# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 30 07:18:03 2020
#   Inital geometry file: a 114 line input string
#   Ligand name: 2-amino-7-(1,1-dioxo-1lambda~6~-thian-4-yl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Nc1nc2Oc3ccc(cc3C(=O)c2cc1C(O)=O)C4CC[S](=O)(=O)CC4
#
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
 F8S  F8S  '2-amino-7-(1,1-dioxo-1lambda~6~-thian-4-yl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid'  ligand  42  27  .  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_F8S
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
 F8S  C02  C  CR6    0   0.465  -5.2611   1.0857  -0.0665
 F8S  C04  C  CR66   0   0.481  -2.9837   1.0425  -0.0549
 F8S  C06  C  CR6    0   0.342  -0.6502   1.2285  -0.0540
 F8S  C07  C  C1     0  -0.313   0.4438   2.0874  -0.0872
 F8S  C08  C  C1     0  -0.307   1.7160   1.5563  -0.0587
 F8S  C09  C  C      0   0.212   1.9327   0.1727   0.0045
 F8S  C10  C  CH1    0  -0.351   3.3289  -0.3947   0.0357
 F8S  C11  C  CH2    0  -0.441   4.0786  -0.0687  -1.2622
 F8S  C12  C  CH2    0  -0.617   5.4555  -0.7181  -1.3317
 F8S  C16  C  CH2    0  -0.618   5.4618  -0.5512   1.4233
 F8S  C17  C  CH2    0  -0.440   4.0839   0.0830   1.2828
 F8S  C18  C  C1     0  -0.396   0.8300  -0.6574   0.0353
 F8S  C19  C  CR6    0  -0.086  -0.4724  -0.1498   0.0066
 F8S  C20  C  CR6    0   0.415  -1.6421  -1.0415   0.0388
 F8S  C22  C  CR66   0  -0.252  -2.9124  -0.3501   0.0033
 F8S  C23  C  CR16   0  -0.207  -4.1473  -1.0194   0.0225
 F8S  C24  C  CR6    0  -0.267  -5.3380  -0.3479  -0.0122
 F8S  C25  C  C      0   0.454  -6.6465  -1.1206   0.0065
 F8S  N01  N  NH2    0  -0.820  -6.3627   1.8265  -0.0965
 F8S  N03  N  N      0  -0.485  -4.0908   1.7377  -0.0876
 F8S  O05  O  O      0  -0.455  -1.8755   1.8034  -0.0836
 F8S  O21  O  O      0  -0.437  -1.5346  -2.2597   0.0907
 F8S  O26  O  OC    -1  -0.574  -6.5626  -2.3572   0.0649
 F8S  O27  O  O      0  -0.600  -7.7086  -0.4551  -0.0402
 F8S  S13  S  S      0   1.216   6.4897  -0.1649   0.0150
 F8S  H1   H  H      0   0.281   0.2916   3.1579  -0.1335
 F8S  H2   H  H      0   0.266   2.5576   2.2376  -0.0851
 F8S  H3   H  HCH1   0   0.264   3.2404  -1.4851   0.0996
 F8S  H4   H  HCH2   0   0.279   3.5033  -0.4350  -2.1142
 F8S  H5   H  HCH2   0   0.301   5.3953  -1.8055  -1.2614
 F8S  H6   H  HCH2   0   0.323   5.9938  -0.1804   2.3018
 F8S  H7   H  HCH2   0   0.301   5.4056  -1.6394   1.4882
 F8S  H8   H  HCH2   0   0.254   4.1817   1.1709   1.2814
 F8S  H9   H  HCH2   0   0.279   3.5123  -0.1787   2.1747
 F8S  H10  H  H      0   0.262   0.9629  -1.7313   0.0821
 F8S  H11  H  HCR6   0   0.263  -4.1555  -2.1008   0.0640
 F8S  H12  H  HNH2   0   0.413  -7.2487   1.3309  -0.0902
 F8S  H13  H  HNH2   0   0.392  -6.3008   2.8288  -0.1381
 F8S  H15  H  HCH2   0   0.255   4.1747   1.0120  -1.3917
 F8S  H16  H  HCH2   0   0.323   5.9832  -0.4578  -2.2513
 F8S  O14  O  OS     0  -0.689   6.6237   1.2920  -0.0756
 F8S  O15  O  OS     0  -0.684   7.7142  -0.9655   0.0636

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
 F8S  O27  C25  deloc     1.254  0.020  1.254
 F8S  N01  C02  single    1.328  0.020  1.328
 F8S  C25  O26  deloc     1.241  0.020  1.241
 F8S  C25  C24  single    1.520  0.020  1.520
 F8S  C02  C24  aromatic  1.437  0.020  1.437
 F8S  C02  N03  aromatic  1.340  0.020  1.340
 F8S  C24  C23  aromatic  1.367  0.020  1.367
 F8S  N03  C04  aromatic  1.308  0.020  1.308
 F8S  C23  C22  aromatic  1.405  0.020  1.405
 F8S  C04  C22  aromatic  1.396  0.020  1.396
 F8S  C04  O05  single    1.345  0.020  1.345
 F8S  C22  C20  single    1.447  0.020  1.447
 F8S  O05  C06  single    1.354  0.020  1.354
 F8S  C20  O21  double    1.224  0.020  1.224
 F8S  C20  C19  single    1.471  0.020  1.471
 F8S  C06  C19  aromatic  1.391  0.020  1.391
 F8S  C06  C07  aromatic  1.391  0.020  1.391
 F8S  C19  C18  aromatic  1.398  0.020  1.398
 F8S  C07  C08  aromatic  1.379  0.020  1.379
 F8S  C08  C09  aromatic  1.402  0.020  1.402
 F8S  C18  C09  aromatic  1.381  0.020  1.381
 F8S  C09  C10  single    1.507  0.020  1.507
 F8S  C10  C17  single    1.534  0.020  1.534
 F8S  C10  C11  single    1.534  0.020  1.534
 F8S  C17  C16  single    1.523  0.020  1.523
 F8S  C11  C12  single    1.524  0.020  1.524
 F8S  C16  S13  single    1.786  0.020  1.786
 F8S  C12  S13  single    1.786  0.020  1.786
 F8S  O15  S13  double    1.464  0.020  1.464
 F8S  S13  O14  double    1.466  0.020  1.466
 F8S  C07  H1   single    0.930  0.020  1.080
 F8S  C08  H2   single    0.930  0.020  1.080
 F8S  C10  H3   single    0.970  0.020  1.090
 F8S  C11  H4   single    0.970  0.020  1.090
 F8S  C12  H5   single    0.970  0.020  1.090
 F8S  C16  H6   single    0.970  0.020  1.090
 F8S  C16  H7   single    0.970  0.020  1.090
 F8S  C17  H8   single    0.970  0.020  1.090
 F8S  C17  H9   single    0.970  0.020  1.090
 F8S  C18  H10  single    0.930  0.020  1.080
 F8S  C23  H11  single    0.930  0.020  1.080
 F8S  N01  H12  single    0.860  0.020  1.020
 F8S  N01  H13  single    0.860  0.020  1.020
 F8S  C11  H15  single    0.970  0.020  1.090
 F8S  C12  H16  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
 F8S  N03  C02  N01  116.92  3.000
 F8S  N03  C02  C24  122.20  3.000
 F8S  N01  C02  C24  120.88  3.000
 F8S  O05  C04  N03  113.36  3.000
 F8S  O05  C04  C22  121.56  3.000
 F8S  N03  C04  C22  125.08  3.000
 F8S  O05  C06  C19  122.51  3.000
 F8S  C19  C06  C07  120.81  3.000
 F8S  O05  C06  C07  116.68  3.000
 F8S  H1   C07  C08  120.78  3.000
 F8S  H1   C07  C06  120.07  3.000
 F8S  C08  C07  C06  119.15  3.000
 F8S  H2   C08  C09  120.12  3.000
 F8S  H2   C08  C07  118.30  3.000
 F8S  C09  C08  C07  121.58  3.000
 F8S  C18  C09  C10  120.87  3.000
 F8S  C10  C09  C08  121.04  3.000
 F8S  C18  C09  C08  118.09  3.000
 F8S  H3   C10  C17  107.59  3.000
 F8S  H3   C10  C11  107.47  3.000
 F8S  C17  C10  C11  112.40  3.000
 F8S  H3   C10  C09  107.51  3.000
 F8S  C11  C10  C09  110.80  3.000
 F8S  C17  C10  C09  110.82  3.000
 F8S  H15  C11  H4   106.60  3.000
 F8S  H15  C11  C12  109.67  3.000
 F8S  H4   C11  C12  107.31  3.000
 F8S  H15  C11  C10  110.70  3.000
 F8S  H4   C11  C10  109.37  3.000
 F8S  C12  C11  C10  112.93  3.000
 F8S  H16  C12  H5   108.57  3.000
 F8S  H16  C12  S13  106.34  3.000
 F8S  H5   C12  S13  106.98  3.000
 F8S  H16  C12  C11  111.93  3.000
 F8S  H5   C12  C11  111.83  3.000
 F8S  S13  C12  C11  110.91  3.000
 F8S  H7   C16  H6   108.41  3.000
 F8S  H7   C16  S13  106.99  3.000
 F8S  H6   C16  S13  106.30  3.000
 F8S  H7   C16  C17  111.96  3.000
 F8S  H6   C16  C17  111.93  3.000
 F8S  S13  C16  C17  110.97  3.000
 F8S  H9   C17  H8   106.67  3.000
 F8S  H9   C17  C16  107.37  3.000
 F8S  H8   C17  C16  109.49  3.000
 F8S  H9   C17  C10  109.39  3.000
 F8S  H8   C17  C10  110.68  3.000
 F8S  C16  C17  C10  112.98  3.000
 F8S  H10  C18  C19  118.37  3.000
 F8S  H10  C18  C09  119.94  3.000
 F8S  C19  C18  C09  121.69  3.000
 F8S  C20  C19  C18  121.34  3.000
 F8S  C18  C19  C06  118.66  3.000
 F8S  C20  C19  C06  119.99  3.000
 F8S  O21  C20  C22  123.63  3.000
 F8S  O21  C20  C19  122.30  3.000
 F8S  C22  C20  C19  114.08  3.000
 F8S  C23  C22  C20  122.95  3.000
 F8S  C20  C22  C04  121.51  3.000
 F8S  C23  C22  C04  115.54  3.000
 F8S  H11  C23  C24  119.02  3.000
 F8S  H11  C23  C22  118.90  3.000
 F8S  C24  C23  C22  122.08  3.000
 F8S  C25  C24  C23  119.98  3.000
 F8S  C23  C24  C02  116.39  3.000
 F8S  C25  C24  C02  123.63  3.000
 F8S  O27  C25  O26  126.00  3.000
 F8S  O26  C25  C24  116.69  3.000
 F8S  O27  C25  C24  117.32  3.000
 F8S  H13  N01  H12  122.74  3.000
 F8S  H13  N01  C02  120.42  3.000
 F8S  H12  N01  C02  116.84  3.000
 F8S  C04  N03  C02  118.71  3.000
 F8S  C06  O05  C04  120.34  3.000
 F8S  O15  S13  O14  117.98  3.000
 F8S  O14  S13  C16  108.44  3.000
 F8S  O15  S13  C16  109.69  3.000
 F8S  O14  S13  C12  108.31  3.000
 F8S  O15  S13  C12  109.88  3.000
 F8S  C16  S13  C12  101.20  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
 F8S  CONST_01  C22  C23  C24  C02    0.00   0.0  0
 F8S  CONST_02  C22  C04  N03  C02    0.00   0.0  0
 F8S  CONST_03  C24  C02  N03  C04    0.00   0.0  0
 F8S  CONST_04  C24  C23  C22  C04    0.00   0.0  0
 F8S  CONST_05  C09  C18  C19  C06    0.00   0.0  0
 F8S  CONST_06  C09  C08  C07  C06    0.00   0.0  0
 F8S  CONST_07  C18  C19  C06  C07    0.00   0.0  0
 F8S  CONST_08  C18  C09  C08  C07    0.00   0.0  0
 F8S  CONST_09  C19  C06  C07  C08    0.00   0.0  0
 F8S  CONST_10  C19  C18  C09  C08    0.00   0.0  0
 F8S  CONST_11  N03  C02  C24  C23    0.00   0.0  0
 F8S  CONST_12  N03  C04  C22  C23    0.00   0.0  0
 F8S  CONST_13  C10  C09  C08  C07  180.00   0.0  0
 F8S  CONST_14  C19  C18  C09  C10  180.00   0.0  0
 F8S  CONST_15  N01  C02  N03  C04  180.00   0.0  0
 F8S  CONST_16  C25  C24  C23  C22  180.00   0.0  0
 F8S  CONST_17  N01  C02  C24  C23  180.00   0.0  0
 F8S  CONST_18  N03  C02  C24  C25  180.00   0.0  0
 F8S  CONST_19  H11  C23  C24  C02  180.00   0.0  0
 F8S  CONST_20  H10  C18  C19  C06  180.00   0.0  0
 F8S  CONST_21  H2   C08  C07  C06  180.00   0.0  0
 F8S  CONST_22  H1   C07  C08  C09  180.00   0.0  0
 F8S  CONST_23  H12  N01  C02  C24    0.00   0.0  0
 F8S  CONST_24  H13  N01  C02  C24  180.00   0.0  0
 F8S  Var_01    C19  C20  C22  C04   -0.06  30.0  1
 F8S  Var_02    C19  C06  O05  C04   -0.01  30.0  1
 F8S  Var_03    N03  C04  O05  C06  179.92  30.0  1
 F8S  Var_04    C22  C20  C19  C06   -0.06  30.0  1
 F8S  Var_05    S13  C16  C17  C10   59.97  30.0  1
 F8S  Var_06    S13  C12  C11  C10  -60.15  30.0  1
 F8S  Var_07    C16  S13  C12  C11   54.42  30.0  1
 F8S  Var_08    C17  C16  S13  C12  -54.34  30.0  1
 F8S  Var_09    O27  C25  C24  C02    0.64  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
 F8S  chir_01  C10  C09  C17  C11  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
 F8S  plan-1  C06  0.020
 F8S  plan-1  C07  0.020
 F8S  plan-1  C08  0.020
 F8S  plan-1  C09  0.020
 F8S  plan-1  C10  0.020
 F8S  plan-1  C18  0.020
 F8S  plan-1  C19  0.020
 F8S  plan-1  C20  0.020
 F8S  plan-1  O05  0.020
 F8S  plan-1  H1   0.020
 F8S  plan-1  H2   0.020
 F8S  plan-1  H10  0.020
 F8S  plan-2  C02  0.020
 F8S  plan-2  N01  0.020
 F8S  plan-2  H12  0.020
 F8S  plan-2  H13  0.020
 F8S  plan-3  C02  0.020
 F8S  plan-3  C04  0.020
 F8S  plan-3  C20  0.020
 F8S  plan-3  C22  0.020
 F8S  plan-3  C23  0.020
 F8S  plan-3  C24  0.020
 F8S  plan-3  C25  0.020
 F8S  plan-3  N01  0.020
 F8S  plan-3  N03  0.020
 F8S  plan-3  O05  0.020
 F8S  plan-3  H11  0.020
 F8S  plan-4  C19  0.020
 F8S  plan-4  C20  0.020
 F8S  plan-4  C22  0.020
 F8S  plan-4  O21  0.020
 F8S  plan-5  C24  0.020
 F8S  plan-5  C25  0.020
 F8S  plan-5  O26  0.020
 F8S  plan-5  O27  0.020

