# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 19 07:00:05 2020
#   Inital geometry file: a 111 line input string
#   Ligand name: 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)c3csc4NC(=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
 C1V  C1V  4-hydroxy-3-(2'-hydroxybiphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile  ligand  38  26  .  2021-08-07  2021-08-07  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_C1V
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
 C1V  OAD  O  OH1   0  -0.550  -1.3647   1.6557   0.3882
 C1V  CAT  C  CR6   0   0.462  -2.4851   0.9941   0.2125
 C1V  CAZ  C  CR56  0  -0.010  -2.3912  -0.4095   0.0195
 C1V  CAU  C  CR6   0  -0.356  -3.7381   1.5875   0.2203
 C1V  CAE  C  CSP   0   0.040  -3.8599   2.9826   0.4030
 C1V  NAA  N  NS    0  -0.245  -3.9253   4.1251   0.5550
 C1V  CAX  C  CR6   0   0.543  -4.9690   0.8434   0.0636
 C1V  OAB  O  O     0  -0.459  -6.0806   1.3446   0.0635
 C1V  NAO  N  NR16  0  -0.735  -4.7961  -0.5178  -0.0806
 C1V  CAY  C  CR56  0   0.108  -3.5810  -1.1060  -0.0947
 C1V  SAP  S  S2    0   0.294  -3.3398  -2.7957  -0.2214
 C1V  CAN  C  CR15  0  -0.553  -1.6253  -2.5818  -0.1321
 C1V  CAW  C  CR5   0   0.209  -1.2470  -1.2866  -0.0145
 C1V  CAS  C  CR6   0   0.036   0.1727  -0.8931   0.0390
 C1V  CAL  C  CR16  0  -0.280   1.0040  -1.4143   1.0250
 C1V  CAJ  C  CR16  0  -0.290   2.3542  -1.0965   1.0516
 C1V  CAK  C  CR16  0  -0.266   0.7258  -0.0491  -0.9232
 C1V  CAI  C  CR16  0  -0.280   2.0732   0.2634  -0.8983
 C1V  CAR  C  CR6   0   0.090   2.9115  -0.2526   0.0931
 C1V  CAV  C  CR6   0  -0.045   4.3438   0.1068   0.1704
 C1V  CAM  C  CR16  0  -0.286   4.8797   0.5659   1.3727
 C1V  CAG  C  CR16  0  -0.273   6.2199   0.8999   1.4969
 C1V  CAF  C  CR16  0  -0.251   7.0534   0.7715   0.3950
 C1V  CAH  C  CR16  0  -0.378   6.5486   0.3109  -0.8111
 C1V  CAQ  C  CR6   0   0.323   5.2021  -0.0240  -0.9304
 C1V  OAC  O  OH1   0  -0.623   4.6892  -0.5000  -2.0816
 C1V  HAD  H  HOH1  0   0.498  -1.4974   2.6063   0.5132
 C1V  HAO  H  HNR6  0   0.435  -5.6337  -1.0766  -0.1823
 C1V  HAN  H  HCR5  0   0.310  -0.9843  -3.4470  -0.2053
 C1V  HAL  H  HCR6  0   0.255   0.5933  -2.0695   1.7830
 C1V  HAK  H  HCR6  0   0.253   0.1016   0.3626  -1.7061
 C1V  HAJ  H  HCR6  0   0.256   2.9817  -1.5201   1.8260
 C1V  HAI  H  HCR6  0   0.252   2.4714   0.9291  -1.6522
 C1V  HAM  H  HCR6  0   0.256   4.2201   0.6745   2.2252
 C1V  HAG  H  HCR6  0   0.254   6.6056   1.2602   2.4409
 C1V  HAF  H  HCR6  0   0.261   8.1024   1.0272   0.4683
 C1V  HAH  H  HCR6  0   0.270   7.2068   0.2022  -1.6662
 C1V  HAC  H  HOH1  0   0.476   5.3781  -0.5597  -2.7532

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
 C1V  OAD  CAT  single    1.313  0.020  1.313
 C1V  CAT  CAZ  single    1.420  0.020  1.420
 C1V  CAT  CAU  double    1.386  0.020  1.386
 C1V  CAZ  CAY  aromatic  1.383  0.020  1.383
 C1V  CAZ  CAW  aromatic  1.442  0.020  1.442
 C1V  CAU  CAE  single    1.412  0.020  1.412
 C1V  CAU  CAX  single    1.447  0.020  1.447
 C1V  CAE  NAA  triple    1.154  0.020  1.154
 C1V  CAX  OAB  double    1.219  0.020  1.219
 C1V  CAX  NAO  single    1.380  0.020  1.380
 C1V  NAO  CAY  single    1.350  0.020  1.350
 C1V  CAY  SAP  aromatic  1.712  0.020  1.712
 C1V  SAP  CAN  aromatic  1.730  0.020  1.730
 C1V  CAN  CAW  aromatic  1.354  0.020  1.354
 C1V  CAW  CAS  single    1.474  0.020  1.474
 C1V  CAS  CAL  aromatic  1.391  0.020  1.391
 C1V  CAS  CAK  aromatic  1.394  0.020  1.394
 C1V  CAL  CAJ  aromatic  1.387  0.020  1.387
 C1V  CAJ  CAR  aromatic  1.393  0.020  1.393
 C1V  CAK  CAI  aromatic  1.383  0.020  1.383
 C1V  CAI  CAR  aromatic  1.397  0.020  1.397
 C1V  CAR  CAV  single    1.479  0.020  1.479
 C1V  CAV  CAM  aromatic  1.394  0.020  1.394
 C1V  CAV  CAQ  aromatic  1.402  0.020  1.402
 C1V  CAM  CAG  aromatic  1.387  0.020  1.387
 C1V  CAG  CAF  aromatic  1.388  0.020  1.388
 C1V  CAF  CAH  aromatic  1.386  0.020  1.386
 C1V  CAH  CAQ  aromatic  1.393  0.020  1.393
 C1V  CAQ  OAC  single    1.347  0.020  1.347
 C1V  OAD  HAD  single    0.850  0.020  0.980
 C1V  NAO  HAO  single    0.860  0.020  1.020
 C1V  CAN  HAN  single    0.930  0.020  1.080
 C1V  CAL  HAL  single    0.930  0.020  1.080
 C1V  CAK  HAK  single    0.930  0.020  1.080
 C1V  CAJ  HAJ  single    0.930  0.020  1.080
 C1V  CAI  HAI  single    0.930  0.020  1.080
 C1V  CAM  HAM  single    0.930  0.020  1.080
 C1V  CAG  HAG  single    0.930  0.020  1.080
 C1V  CAF  HAF  single    0.930  0.020  1.080
 C1V  CAH  HAH  single    0.930  0.020  1.080
 C1V  OAC  HAC  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
 C1V  HAD  OAD  CAT  113.27  3.000
 C1V  CAU  CAT  CAZ  118.92  3.000
 C1V  CAU  CAT  OAD  123.70  3.000
 C1V  CAZ  CAT  OAD  117.38  3.000
 C1V  CAW  CAZ  CAY  111.98  3.000
 C1V  CAW  CAZ  CAT  131.06  3.000
 C1V  CAY  CAZ  CAT  116.87  3.000
 C1V  CAX  CAU  CAE  116.66  3.000
 C1V  CAX  CAU  CAT  123.24  3.000
 C1V  CAE  CAU  CAT  120.10  3.000
 C1V  NAA  CAE  CAU  180.00  3.000
 C1V  NAO  CAX  OAB  121.32  3.000
 C1V  NAO  CAX  CAU  114.33  3.000
 C1V  OAB  CAX  CAU  124.34  3.000
 C1V  HAO  NAO  CAY  120.22  3.000
 C1V  HAO  NAO  CAX  116.84  3.000
 C1V  CAY  NAO  CAX  122.94  3.000
 C1V  SAP  CAY  NAO  123.90  3.000
 C1V  SAP  CAY  CAZ  112.45  3.000
 C1V  NAO  CAY  CAZ  123.63  3.000
 C1V  CAN  SAP  CAY   90.79  3.000
 C1V  HAN  CAN  CAW  127.35  3.000
 C1V  HAN  CAN  SAP  119.08  3.000
 C1V  CAW  CAN  SAP  113.55  3.000
 C1V  CAS  CAW  CAN  121.83  3.000
 C1V  CAS  CAW  CAZ  126.93  3.000
 C1V  CAN  CAW  CAZ  111.23  3.000
 C1V  CAK  CAS  CAL  118.61  3.000
 C1V  CAK  CAS  CAW  121.24  3.000
 C1V  CAL  CAS  CAW  120.08  3.000
 C1V  HAL  CAL  CAJ  119.63  3.000
 C1V  HAL  CAL  CAS  119.75  3.000
 C1V  CAJ  CAL  CAS  120.62  3.000
 C1V  HAJ  CAJ  CAR  119.81  3.000
 C1V  HAJ  CAJ  CAL  119.21  3.000
 C1V  CAR  CAJ  CAL  120.98  3.000
 C1V  HAK  CAK  CAI  119.26  3.000
 C1V  HAK  CAK  CAS  120.03  3.000
 C1V  CAI  CAK  CAS  120.71  3.000
 C1V  HAI  CAI  CAR  120.07  3.000
 C1V  HAI  CAI  CAK  119.01  3.000
 C1V  CAR  CAI  CAK  120.92  3.000
 C1V  CAV  CAR  CAI  121.91  3.000
 C1V  CAV  CAR  CAJ  119.91  3.000
 C1V  CAI  CAR  CAJ  118.15  3.000
 C1V  CAQ  CAV  CAM  118.20  3.000
 C1V  CAQ  CAV  CAR  121.96  3.000
 C1V  CAM  CAV  CAR  119.83  3.000
 C1V  HAM  CAM  CAG  119.59  3.000
 C1V  HAM  CAM  CAV  118.53  3.000
 C1V  CAG  CAM  CAV  121.87  3.000
 C1V  HAG  CAG  CAF  120.65  3.000
 C1V  HAG  CAG  CAM  120.20  3.000
 C1V  CAF  CAG  CAM  119.15  3.000
 C1V  HAF  CAF  CAH  119.37  3.000
 C1V  HAF  CAF  CAG  120.44  3.000
 C1V  CAH  CAF  CAG  120.20  3.000
 C1V  HAH  CAH  CAQ  119.68  3.000
 C1V  HAH  CAH  CAF  119.88  3.000
 C1V  CAQ  CAH  CAF  120.43  3.000
 C1V  OAC  CAQ  CAH  121.75  3.000
 C1V  OAC  CAQ  CAV  118.09  3.000
 C1V  CAH  CAQ  CAV  120.15  3.000
 C1V  HAC  OAC  CAQ  110.19  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
 C1V  CONST_01  CAN  SAP  CAY  CAZ    0.00  0.0  0
 C1V  CONST_02  SAP  CAN  CAW  CAZ    0.00  0.0  0
 C1V  CONST_05  CAN  CAW  CAZ  CAY    0.00  0.0  0
 C1V  CONST_06  CAS  CAW  CAZ  CAY  180.00  0.0  0
 C1V  CONST_07  CAW  CAN  SAP  CAY    0.00  0.0  0
 C1V  CONST_08  CAW  CAZ  CAY  SAP    0.00  0.0  0
 C1V  CONST_09  CAS  CAW  CAN  SAP  180.00  0.0  0
 C1V  CONST_12  CAJ  CAL  CAS  CAW  180.00  0.0  0
 C1V  CONST_13  CAI  CAK  CAS  CAW  180.00  0.0  0
 C1V  CONST_14  CAR  CAJ  CAL  CAS    0.00  0.0  0
 C1V  CONST_15  CAR  CAI  CAK  CAS    0.00  0.0  0
 C1V  CONST_16  CAI  CAK  CAS  CAL    0.00  0.0  0
 C1V  CONST_17  CAI  CAR  CAJ  CAL    0.00  0.0  0
 C1V  CONST_18  CAV  CAR  CAJ  CAL  180.00  0.0  0
 C1V  CONST_19  CAK  CAS  CAL  CAJ    0.00  0.0  0
 C1V  CONST_20  CAK  CAI  CAR  CAJ    0.00  0.0  0
 C1V  CONST_23  CAV  CAR  CAI  CAK  180.00  0.0  0
 C1V  CONST_26  CAG  CAM  CAV  CAR  180.00  0.0  0
 C1V  CONST_27  CAH  CAQ  CAV  CAR  180.00  0.0  0
 C1V  CONST_28  CAF  CAG  CAM  CAV    0.00  0.0  0
 C1V  CONST_29  CAF  CAH  CAQ  CAV    0.00  0.0  0
 C1V  CONST_30  CAH  CAQ  CAV  CAM    0.00  0.0  0
 C1V  CONST_31  CAH  CAF  CAG  CAM    0.00  0.0  0
 C1V  CONST_32  CAQ  CAV  CAM  CAG    0.00  0.0  0
 C1V  CONST_33  CAQ  CAH  CAF  CAG    0.00  0.0  0
 C1V  CONST_34  CAS  CAW  CAZ  CAT    0.00  0.0  0
 C1V  CONST_35  CAY  NAO  CAX  CAU    0.00  0.0  0
 C1V  CONST_36  OAC  CAQ  CAV  CAR    0.00  0.0  0
 C1V  CONST_37  OAC  CAQ  CAV  CAM  180.00  0.0  0
 C1V  CONST_38  OAC  CAQ  CAH  CAF  180.00  0.0  0
 C1V  CONST_39  CAY  NAO  CAX  OAB  180.00  0.0  0
 C1V  CONST_40  HAN  CAN  CAW  CAZ  180.00  0.0  0
 C1V  CONST_41  HAL  CAL  CAS  CAW    0.00  0.0  0
 C1V  CONST_42  HAK  CAK  CAS  CAW    0.00  0.0  0
 C1V  CONST_43  HAJ  CAJ  CAL  CAS  180.00  0.0  0
 C1V  CONST_44  HAI  CAI  CAK  CAS  180.00  0.0  0
 C1V  CONST_45  HAM  CAM  CAV  CAR    0.00  0.0  0
 C1V  CONST_46  HAG  CAG  CAM  CAV  180.00  0.0  0
 C1V  CONST_47  HAH  CAH  CAQ  CAV  180.00  0.0  0
 C1V  CONST_48  HAF  CAF  CAG  CAM  180.00  0.0  0
 C1V  CONST_49  HAO  NAO  CAX  CAU  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
 C1V  plan-1  CAW  0.020
 C1V  plan-1  CAS  0.020
 C1V  plan-1  CAL  0.020
 C1V  plan-1  CAJ  0.020
 C1V  plan-1  CAK  0.020
 C1V  plan-1  CAI  0.020
 C1V  plan-1  CAR  0.020
 C1V  plan-1  CAV  0.020
 C1V  plan-1  HAL  0.020
 C1V  plan-1  HAK  0.020
 C1V  plan-1  HAJ  0.020
 C1V  plan-1  HAI  0.020
 C1V  plan-2  CAR  0.020
 C1V  plan-2  CAV  0.020
 C1V  plan-2  CAM  0.020
 C1V  plan-2  CAG  0.020
 C1V  plan-2  CAF  0.020
 C1V  plan-2  CAH  0.020
 C1V  plan-2  CAQ  0.020
 C1V  plan-2  OAC  0.020
 C1V  plan-2  HAM  0.020
 C1V  plan-2  HAG  0.020
 C1V  plan-2  HAF  0.020
 C1V  plan-2  HAH  0.020
 C1V  plan-3  OAD  0.020
 C1V  plan-3  CAT  0.020
 C1V  plan-3  CAZ  0.020
 C1V  plan-3  CAU  0.020
 C1V  plan-3  CAE  0.020
 C1V  plan-3  NAA  0.020
 C1V  plan-3  CAX  0.020
 C1V  plan-3  OAB  0.020
 C1V  plan-3  NAO  0.020
 C1V  plan-3  CAY  0.020
 C1V  plan-3  SAP  0.020
 C1V  plan-3  CAN  0.020
 C1V  plan-3  CAW  0.020
 C1V  plan-3  CAS  0.020
 C1V  plan-3  HAO  0.020
 C1V  plan-3  HAN  0.020

