# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 09:49:05 2022
#   Inital geometry file: a 126 line input string
#   Ligand name: 3-phenoxy-~{N}-[(~{E})-(5-pyrimidin-2-ylsulfanylfuran-2-yl)methylideneamino]benzamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O=C(N/N=C/c1oc(Sc2ncccn2)cc1)c3cccc(Oc4ccccc4)c3
#
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
 1RI  1RI  "3-phenoxy-~{N}-[(~{E})-(5-pyrimidin-2-ylsulfanylfuran-2-yl)methylideneamino]benzamide"  ligand  46  30  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_1RI
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
 1RI  N1   N  NH1   0  -0.522   2.9268   -7.3682  -15.8610
 1RI  N3   N  N     0  -0.401  -3.2462   -2.8985  -18.4713
 1RI  C4   C  CR6   0   0.378   3.2989  -11.3976  -13.3689
 1RI  C5   C  CR6   0   0.323   3.1919  -12.8314  -11.4934
 1RI  C6   C  CR16  0  -0.306   3.7554  -12.0419  -10.4985
 1RI  C7   C  CR16  0  -0.247   4.2970  -12.6522   -9.3768
 1RI  C8   C  CR16  0  -0.260   4.2707  -14.0350   -9.2427
 1RI  C10  C  CR16  0  -0.323   3.1607  -14.2123  -11.3739
 1RI  C13  C  CR16  0  -0.300   4.5852   -9.6001  -15.0546
 1RI  C15  C  CR5   0   0.341   2.2249   -4.2242  -17.4176
 1RI  C17  C  CR15  0  -0.293   1.6540   -2.3330  -18.4379
 1RI  C20  C  CR16  0  -0.015  -4.1561   -2.7546  -17.5164
 1RI  C21  C  CR16  0  -0.348  -3.8131   -2.7026  -16.1750
 1RI  C22  C  CR16  0  -0.009  -2.4648   -2.8097  -15.8816
 1RI  C1   C  C     0   0.533   2.3468   -8.5839  -15.6556
 1RI  C11  C  CR16  0  -0.322   4.6830  -11.4467  -13.5040
 1RI  C12  C  CR16  0  -0.231   5.3128  -10.5468  -14.3493
 1RI  C16  C  CR15  0  -0.339   2.6727   -2.9622  -17.6792
 1RI  C18  C  CR5   0   0.145   0.6685   -3.2570  -18.5784
 1RI  C19  C  CR6   0   0.230  -1.9906   -2.9865  -18.0664
 1RI  C2   C  CR6   0  -0.041   3.1998   -9.5585  -14.9145
 1RI  C3   C  CR16  0  -0.358   2.5568  -10.4662  -14.0799
 1RI  C9   C  CR16  0  -0.248   3.6979  -14.8100  -10.2413
 1RI  N2   N  N     0  -0.182   2.2790   -6.4254  -16.5608
 1RI  N4   N  N     0  -0.383  -1.5431   -2.9543  -16.8281
 1RI  O1   O  O     0  -0.438   1.2234   -8.8560  -16.0262
 1RI  O3   O  O     0  -0.399   1.0132   -4.4122  -17.9710
 1RI  S1   S  S2    0   0.106  -0.8470   -3.1772  -19.4087
 1RI  H1   H  HNH1  0   0.420   3.8136   -7.1464  -15.4205
 1RI  H2   H  HCR6  0   0.278   3.7708  -10.9632  -10.5938
 1RI  H3   H  HCR6  0   0.262   4.7377  -12.0399   -8.6008
 1RI  H4   H  HCR6  0   0.258   4.6918  -14.5039   -8.3634
 1RI  H5   H  HCR6  0   0.269   2.7159  -14.8124  -12.1576
 1RI  H6   H  HCR6  0   0.268   5.1029   -8.9309  -15.7294
 1RI  H7   H  HCR5  0   0.286   1.6395   -1.3260  -18.8209
 1RI  H9   H  HCR6  0   0.289  -4.5565   -2.5844  -15.4010
 1RI  H10  H  HCR6  0   0.288  -2.1091   -2.7804  -14.8583
 1RI  H11  H  HCR6  0   0.288   5.2697  -12.1800  -12.9660
 1RI  H12  H  HCR6  0   0.271   6.3870  -10.5952  -14.4674
 1RI  H14  H  HCR5  0   0.278   3.6136   -2.5411  -17.3630
 1RI  H15  H  HCR6  0   0.274   1.4800  -10.4449  -13.9700
 1RI  H16  H  HCR6  0   0.262   3.6750  -15.8878  -10.1475
 1RI  O2   O  O2    0  -0.507   2.5990  -12.2711  -12.5954
 1RI  C14  C  C1    0  -0.139   2.8481   -5.2926  -16.6828
 1RI  H8   H  HCR6  0   0.288  -5.1893   -2.6794  -17.8349
 1RI  H13  H  H     0   0.275   3.8187   -5.0545  -16.2448

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
 1RI  S1   C18  single    1.730  0.020  1.730
 1RI  S1   C19  single    1.774  0.020  1.774
 1RI  N3   C19  aromatic  1.322  0.020  1.322
 1RI  N3   C20  aromatic  1.327  0.020  1.327
 1RI  C18  C17  aromatic  1.358  0.020  1.358
 1RI  C18  O3   aromatic  1.350  0.020  1.350
 1RI  C17  C16  aromatic  1.417  0.020  1.417
 1RI  C19  N4   aromatic  1.317  0.020  1.317
 1RI  C20  C21  aromatic  1.386  0.020  1.386
 1RI  O3   C15  aromatic  1.345  0.020  1.345
 1RI  C16  C15  aromatic  1.364  0.020  1.364
 1RI  C15  C14  single    1.439  0.020  1.439
 1RI  N4   C22  aromatic  1.329  0.020  1.329
 1RI  C21  C22  aromatic  1.384  0.020  1.384
 1RI  C14  N2   double    1.274  0.020  1.274
 1RI  N2   N1   single    1.341  0.020  1.341
 1RI  N1   C1   single    1.363  0.020  1.363
 1RI  O1   C1   double    1.214  0.020  1.214
 1RI  C1   C2   single    1.492  0.020  1.492
 1RI  C13  C2   aromatic  1.393  0.020  1.393
 1RI  C13  C12  aromatic  1.387  0.020  1.387
 1RI  C2   C3   aromatic  1.391  0.020  1.391
 1RI  C12  C11  aromatic  1.386  0.020  1.386
 1RI  C3   C4   aromatic  1.387  0.020  1.387
 1RI  C11  C4   aromatic  1.392  0.020  1.392
 1RI  C4   O2   single    1.361  0.020  1.361
 1RI  O2   C5   single    1.371  0.020  1.371
 1RI  C5   C10  aromatic  1.386  0.020  1.386
 1RI  C5   C6   aromatic  1.389  0.020  1.389
 1RI  C10  C9   aromatic  1.389  0.020  1.389
 1RI  C6   C7   aromatic  1.387  0.020  1.387
 1RI  C9   C8   aromatic  1.388  0.020  1.388
 1RI  C7   C8   aromatic  1.390  0.020  1.390
 1RI  N1   H1   single    0.860  0.020  1.020
 1RI  C6   H2   single    0.930  0.020  1.080
 1RI  C7   H3   single    0.930  0.020  1.080
 1RI  C8   H4   single    0.930  0.020  1.080
 1RI  C10  H5   single    0.930  0.020  1.080
 1RI  C13  H6   single    0.930  0.020  1.080
 1RI  C17  H7   single    0.930  0.020  1.080
 1RI  C20  H8   single    0.930  0.020  1.080
 1RI  C21  H9   single    0.930  0.020  1.080
 1RI  C22  H10  single    0.930  0.020  1.080
 1RI  C11  H11  single    0.930  0.020  1.080
 1RI  C12  H12  single    0.930  0.020  1.080
 1RI  C14  H13  single    0.930  0.020  1.080
 1RI  C16  H14  single    0.930  0.020  1.080
 1RI  C3   H15  single    0.930  0.020  1.080
 1RI  C9   H16  single    0.930  0.020  1.080

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
 1RI  H1   N1   N2   119.67  3.000
 1RI  H1   N1   C1   120.11  3.000
 1RI  N2   N1   C1   120.02  3.000
 1RI  C19  N3   C20  115.98  3.000
 1RI  O2   C4   C3   116.57  3.000
 1RI  O2   C4   C11  122.97  3.000
 1RI  C3   C4   C11  120.41  3.000
 1RI  O2   C5   C10  117.81  3.000
 1RI  C10  C5   C6   120.88  3.000
 1RI  O2   C5   C6   121.24  3.000
 1RI  H2   C6   C7   120.25  3.000
 1RI  H2   C6   C5   120.58  3.000
 1RI  C7   C6   C5   119.17  3.000
 1RI  H3   C7   C8   120.10  3.000
 1RI  H3   C7   C6   119.34  3.000
 1RI  C8   C7   C6   120.56  3.000
 1RI  H4   C8   C9   120.23  3.000
 1RI  H4   C8   C7   120.16  3.000
 1RI  C9   C8   C7   119.61  3.000
 1RI  H5   C10  C9   120.71  3.000
 1RI  H5   C10  C5   119.93  3.000
 1RI  C9   C10  C5   119.36  3.000
 1RI  H6   C13  C2   121.33  3.000
 1RI  H6   C13  C12  119.22  3.000
 1RI  C2   C13  C12  119.41  3.000
 1RI  O3   C15  C16  110.24  3.000
 1RI  C16  C15  C14  129.99  3.000
 1RI  O3   C15  C14  119.76  3.000
 1RI  H7   C17  C18  126.10  3.000
 1RI  H7   C17  C16  127.94  3.000
 1RI  C18  C17  C16  105.96  3.000
 1RI  H8   C20  C21  121.19  3.000
 1RI  H8   C20  N3   116.73  3.000
 1RI  C21  C20  N3   122.08  3.000
 1RI  H9   C21  C22  121.83  3.000
 1RI  H9   C21  C20  121.85  3.000
 1RI  C22  C21  C20  116.33  3.000
 1RI  H10  C22  N4   116.60  3.000
 1RI  H10  C22  C21  121.18  3.000
 1RI  N4   C22  C21  122.22  3.000
 1RI  O1   C1   C2   122.30  3.000
 1RI  C2   C1   N1   114.47  3.000
 1RI  O1   C1   N1   123.23  3.000
 1RI  H11  C11  C12  119.78  3.000
 1RI  H11  C11  C4   120.99  3.000
 1RI  C12  C11  C4   119.23  3.000
 1RI  H12  C12  C11  119.26  3.000
 1RI  H12  C12  C13  119.74  3.000
 1RI  C11  C12  C13  120.99  3.000
 1RI  H14  C16  C17  127.64  3.000
 1RI  H14  C16  C15  126.26  3.000
 1RI  C17  C16  C15  106.10  3.000
 1RI  S1   C18  O3   118.63  3.000
 1RI  O3   C18  C17  110.51  3.000
 1RI  S1   C18  C17  130.84  3.000
 1RI  S1   C19  N4   119.68  3.000
 1RI  N4   C19  N3   127.51  3.000
 1RI  S1   C19  N3   112.81  3.000
 1RI  C3   C2   C1   117.39  3.000
 1RI  C3   C2   C13  120.05  3.000
 1RI  C1   C2   C13  122.55  3.000
 1RI  H15  C3   C2   120.53  3.000
 1RI  H15  C3   C4   119.56  3.000
 1RI  C2   C3   C4   119.90  3.000
 1RI  H16  C9   C10  119.42  3.000
 1RI  H16  C9   C8   120.17  3.000
 1RI  C10  C9   C8   120.41  3.000
 1RI  C14  N2   N1   117.35  3.000
 1RI  C19  N4   C22  115.89  3.000
 1RI  C18  O3   C15  107.18  3.000
 1RI  C19  S1   C18  101.92  3.000
 1RI  C5   O2   C4   119.79  3.000
 1RI  H13  C14  N2   123.58  3.000
 1RI  H13  C14  C15  115.36  3.000
 1RI  N2   C14  C15  121.06  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
 1RI  CONST_01  C22  N4   C19  N3      0.00   0.0  0
 1RI  CONST_02  C22  C21  C20  N3      0.00   0.0  0
 1RI  CONST_03  C13  C2   C3   C4      0.00   0.0  0
 1RI  CONST_04  C13  C12  C11  C4      0.00   0.0  0
 1RI  CONST_05  C8   C9   C10  C5      0.00   0.0  0
 1RI  CONST_06  C8   C7   C6   C5      0.00   0.0  0
 1RI  CONST_07  C9   C10  C5   C6      0.00   0.0  0
 1RI  CONST_08  C9   C8   C7   C6      0.00   0.0  0
 1RI  CONST_09  C10  C5   C6   C7      0.00   0.0  0
 1RI  CONST_10  C10  C9   C8   C7      0.00   0.0  0
 1RI  CONST_11  C17  C18  O3   C15     0.00   0.0  0
 1RI  CONST_12  C18  C17  C16  C15     0.00   0.0  0
 1RI  CONST_13  O3   C15  C16  C17     0.00   0.0  0
 1RI  CONST_14  N4   C19  N3   C20     0.00   0.0  0
 1RI  CONST_15  N4   C22  C21  C20     0.00   0.0  0
 1RI  CONST_16  C19  N3   C20  C21     0.00   0.0  0
 1RI  CONST_17  C19  N4   C22  C21     0.00   0.0  0
 1RI  CONST_18  C2   C13  C12  C11     0.00   0.0  0
 1RI  CONST_19  C2   C3   C4   C11     0.00   0.0  0
 1RI  CONST_20  C3   C2   C13  C12     0.00   0.0  0
 1RI  CONST_21  C3   C4   C11  C12     0.00   0.0  0
 1RI  CONST_22  O3   C18  C17  C16     0.00   0.0  0
 1RI  CONST_23  C18  O3   C15  C16     0.00   0.0  0
 1RI  CONST_24  C1   C2   C3   C4    180.00   0.0  0
 1RI  CONST_25  O2   C5   C6   C7    180.00   0.0  0
 1RI  CONST_26  S1   C18  O3   C15   180.00   0.0  0
 1RI  CONST_27  C14  C15  C16  C17   180.00   0.0  0
 1RI  CONST_28  S1   C19  N3   C20   180.00   0.0  0
 1RI  CONST_29  S1   C19  N4   C22   180.00   0.0  0
 1RI  CONST_30  C12  C13  C2   C1    180.00   0.0  0
 1RI  CONST_31  O2   C4   C11  C12   180.00   0.0  0
 1RI  CONST_32  C18  O3   C15  C14   180.00   0.0  0
 1RI  CONST_33  S1   C18  C17  C16   180.00   0.0  0
 1RI  CONST_34  O2   C4   C3   C2    180.00   0.0  0
 1RI  CONST_35  O2   C5   C10  C9    180.00   0.0  0
 1RI  CONST_36  H9   C21  C20  N3    180.00   0.0  0
 1RI  CONST_37  H12  C12  C11  C4    180.00   0.0  0
 1RI  CONST_38  H16  C9   C10  C5    180.00   0.0  0
 1RI  CONST_39  H3   C7   C6   C5    180.00   0.0  0
 1RI  CONST_40  H5   C10  C5   C6    180.00   0.0  0
 1RI  CONST_41  H4   C8   C7   C6    180.00   0.0  0
 1RI  CONST_42  H16  C9   C8   C7    180.00   0.0  0
 1RI  CONST_43  H5   C10  C9   C8    180.00   0.0  0
 1RI  CONST_44  H2   C6   C7   C8    180.00   0.0  0
 1RI  CONST_45  H2   C6   C5   C10   180.00   0.0  0
 1RI  CONST_46  H4   C8   C9   C10   180.00   0.0  0
 1RI  CONST_47  H15  C3   C2   C13   180.00   0.0  0
 1RI  CONST_48  H11  C11  C12  C13   180.00   0.0  0
 1RI  CONST_49  H7   C17  C16  C15   180.00   0.0  0
 1RI  CONST_50  H10  C22  C21  C20   180.00   0.0  0
 1RI  CONST_51  H8   C20  C21  C22   180.00   0.0  0
 1RI  CONST_52  H6   C13  C12  C11   180.00   0.0  0
 1RI  CONST_53  H15  C3   C4   C11   180.00   0.0  0
 1RI  CONST_54  H14  C16  C17  C18   180.00   0.0  0
 1RI  CONST_55  H8   C20  N3   C19   180.00   0.0  0
 1RI  CONST_56  H10  C22  N4   C19   180.00   0.0  0
 1RI  CONST_57  H12  C12  C13  C2    180.00   0.0  0
 1RI  CONST_58  H6   C13  C2   C3    180.00   0.0  0
 1RI  CONST_59  H11  C11  C4   C3    180.00   0.0  0
 1RI  CONST_60  H3   C7   C8   C9    180.00   0.0  0
 1RI  CONST_61  H9   C21  C22  N4    180.00   0.0  0
 1RI  CONST_62  H7   C17  C18  O3    180.00   0.0  0
 1RI  CONST_63  H14  C16  C15  O3    180.00   0.0  0
 1RI  CONST_64  N2   N1   C1   C2    180.00   0.0  0
 1RI  CONST_65  H1   N1   C1   C2      0.00   0.0  0
 1RI  CONST_66  O1   C1   N1   N2      0.00   0.0  0
 1RI  CONST_67  H1   N1   C1   O1    180.00   0.0  0
 1RI  Var_01    C18  S1   C19  N3    179.85  30.0  2
 1RI  Var_02    C10  C5   O2   C4   -127.59  30.0  2
 1RI  Var_03    C6   C5   O2   C4     55.14  30.0  2
 1RI  Var_04    C3   C4   O2   C5   -153.65  30.0  1
 1RI  Var_05    C11  C4   O2   C5     28.99  30.0  1
 1RI  Var_06    C19  S1   C18  C17  -104.18  30.0  1
 1RI  Var_07    N4   C19  S1   C18    -0.50  30.0  2
 1RI  Var_08    O3   C18  S1   C19    77.71  30.0  2
 1RI  Var_09    C13  C2   C1   N1    -34.18  30.0  2
 1RI  Var_10    C3   C2   C1   N1    147.18  30.0  2
 1RI  Var_11    O1   C1   C2   C13   146.70  30.0  2
 1RI  Var_12    N2   C14  C15  C16  -178.80  30.0  2
 1RI  Var_13    O1   C1   C2   C3    -31.95  30.0  2
 1RI  Var_14    O3   C15  C14  N2      0.95  30.0  2
 1RI  Var_15    H13  C14  C15  C16     1.64  30.0  2
 1RI  Var_16    H13  C14  C15  O3   -178.61  30.0  2
 1RI  Var_17    C15  C14  N2   N1    179.97   0.0  2
 1RI  Var_18    C14  N2   N1   C1    177.64  30.0  1
 1RI  Var_19    H13  C14  N2   N1     -0.51   0.0  2
 1RI  Var_20    H1   N1   N2   C14     2.77  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
 1RI  plan-1  C15  0.020
 1RI  plan-1  C17  0.020
 1RI  plan-1  C16  0.020
 1RI  plan-1  C18  0.020
 1RI  plan-1  O3   0.020
 1RI  plan-1  S1   0.020
 1RI  plan-1  H7   0.020
 1RI  plan-1  H14  0.020
 1RI  plan-1  C14  0.020
 1RI  plan-2  N3   0.020
 1RI  plan-2  C20  0.020
 1RI  plan-2  C21  0.020
 1RI  plan-2  C22  0.020
 1RI  plan-2  C19  0.020
 1RI  plan-2  N4   0.020
 1RI  plan-2  S1   0.020
 1RI  plan-2  H9   0.020
 1RI  plan-2  H10  0.020
 1RI  plan-2  H8   0.020
 1RI  plan-3  C5   0.020
 1RI  plan-3  C6   0.020
 1RI  plan-3  C7   0.020
 1RI  plan-3  C8   0.020
 1RI  plan-3  C10  0.020
 1RI  plan-3  C9   0.020
 1RI  plan-3  H2   0.020
 1RI  plan-3  H3   0.020
 1RI  plan-3  H4   0.020
 1RI  plan-3  H5   0.020
 1RI  plan-3  H16  0.020
 1RI  plan-3  O2   0.020
 1RI  plan-4  C4   0.020
 1RI  plan-4  C13  0.020
 1RI  plan-4  C1   0.020
 1RI  plan-4  C11  0.020
 1RI  plan-4  C12  0.020
 1RI  plan-4  C2   0.020
 1RI  plan-4  C3   0.020
 1RI  plan-4  H6   0.020
 1RI  plan-4  H11  0.020
 1RI  plan-4  H12  0.020
 1RI  plan-4  H15  0.020
 1RI  plan-4  O2   0.020
 1RI  plan-5  N1   0.020
 1RI  plan-5  C1   0.020
 1RI  plan-5  C2   0.020
 1RI  plan-5  N2   0.020
 1RI  plan-5  O1   0.020
 1RI  plan-5  H1   0.020
 1RI  plan-6  N1   0.020
 1RI  plan-6  C15  0.020
 1RI  plan-6  N2   0.020
 1RI  plan-6  C14  0.020
 1RI  plan-6  H13  0.020

