# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar  8 14:24:48 2022
#   Inital geometry file: a 111 line input string
#   Ligand name: 2-chloro-4-hydroxy-3-(2'-hydroxybiphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccccc1c2ccc(cc2)c3c(Cl)sc4NC(=O)C(=C(O)c34)C#N
#
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
 32J  32J  2-chloro-4-hydroxy-3-(2'-hydroxybiphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile  ligand  38  27  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_32J
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
 32J  C4   C   CR6   0  -0.353   3.4710   2.0330   0.1578
 32J  N2   N   NS    0  -0.243   3.4453   4.5870   0.4063
 32J  C7   C   CR5   0  -0.388   1.6895  -2.2752  -0.1532
 32J  C6   C   CR5   0   0.306   1.2098  -1.0142  -0.0588
 32J  C9   C   CR16  0  -0.267  -0.9887  -0.9968   1.1009
 32J  C13  C   CR16  0  -0.251  -0.8513  -0.1226  -1.1281
 32J  C20  C   CSP   0   0.042   3.4774   3.4387   0.2940
 32J  C8   C   CR6   0   0.042  -0.2292  -0.6955  -0.0246
 32J  C18  C   CR16  0  -0.333  -6.2906   1.6835  -0.1537
 32J  C16  C   CR16  0  -0.270  -6.7019  -0.6301   0.3670
 32J  C19  C   CR6   0   0.309  -4.9184   1.4448  -0.1766
 32J  C1   C   CR56  0  -0.021   2.2921  -0.0662  -0.0135
 32J  C2   C   CR56  0   0.111   3.5313  -0.6710  -0.0868
 32J  N1   N   NR16  0  -0.738   4.6963   0.0063  -0.0522
 32J  C3   C   CR6   0   0.545   4.7596   1.3816   0.0661
 32J  C5   C   CR6   0   0.465   2.2680   1.3465   0.1253
 32J  S1   S   S2    0   0.354   3.4253  -2.3778  -0.2024
 32J  C10  C   CR16  0  -0.275  -2.3446  -0.7116   1.1297
 32J  C11  C   CR6   0   0.019  -2.9749  -0.1310   0.0302
 32J  C12  C   CR16  0  -0.308  -2.2087   0.1527  -1.1031
 32J  C14  C   CR6   0  -0.044  -4.4264   0.1542   0.0605
 32J  C15  C   CR16  0  -0.285  -5.3366  -0.8641   0.3415
 32J  C17  C   CR16  0  -0.250  -7.1746   0.6510   0.1108
 32J  O2   O   OH1   0  -0.546   1.0920   1.9208   0.2202
 32J  O3   O   O     0  -0.455   5.8290   1.9649   0.0915
 32J  CL1  CL  CL    0  -0.052   0.7866  -3.7129  -0.2594
 32J  H1   H   HCR6  0   0.262  -0.5161  -1.4408   1.9676
 32J  H2   H   HCR6  0   0.260  -0.2777   0.1000  -2.0186
 32J  H3   H   HCR6  0   0.264  -6.6552   2.6866  -0.3377
 32J  H4   H   HCR6  0   0.254  -7.3887  -1.4388   0.5774
 32J  H5   H   HNR6  0   0.438   5.5778  -0.4871  -0.1164
 32J  H6   H   HCR6  0   0.261  -2.9179  -0.9352   2.0206
 32J  H7   H   HCR6  0   0.276  -2.6782   0.5613  -1.9897
 32J  H8   H   HCR6  0   0.258  -4.9589  -1.8620   0.5288
 32J  H9   H   HCR6  0   0.259  -8.2381   0.8515   0.1225
 32J  H10  H   HOH1  0   0.472  -3.1889   2.2680  -0.3087
 32J  H11  H   HOH1  0   0.498   1.1440   2.8828   0.3153
 32J  O1   O   OH1   0  -0.619  -4.1182   2.5045  -0.4145

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
 32J  C16  C15  aromatic  1.385  0.020  1.385
 32J  C16  C17  aromatic  1.389  0.020  1.389
 32J  C15  C14  aromatic  1.394  0.020  1.394
 32J  C10  C9   aromatic  1.386  0.020  1.386
 32J  C10  C11  aromatic  1.394  0.020  1.394
 32J  C9   C8   aromatic  1.391  0.020  1.391
 32J  O3   C3   double    1.218  0.020  1.218
 32J  C17  C18  aromatic  1.385  0.020  1.385
 32J  S1   C2   aromatic  1.714  0.020  1.714
 32J  S1   C7   aromatic  1.739  0.020  1.739
 32J  N1   C3   single    1.382  0.020  1.382
 32J  N1   C2   single    1.348  0.020  1.348
 32J  C3   C4   single    1.447  0.020  1.447
 32J  C2   C1   aromatic  1.381  0.020  1.381
 32J  CL1  C7   single    1.701  0.020  1.701
 32J  C7   C6   aromatic  1.352  0.020  1.352
 32J  C14  C11  single    1.480  0.020  1.480
 32J  C14  C19  aromatic  1.401  0.020  1.401
 32J  C11  C12  aromatic  1.397  0.020  1.397
 32J  C1   C6   aromatic  1.440  0.020  1.440
 32J  C1   C5   single    1.420  0.020  1.420
 32J  C6   C8   single    1.474  0.020  1.474
 32J  C8   C13  aromatic  1.390  0.020  1.390
 32J  C4   C5   double    1.385  0.020  1.385
 32J  C4   C20  single    1.412  0.020  1.412
 32J  C5   O2   single    1.312  0.020  1.312
 32J  C20  N2   triple    1.154  0.020  1.154
 32J  C12  C13  aromatic  1.385  0.020  1.385
 32J  C18  C19  aromatic  1.393  0.020  1.393
 32J  C19  O1   single    1.349  0.020  1.349
 32J  C9   H1   single    0.930  0.020  1.080
 32J  C13  H2   single    0.930  0.020  1.080
 32J  C18  H3   single    0.930  0.020  1.080
 32J  C16  H4   single    0.930  0.020  1.080
 32J  N1   H5   single    0.860  0.020  1.020
 32J  C10  H6   single    0.930  0.020  1.080
 32J  C12  H7   single    0.930  0.020  1.080
 32J  C15  H8   single    0.930  0.020  1.080
 32J  C17  H9   single    0.930  0.020  1.080
 32J  O1   H10  single    0.850  0.020  0.980
 32J  O2   H11  single    0.850  0.020  0.980

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
 32J  C5   C4   C3   123.28  3.000
 32J  C5   C4   C20  119.96  3.000
 32J  C3   C4   C20  116.76  3.000
 32J  CL1  C7   S1   118.56  3.000
 32J  CL1  C7   C6   127.16  3.000
 32J  S1   C7   C6   114.26  3.000
 32J  C1   C6   C8   126.21  3.000
 32J  C8   C6   C7   123.33  3.000
 32J  C1   C6   C7   110.46  3.000
 32J  H1   C9   C10  119.66  3.000
 32J  H1   C9   C8   119.89  3.000
 32J  C10  C9   C8   120.44  3.000
 32J  H2   C13  C12  119.56  3.000
 32J  H2   C13  C8   120.04  3.000
 32J  C12  C13  C8   120.40  3.000
 32J  N2   C20  C4   180.00  3.000
 32J  C13  C8   C9   119.16  3.000
 32J  C13  C8   C6   120.49  3.000
 32J  C9   C8   C6   120.33  3.000
 32J  H3   C18  C17  120.54  3.000
 32J  H3   C18  C19  119.18  3.000
 32J  C17  C18  C19  120.28  3.000
 32J  H4   C16  C17  120.62  3.000
 32J  H4   C16  C15  120.20  3.000
 32J  C17  C16  C15  119.19  3.000
 32J  O1   C19  C14  123.03  3.000
 32J  O1   C19  C18  116.91  3.000
 32J  C14  C19  C18  120.06  3.000
 32J  C5   C1   C2   117.15  3.000
 32J  C5   C1   C6   130.21  3.000
 32J  C2   C1   C6   112.62  3.000
 32J  S1   C2   N1   123.75  3.000
 32J  N1   C2   C1   123.65  3.000
 32J  S1   C2   C1   112.59  3.000
 32J  H5   N1   C3   116.79  3.000
 32J  H5   N1   C2   120.40  3.000
 32J  C3   N1   C2   122.81  3.000
 32J  O3   C3   N1   121.23  3.000
 32J  N1   C3   C4   114.38  3.000
 32J  O3   C3   C4   124.39  3.000
 32J  O2   C5   C1   117.25  3.000
 32J  O2   C5   C4   124.03  3.000
 32J  C1   C5   C4   118.72  3.000
 32J  C2   S1   C7    90.06  3.000
 32J  H6   C10  C11  119.71  3.000
 32J  H6   C10  C9   119.52  3.000
 32J  C11  C10  C9   120.77  3.000
 32J  C14  C11  C12  121.04  3.000
 32J  C12  C11  C10  118.45  3.000
 32J  C14  C11  C10  120.51  3.000
 32J  H7   C12  C11  120.18  3.000
 32J  H7   C12  C13  119.00  3.000
 32J  C11  C12  C13  120.78  3.000
 32J  C15  C14  C11  120.25  3.000
 32J  C11  C14  C19  121.23  3.000
 32J  C15  C14  C19  118.52  3.000
 32J  H8   C15  C14  118.68  3.000
 32J  H8   C15  C16  119.74  3.000
 32J  C14  C15  C16  121.57  3.000
 32J  H9   C17  C16  120.21  3.000
 32J  H9   C17  C18  119.42  3.000
 32J  C16  C17  C18  120.37  3.000
 32J  H11  O2   C5   113.20  3.000
 32J  H10  O1   C19  111.07  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
 32J  CONST_01  C1   C2   S1   C7     0.00  0.0  0
 32J  CONST_02  C2   C1   C6   C7     0.00  0.0  0
 32J  CONST_05  C2   S1   C7   C6     0.00  0.0  0
 32J  CONST_06  S1   C2   C1   C6     0.00  0.0  0
 32J  CONST_07  C10  C9   C8   C6   180.00  0.0  0
 32J  CONST_08  C12  C13  C8   C6   180.00  0.0  0
 32J  CONST_09  C14  C11  C10  C9   180.00  0.0  0
 32J  CONST_10  C12  C11  C10  C9     0.00  0.0  0
 32J  CONST_12  C12  C13  C8   C9     0.00  0.0  0
 32J  CONST_13  C10  C9   C8   C13    0.00  0.0  0
 32J  CONST_15  C10  C11  C12  C13    0.00  0.0  0
 32J  CONST_16  C14  C11  C12  C13  180.00  0.0  0
 32J  CONST_17  C11  C10  C9   C8     0.00  0.0  0
 32J  CONST_18  S1   C7   C6   C8   180.00  0.0  0
 32J  CONST_19  C2   C1   C6   C8   180.00  0.0  0
 32J  CONST_20  C11  C12  C13  C8     0.00  0.0  0
 32J  CONST_21  C15  C16  C17  C18    0.00  0.0  0
 32J  CONST_22  C15  C14  C19  C18    0.00  0.0  0
 32J  CONST_23  C11  C14  C19  C18  180.00  0.0  0
 32J  CONST_24  C11  C14  C15  C16  180.00  0.0  0
 32J  CONST_25  C19  C14  C15  C16    0.00  0.0  0
 32J  CONST_26  C19  C18  C17  C16    0.00  0.0  0
 32J  CONST_29  S1   C7   C6   C1     0.00  0.0  0
 32J  CONST_32  C17  C16  C15  C14    0.00  0.0  0
 32J  CONST_33  C17  C18  C19  C14    0.00  0.0  0
 32J  CONST_34  C5   C1   C6   C8     0.00  0.0  0
 32J  CONST_35  C2   N1   C3   C4     0.00  0.0  0
 32J  CONST_36  CL1  C7   C6   C8     0.00  0.0  0
 32J  CONST_37  CL1  C7   C6   C1   180.00  0.0  0
 32J  CONST_38  CL1  C7   S1   C2   180.00  0.0  0
 32J  CONST_39  O1   C19  C14  C11    0.00  0.0  0
 32J  CONST_40  O1   C19  C14  C15  180.00  0.0  0
 32J  CONST_41  O1   C19  C18  C17  180.00  0.0  0
 32J  CONST_42  O3   C3   N1   C2   180.00  0.0  0
 32J  CONST_43  H1   C9   C8   C6     0.00  0.0  0
 32J  CONST_44  H2   C13  C8   C6     0.00  0.0  0
 32J  CONST_45  H6   C10  C9   C8   180.00  0.0  0
 32J  CONST_46  H7   C12  C13  C8   180.00  0.0  0
 32J  CONST_47  H4   C16  C17  C18  180.00  0.0  0
 32J  CONST_48  H3   C18  C17  C16  180.00  0.0  0
 32J  CONST_49  H8   C15  C14  C19  180.00  0.0  0
 32J  CONST_50  H9   C17  C18  C19  180.00  0.0  0
 32J  CONST_51  H5   N1   C3   C4   180.00  0.0  0

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
 32J  plan-1  C18  0.020
 32J  plan-1  C16  0.020
 32J  plan-1  C19  0.020
 32J  plan-1  C11  0.020
 32J  plan-1  C14  0.020
 32J  plan-1  C15  0.020
 32J  plan-1  C17  0.020
 32J  plan-1  H3   0.020
 32J  plan-1  H4   0.020
 32J  plan-1  H8   0.020
 32J  plan-1  H9   0.020
 32J  plan-1  O1   0.020
 32J  plan-2  C6   0.020
 32J  plan-2  C9   0.020
 32J  plan-2  C13  0.020
 32J  plan-2  C8   0.020
 32J  plan-2  C10  0.020
 32J  plan-2  C11  0.020
 32J  plan-2  C12  0.020
 32J  plan-2  C14  0.020
 32J  plan-2  H1   0.020
 32J  plan-2  H2   0.020
 32J  plan-2  H6   0.020
 32J  plan-2  H7   0.020
 32J  plan-3  C4   0.020
 32J  plan-3  N2   0.020
 32J  plan-3  C7   0.020
 32J  plan-3  C6   0.020
 32J  plan-3  C20  0.020
 32J  plan-3  C8   0.020
 32J  plan-3  C1   0.020
 32J  plan-3  C2   0.020
 32J  plan-3  N1   0.020
 32J  plan-3  C3   0.020
 32J  plan-3  C5   0.020
 32J  plan-3  S1   0.020
 32J  plan-3  O2   0.020
 32J  plan-3  O3   0.020
 32J  plan-3  CL1  0.020
 32J  plan-3  H5   0.020

