# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 21:24:19 2021
#   Inital geometry file: a 80 line input string
#   Ligand name: 5-ethyl-~{N}-(1~{H}-indol-5-ylmethyl)-1,3,4-thiadiazol-2-amine
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1sc(NCc2ccc3[nH]ccc3c2)nn1
#
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
 O1E  O1E  5-ethyl-~{N}-(1~{H}-indol-5-ylmethyl)-1,3,4-thiadiazol-2-amine  ligand  32  18  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_O1E
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
 O1E  C4   C  CH2   0  -0.405  11.8775  18.4098  21.5900
 O1E  C5   C  CR6   0   0.105  11.0481  17.2224  21.1709
 O1E  C6   C  CR16  0  -0.316  10.5447  16.3309  22.1405
 O1E  N1   N  N     0  -0.336  13.1465  17.5104  24.0130
 O1E  C7   C  CR16  0  -0.292   9.8186  15.2106  21.7910
 O1E  C8   C  CR56  0   0.336   9.5923  14.9837  20.4341
 O1E  N2   N  NH1   0  -0.641  13.2913  18.1019  21.7451
 O1E  C9   C  CR15  0  -0.028   8.9622  14.1872  18.4511
 O1E  C10  C  CR15  0  -0.422   9.6581  15.3301  18.1802
 O1E  C11  C  CR56  0   0.077  10.0769  15.8620  19.4394
 O1E  C12  C  CR16  0  -0.402  10.8100  16.9888  19.8283
 O1E  N3   N  NR15  0  -0.678   8.9210  13.9797  19.8003
 O1E  N    N  N     0  -0.247  13.9037  16.9977  25.0107
 O1E  C    C  CH3   0  -0.666  16.5590  14.6753  25.1339
 O1E  C2   C  CR5   0   0.087  15.0955  16.6679  24.6660
 O1E  C3   C  CR5   0   0.335  13.7850  17.5803  22.8814
 O1E  S    S  S2    0   0.134  15.4169  16.9808  22.9777
 O1E  H7   H  HCH2  0   0.272  11.8071  19.1990  20.8411
 O1E  H6   H  HCH2  0   0.267  11.5182  18.8292  22.5291
 O1E  H8   H  HCR6  0   0.248  10.7380  16.5334  23.1861
 O1E  H9   H  HCR6  0   0.258   9.4372  14.5359  22.5471
 O1E  H5   H  HNH1  0   0.405  13.8012  17.9266  20.8946
 O1E  H11  H  HCR5  0   0.281   8.4852  13.4937  17.7773
 O1E  H12  H  HCR5  0   0.247   9.8489  15.7414  17.2019
 O1E  H13  H  HCR6  0   0.241  11.1877  17.6772  19.0799
 O1E  H10  H  HNR5  0   0.410   8.4676  13.2021  20.2498
 O1E  H2   H  HCH3  0   0.245  17.2972  14.2803  25.8307
 O1E  H1   H  HCH3  0   0.237  15.7136  13.9882  25.1119
 O1E  H    H  HCH3  0   0.229  17.0143  14.6825  24.1428
 O1E  H4   H  HCH2  0   0.263  16.9900  16.7346  25.6118
 O1E  H3   H  HCH2  0   0.265  15.6932  16.0413  26.5681
 O1E  C1   C  CH2   0  -0.510  16.1220  16.0727  25.5657

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
 O1E  C10  C9   aromatic  1.365  0.020  1.365
 O1E  C10  C11  aromatic  1.430  0.020  1.430
 O1E  C9   N3   aromatic  1.366  0.020  1.366
 O1E  C11  C12  aromatic  1.399  0.020  1.399
 O1E  C11  C8   aromatic  1.413  0.020  1.413
 O1E  C12  C5   aromatic  1.383  0.020  1.383
 O1E  N3   C8   aromatic  1.364  0.020  1.364
 O1E  C8   C7   aromatic  1.394  0.020  1.394
 O1E  C5   C4   single    1.508  0.020  1.508
 O1E  C5   C6   aromatic  1.410  0.020  1.410
 O1E  C4   N2   single    1.455  0.020  1.455
 O1E  N2   C3   single    1.344  0.020  1.344
 O1E  C7   C6   aromatic  1.380  0.020  1.380
 O1E  C3   S    aromatic  1.741  0.020  1.741
 O1E  C3   N1   aromatic  1.301  0.020  1.301
 O1E  S    C2   aromatic  1.747  0.020  1.747
 O1E  N1   N    aromatic  1.353  0.020  1.353
 O1E  C2   N    aromatic  1.284  0.020  1.284
 O1E  C2   C1   single    1.489  0.020  1.489
 O1E  C    C1   single    1.526  0.020  1.526
 O1E  C4   H7   single    0.970  0.020  1.090
 O1E  C4   H6   single    0.970  0.020  1.090
 O1E  C6   H8   single    0.930  0.020  1.080
 O1E  C7   H9   single    0.930  0.020  1.080
 O1E  N2   H5   single    0.890  0.020  1.040
 O1E  C9   H11  single    0.930  0.020  1.080
 O1E  C10  H12  single    0.930  0.020  1.080
 O1E  C12  H13  single    0.930  0.020  1.080
 O1E  N3   H10  single    0.860  0.020  1.020
 O1E  C    H2   single    0.970  0.020  1.090
 O1E  C    H1   single    0.970  0.020  1.090
 O1E  C    H    single    0.970  0.020  1.090
 O1E  C1   H4   single    0.970  0.020  1.090
 O1E  C1   H3   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
 O1E  H6   C4   H7   106.99  3.000
 O1E  H6   C4   N2   108.06  3.000
 O1E  H7   C4   N2   106.80  3.000
 O1E  H6   C4   C5   111.18  3.000
 O1E  H7   C4   C5   110.09  3.000
 O1E  N2   C4   C5   113.41  3.000
 O1E  C12  C5   C6   119.94  3.000
 O1E  C6   C5   C4   120.20  3.000
 O1E  C12  C5   C4   119.83  3.000
 O1E  H8   C6   C7   119.37  3.000
 O1E  H8   C6   C5   118.83  3.000
 O1E  C7   C6   C5   121.80  3.000
 O1E  C3   N1   N    112.76  3.000
 O1E  H9   C7   C8   121.40  3.000
 O1E  H9   C7   C6   120.96  3.000
 O1E  C8   C7   C6   117.64  3.000
 O1E  N3   C8   C11  107.41  3.000
 O1E  N3   C8   C7   130.68  3.000
 O1E  C11  C8   C7   121.90  3.000
 O1E  H5   N2   C3   117.41  3.000
 O1E  H5   N2   C4   116.03  3.000
 O1E  C3   N2   C4   121.94  3.000
 O1E  H11  C9   N3   120.42  3.000
 O1E  H11  C9   C10  129.79  3.000
 O1E  N3   C9   C10  109.79  3.000
 O1E  H12  C10  C11  127.25  3.000
 O1E  H12  C10  C9   126.12  3.000
 O1E  C11  C10  C9   106.62  3.000
 O1E  C12  C11  C10  134.25  3.000
 O1E  C12  C11  C8   118.99  3.000
 O1E  C10  C11  C8   106.76  3.000
 O1E  H13  C12  C11  120.11  3.000
 O1E  H13  C12  C5   120.16  3.000
 O1E  C11  C12  C5   119.72  3.000
 O1E  H10  N3   C9   124.92  3.000
 O1E  H10  N3   C8   125.67  3.000
 O1E  C9   N3   C8   109.41  3.000
 O1E  C2   N    N1   114.76  3.000
 O1E  H    C    H1   108.04  3.000
 O1E  H    C    H2   107.50  3.000
 O1E  H1   C    H2   108.06  3.000
 O1E  H    C    C1   111.75  3.000
 O1E  H1   C    C1   111.15  3.000
 O1E  H2   C    C1   110.19  3.000
 O1E  S    C2   C1   121.92  3.000
 O1E  C1   C2   N    125.48  3.000
 O1E  S    C2   N    112.60  3.000
 O1E  S    C3   N2   121.64  3.000
 O1E  S    C3   N1   113.17  3.000
 O1E  N2   C3   N1   125.15  3.000
 O1E  C3   S    C2    86.71  3.000
 O1E  H3   C1   H4   106.92  3.000
 O1E  H3   C1   C2   107.20  3.000
 O1E  H4   C1   C2   109.33  3.000
 O1E  H3   C1   C    110.25  3.000
 O1E  H4   C1   C    109.82  3.000
 O1E  C2   C1   C    113.10  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
 O1E  CONST_01  C10  C11  C12  C5    180.00   0.0  0
 O1E  CONST_02  C8   C11  C12  C5      0.00   0.0  0
 O1E  CONST_03  C8   C7   C6   C5      0.00   0.0  0
 O1E  CONST_04  C11  C12  C5   C6      0.00   0.0  0
 O1E  CONST_05  C11  C8   C7   C6      0.00   0.0  0
 O1E  CONST_06  N3   C8   C7   C6    180.00   0.0  0
 O1E  CONST_07  C2   S    C3   N1      0.00   0.0  0
 O1E  CONST_08  S    C2   N    N1      0.00   0.0  0
 O1E  CONST_09  C10  C11  C8   C7    180.00   0.0  0
 O1E  CONST_10  C12  C11  C8   C7      0.00   0.0  0
 O1E  CONST_11  C9   N3   C8   C7    180.00   0.0  0
 O1E  CONST_12  C12  C5   C6   C7      0.00   0.0  0
 O1E  CONST_13  C9   C10  C11  C8      0.00   0.0  0
 O1E  CONST_14  C10  C9   N3   C8      0.00   0.0  0
 O1E  CONST_15  C12  C11  C10  C9    180.00   0.0  0
 O1E  CONST_16  C11  C8   N3   C9      0.00   0.0  0
 O1E  CONST_17  N3   C8   C11  C10     0.00   0.0  0
 O1E  CONST_18  N3   C9   C10  C11     0.00   0.0  0
 O1E  CONST_19  N3   C8   C11  C12   180.00   0.0  0
 O1E  CONST_20  S    C3   N1   N       0.00   0.0  0
 O1E  CONST_21  C3   S    C2   N       0.00   0.0  0
 O1E  CONST_22  C3   N1   N    C2      0.00   0.0  0
 O1E  CONST_23  C11  C12  C5   C4    180.00   0.0  0
 O1E  CONST_24  C7   C6   C5   C4    180.00   0.0  0
 O1E  CONST_25  C1   C2   N    N1    180.00   0.0  0
 O1E  CONST_26  C2   S    C3   N2    180.00   0.0  0
 O1E  CONST_27  N    N1   C3   N2    180.00   0.0  0
 O1E  CONST_28  C3   S    C2   C1    180.00   0.0  0
 O1E  CONST_29  H9   C7   C6   C5    180.00   0.0  0
 O1E  CONST_30  H13  C12  C5   C6    180.00   0.0  0
 O1E  CONST_31  H10  N3   C8   C7      0.00   0.0  0
 O1E  CONST_32  H12  C10  C11  C8    180.00   0.0  0
 O1E  CONST_33  H11  C9   N3   C8    180.00   0.0  0
 O1E  CONST_34  H8   C6   C7   C8    180.00   0.0  0
 O1E  CONST_35  S    C3   N2   C4    180.00   0.0  0
 O1E  CONST_36  N1   C3   N2   C4      0.00   0.0  0
 O1E  CONST_37  H5   N2   C3   N1    180.00   0.0  0
 O1E  Var_01    C3   N2   C4   C5    -84.20  30.0  3
 O1E  Var_02    N2   C4   C5   C6     85.65  30.0  2
 O1E  Var_03    C    C1   C2   N     117.78  30.0  2
 O1E  Var_04    H2   C    C1   C2   -179.17  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
 O1E  plan-1  N1   0.020
 O1E  plan-1  N2   0.020
 O1E  plan-1  N    0.020
 O1E  plan-1  C2   0.020
 O1E  plan-1  C3   0.020
 O1E  plan-1  S    0.020
 O1E  plan-1  C1   0.020
 O1E  plan-2  C4   0.020
 O1E  plan-2  C5   0.020
 O1E  plan-2  C6   0.020
 O1E  plan-2  C7   0.020
 O1E  plan-2  C8   0.020
 O1E  plan-2  C9   0.020
 O1E  plan-2  C10  0.020
 O1E  plan-2  C11  0.020
 O1E  plan-2  C12  0.020
 O1E  plan-2  N3   0.020
 O1E  plan-2  H8   0.020
 O1E  plan-2  H9   0.020
 O1E  plan-2  H11  0.020
 O1E  plan-2  H12  0.020
 O1E  plan-2  H13  0.020
 O1E  plan-2  H10  0.020
 O1E  plan-3  C4   0.020
 O1E  plan-3  N2   0.020
 O1E  plan-3  C3   0.020
 O1E  plan-3  H5   0.020

