_FSN
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
 FSN  O21   O  O     0  -0.415   0.2600   1.0192  -0.9553
 FSN  C20   C  CR5   0   0.608   0.4377  -0.1061  -0.5630
 FSN  N19   N  NR5   0  -0.517   1.2667  -0.4422   0.4846
 FSN  C23   C  CH2   0  -0.433   2.0007   0.5414   1.2643
 FSN  C24   C  CR6   0   0.124   3.3278   0.8835   0.6398
 FSN  C32   C  CR16  0  -0.275   3.4455   1.9632  -0.2308
 FSN  C31   C  CR16  0  -0.399   4.6593   2.2720  -0.8279
 FSN  C30   C  CR6   0   0.520   5.7553   1.4821  -0.5409
 FSN  F29   F  F     0  -0.315   6.9340   1.7725  -1.1146
 FSN  C26   C  CR16  0  -0.399   5.6789   0.4058   0.3219
 FSN  C25   C  CR16  0  -0.275   4.4567   0.1145   0.9101
 FSN  C17   C  CR5   0   0.601   1.3813  -1.8020   0.6660
 FSN  O18   O  O     0  -0.428   2.0433  -2.3224   1.5299
 FSN  C16   C  CR15  0  -0.399   0.5583  -2.5026  -0.3918
 FSN  C15   C  CH1   0  -0.111  -0.5213  -3.3827   0.2160
 FSN  N11   N  NT    0  -0.414  -1.6170  -2.4530   0.4661
 FSN  C12   C  CH2   0  -0.334  -2.7930  -3.3046   0.5930
 FSN  C13   C  CH2   0  -0.479  -2.6121  -4.4391  -0.4384
 FSN  C14   C  CH2   0  -0.461  -1.0939  -4.4853  -0.6991
 FSN  C10   C  CH1   0  -0.099  -1.6768  -1.5642  -0.6876
 FSN  C7    C  CR6   0   0.124  -2.4134  -0.2864  -0.3867
 FSN  C8    C  CR16  0  -0.283  -3.0347   0.4103  -1.4179
 FSN  C9    C  CR16  0  -0.252  -3.6726   1.6131  -1.1776
 FSN  C4    C  CR6   0  -0.001  -3.7086   2.1306   0.1160
 FSN  C5    C  CR16  0  -0.245  -3.1012   1.4317   1.1566
 FSN  C6    C  CR16  0  -0.281  -2.4562   0.2342   0.9024
 FSN  C3    C  C     0   0.583  -4.3886   3.4066   0.3806
 FSN  N1    N  NC2   1  -0.763  -4.3169   4.3664  -0.5094
 FSN  N2    N  NH2   0  -0.764  -5.0508   3.5631   1.5013
 FSN  C22   C  CR15  0  -0.425  -0.1886  -1.3699  -1.1000
 FSN  H231  H  HCH2  0   0.290   1.3757   1.4282   1.3561
 FSN  H232  H  HCH2  0   0.292   2.1346   0.1348   2.2658
 FSN  H32   H  HCR6  0   0.265   2.5824   2.5785  -0.4492
 FSN  H31   H  HCR6  0   0.281   4.7487   3.1135  -1.5022
 FSN  H26   H  HCR6  0   0.281   6.5557  -0.1914   0.5356
 FSN  H25   H  HCR6  0   0.265   4.3893  -0.7221   1.5934
 FSN  H16   H  HCR5  0   0.329   1.2359  -3.0563  -1.0451
 FSN  H15   H  HCH1  0   0.270  -0.1956  -3.8290   1.1594
 FSN  H121  H  HCH2  0   0.249  -3.7102  -2.7314   0.4531
 FSN  H122  H  HCH2  0   0.247  -2.8193  -3.7105   1.6064
 FSN  H131  H  HCH2  0   0.240  -3.1558  -4.2183  -1.3572
 FSN  H132  H  HCH2  0   0.248  -2.9996  -5.3834  -0.0579
 FSN  H141  H  HCH2  0   0.243  -0.8696  -4.2877  -1.7493
 FSN  H142  H  HCH2  0   0.251  -0.6567  -5.4544  -0.4595
 FSN  H10   H  HCH1  0   0.269  -2.1738  -2.0380  -1.5473
 FSN  H8    H  HCR6  0   0.265  -3.0236   0.0085  -2.4235
 FSN  H9    H  HCR6  0   0.281  -4.1656   2.1253  -1.9940
 FSN  H5    H  HCR6  0   0.278  -3.1029   1.8280   2.1640
 FSN  H6    H  HCR6  0   0.268  -1.9807  -0.3019   1.7124
 FSN  HN11  H  HNC2  0   0.447  -3.7098   4.2839  -1.3085
 FSN  HN12  H  HNC2  0   0.439  -4.8111   5.2393  -0.4003
 FSN  HN21  H  HNH2  0   0.438  -5.4959   4.4356   1.7427
 FSN  HN22  H  HNH2  0   0.447  -5.2194   2.7829   2.1157
 FSN  H22   H  HCR5  0   0.323  -0.0942  -1.3789  -2.1850

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
 FSN  O21  C20   double    1.205  0.020  1.205
 FSN  C20  N19   single    1.378  0.020  1.378
 FSN  C20  C22   single    1.509  0.020  1.509
 FSN  N19  C23   single    1.454  0.020  1.454
 FSN  N19  C17   single    1.377  0.020  1.377
 FSN  C23  C24   single    1.506  0.020  1.506
 FSN  C23  H231  single    0.970  0.020  1.090
 FSN  C23  H232  single    0.970  0.020  1.090
 FSN  C24  C32   aromatic  1.392  0.020  1.392
 FSN  C24  C25   aromatic  1.392  0.020  1.392
 FSN  C32  C31   aromatic  1.388  0.020  1.388
 FSN  C32  H32   single    0.930  0.020  1.080
 FSN  C31  C30   aromatic  1.381  0.020  1.381
 FSN  C31  H31   single    0.930  0.020  1.080
 FSN  C30  F29   single    1.343  0.020  1.343
 FSN  C30  C26   aromatic  1.382  0.020  1.382
 FSN  C26  C25   aromatic  1.387  0.020  1.387
 FSN  C26  H26   single    0.930  0.020  1.080
 FSN  C25  H25   single    0.930  0.020  1.080
 FSN  C17  O18   double    1.206  0.020  1.206
 FSN  C17  C16   single    1.512  0.020  1.512
 FSN  C16  C15   single    1.520  0.020  1.520
 FSN  C16  C22   single    1.531  0.020  1.531
 FSN  C16  H16   single    0.970  0.020  1.090
 FSN  C15  N11   single    1.459  0.020  1.459
 FSN  C15  C14   single    1.543  0.020  1.543
 FSN  C15  H15   single    0.970  0.020  1.090
 FSN  N11  C12   single    1.458  0.020  1.458
 FSN  N11  C10   single    1.458  0.020  1.458
 FSN  C12  C13   single    1.544  0.020  1.544
 FSN  C12  H121  single    0.970  0.020  1.090
 FSN  C12  H122  single    0.970  0.020  1.090
 FSN  C13  C14   single    1.541  0.020  1.541
 FSN  C13  H131  single    0.970  0.020  1.090
 FSN  C13  H132  single    0.970  0.020  1.090
 FSN  C14  H141  single    0.970  0.020  1.090
 FSN  C14  H142  single    0.970  0.020  1.090
 FSN  C10  C7    single    1.505  0.020  1.505
 FSN  C10  C22   single    1.556  0.020  1.556
 FSN  C10  H10   single    0.970  0.020  1.090
 FSN  C7   C8    aromatic  1.391  0.020  1.391
 FSN  C7   C6    aromatic  1.391  0.020  1.391
 FSN  C8   C9    aromatic  1.383  0.020  1.383
 FSN  C8   H8    single    0.930  0.020  1.080
 FSN  C9   C4    aromatic  1.394  0.020  1.394
 FSN  C9   H9    single    0.930  0.020  1.080
 FSN  C4   C5    aromatic  1.393  0.020  1.393
 FSN  C4   C3    single    1.470  0.020  1.470
 FSN  C5   C6    aromatic  1.384  0.020  1.384
 FSN  C5   H5    single    0.930  0.020  1.080
 FSN  C6   H6    single    0.930  0.020  1.080
 FSN  C3   N1    double    1.311  0.020  1.311
 FSN  C3   N2    single    1.311  0.020  1.311
 FSN  N1   HN11  single    0.860  0.020  1.020
 FSN  N1   HN12  single    0.860  0.020  1.020
 FSN  N2   HN21  single    0.860  0.020  1.020
 FSN  N2   HN22  single    0.860  0.020  1.020
 FSN  C22  H22   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
 FSN  C22   C20  N19   108.42  3.000
 FSN  C22   C20  O21   127.23  3.000
 FSN  N19   C20  O21   124.35  3.000
 FSN  C17   N19  C23   123.74  3.000
 FSN  C17   N19  C20   113.04  3.000
 FSN  C23   N19  C20   123.13  3.000
 FSN  H232  C23  H231  107.29  3.000
 FSN  H232  C23  C24   110.96  3.000
 FSN  H231  C23  C24   110.84  3.000
 FSN  H232  C23  N19   107.62  3.000
 FSN  H231  C23  N19   107.84  3.000
 FSN  C24   C23  N19   112.10  3.000
 FSN  C25   C24  C32   118.77  3.000
 FSN  C25   C24  C23   120.56  3.000
 FSN  C32   C24  C23   120.66  3.000
 FSN  H32   C32  C31   118.96  3.000
 FSN  H32   C32  C24   119.99  3.000
 FSN  C31   C32  C24   121.05  3.000
 FSN  H31   C31  C30   120.59  3.000
 FSN  H31   C31  C32   120.90  3.000
 FSN  C30   C31  C32   118.52  3.000
 FSN  C26   C30  F29   118.94  3.000
 FSN  C26   C30  C31   122.11  3.000
 FSN  F29   C30  C31   118.95  3.000
 FSN  H26   C26  C25   120.94  3.000
 FSN  H26   C26  C30   120.56  3.000
 FSN  C25   C26  C30   118.49  3.000
 FSN  H25   C25  C26   119.00  3.000
 FSN  H25   C25  C24   119.93  3.000
 FSN  C26   C25  C24   121.06  3.000
 FSN  C16   C17  O18   126.85  3.000
 FSN  C16   C17  N19   108.67  3.000
 FSN  O18   C17  N19   124.48  3.000
 FSN  H16   C16  C22   113.65  3.000
 FSN  H16   C16  C15   112.73  3.000
 FSN  C22   C16  C15   105.49  3.000
 FSN  H16   C16  C17   108.40  3.000
 FSN  C22   C16  C17   104.27  3.000
 FSN  C15   C16  C17   112.03  3.000
 FSN  H15   C15  C14   109.31  3.000
 FSN  H15   C15  N11   109.64  3.000
 FSN  C14   C15  N11   106.17  3.000
 FSN  H15   C15  C16   111.70  3.000
 FSN  C14   C15  C16   116.12  3.000
 FSN  N11   C15  C16   103.48  3.000
 FSN  C10   N11  C12   113.08  3.000
 FSN  C10   N11  C15   106.49  3.000
 FSN  C12   N11  C15   104.39  3.000
 FSN  H122  C12  H121  107.11  3.000
 FSN  H122  C12  C13   110.46  3.000
 FSN  H121  C12  C13   113.52  3.000
 FSN  H122  C12  N11   108.50  3.000
 FSN  H121  C12  N11   111.12  3.000
 FSN  C13   C12  N11   106.06  3.000
 FSN  H132  C13  H131  107.01  3.000
 FSN  H132  C13  C14   112.55  3.000
 FSN  H131  C13  C14   110.78  3.000
 FSN  H132  C13  C12   111.22  3.000
 FSN  H131  C13  C12   110.84  3.000
 FSN  C14   C13  C12   104.51  3.000
 FSN  H142  C14  H141  106.86  3.000
 FSN  H142  C14  C13   112.63  3.000
 FSN  H141  C14  C13   111.07  3.000
 FSN  H142  C14  C15   110.87  3.000
 FSN  H141  C14  C15   111.40  3.000
 FSN  C13   C14  C15   104.11  3.000
 FSN  H10   C10  C22   106.18  3.000
 FSN  H10   C10  C7    107.51  3.000
 FSN  C22   C10  C7    114.51  3.000
 FSN  H10   C10  N11   111.98  3.000
 FSN  C22   C10  N11   104.27  3.000
 FSN  C7    C10  N11   112.30  3.000
 FSN  C6    C7   C8    119.07  3.000
 FSN  C6    C7   C10   121.20  3.000
 FSN  C8    C7   C10   119.70  3.000
 FSN  H8    C8   C9    119.27  3.000
 FSN  H8    C8   C7    119.87  3.000
 FSN  C9    C8   C7    120.86  3.000
 FSN  H9    C9   C4    120.83  3.000
 FSN  H9    C9   C8    119.38  3.000
 FSN  C4    C9   C8    119.75  3.000
 FSN  C3    C4   C5    120.19  3.000
 FSN  C3    C4   C9    120.09  3.000
 FSN  C5    C4   C9    119.73  3.000
 FSN  H5    C5   C6    119.24  3.000
 FSN  H5    C5   C4    120.72  3.000
 FSN  C6    C5   C4    120.02  3.000
 FSN  H6    C6   C5    119.76  3.000
 FSN  H6    C6   C7    119.67  3.000
 FSN  C5    C6   C7    120.57  3.000
 FSN  N2    C3   N1    121.37  3.000
 FSN  N2    C3   C4    119.42  3.000
 FSN  N1    C3   C4    119.21  3.000
 FSN  HN12  N1   HN11  116.87  3.000
 FSN  HN12  N1   C3    122.22  3.000
 FSN  HN11  N1   C3    120.78  3.000
 FSN  HN22  N2   HN21  116.74  3.000
 FSN  HN22  N2   C3    120.90  3.000
 FSN  HN21  N2   C3    122.05  3.000
 FSN  H22   C22  C10   110.23  3.000
 FSN  H22   C22  C16   114.37  3.000
 FSN  C10   C22  C16   104.57  3.000
 FSN  H22   C22  C20   108.99  3.000
 FSN  C10   C22  C20   114.02  3.000
 FSN  C16   C22  C20   104.63  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
 FSN  CONST_01  C30   C31  C32  C24    0.00   0.0  0
 FSN  CONST_02  C30   C26  C25  C24    0.00   0.0  0
 FSN  CONST_03  C26   C25  C24  C32    0.00   0.0  0
 FSN  CONST_04  C26   C30  C31  C32    0.00   0.0  0
 FSN  CONST_05  C25   C24  C32  C31    0.00   0.0  0
 FSN  CONST_06  C25   C26  C30  C31    0.00   0.0  0
 FSN  CONST_07  C4    C9   C8   C7     0.00   0.0  0
 FSN  CONST_08  C4    C5   C6   C7     0.00   0.0  0
 FSN  CONST_09  C5    C6   C7   C8     0.00   0.0  0
 FSN  CONST_10  C5    C4   C9   C8     0.00   0.0  0
 FSN  CONST_11  C6    C7   C8   C9     0.00   0.0  0
 FSN  CONST_12  C6    C5   C4   C9     0.00   0.0  0
 FSN  CONST_13  C9    C8   C7   C10  180.00   0.0  0
 FSN  CONST_14  C5    C6   C7   C10  180.00   0.0  0
 FSN  CONST_15  C22   C20  N19  C17    0.00   0.0  0
 FSN  CONST_16  C31   C32  C24  C23  180.00   0.0  0
 FSN  CONST_17  C26   C25  C24  C23  180.00   0.0  0
 FSN  CONST_18  F29   C30  C31  C32  180.00   0.0  0
 FSN  CONST_19  C25   C26  C30  F29  180.00   0.0  0
 FSN  CONST_20  C3    C4   C9   C8   180.00   0.0  0
 FSN  CONST_21  C3    C4   C5   C6   180.00   0.0  0
 FSN  CONST_22  C17   N19  C20  O21  180.00   0.0  0
 FSN  CONST_23  C22   C20  N19  C23  180.00   0.0  0
 FSN  CONST_24  H31   C31  C32  C24  180.00   0.0  0
 FSN  CONST_25  H26   C26  C25  C24  180.00   0.0  0
 FSN  CONST_26  H25   C25  C24  C32  180.00   0.0  0
 FSN  CONST_27  H32   C32  C31  C30  180.00   0.0  0
 FSN  CONST_28  H8    C8   C7   C10    0.00   0.0  0
 FSN  CONST_29  H6    C6   C7   C10    0.00   0.0  0
 FSN  CONST_30  H9    C9   C8   C7   180.00   0.0  0
 FSN  CONST_31  H5    C5   C6   C7   180.00   0.0  0
 FSN  CONST_32  C23   N19  C20  O21    0.00   0.0  0
 FSN  CONST_33  HN11  N1   C3   C4     0.00   0.0  0
 FSN  CONST_34  HN12  N1   C3   C4   180.00   0.0  0
 FSN  CONST_35  HN21  N2   C3   C4   180.00   0.0  0
 FSN  CONST_36  HN22  N2   C3   C4     0.00   0.0  0
 FSN  Var_01    C16   C17  N19  C20    1.16  30.0  1
 FSN  Var_02    C13   C12  N11  C15  -37.37  30.0  1
 FSN  Var_03    C12   C13  C14  C15    0.60  30.0  1
 FSN  Var_04    C14   C13  C12  N11   22.20  30.0  1
 FSN  Var_05    C24   C23  N19  C20  -86.60  30.0  3
 FSN  Var_06    C32   C24  C23  N19   92.88  30.0  2
 FSN  Var_07    N1    C3   C4   C9   -36.84  30.0  2

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
 FSN  chir_01  C16  C17  C15  C22  negativ
 FSN  chir_02  C15  N11  C16  C14  positiv
 FSN  chir_03  C10  N11  C22  C7   positiv
 FSN  chir_04  C22  C10  C16  C20  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
 FSN  plan-1  C23   0.020
 FSN  plan-1  C24   0.020
 FSN  plan-1  C32   0.020
 FSN  plan-1  C31   0.020
 FSN  plan-1  C30   0.020
 FSN  plan-1  F29   0.020
 FSN  plan-1  C26   0.020
 FSN  plan-1  C25   0.020
 FSN  plan-1  H32   0.020
 FSN  plan-1  H31   0.020
 FSN  plan-1  H26   0.020
 FSN  plan-1  H25   0.020
 FSN  plan-2  C10   0.020
 FSN  plan-2  C7    0.020
 FSN  plan-2  C8    0.020
 FSN  plan-2  C9    0.020
 FSN  plan-2  C4    0.020
 FSN  plan-2  C5    0.020
 FSN  plan-2  C6    0.020
 FSN  plan-2  C3    0.020
 FSN  plan-2  H8    0.020
 FSN  plan-2  H9    0.020
 FSN  plan-2  H5    0.020
 FSN  plan-2  H6    0.020
 FSN  plan-3  N19   0.020
 FSN  plan-3  C17   0.020
 FSN  plan-3  O18   0.020
 FSN  plan-3  C16   0.020
 FSN  plan-4  C4    0.020
 FSN  plan-4  C3    0.020
 FSN  plan-4  N1    0.020
 FSN  plan-4  N2    0.020
 FSN  plan-4  HN11  0.020
 FSN  plan-4  HN12  0.020
 FSN  plan-4  HN21  0.020
 FSN  plan-4  HN22  0.020
 FSN  plan-5  O21   0.020
 FSN  plan-5  C20   0.020
 FSN  plan-5  N19   0.020
 FSN  plan-5  C23   0.020
 FSN  plan-5  C17   0.020
 FSN  plan-5  C22   0.020

