# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX
#   - file written: Thu May  7 14:56:05 2020
#   Inital geometry file: a 145 line input string
#   Ligand name: N-[(4S)-2-[(E)-N-[3-[bis(fluoranyl)methoxy]phenyl]-N'-cyano-carbamimidoyl]-5-(4-chlorophenyl)-3,4-dihydropyrazol-4-yl]-N-ethyl-2-oxidanyl-ethanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN([C@H]1CN(N=C1c2ccc(Cl)cc2)C(Nc3cccc(OC(F)F)c3)=NC#N)C(=O)CO
#
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
 I9H  I9H  N-[(4S)-2-[(E)-N-[3-[bis(fluoranyl)methoxy]phenyl]-N'-cyano-carbamimidoyl]-5-(4-chlorophenyl)-3,4-dihydropyrazol-4-yl]-N-ethyl-2-oxidanyl-ethanamide  ligand  55  34  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_I9H
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
 I9H  CAG   C   CR16  0  -0.288   2.4604  -2.4297  -0.1496
 I9H  CAL   C   CR16  0  -0.191   3.3125  -3.4858  -0.4087
 I9H  CAR   C   CR6   0  -0.048   4.6695  -3.3428  -0.1485
 I9H  CL1   CL  CL    0  -0.114   5.7390  -4.6611  -0.4741
 I9H  CAM   C   CR16  0  -0.188   5.1781  -2.1620   0.3668
 I9H  CAH   C   CR16  0  -0.317   4.3143  -1.1093   0.6231
 I9H  CAC   C   CR6   0   0.072   2.9479  -1.2271   0.3700
 I9H  CAA   C   CR5   0   0.300   2.0501  -0.1126   0.6408
 I9H  NAD   N   N     0  -0.246   0.7795  -0.2206   0.5552
 I9H  CAB   C   CR15  0  -0.283   2.4993   1.2991   0.9601
 I9H  NAF   N   NT    0  -0.465   3.1711   1.9057  -0.1755
 I9H  CAK   C   CH2   0  -0.351   2.5646   1.8201  -1.5017
 I9H  CAQ   C   CH3   0  -0.657   1.5832   2.9355  -1.8357
 I9H  CAJ   C   C     0   0.541   4.3247   2.5896   0.0582
 I9H  OAP   O   O     0  -0.482   4.8007   2.7144   1.1719
 I9H  CAO   C   CH2   0  -0.279   5.0284   3.1754  -1.1562
 I9H  OAU   O   OH1   0  -0.656   6.1374   3.8936  -0.7069
 I9H  CAE   C   CH2   0  -0.270   1.1651   1.9361   1.3707
 I9H  NAI   N   NR5   0  -0.375   0.2095   0.9769   0.8316
 I9H  CAN   C   C     0   0.757  -1.1277   1.1351   0.7722
 I9H  NAT   N   N     0  -0.513  -1.5709   2.3372   1.0341
 I9H  CAX   C   CSP   0   0.197  -2.8241   2.6237   1.2498
 I9H  NBA   N   NS    0  -0.379  -3.8951   3.0076   1.4879
 I9H  NAS   N   NH1   0  -0.750  -1.8472   0.0431   0.4571
 I9H  CAW   C   CR6   0   0.316  -3.1403   0.0478  -0.1042
 I9H  CAY   C   CR16  0  -0.379  -4.0655  -0.8708   0.3673
 I9H  CAZ   C   CR16  0  -0.269  -3.4725   0.9109  -1.1420
 I9H  CBC   C   CR16  0  -0.242  -4.7452   0.8496  -1.6798
 I9H  CBD   C   CR16  0  -0.349  -5.6856  -0.0680  -1.2302
 I9H  CBB   C   CR6   0   0.372  -5.3285  -0.9355  -0.2053
 I9H  OBE   O   O2    0  -0.497  -6.1309  -1.9133   0.3311
 I9H  CBF   C   CH1   0   0.666  -7.4680  -1.9702   0.1300
 I9H  FBH   F   F     0  -0.336  -8.0641  -0.7947   0.4284
 I9H  FBG   F   F     0  -0.340  -7.7649  -2.2268  -1.1667
 I9H  HAG   H   HCR6  0   0.273   1.4051  -2.5427  -0.3584
 I9H  HAL   H   HCR6  0   0.288   2.9244  -4.4104  -0.8129
 I9H  HAM   H   HCR6  0   0.289   6.2349  -2.0573   0.5691
 I9H  HAH   H   HCR6  0   0.265   4.7270  -0.1994   1.0376
 I9H  HAB   H   HCR5  0   0.323   3.1888   1.3226   1.8006
 I9H  HAE1  H   HCH2  0   0.304   1.0725   1.9728   2.4573
 I9H  HAE2  H   HCH2  0   0.294   1.0146   2.9362   0.9760
 I9H  HAK1  H   HCH2  0   0.274   3.3528   1.7875  -2.2518
 I9H  HAK2  H   HCH2  0   0.274   2.0648   0.8557  -1.5909
 I9H  HAQ1  H   HCH3  0   0.230   0.6993   2.9208  -1.1987
 I9H  HAQ2  H   HCH3  0   0.236   2.0426   3.9201  -1.7491
 I9H  HAQ3  H   HCH3  0   0.248   1.2424   2.8166  -2.8641
 I9H  HAO1  H   HCH2  0   0.243   5.3123   2.3475  -1.8214
 I9H  HAO2  H   HCH2  0   0.240   4.3292   3.8037  -1.7223
 I9H  HAU   H   HOH1  0   0.462   6.5894   4.2392  -1.4822
 I9H  HAS   H   HNH1  0   0.431  -1.3440  -0.8345   0.4467
 I9H  HAY   H   HCR6  0   0.289  -3.8067  -1.5380   1.1799
 I9H  HAZ   H   HCR6  0   0.278  -2.7499   1.6121  -1.5378
 I9H  HBC   H   HCR6  0   0.274  -5.0136   1.5193  -2.4856
 I9H  HBD   H   HCR6  0   0.289  -6.6551  -0.0870  -1.7039
 I9H  HBF   H   HCH1  0   0.241  -7.8733  -2.7618   0.7564

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
 I9H  CAG  CAL   aromatic  1.382  0.020  1.382
 I9H  CAG  CAC   aromatic  1.398  0.020  1.398
 I9H  CAL  CAR   aromatic  1.389  0.020  1.389
 I9H  CAR  CL1   single    1.729  0.020  1.729
 I9H  CAR  CAM   aromatic  1.385  0.020  1.385
 I9H  CAM  CAH   aromatic  1.386  0.020  1.386
 I9H  CAH  CAC   aromatic  1.395  0.020  1.395
 I9H  CAC  CAA   single    1.456  0.020  1.456
 I9H  CAA  NAD   double    1.278  0.020  1.278
 I9H  CAA  CAB   single    1.516  0.020  1.516
 I9H  NAD  NAI   single    1.355  0.020  1.355
 I9H  CAB  NAF   single    1.452  0.020  1.452
 I9H  CAB  CAE   single    1.534  0.020  1.534
 I9H  NAF  CAK   single    1.461  0.020  1.461
 I9H  NAF  CAJ   single    1.361  0.020  1.361
 I9H  CAK  CAQ   single    1.523  0.020  1.523
 I9H  CAJ  OAP   double    1.218  0.020  1.218
 I9H  CAJ  CAO   single    1.521  0.020  1.521
 I9H  CAO  OAU   single    1.396  0.020  1.396
 I9H  CAE  NAI   single    1.457  0.020  1.457
 I9H  NAI  CAN   single    1.348  0.020  1.348
 I9H  CAN  NAT   double    1.308  0.020  1.308
 I9H  CAN  NAS   single    1.345  0.020  1.345
 I9H  NAT  CAX   single    1.304  0.020  1.304
 I9H  CAX  NBA   triple    1.162  0.020  1.162
 I9H  NAS  CAW   single    1.410  0.020  1.410
 I9H  CAW  CAY   aromatic  1.386  0.020  1.386
 I9H  CAW  CAZ   aromatic  1.390  0.020  1.390
 I9H  CAY  CBB   aromatic  1.388  0.020  1.388
 I9H  CAZ  CBC   aromatic  1.383  0.020  1.383
 I9H  CBC  CBD   aromatic  1.389  0.020  1.389
 I9H  CBD  CBB   aromatic  1.389  0.020  1.389
 I9H  CBB  OBE   single    1.374  0.020  1.374
 I9H  OBE  CBF   single    1.353  0.020  1.353
 I9H  CBF  FBH   single    1.351  0.020  1.351
 I9H  CBF  FBG   single    1.355  0.020  1.355
 I9H  CAG  HAG   single    0.930  0.020  1.080
 I9H  CAL  HAL   single    0.930  0.020  1.080
 I9H  CAM  HAM   single    0.930  0.020  1.080
 I9H  CAH  HAH   single    0.930  0.020  1.080
 I9H  CAB  HAB   single    0.970  0.020  1.090
 I9H  CAE  HAE1  single    0.970  0.020  1.090
 I9H  CAE  HAE2  single    0.970  0.020  1.090
 I9H  CAK  HAK1  single    0.970  0.020  1.090
 I9H  CAK  HAK2  single    0.970  0.020  1.090
 I9H  CAQ  HAQ1  single    0.970  0.020  1.090
 I9H  CAQ  HAQ2  single    0.970  0.020  1.090
 I9H  CAQ  HAQ3  single    0.970  0.020  1.090
 I9H  CAO  HAO1  single    0.970  0.020  1.090
 I9H  CAO  HAO2  single    0.970  0.020  1.090
 I9H  OAU  HAU   single    0.850  0.020  0.980
 I9H  NAS  HAS   single    0.860  0.020  1.020
 I9H  CAY  HAY   single    0.930  0.020  1.080
 I9H  CAZ  HAZ   single    0.930  0.020  1.080
 I9H  CBC  HBC   single    0.930  0.020  1.080
 I9H  CBD  HBD   single    0.930  0.020  1.080
 I9H  CBF  HBF   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
 I9H  HAG   CAG  CAC   120.13  3.000
 I9H  HAG   CAG  CAL   119.06  3.000
 I9H  CAC   CAG  CAL   120.82  3.000
 I9H  HAL   CAL  CAR   120.58  3.000
 I9H  HAL   CAL  CAG   120.16  3.000
 I9H  CAR   CAL  CAG   119.26  3.000
 I9H  CAM   CAR  CL1   119.54  3.000
 I9H  CAM   CAR  CAL   121.08  3.000
 I9H  CL1   CAR  CAL   119.38  3.000
 I9H  HAM   CAM  CAH   120.08  3.000
 I9H  HAM   CAM  CAR   120.74  3.000
 I9H  CAH   CAM  CAR   119.18  3.000
 I9H  HAH   CAH  CAC   120.96  3.000
 I9H  HAH   CAH  CAM   118.17  3.000
 I9H  CAC   CAH  CAM   120.86  3.000
 I9H  CAA   CAC  CAH   120.37  3.000
 I9H  CAA   CAC  CAG   120.82  3.000
 I9H  CAH   CAC  CAG   118.81  3.000
 I9H  CAB   CAA  NAD   112.80  3.000
 I9H  CAB   CAA  CAC   124.70  3.000
 I9H  NAD   CAA  CAC   122.39  3.000
 I9H  NAI   NAD  CAA   109.26  3.000
 I9H  HAB   CAB  CAE   109.61  3.000
 I9H  HAB   CAB  NAF   107.58  3.000
 I9H  CAE   CAB  NAF   115.98  3.000
 I9H  HAB   CAB  CAA   111.77  3.000
 I9H  CAE   CAB  CAA   100.68  3.000
 I9H  NAF   CAB  CAA   111.19  3.000
 I9H  CAJ   NAF  CAK   122.49  3.000
 I9H  CAJ   NAF  CAB   117.88  3.000
 I9H  CAK   NAF  CAB   119.56  3.000
 I9H  HAK2  CAK  HAK1  104.43  3.000
 I9H  HAK2  CAK  CAQ   109.55  3.000
 I9H  HAK1  CAK  CAQ   109.72  3.000
 I9H  HAK2  CAK  NAF   108.46  3.000
 I9H  HAK1  CAK  NAF   109.07  3.000
 I9H  CAQ   CAK  NAF   115.07  3.000
 I9H  HAQ3  CAQ  HAQ2  107.77  3.000
 I9H  HAQ3  CAQ  HAQ1  107.25  3.000
 I9H  HAQ2  CAQ  HAQ1  107.91  3.000
 I9H  HAQ3  CAQ  CAK   109.18  3.000
 I9H  HAQ2  CAQ  CAK   111.88  3.000
 I9H  HAQ1  CAQ  CAK   112.63  3.000
 I9H  CAO   CAJ  OAP   120.66  3.000
 I9H  CAO   CAJ  NAF   116.65  3.000
 I9H  OAP   CAJ  NAF   122.68  3.000
 I9H  HAO2  CAO  HAO1  106.48  3.000
 I9H  HAO2  CAO  OAU   112.19  3.000
 I9H  HAO1  CAO  OAU   112.17  3.000
 I9H  HAO2  CAO  CAJ   109.73  3.000
 I9H  HAO1  CAO  CAJ   108.21  3.000
 I9H  OAU   CAO  CAJ   107.99  3.000
 I9H  HAU   OAU  CAO   107.39  3.000
 I9H  HAE2  CAE  HAE1  108.62  3.000
 I9H  HAE2  CAE  NAI   112.39  3.000
 I9H  HAE1  CAE  NAI   109.56  3.000
 I9H  HAE2  CAE  CAB   113.93  3.000
 I9H  HAE1  CAE  CAB   110.74  3.000
 I9H  NAI   CAE  CAB   101.42  3.000
 I9H  CAN   NAI  CAE   126.13  3.000
 I9H  CAN   NAI  NAD   120.81  3.000
 I9H  CAE   NAI  NAD   112.42  3.000
 I9H  NAS   CAN  NAT   127.73  3.000
 I9H  NAS   CAN  NAI   116.47  3.000
 I9H  NAT   CAN  NAI   115.80  3.000
 I9H  CAX   NAT  CAN   124.12  3.000
 I9H  NBA   CAX  NAT   180.00  3.000
 I9H  HAS   NAS  CAW   117.07  3.000
 I9H  HAS   NAS  CAN   116.14  3.000
 I9H  CAW   NAS  CAN   125.54  3.000
 I9H  CAZ   CAW  CAY   120.39  3.000
 I9H  CAZ   CAW  NAS   121.24  3.000
 I9H  CAY   CAW  NAS   118.33  3.000
 I9H  HAY   CAY  CBB   119.89  3.000
 I9H  HAY   CAY  CAW   120.27  3.000
 I9H  CBB   CAY  CAW   119.85  3.000
 I9H  HAZ   CAZ  CBC   120.08  3.000
 I9H  HAZ   CAZ  CAW   121.06  3.000
 I9H  CBC   CAZ  CAW   118.86  3.000
 I9H  HBC   CBC  CBD   118.83  3.000
 I9H  HBC   CBC  CAZ   119.38  3.000
 I9H  CBD   CBC  CAZ   121.78  3.000
 I9H  HBD   CBD  CBB   122.94  3.000
 I9H  HBD   CBD  CBC   118.55  3.000
 I9H  CBB   CBD  CBC   118.51  3.000
 I9H  OBE   CBB  CBD   125.60  3.000
 I9H  OBE   CBB  CAY   113.80  3.000
 I9H  CBD   CBB  CAY   120.60  3.000
 I9H  CBF   OBE  CBB   123.30  3.000
 I9H  HBF   CBF  FBG   109.37  3.000
 I9H  HBF   CBF  FBH   109.96  3.000
 I9H  FBG   CBF  FBH   106.23  3.000
 I9H  HBF   CBF  OBE   108.25  3.000
 I9H  FBG   CBF  OBE   111.51  3.000
 I9H  FBH   CBF  OBE   111.50  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
 I9H  CONST_01  CAM   CAR  CAL  CAG    0.00   0.0  0
 I9H  CONST_02  CAM   CAH  CAC  CAG    0.00   0.0  0
 I9H  CONST_03  CAH   CAC  CAG  CAL    0.00   0.0  0
 I9H  CONST_04  CAH   CAM  CAR  CAL    0.00   0.0  0
 I9H  CONST_05  CAC   CAG  CAL  CAR    0.00   0.0  0
 I9H  CONST_06  CAC   CAH  CAM  CAR    0.00   0.0  0
 I9H  CONST_07  CBD   CBB  CAY  CAW    0.00   0.0  0
 I9H  CONST_08  CBD   CBC  CAZ  CAW    0.00   0.0  0
 I9H  CONST_09  CBC   CAZ  CAW  CAY    0.00   0.0  0
 I9H  CONST_10  CBC   CBD  CBB  CAY    0.00   0.0  0
 I9H  CONST_11  CBB   CAY  CAW  CAZ    0.00   0.0  0
 I9H  CONST_12  CBB   CBD  CBC  CAZ    0.00   0.0  0
 I9H  CONST_13  CAA   CAC  CAG  CAL  180.00   0.0  0
 I9H  CONST_14  CAA   CAC  CAH  CAM  180.00   0.0  0
 I9H  CONST_15  CL1   CAR  CAL  CAG  180.00   0.0  0
 I9H  CONST_16  CAH   CAM  CAR  CL1  180.00   0.0  0
 I9H  CONST_17  CBB   CAY  CAW  NAS  180.00   0.0  0
 I9H  CONST_18  CBC   CAZ  CAW  NAS  180.00   0.0  0
 I9H  CONST_19  OBE   CBB  CAY  CAW  180.00   0.0  0
 I9H  CONST_20  OBE   CBB  CBD  CBC  180.00   0.0  0
 I9H  CONST_21  HAH   CAH  CAC  CAG  180.00   0.0  0
 I9H  CONST_22  HAM   CAM  CAR  CAL  180.00   0.0  0
 I9H  CONST_23  HAG   CAG  CAL  CAR  180.00   0.0  0
 I9H  CONST_24  HAL   CAL  CAR  CAM  180.00   0.0  0
 I9H  CONST_25  HBC   CBC  CAZ  CAW  180.00   0.0  0
 I9H  CONST_26  HAZ   CAZ  CAW  CAY  180.00   0.0  0
 I9H  CONST_27  HBD   CBD  CBB  CAY  180.00   0.0  0
 I9H  CONST_28  HAY   CAY  CAW  CAZ  180.00   0.0  0
 I9H  CONST_32  NAT   CAN  NAI  NAD  180.00   0.0  0
 I9H  CONST_33  NAS   CAN  NAI  NAD    0.00   0.0  0
 I9H  CONST_34  NAT   CAN  NAI  CAE    0.00   0.0  0
 I9H  CONST_35  NAS   CAN  NAI  CAE  180.00   0.0  0
 I9H  CONST_37  OAP   CAJ  NAF  CAB    0.00   0.0  0
 I9H  CONST_38  CAO   CAJ  NAF  CAB  180.00   0.0  0
 I9H  CONST_40  CAX   NAT  CAN  NAI  180.00   0.0  0
 I9H  CONST_41  OAP   CAJ  NAF  CAK  180.00   0.0  0
 I9H  CONST_42  CAO   CAJ  NAF  CAK    0.00   0.0  0
 I9H  CONST_43  NAS   CAN  NAT  CAX    0.00   0.0  0
 I9H  Var_01    NAD   CAA  CAC  CAG    7.54  30.0  2
 I9H  Var_02    CAE   NAI  NAD  CAA  -10.47  30.0  1
 I9H  Var_03    CAB   CAE  NAI  NAD   17.77  30.0  1
 I9H  Var_04    CAQ   CAK  NAF  CAB   87.84  30.0  3
 I9H  Var_05    FBH   CBF  OBE  CBB  -52.23  30.0  3
 I9H  Var_06    OAU   CAO  CAJ  NAF  176.76  30.0  3
 I9H  Var_07    HAQ1  CAQ  CAK  NAF  -64.78  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 I9H  chir_01  CAB  CAA  NAF  CAE  negativ

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
 I9H  plan-1  CAG  0.020
 I9H  plan-1  CAL  0.020
 I9H  plan-1  CAR  0.020
 I9H  plan-1  CL1  0.020
 I9H  plan-1  CAM  0.020
 I9H  plan-1  CAH  0.020
 I9H  plan-1  CAC  0.020
 I9H  plan-1  CAA  0.020
 I9H  plan-1  HAG  0.020
 I9H  plan-1  HAL  0.020
 I9H  plan-1  HAM  0.020
 I9H  plan-1  HAH  0.020
 I9H  plan-2  NAS  0.020
 I9H  plan-2  CAW  0.020
 I9H  plan-2  CAY  0.020
 I9H  plan-2  CAZ  0.020
 I9H  plan-2  CBC  0.020
 I9H  plan-2  CBD  0.020
 I9H  plan-2  CBB  0.020
 I9H  plan-2  OBE  0.020
 I9H  plan-2  HAY  0.020
 I9H  plan-2  HAZ  0.020
 I9H  plan-2  HBC  0.020
 I9H  plan-2  HBD  0.020
 I9H  plan-3  NAD  0.020
 I9H  plan-3  CAE  0.020
 I9H  plan-3  NAI  0.020
 I9H  plan-3  CAN  0.020
 I9H  plan-3  NAT  0.020
 I9H  plan-3  CAX  0.020
 I9H  plan-3  NAS  0.020
 I9H  plan-3  CAW  0.020
 I9H  plan-3  HAS  0.020
 I9H  plan-4  CAB  0.020
 I9H  plan-4  NAF  0.020
 I9H  plan-4  CAK  0.020
 I9H  plan-4  CAJ  0.020
 I9H  plan-4  OAP  0.020
 I9H  plan-4  CAO  0.020

