# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 04:53:01 2020
#   Inital geometry file: a 126 line input string
#   Ligand name: 5-[(ethylcarbamothioyl)amino]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=S)Nc1ccc(c(c1)C(O)=O)C2=C3C=CC(=O)C=C3Oc4cc(O)ccc24
#
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
 FLG  FLG  '5-[(ethylcarbamothioyl)amino]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid'  ligand  48  31  .  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_FLG
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
 FLG  S1    S  S1     0  -0.440   8.3920  -0.4630   8.2255
 FLG  C21   C  C      0   0.327   7.0025  -1.3875   7.9867
 FLG  N1    N  NH1    0  -0.690   5.8092  -0.7726   7.8041
 FLG  C17   C  CR6    0   0.323   4.7106  -1.2154   7.0411
 FLG  C18   C  CR16   0  -0.325   4.8750  -1.9811   5.8944
 FLG  C19   C  CR6    0  -0.106   3.7804  -2.3799   5.1383
 FLG  C20   C  C      0   0.411   3.9818  -3.2315   3.8940
 FLG  O4    O  OC    -1  -0.575   5.1478  -3.5487   3.6048
 FLG  O5    O  O      0  -0.560   2.9396  -3.5277   3.2804
 FLG  C16   C  CR16   0  -0.291   3.4328  -0.8198   7.4238
 FLG  C15   C  CR16   0  -0.274   2.3407  -1.1996   6.6650
 FLG  C14   C  CR6    0  -0.062   2.5015  -1.9865   5.5269
 FLG  C10   C  CR6    0   0.314   1.2792  -2.3412   4.7676
 FLG  C9    C  CR6    0  -0.076   0.4522  -3.3550   5.1888
 FLG  C4    C  CR6    0   0.421  -0.8005  -3.5766   4.5302
 FLG  O2    O  O      0  -0.476  -1.1818  -2.7535   3.5305
 FLG  C5    C  C1     0  -0.548  -1.6444  -4.5856   4.8741
 FLG  C8    C  C1     0  -0.279   0.7861  -4.2601   6.2475
 FLG  C7    C  C1     0  -0.398  -0.0351  -5.2681   6.6053
 FLG  C6    C  C      0   0.373  -1.3152  -5.4994   5.9395
 FLG  O3    O  OC     0  -0.511  -2.0623  -6.4250   6.2780
 FLG  C11   C  CR66   0   0.009   0.8382  -1.4889   3.7069
 FLG  C3    C  CR66   0   0.373  -0.4053  -1.7373   3.1150
 FLG  C2    C  CR16   0  -0.437  -0.9022  -0.9593   2.0831
 FLG  C12   C  CR16   0  -0.316   1.5859  -0.4133   3.2080
 FLG  C13   C  CR16   0  -0.378   1.1187   0.3705   2.1821
 FLG  C1    C  CR6    0   0.373  -0.1361   0.0986   1.6134
 FLG  O1    O  OH1    0  -0.613  -0.6395   0.8296   0.6141
 FLG  N2    N  NH1    0  -0.567   7.0492  -2.7200   8.0053
 FLG  C22   C  CH2    0  -0.281   5.9651  -3.6590   8.2564
 FLG  C23   C  CH3    0  -0.685   6.4802  -4.8349   9.0658
 FLG  H18   H  HCR6   0   0.277   5.8635  -2.2738   5.5652
 FLG  H16   H  HCR6   0   0.275   3.2934  -0.2198   8.3141
 FLG  H15   H  HCR6   0   0.262   1.3495  -0.8877   6.9696
 FLG  H5    H  H      0   0.261  -2.5857  -4.7071   4.3521
 FLG  H8    H  H      0   0.262   1.7304  -4.1246   6.7589
 FLG  H7    H  H      0   0.256   0.2450  -5.9419   7.4057
 FLG  H2    H  HCR6   0   0.289  -1.8707  -1.1764   1.6509
 FLG  H12   H  HCR6   0   0.271   2.5540  -0.1967   3.6389
 FLG  H13   H  HCR6   0   0.284   1.7185   1.1925   1.8107
 FLG  H221  H  HCH2   0   0.255   5.1724  -3.1507   8.8052
 FLG  H222  H  HCH2   0   0.250   5.5319  -4.0110   7.3174
 FLG  H231  H  HCH3   0   0.237   7.2836  -5.3556   8.5424
 FLG  H232  H  HCH3   0   0.239   6.8532  -4.5153  10.0387
 FLG  H233  H  HCH3   0   0.249   5.6744  -5.5492   9.2285
 FLG  HN1   H  HNH1   0   0.406   7.9828  -3.0953   8.0725
 FLG  HO1   H  HOH1   0   0.484  -0.0299   1.5334   0.3628
 FLG  HN2   H  HNH1   0   0.411   5.8254   0.2153   8.0088

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
 FLG  S1   C21   double    1.686  0.020  1.686
 FLG  C21  N2    single    1.333  0.020  1.333
 FLG  C21  N1    single    1.355  0.020  1.355
 FLG  N1   C17   single    1.409  0.020  1.409
 FLG  C17  C18   aromatic  1.389  0.020  1.389
 FLG  C17  C16   aromatic  1.391  0.020  1.391
 FLG  C18  C19   aromatic  1.389  0.020  1.389
 FLG  C18  H18   single    0.930  0.020  1.080
 FLG  C19  C20   single    1.521  0.020  1.521
 FLG  C19  C14   aromatic  1.393  0.020  1.393
 FLG  C20  O4    deloc     1.242  0.020  1.242
 FLG  C20  O5    deloc     1.245  0.020  1.245
 FLG  C16  C15   aromatic  1.383  0.020  1.383
 FLG  C16  H16   single    0.930  0.020  1.080
 FLG  C15  C14   aromatic  1.393  0.020  1.393
 FLG  C15  H15   single    0.930  0.020  1.080
 FLG  C14  C10   single    1.482  0.020  1.482
 FLG  C10  C9    aromatic  1.374  0.020  1.374
 FLG  C10  C11   aromatic  1.430  0.020  1.430
 FLG  C9   C4    aromatic  1.432  0.020  1.432
 FLG  C9   C8    aromatic  1.432  0.020  1.432
 FLG  C4   O2    aromatic  1.350  0.020  1.350
 FLG  C4   C5    aromatic  1.360  0.020  1.360
 FLG  O2   C3    aromatic  1.345  0.020  1.345
 FLG  C5   C6    aromatic  1.442  0.020  1.442
 FLG  C5   H5    single    0.930  0.020  1.080
 FLG  C8   C7    aromatic  1.348  0.020  1.348
 FLG  C8   H8    single    0.930  0.020  1.080
 FLG  C7   C6    aromatic  1.461  0.020  1.461
 FLG  C7   H7    single    0.930  0.020  1.080
 FLG  C6   O3    double    1.237  0.020  1.237
 FLG  C11  C3    aromatic  1.399  0.020  1.399
 FLG  C11  C12   aromatic  1.402  0.020  1.402
 FLG  C3   C2    aromatic  1.385  0.020  1.385
 FLG  C2   C1    aromatic  1.388  0.020  1.388
 FLG  C2   H2    single    0.930  0.020  1.080
 FLG  C12  C13   aromatic  1.373  0.020  1.373
 FLG  C12  H12   single    0.930  0.020  1.080
 FLG  C13  C1    aromatic  1.404  0.020  1.404
 FLG  C13  H13   single    0.930  0.020  1.080
 FLG  C1   O1    single    1.336  0.020  1.336
 FLG  N2   C22   single    1.456  0.020  1.456
 FLG  C22  C23   single    1.518  0.020  1.518
 FLG  C22  H221  single    0.970  0.020  1.090
 FLG  C22  H222  single    0.970  0.020  1.090
 FLG  C23  H231  single    0.970  0.020  1.090
 FLG  C23  H232  single    0.970  0.020  1.090
 FLG  C23  H233  single    0.970  0.020  1.090
 FLG  HN1  N2    single    0.860  0.020  1.020
 FLG  HO1  O1    single    0.850  0.020  0.980
 FLG  HN2  N1    single    0.890  0.020  1.040

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
 FLG  N2    C21  N1    119.10  3.000
 FLG  N1    C21  S1    119.74  3.000
 FLG  N2    C21  S1    121.14  3.000
 FLG  HN2   N1   C17   115.48  3.000
 FLG  HN2   N1   C21   113.76  3.000
 FLG  C17   N1   C21   128.10  3.000
 FLG  C16   C17  C18   119.52  3.000
 FLG  C16   C17  N1    118.54  3.000
 FLG  C18   C17  N1    121.88  3.000
 FLG  H18   C18  C19   118.47  3.000
 FLG  H18   C18  C17   120.56  3.000
 FLG  C19   C18  C17   120.97  3.000
 FLG  C14   C19  C20   120.51  3.000
 FLG  C14   C19  C18   119.38  3.000
 FLG  C20   C19  C18   120.11  3.000
 FLG  O5    C20  O4    127.59  3.000
 FLG  O5    C20  C19   115.18  3.000
 FLG  O4    C20  C19   117.23  3.000
 FLG  H16   C16  C15   120.11  3.000
 FLG  H16   C16  C17   120.14  3.000
 FLG  C15   C16  C17   119.75  3.000
 FLG  H15   C15  C14   119.88  3.000
 FLG  H15   C15  C16   119.30  3.000
 FLG  C14   C15  C16   120.81  3.000
 FLG  C10   C14  C15   117.30  3.000
 FLG  C10   C14  C19   123.13  3.000
 FLG  C15   C14  C19   119.56  3.000
 FLG  C11   C10  C9    118.77  3.000
 FLG  C11   C10  C14   119.45  3.000
 FLG  C9    C10  C14   121.05  3.000
 FLG  C8    C9   C4    116.48  3.000
 FLG  C8    C9   C10   123.52  3.000
 FLG  C4    C9   C10   119.96  3.000
 FLG  C5    C4   O2    117.68  3.000
 FLG  C5    C4   C9    122.77  3.000
 FLG  O2    C4   C9    119.55  3.000
 FLG  C3    O2   C4    121.77  3.000
 FLG  H5    C5   C6    118.91  3.000
 FLG  H5    C5   C4    120.05  3.000
 FLG  C6    C5   C4    121.04  3.000
 FLG  H8    C8   C7    119.97  3.000
 FLG  H8    C8   C9    118.27  3.000
 FLG  C7    C8   C9    121.76  3.000
 FLG  H7    C7   C6    117.69  3.000
 FLG  H7    C7   C8    120.24  3.000
 FLG  C6    C7   C8    122.07  3.000
 FLG  O3    C6   C7    121.53  3.000
 FLG  O3    C6   C5    122.59  3.000
 FLG  C7    C6   C5    115.87  3.000
 FLG  C12   C11  C3    117.37  3.000
 FLG  C12   C11  C10   123.83  3.000
 FLG  C3    C11  C10   118.80  3.000
 FLG  C2    C3   C11   122.30  3.000
 FLG  C2    C3   O2    116.59  3.000
 FLG  C11   C3   O2    121.11  3.000
 FLG  H2    C2   C1    120.76  3.000
 FLG  H2    C2   C3    120.40  3.000
 FLG  C1    C2   C3    118.84  3.000
 FLG  H12   C12  C13   119.21  3.000
 FLG  H12   C12  C11   119.30  3.000
 FLG  C13   C12  C11   121.49  3.000
 FLG  H13   C13  C1    120.19  3.000
 FLG  H13   C13  C12   120.06  3.000
 FLG  C1    C13  C12   119.75  3.000
 FLG  O1    C1   C13   122.24  3.000
 FLG  O1    C1   C2    117.51  3.000
 FLG  C13   C1   C2    120.24  3.000
 FLG  HO1   O1   C1    110.85  3.000
 FLG  HN1   N2   C22   115.96  3.000
 FLG  HN1   N2   C21   113.91  3.000
 FLG  C22   N2   C21   128.37  3.000
 FLG  H222  C22  H221  107.14  3.000
 FLG  H222  C22  C23   110.08  3.000
 FLG  H221  C22  C23   109.85  3.000
 FLG  H222  C22  N2    110.79  3.000
 FLG  H221  C22  N2    109.12  3.000
 FLG  C23   C22  N2    109.81  3.000
 FLG  H233  C23  H232  108.19  3.000
 FLG  H233  C23  H231  107.66  3.000
 FLG  H232  C23  H231  108.42  3.000
 FLG  H233  C23  C22   109.68  3.000
 FLG  H232  C23  C22   111.41  3.000
 FLG  H231  C23  C22   111.34  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
 FLG  CONST_01  C14   C19  C18  C17     0.00   0.0  0
 FLG  CONST_02  C14   C15  C16  C17     0.00   0.0  0
 FLG  CONST_03  C15   C16  C17  C18     0.00   0.0  0
 FLG  CONST_04  C15   C14  C19  C18     0.00   0.0  0
 FLG  CONST_05  C10   C14  C19  C18   180.00   0.0  0
 FLG  CONST_06  C16   C17  C18  C19     0.00   0.0  0
 FLG  CONST_07  C16   C15  C14  C19     0.00   0.0  0
 FLG  CONST_10  C10   C14  C15  C16   180.00   0.0  0
 FLG  CONST_13  C4    C9   C10  C14   180.00   0.0  0
 FLG  CONST_14  C8    C9   C10  C14     0.00   0.0  0
 FLG  CONST_15  C3    C11  C10  C14   180.00   0.0  0
 FLG  CONST_16  C12   C11  C10  C14     0.00   0.0  0
 FLG  CONST_17  O2    C4   C9   C10     0.00   0.0  0
 FLG  CONST_18  C5    C4   C9   C10   180.00   0.0  0
 FLG  CONST_19  C7    C8   C9   C10   180.00   0.0  0
 FLG  CONST_20  O2    C3   C11  C10     0.00   0.0  0
 FLG  CONST_21  C2    C3   C11  C10   180.00   0.0  0
 FLG  CONST_22  C13   C12  C11  C10   180.00   0.0  0
 FLG  CONST_23  C3    C11  C10  C9      0.00   0.0  0
 FLG  CONST_24  C12   C11  C10  C9    180.00   0.0  0
 FLG  CONST_25  C3    O2   C4   C9      0.00   0.0  0
 FLG  CONST_26  C6    C5   C4   C9      0.00   0.0  0
 FLG  CONST_27  C6    C7   C8   C9      0.00   0.0  0
 FLG  CONST_28  C11   C10  C9   C4      0.00   0.0  0
 FLG  CONST_29  C7    C8   C9   C4      0.00   0.0  0
 FLG  CONST_30  C11   C3   O2   C4      0.00   0.0  0
 FLG  CONST_31  C2    C3   O2   C4    180.00   0.0  0
 FLG  CONST_32  C7    C6   C5   C4      0.00   0.0  0
 FLG  CONST_33  C8    C9   C4   O2    180.00   0.0  0
 FLG  CONST_34  C6    C5   C4   O2    180.00   0.0  0
 FLG  CONST_35  C12   C11  C3   O2    180.00   0.0  0
 FLG  CONST_36  C1    C2   C3   O2    180.00   0.0  0
 FLG  CONST_37  C8    C9   C4   C5      0.00   0.0  0
 FLG  CONST_38  C3    O2   C4   C5    180.00   0.0  0
 FLG  CONST_39  C8    C7   C6   C5      0.00   0.0  0
 FLG  CONST_40  C11   C10  C9   C8    180.00   0.0  0
 FLG  CONST_41  C1    C2   C3   C11     0.00   0.0  0
 FLG  CONST_42  C1    C13  C12  C11     0.00   0.0  0
 FLG  CONST_43  C13   C12  C11  C3      0.00   0.0  0
 FLG  CONST_44  C13   C1   C2   C3      0.00   0.0  0
 FLG  CONST_45  C12   C11  C3   C2      0.00   0.0  0
 FLG  CONST_46  C12   C13  C1   C2      0.00   0.0  0
 FLG  CONST_47  C19   C18  C17  N1    180.00   0.0  0
 FLG  CONST_48  C15   C16  C17  N1    180.00   0.0  0
 FLG  CONST_49  C20   C19  C18  C17   180.00   0.0  0
 FLG  CONST_50  C15   C14  C19  C20   180.00   0.0  0
 FLG  CONST_51  C10   C14  C19  C20     0.00   0.0  0
 FLG  CONST_52  O3    C6   C5   C4    180.00   0.0  0
 FLG  CONST_53  O3    C6   C7   C8    180.00   0.0  0
 FLG  CONST_54  O1    C1   C2   C3    180.00   0.0  0
 FLG  CONST_55  O1    C1   C13  C12   180.00   0.0  0
 FLG  CONST_56  H15   C15  C16  C17   180.00   0.0  0
 FLG  CONST_57  H16   C16  C17  C18   180.00   0.0  0
 FLG  CONST_58  H18   C18  C17  C16   180.00   0.0  0
 FLG  CONST_59  H8    C8   C9   C10     0.00   0.0  0
 FLG  CONST_60  H12   C12  C11  C10     0.00   0.0  0
 FLG  CONST_61  H5    C5   C4   C9    180.00   0.0  0
 FLG  CONST_62  H7    C7   C8   C9    180.00   0.0  0
 FLG  CONST_63  H2    C2   C3   O2      0.00   0.0  0
 FLG  CONST_64  H13   C13  C12  C11   180.00   0.0  0
 FLG  CONST_72  HN1   N2   C21  S1      0.00   0.0  0
 FLG  Var_01    O4    C20  C19  C18     0.44  30.0  2
 FLG  Var_02    C23   C22  N2   C21  -142.25  30.0  3
 FLG  Var_03    H231  C23  C22  N2    -59.37  30.0  3

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
 FLG  plan-1  N1   0.020
 FLG  plan-1  C17  0.020
 FLG  plan-1  C18  0.020
 FLG  plan-1  C19  0.020
 FLG  plan-1  C20  0.020
 FLG  plan-1  C16  0.020
 FLG  plan-1  C15  0.020
 FLG  plan-1  C14  0.020
 FLG  plan-1  C10  0.020
 FLG  plan-1  H18  0.020
 FLG  plan-1  H16  0.020
 FLG  plan-1  H15  0.020
 FLG  plan-2  C10  0.020
 FLG  plan-2  O2   0.020
 FLG  plan-2  C11  0.020
 FLG  plan-2  C3   0.020
 FLG  plan-2  C2   0.020
 FLG  plan-2  C12  0.020
 FLG  plan-2  C13  0.020
 FLG  plan-2  C1   0.020
 FLG  plan-2  O1   0.020
 FLG  plan-2  H2   0.020
 FLG  plan-2  H12  0.020
 FLG  plan-2  H13  0.020
 FLG  plan-3  S1   0.020
 FLG  plan-3  C21  0.020
 FLG  plan-3  N1   0.020
 FLG  plan-3  C17  0.020
 FLG  plan-3  N2   0.020
 FLG  plan-3  C22  0.020
 FLG  plan-3  HN1  0.020
 FLG  plan-3  HN2  0.020
 FLG  plan-4  C10  0.020
 FLG  plan-4  C9   0.020
 FLG  plan-4  C4   0.020
 FLG  plan-4  O2   0.020
 FLG  plan-4  C5   0.020
 FLG  plan-4  C8   0.020
 FLG  plan-4  C7   0.020
 FLG  plan-4  C6   0.020
 FLG  plan-4  O3   0.020
 FLG  plan-4  H5   0.020
 FLG  plan-4  H8   0.020
 FLG  plan-4  H7   0.020
 FLG  plan-5  C19  0.020
 FLG  plan-5  C20  0.020
 FLG  plan-5  O4   0.020
 FLG  plan-5  O5   0.020

