# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 17:44:32 2022
#   Inital geometry file: a 89 line input string
#   Ligand name: 4-chloranyl-~{N}-[2-(4-chlorophenyl)ethyl]thieno[2,3-c]pyridine-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1ccc(CCNC(=O)c2sc3cncc(Cl)c3c2)cc1
#
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
 8DS  8DS  "4-chloranyl-N-[2-(4-chlorophenyl)ethyl]thieno[2,3-c]pyridine-2-carboxamide"
  ligand  34  22  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_8DS
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
 8DS  C2    C   C     0   0.561  35.8099  -4.2633  52.6289
 8DS  C4    C   CH2   0  -0.301  36.0429  -6.6276  52.0263
 8DS  C5    C   CH2   0  -0.518  34.9951  -7.5148  52.7118
 8DS  C6    C   CR6   0   0.129  34.5372  -6.9300  54.0153
 8DS  C7    C   CR16  0  -0.309  33.4622  -6.0457  54.0600
 8DS  C8    C   CR16  0  -0.199  33.0858  -5.4272  55.2436
 8DS  C11   C   CR16  0  -0.301  35.2217  -7.1954  55.1981
 8DS  C15   C   CR56  0  -0.328  34.1913  -0.7345  52.7517
 8DS  C16   C   CR56  0   0.423  33.3767  -1.4913  51.8951
 8DS  C17   C   CR15  0  -0.238  33.8552  -2.8240  51.7348
 8DS  C18   C   CR6   0  -0.210  32.2603  -0.8477  51.3535
 8DS  O1    O   O     0  -0.467  36.6708  -4.2664  53.4969
 8DS  N3    N   NH1   0  -0.640  35.5487  -5.2876  51.8057
 8DS  C9    C   CR6   0  -0.054  33.7933  -5.7047  56.4016
 8DS  C10   C   CR16  0  -0.198  34.8575  -6.5930  56.3928
 8DS  CL12  CL  CL    0  -0.135  33.3371  -4.9318  57.8869
 8DS  C13   C   CR5   0  -0.276  34.9903  -3.0391  52.4461
 8DS  S14   S   S2    0   0.295  35.5177  -1.6602  53.3505
 8DS  C20   C   CR16  0  -0.046  32.0255   0.4705  51.6774
 8DS  N21   N   N     0  -0.401  32.8191   1.1715  52.4949
 8DS  C22   C   CR16  0  -0.070  33.8764   0.5948  53.0266
 8DS  H1    H   HCH2  0   0.264  36.3168  -7.0627  51.0648
 8DS  H2    H   HCH2  0   0.259  36.9479  -6.5727  52.6281
 8DS  H3    H   HCH2  0   0.256  34.1459  -7.6460  52.0372
 8DS  H4    H   HCH2  0   0.260  35.4361  -8.5023  52.8636
 8DS  H5    H   HCR6  0   0.262  32.9051  -5.8274  53.1568
 8DS  H6    H   HCR6  0   0.275  32.2524  -4.7377  55.2582
 8DS  H7    H   HCR6  0   0.258  36.0603  -7.8816  55.1915
 8DS  H8    H   HCR5  0   0.287  33.3537  -3.5669  51.1310
 8DS  H9    H   HNH1  0   0.414  34.8235  -5.1859  51.1130
 8DS  H10   H   HCR6  0   0.275  35.3997  -6.8117  57.3030
 8DS  H11   H   HCR6  0   0.288  31.1667   0.9880  51.2664
 8DS  H12   H   HCR6  0   0.286  34.4956   1.1925  53.6860
 8DS  CL19  CL  CL    0  -0.103  31.1972  -1.6952  50.2981

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
 8DS  CL19  C18   single    1.721  0.020  1.721
 8DS  C20   C18   aromatic  1.378  0.020  1.378
 8DS  C20   N21   aromatic  1.338  0.020  1.338
 8DS  C18   C16   aromatic  1.398  0.020  1.398
 8DS  N21   C22   aromatic  1.316  0.020  1.316
 8DS  C16   C15   aromatic  1.404  0.020  1.404
 8DS  C16   C17   aromatic  1.425  0.020  1.425
 8DS  C22   C15   aromatic  1.393  0.020  1.393
 8DS  N3    C4    single    1.445  0.020  1.445
 8DS  N3    C2    single    1.340  0.020  1.340
 8DS  C4    C5    single    1.535  0.020  1.535
 8DS  C15   S14   aromatic  1.725  0.020  1.725
 8DS  C17   C13   aromatic  1.357  0.020  1.357
 8DS  C13   S14   aromatic  1.731  0.020  1.731
 8DS  C13   C2    single    1.484  0.020  1.484
 8DS  C5    C6    single    1.500  0.020  1.500
 8DS  C2    O1    double    1.223  0.020  1.223
 8DS  C6    C7    aromatic  1.393  0.020  1.393
 8DS  C6    C11   aromatic  1.392  0.020  1.392
 8DS  C7    C8    aromatic  1.387  0.020  1.387
 8DS  C11   C10   aromatic  1.387  0.020  1.387
 8DS  C8    C9    aromatic  1.385  0.020  1.385
 8DS  C10   C9    aromatic  1.386  0.020  1.386
 8DS  C9    CL12  single    1.735  0.020  1.735
 8DS  C4    H1    single    0.970  0.020  1.090
 8DS  C4    H2    single    0.970  0.020  1.090
 8DS  C5    H3    single    0.970  0.020  1.090
 8DS  C5    H4    single    0.970  0.020  1.090
 8DS  C7    H5    single    0.930  0.020  1.080
 8DS  C8    H6    single    0.930  0.020  1.080
 8DS  C11   H7    single    0.930  0.020  1.080
 8DS  C17   H8    single    0.930  0.020  1.080
 8DS  N3    H9    single    0.860  0.020  1.020
 8DS  C10   H10   single    0.930  0.020  1.080
 8DS  C20   H11   single    0.930  0.020  1.080
 8DS  C22   H12   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
 8DS  C13   C2   N3    116.56  3.000
 8DS  C13   C2   O1    118.58  3.000
 8DS  N3    C2   O1    124.86  3.000
 8DS  H2    C4   H1    107.39  3.000
 8DS  H2    C4   N3    108.79  3.000
 8DS  H1    C4   N3    108.74  3.000
 8DS  H2    C4   C5    110.49  3.000
 8DS  H1    C4   C5    109.56  3.000
 8DS  N3    C4   C5    111.76  3.000
 8DS  H4    C5   H3    106.93  3.000
 8DS  H4    C5   C6    110.79  3.000
 8DS  H3    C5   C6    110.25  3.000
 8DS  H4    C5   C4    108.01  3.000
 8DS  H3    C5   C4    108.93  3.000
 8DS  C6    C5   C4    111.78  3.000
 8DS  C11   C6   C7    118.25  3.000
 8DS  C11   C6   C5    120.92  3.000
 8DS  C7    C6   C5    120.73  3.000
 8DS  H5    C7   C8    118.81  3.000
 8DS  H5    C7   C6    119.87  3.000
 8DS  C8    C7   C6    121.32  3.000
 8DS  H6    C8   C9    120.66  3.000
 8DS  H6    C8   C7    120.31  3.000
 8DS  C9    C8   C7    119.03  3.000
 8DS  H7    C11  C10   118.92  3.000
 8DS  H7    C11  C6    119.74  3.000
 8DS  C10   C11  C6    121.34  3.000
 8DS  C22   C15  S14   128.12  3.000
 8DS  S14   C15  C16   111.64  3.000
 8DS  C22   C15  C16   120.24  3.000
 8DS  C18   C16  C17   130.93  3.000
 8DS  C17   C16  C15   112.21  3.000
 8DS  C18   C16  C15   116.85  3.000
 8DS  H8    C17  C13   124.90  3.000
 8DS  H8    C17  C16   123.36  3.000
 8DS  C13   C17  C16   111.73  3.000
 8DS  C20   C18  CL19  120.66  3.000
 8DS  C20   C18  C16   119.06  3.000
 8DS  CL19  C18  C16   120.28  3.000
 8DS  H9    N3   C4    116.39  3.000
 8DS  H9    N3   C2    119.04  3.000
 8DS  C4    N3   C2    123.26  3.000
 8DS  CL12  C9   C10   119.51  3.000
 8DS  CL12  C9   C8    119.48  3.000
 8DS  C10   C9   C8    121.01  3.000
 8DS  H10   C10  C9    120.59  3.000
 8DS  H10   C10  C11   120.36  3.000
 8DS  C9    C10  C11   119.04  3.000
 8DS  S14   C13  C17   113.73  3.000
 8DS  S14   C13  C2    115.10  3.000
 8DS  C17   C13  C2    131.09  3.000
 8DS  C13   S14  C15    90.68  3.000
 8DS  H11   C20  N21   116.86  3.000
 8DS  H11   C20  C18   120.19  3.000
 8DS  N21   C20  C18   122.95  3.000
 8DS  C22   N21  C20   119.59  3.000
 8DS  H12   C22  N21   117.57  3.000
 8DS  H12   C22  C15   121.12  3.000
 8DS  N21   C22  C15   121.31  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
 8DS  CONST_01  C9    C8   C7   C6       0.00   0.0  0
 8DS  CONST_02  C9    C10  C11  C6       0.00   0.0  0
 8DS  CONST_03  C10   C11  C6   C7       0.00   0.0  0
 8DS  CONST_04  C10   C9   C8   C7       0.00   0.0  0
 8DS  CONST_05  C11   C6   C7   C8       0.00   0.0  0
 8DS  CONST_06  C11   C10  C9   C8       0.00   0.0  0
 8DS  CONST_07  C20   C18  C16  C15      0.00   0.0  0
 8DS  CONST_08  C13   C17  C16  C15      0.00   0.0  0
 8DS  CONST_09  C20   N21  C22  C15      0.00   0.0  0
 8DS  CONST_10  C17   C13  S14  C15      0.00   0.0  0
 8DS  CONST_11  N21   C20  C18  C16      0.00   0.0  0
 8DS  CONST_12  N21   C22  C15  C16      0.00   0.0  0
 8DS  CONST_13  C13   S14  C15  C16      0.00   0.0  0
 8DS  CONST_14  S14   C13  C17  C16      0.00   0.0  0
 8DS  CONST_15  C20   C18  C16  C17    180.00   0.0  0
 8DS  CONST_16  C22   C15  C16  C17    180.00   0.0  0
 8DS  CONST_17  S14   C15  C16  C17      0.00   0.0  0
 8DS  CONST_18  C22   N21  C20  C18      0.00   0.0  0
 8DS  CONST_19  C22   C15  C16  C18      0.00   0.0  0
 8DS  CONST_20  S14   C15  C16  C18    180.00   0.0  0
 8DS  CONST_21  C13   C17  C16  C18    180.00   0.0  0
 8DS  CONST_22  C22   C15  S14  C13    180.00   0.0  0
 8DS  CONST_23  N21   C22  C15  S14    180.00   0.0  0
 8DS  CONST_24  C16   C17  C13  C2     180.00   0.0  0
 8DS  CONST_25  C15   S14  C13  C2     180.00   0.0  0
 8DS  CONST_26  C8    C7   C6   C5     180.00   0.0  0
 8DS  CONST_27  C10   C11  C6   C5     180.00   0.0  0
 8DS  CONST_28  CL12  C9   C8   C7     180.00   0.0  0
 8DS  CONST_29  CL12  C9   C10  C11    180.00   0.0  0
 8DS  CONST_30  CL19  C18  C16  C15    180.00   0.0  0
 8DS  CONST_31  CL19  C18  C16  C17      0.00   0.0  0
 8DS  CONST_32  N21   C20  C18  CL19   180.00   0.0  0
 8DS  CONST_33  H6    C8   C7   C6     180.00   0.0  0
 8DS  CONST_34  H10   C10  C11  C6     180.00   0.0  0
 8DS  CONST_35  H7    C11  C6   C7     180.00   0.0  0
 8DS  CONST_36  H10   C10  C9   C8     180.00   0.0  0
 8DS  CONST_37  H5    C7   C6   C11    180.00   0.0  0
 8DS  CONST_38  H8    C17  C16  C15    180.00   0.0  0
 8DS  CONST_39  H11   C20  C18  C16    180.00   0.0  0
 8DS  CONST_40  H12   C22  C15  C16    180.00   0.0  0
 8DS  CONST_41  H8    C17  C16  C18      0.00   0.0  0
 8DS  CONST_42  H5    C7   C8   C9     180.00   0.0  0
 8DS  CONST_43  H7    C11  C10  C9     180.00   0.0  0
 8DS  CONST_44  H6    C8   C9   C10    180.00   0.0  0
 8DS  CONST_45  H12   C22  C15  S14      0.00   0.0  0
 8DS  CONST_46  H8    C17  C13  S14    180.00   0.0  0
 8DS  CONST_47  H12   C22  N21  C20    180.00   0.0  0
 8DS  CONST_48  H11   C20  N21  C22    180.00   0.0  0
 8DS  CONST_49  C13   C2   N3   C4     180.00   0.0  0
 8DS  CONST_50  H9    N3   C2   C13      0.00   0.0  0
 8DS  CONST_51  O1    C2   N3   C4       0.00   0.0  0
 8DS  CONST_52  H9    N3   C2   O1     180.00   0.0  0
 8DS  Var_01    C7    C6   C5   C4      88.90  30.0  2
 8DS  Var_02    C11   C6   C5   C4     -87.36  30.0  2
 8DS  Var_03    N3    C2   C13  C17     12.62  30.0  2
 8DS  Var_04    O1    C2   C13  C17   -168.01  30.0  2
 8DS  Var_05    S14   C13  C2   O1       8.59  30.0  2
 8DS  Var_06    S14   C13  C2   N3    -170.79  30.0  2
 8DS  Var_07    H3    C5   C6   C7     -32.42  30.0  3
 8DS  Var_08    H4    C5   C6   C7    -150.59  30.0  3
 8DS  Var_09    H3    C5   C6   C11    151.32  30.0  3
 8DS  Var_10    H4    C5   C6   C11     33.15  30.0  3
 8DS  Var_11    N3    C4   C5   C6     -56.91  30.0  1
 8DS  Var_12    H1    C4   C5   C6    -177.51  30.0  1
 8DS  Var_13    H2    C4   C5   C6      64.37  30.0  1
 8DS  Var_14    C5    C4   N3   C2      97.20  30.0  3
 8DS  Var_15    H1    C4   N3   C2    -141.73  30.0  3
 8DS  Var_16    H2    C4   N3   C2     -25.07  30.0  3
 8DS  Var_17    H9    N3   C4   C5     -69.55  30.0  2
 8DS  Var_18    H3    C5   C4   N3      65.16  30.0  3
 8DS  Var_19    H4    C5   C4   N3    -179.04  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
 8DS  plan-1  C5    0.020
 8DS  plan-1  C6    0.020
 8DS  plan-1  C7    0.020
 8DS  plan-1  C8    0.020
 8DS  plan-1  C11   0.020
 8DS  plan-1  C9    0.020
 8DS  plan-1  C10   0.020
 8DS  plan-1  CL12  0.020
 8DS  plan-1  H5    0.020
 8DS  plan-1  H6    0.020
 8DS  plan-1  H7    0.020
 8DS  plan-1  H10   0.020
 8DS  plan-2  C2    0.020
 8DS  plan-2  C15   0.020
 8DS  plan-2  C16   0.020
 8DS  plan-2  C17   0.020
 8DS  plan-2  C18   0.020
 8DS  plan-2  C13   0.020
 8DS  plan-2  S14   0.020
 8DS  plan-2  C20   0.020
 8DS  plan-2  N21   0.020
 8DS  plan-2  C22   0.020
 8DS  plan-2  H8    0.020
 8DS  plan-2  H11   0.020
 8DS  plan-2  H12   0.020
 8DS  plan-2  CL19  0.020
 8DS  plan-3  C2    0.020
 8DS  plan-3  C4    0.020
 8DS  plan-3  O1    0.020
 8DS  plan-3  N3    0.020
 8DS  plan-3  C13   0.020
 8DS  plan-3  H9    0.020

