# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 20 08:35:30 2020
#   Inital geometry file: a 129 line input string
#   Ligand name: ~{N}-[2,4-bis(fluoranyl)-3-[4-(3-methoxy-1~{H}-pyrazolo[3,4-b]pyridin-5-yl)-1,2,3-triazol-1-yl]phenyl]-3-bromanyl-benzenesulfonamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1n[nH]c2ncc(cc12)c3cn(nn3)c4c(F)ccc(N[S](=O)(=O)c5cccc(Br)c5)c4F
#
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
 C9O  C9O  ~{N}-[2,4-bis(fluoranyl)-3-[4-(3-methoxy-1~{H}-pyrazolo[3,4-b]pyridin-5-yl)-1,2,3-triazol-1-yl]phenyl]-3-bromanyl-benzenesulfonamide  ligand  49  35  .  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_C9O
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
 C9O  C10  C   CR6   0   0.583  -0.3045  -3.8796   0.0892
 C9O  C15  C   CR5   0   0.177   2.8990  -0.9205  -0.1343
 C9O  C17  C   CR16  0  -0.215   4.9604   0.4243  -0.4013
 C9O  C22  C   CR5   0   0.444   7.1621   1.8332  -0.1710
 C9O  C24  C   CH3   0  -0.423   8.6545   2.8801  -1.6399
 C9O  C26  C   CR16  0  -0.098   4.2475  -0.1746   1.8213
 C9O  C02  C   CR6   0  -0.101  -2.4489   2.0683   0.5318
 C9O  C03  C   CR16  0  -0.206  -3.3701   1.2247  -0.0657
 C9O  C04  C   CR6   0  -0.204  -3.5633  -0.0306   0.4948
 C9O  N06  N   NC1   0  -0.790  -3.6927  -1.9562  -1.4342
 C9O  C07  C   CR6   0   0.065  -2.5471  -2.6163  -0.9423
 C9O  C08  C   CR16  0  -0.234  -2.6388  -3.8827  -0.3779
 C9O  C09  C   CR16  0  -0.441  -1.5261  -4.5168   0.1503
 C9O  F11  F   F     0  -0.281   0.7828  -4.4657   0.5769
 C9O  C12  C   CR6   0  -0.049  -0.1706  -2.6193  -0.4746
 C9O  N13  N   NR5   0  -0.361   1.0748  -1.9706  -0.5324
 C9O  C14  C   CR15  0  -0.086   1.8001  -1.4609   0.4837
 C9O  C16  C   CR6   0  -0.062   4.0471  -0.2152   0.4233
 C9O  C18  C   CR56  0  -0.161   6.0210   1.0721   0.2148
 C9O  C19  C   CR56  0   0.546   6.1037   1.0413   1.6177
 C9O  N20  N   NR15  0  -0.538   7.2045   1.7345   1.9543
 C9O  N21  N   N     0  -0.279   7.8495   2.2147   0.8676
 C9O  N25  N   N     0  -0.420   5.2435   0.4342   2.4294
 C9O  N27  N   N     0  -0.314   2.7642  -1.1368  -1.4674
 C9O  N28  N   N     0  -0.069   1.6748  -1.7630  -1.7013
 C9O  C29  C   CR6   0   0.605  -1.3038  -1.9988  -0.9722
 C9O  F30  F   F     0  -0.271  -1.1893  -0.7807  -1.4839
 C9O  O31  O   OS    0  -0.629  -5.0745  -2.1531   0.6507
 C9O  O32  O   OS    0  -0.636  -5.6261  -0.4261  -1.1031
 C9O  C33  C   CR16  0  -0.231  -2.8693  -0.4499   1.6208
 C9O  C34  C   CR16  0  -0.236  -1.9477   0.4142   2.1924
 C9O  C35  C   CR16  0  -0.206  -1.7307   1.6733   1.6532
 C9O  H1   H   HCR6  0   0.273   4.8436   0.4190  -1.4773
 C9O  H2   H   HCH3  0   0.233   8.5778   3.8641  -1.1740
 C9O  H3   H   HCH3  0   0.233   9.5383   2.3722  -1.2499
 C9O  H4   H   HCH3  0   0.252   8.7521   2.9970  -2.7155
 C9O  H5   H   HCR6  0   0.264   3.5416  -0.6814   2.4711
 C9O  H6   H   HCR6  0   0.309  -3.9209   1.5325  -0.9445
 C9O  H7   H   HNC1  0   0.430  -3.5626  -1.4139  -2.2830
 C9O  H8   H   HCR6  0   0.305  -3.5979  -4.3799  -0.3537
 C9O  H9   H   HCR6  0   0.308  -1.6051  -5.5011   0.5902
 C9O  H10  H   HCR5  0   0.321   1.4777  -1.5097   1.5096
 C9O  H11  H   HNR5  0   0.417   7.5768   1.9027   2.8743
 C9O  H12  H   HCR6  0   0.299  -3.0393  -1.4258   2.0537
 C9O  H13  H   HCR6  0   0.289  -1.3950   0.1069   3.0693
 C9O  H14  H   HCR6  0   0.296  -1.0088   2.3357   2.1110
 C9O  O23  O   O2    0  -0.464   7.4766   2.1117  -1.4284
 C9O  S05  S   S     0   1.371  -4.6547  -1.1643  -0.3213
 C9O  BR1  BR  BR    0  -0.014  -2.1656   3.7825  -0.1941

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
 C9O  C24  O23  single    1.422  0.020  1.422
 C9O  N21  N20  aromatic  1.352  0.020  1.352
 C9O  N21  C22  aromatic  1.303  0.020  1.303
 C9O  N20  C19  aromatic  1.344  0.020  1.344
 C9O  C22  O23  single    1.326  0.020  1.326
 C9O  C22  C18  aromatic  1.425  0.020  1.425
 C9O  C19  C18  aromatic  1.406  0.020  1.406
 C9O  C19  N25  aromatic  1.329  0.020  1.329
 C9O  C18  C17  aromatic  1.387  0.020  1.387
 C9O  N25  C26  aromatic  1.316  0.020  1.316
 C9O  C17  C16  aromatic  1.387  0.020  1.387
 C9O  C26  C16  aromatic  1.413  0.020  1.413
 C9O  C16  C15  single    1.458  0.020  1.458
 C9O  C15  N27  aromatic  1.357  0.020  1.357
 C9O  C15  C14  aromatic  1.372  0.020  1.372
 C9O  N27  N28  aromatic  1.278  0.020  1.278
 C9O  C14  N13  aromatic  1.348  0.020  1.348
 C9O  N28  N13  aromatic  1.330  0.020  1.330
 C9O  N13  C12  single    1.405  0.020  1.405
 C9O  F30  C29  single    1.326  0.020  1.326
 C9O  C12  C29  aromatic  1.384  0.020  1.384
 C9O  C12  C10  aromatic  1.387  0.020  1.387
 C9O  F11  C10  single    1.328  0.020  1.328
 C9O  C29  C07  aromatic  1.389  0.020  1.389
 C9O  C10  C09  aromatic  1.379  0.020  1.379
 C9O  C07  N06  single    1.411  0.020  1.411
 C9O  C07  C08  aromatic  1.390  0.020  1.390
 C9O  C09  C08  aromatic  1.385  0.020  1.385
 C9O  N06  S05  single    1.671  0.020  1.671
 C9O  C33  C34  aromatic  1.387  0.020  1.387
 C9O  C33  C04  aromatic  1.388  0.020  1.388
 C9O  C34  C35  aromatic  1.387  0.020  1.387
 C9O  S05  C04  single    1.773  0.020  1.773
 C9O  S05  O31  double    1.449  0.020  1.449
 C9O  S05  O32  double    1.449  0.020  1.449
 C9O  C04  C03  aromatic  1.388  0.020  1.388
 C9O  C35  C02  aromatic  1.389  0.020  1.389
 C9O  C03  C02  aromatic  1.385  0.020  1.385
 C9O  C02  BR1  single    1.883  0.020  1.883
 C9O  C17  H1   single    0.930  0.020  1.080
 C9O  C24  H2   single    0.970  0.020  1.090
 C9O  C24  H3   single    0.970  0.020  1.090
 C9O  C24  H4   single    0.970  0.020  1.090
 C9O  C26  H5   single    0.930  0.020  1.080
 C9O  C03  H6   single    0.930  0.020  1.080
 C9O  N06  H7   single    0.890  0.020  1.040
 C9O  C08  H8   single    0.930  0.020  1.080
 C9O  C09  H9   single    0.930  0.020  1.080
 C9O  C14  H10  single    0.930  0.020  1.080
 C9O  N20  H11  single    0.860  0.020  1.020
 C9O  C33  H12  single    0.930  0.020  1.080
 C9O  C34  H13  single    0.930  0.020  1.080
 C9O  C35  H14  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
 C9O  C12  C10  F11  118.11  3.000
 C9O  F11  C10  C09  120.33  3.000
 C9O  C12  C10  C09  121.56  3.000
 C9O  N27  C15  C16  122.06  3.000
 C9O  N27  C15  C14  107.47  3.000
 C9O  C16  C15  C14  130.46  3.000
 C9O  H1   C17  C18  121.76  3.000
 C9O  H1   C17  C16  121.19  3.000
 C9O  C18  C17  C16  117.05  3.000
 C9O  O23  C22  N21  124.72  3.000
 C9O  O23  C22  C18  123.98  3.000
 C9O  N21  C22  C18  111.30  3.000
 C9O  H4   C24  H3   109.34  3.000
 C9O  H4   C24  H2   109.38  3.000
 C9O  H3   C24  H2   108.90  3.000
 C9O  H4   C24  O23  106.25  3.000
 C9O  H3   C24  O23  111.48  3.000
 C9O  H2   C24  O23  111.43  3.000
 C9O  H5   C26  N25  115.57  3.000
 C9O  H5   C26  C16  119.14  3.000
 C9O  N25  C26  C16  125.29  3.000
 C9O  C35  C02  C03  121.28  3.000
 C9O  C03  C02  BR1  119.23  3.000
 C9O  C35  C02  BR1  119.49  3.000
 C9O  H6   C03  C04  120.95  3.000
 C9O  H6   C03  C02  121.06  3.000
 C9O  C04  C03  C02  117.99  3.000
 C9O  C33  C04  S05  119.23  3.000
 C9O  S05  C04  C03  118.56  3.000
 C9O  C33  C04  C03  122.09  3.000
 C9O  H7   N06  C07  115.93  3.000
 C9O  H7   N06  S05  112.17  3.000
 C9O  C07  N06  S05  117.20  3.000
 C9O  C29  C07  C08  118.24  3.000
 C9O  C08  C07  N06  120.96  3.000
 C9O  C29  C07  N06  120.77  3.000
 C9O  H8   C08  C09  119.59  3.000
 C9O  H8   C08  C07  119.14  3.000
 C9O  C09  C08  C07  121.26  3.000
 C9O  H9   C09  C08  120.88  3.000
 C9O  H9   C09  C10  120.23  3.000
 C9O  C08  C09  C10  118.89  3.000
 C9O  C29  C12  N13  120.24  3.000
 C9O  C29  C12  C10  118.31  3.000
 C9O  N13  C12  C10  121.44  3.000
 C9O  N28  N13  C14  111.14  3.000
 C9O  N28  N13  C12  120.52  3.000
 C9O  C14  N13  C12  128.32  3.000
 C9O  H10  C14  N13  122.68  3.000
 C9O  H10  C14  C15  133.41  3.000
 C9O  N13  C14  C15  103.90  3.000
 C9O  C26  C16  C17  118.80  3.000
 C9O  C26  C16  C15  120.26  3.000
 C9O  C17  C16  C15  120.94  3.000
 C9O  C19  C18  C22  103.58  3.000
 C9O  C19  C18  C17  118.56  3.000
 C9O  C22  C18  C17  137.87  3.000
 C9O  N25  C19  N20  127.79  3.000
 C9O  N25  C19  C18  125.54  3.000
 C9O  N20  C19  C18  106.67  3.000
 C9O  H11  N20  N21  119.92  3.000
 C9O  H11  N20  C19  128.18  3.000
 C9O  N21  N20  C19  111.89  3.000
 C9O  N20  N21  C22  106.56  3.000
 C9O  C19  N25  C26  114.76  3.000
 C9O  N28  N27  C15  110.02  3.000
 C9O  N27  N28  N13  107.46  3.000
 C9O  F30  C29  C12  118.66  3.000
 C9O  C12  C29  C07  121.73  3.000
 C9O  F30  C29  C07  119.61  3.000
 C9O  H12  C33  C34  120.13  3.000
 C9O  H12  C33  C04  121.27  3.000
 C9O  C34  C33  C04  118.59  3.000
 C9O  H13  C34  C35  119.56  3.000
 C9O  H13  C34  C33  119.80  3.000
 C9O  C35  C34  C33  120.64  3.000
 C9O  H14  C35  C34  119.74  3.000
 C9O  H14  C35  C02  120.85  3.000
 C9O  C34  C35  C02  119.41  3.000
 C9O  C24  O23  C22  116.81  3.000
 C9O  O32  S05  O31  121.03  3.000
 C9O  O32  S05  N06  105.55  3.000
 C9O  O31  S05  N06  106.87  3.000
 C9O  O32  S05  C04  109.59  3.000
 C9O  O31  S05  C04  107.82  3.000
 C9O  N06  S05  C04  104.79  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
 C9O  CONST_03  C07  C29  C12  C10    0.00   0.0  0
 C9O  CONST_04  C07  C08  C09  C10    0.00   0.0  0
 C9O  CONST_05  C18  C17  C16  C15  180.00   0.0  0
 C9O  CONST_06  N25  C26  C16  C15  180.00   0.0  0
 C9O  CONST_07  N13  N28  N27  C15    0.00   0.0  0
 C9O  CONST_08  N28  N13  C14  C15    0.00   0.0  0
 C9O  CONST_09  C12  N13  C14  C15  180.00   0.0  0
 C9O  CONST_10  N21  C22  C18  C17  180.00   0.0  0
 C9O  CONST_11  N20  C19  C18  C17  180.00   0.0  0
 C9O  CONST_12  N25  C19  C18  C17    0.00   0.0  0
 C9O  CONST_13  N25  C26  C16  C17    0.00   0.0  0
 C9O  CONST_14  N27  C15  C16  C17    0.00   0.0  0
 C9O  CONST_15  C14  C15  C16  C17  180.00   0.0  0
 C9O  CONST_16  C19  N20  N21  C22    0.00   0.0  0
 C9O  CONST_17  N20  C19  C18  C22    0.00   0.0  0
 C9O  CONST_18  N25  C19  C18  C22  180.00   0.0  0
 C9O  CONST_19  C16  C17  C18  C22  180.00   0.0  0
 C9O  CONST_20  N20  C19  N25  C26  180.00   0.0  0
 C9O  CONST_21  C18  C19  N25  C26    0.00   0.0  0
 C9O  CONST_22  C18  C17  C16  C26    0.00   0.0  0
 C9O  CONST_23  N27  C15  C16  C26  180.00   0.0  0
 C9O  CONST_24  C14  C15  C16  C26    0.00   0.0  0
 C9O  CONST_25  C33  C34  C35  C02    0.00   0.0  0
 C9O  CONST_26  C33  C04  C03  C02    0.00   0.0  0
 C9O  CONST_27  C34  C33  C04  C03    0.00   0.0  0
 C9O  CONST_28  C34  C35  C02  C03    0.00   0.0  0
 C9O  CONST_29  C35  C34  C33  C04    0.00   0.0  0
 C9O  CONST_30  C35  C02  C03  C04    0.00   0.0  0
 C9O  CONST_31  N13  C12  C29  C07  180.00   0.0  0
 C9O  CONST_32  C12  C29  C07  C08    0.00   0.0  0
 C9O  CONST_33  C12  C10  C09  C08    0.00   0.0  0
 C9O  CONST_34  N13  C12  C10  C09  180.00   0.0  0
 C9O  CONST_35  C29  C12  C10  C09    0.00   0.0  0
 C9O  CONST_36  C29  C07  C08  C09    0.00   0.0  0
 C9O  CONST_37  N27  N28  N13  C12  180.00   0.0  0
 C9O  CONST_38  C16  C15  C14  N13  180.00   0.0  0
 C9O  CONST_39  N27  C15  C14  N13    0.00   0.0  0
 C9O  CONST_40  N28  N27  C15  C14    0.00   0.0  0
 C9O  CONST_41  N27  N28  N13  C14    0.00   0.0  0
 C9O  CONST_43  C19  C18  C17  C16    0.00   0.0  0
 C9O  CONST_44  C19  N25  C26  C16    0.00   0.0  0
 C9O  CONST_45  N28  N27  C15  C16  180.00   0.0  0
 C9O  CONST_46  N20  N21  C22  C18    0.00   0.0  0
 C9O  CONST_47  N21  N20  C19  C18    0.00   0.0  0
 C9O  CONST_48  N21  C22  C18  C19    0.00   0.0  0
 C9O  CONST_49  N25  C19  N20  N21  180.00   0.0  0
 C9O  CONST_51  F30  C29  C12  C10  180.00   0.0  0
 C9O  CONST_52  O23  C22  C18  C17    0.00   0.0  0
 C9O  CONST_53  C34  C35  C02  BR1  180.00   0.0  0
 C9O  CONST_54  C04  C03  C02  BR1  180.00   0.0  0
 C9O  CONST_55  S05  C04  C03  C02  180.00   0.0  0
 C9O  CONST_56  C34  C33  C04  S05  180.00   0.0  0
 C9O  CONST_57  C12  C29  C07  N06  180.00   0.0  0
 C9O  CONST_58  C09  C08  C07  N06  180.00   0.0  0
 C9O  CONST_59  F30  C29  C07  C08  180.00   0.0  0
 C9O  CONST_60  F11  C10  C09  C08  180.00   0.0  0
 C9O  CONST_61  N13  C12  C10  F11    0.00   0.0  0
 C9O  CONST_62  C29  C12  C10  F11  180.00   0.0  0
 C9O  CONST_63  F30  C29  C12  N13    0.00   0.0  0
 C9O  CONST_64  O23  C22  C18  C19  180.00   0.0  0
 C9O  CONST_65  O23  C22  N21  N20  180.00   0.0  0
 C9O  CONST_66  H8   C08  C09  C10  180.00   0.0  0
 C9O  CONST_67  H1   C17  C16  C15    0.00   0.0  0
 C9O  CONST_68  H5   C26  C16  C15    0.00   0.0  0
 C9O  CONST_69  H11  N20  N21  C22  180.00   0.0  0
 C9O  CONST_70  H13  C34  C35  C02  180.00   0.0  0
 C9O  CONST_71  H12  C33  C04  C03  180.00   0.0  0
 C9O  CONST_72  H14  C35  C02  C03  180.00   0.0  0
 C9O  CONST_73  H9   C09  C08  C07  180.00   0.0  0
 C9O  CONST_74  H10  C14  N13  C12    0.00   0.0  0
 C9O  CONST_75  H6   C03  C04  C33  180.00   0.0  0
 C9O  Var_01    N21  C22  O23  C24    0.19  30.0  2
 C9O  Var_02    N06  S05  C04  C03   87.13  30.0  1
 C9O  Var_03    C07  N06  S05  C04   56.23  30.0  2
 C9O  Var_04    H2   C24  O23  C22  -61.46  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
 C9O  plan-1  C15  0.020
 C9O  plan-1  C12  0.020
 C9O  plan-1  N13  0.020
 C9O  plan-1  C14  0.020
 C9O  plan-1  C16  0.020
 C9O  plan-1  N27  0.020
 C9O  plan-1  N28  0.020
 C9O  plan-1  H10  0.020
 C9O  plan-2  C10  0.020
 C9O  plan-2  N06  0.020
 C9O  plan-2  C07  0.020
 C9O  plan-2  C08  0.020
 C9O  plan-2  C09  0.020
 C9O  plan-2  F11  0.020
 C9O  plan-2  C12  0.020
 C9O  plan-2  N13  0.020
 C9O  plan-2  C29  0.020
 C9O  plan-2  F30  0.020
 C9O  plan-2  H8   0.020
 C9O  plan-2  H9   0.020
 C9O  plan-3  C02  0.020
 C9O  plan-3  C03  0.020
 C9O  plan-3  C04  0.020
 C9O  plan-3  C33  0.020
 C9O  plan-3  C34  0.020
 C9O  plan-3  C35  0.020
 C9O  plan-3  H6   0.020
 C9O  plan-3  H12  0.020
 C9O  plan-3  H13  0.020
 C9O  plan-3  H14  0.020
 C9O  plan-3  S05  0.020
 C9O  plan-3  BR1  0.020
 C9O  plan-4  C15  0.020
 C9O  plan-4  C17  0.020
 C9O  plan-4  C22  0.020
 C9O  plan-4  C26  0.020
 C9O  plan-4  C16  0.020
 C9O  plan-4  C18  0.020
 C9O  plan-4  C19  0.020
 C9O  plan-4  N20  0.020
 C9O  plan-4  N21  0.020
 C9O  plan-4  N25  0.020
 C9O  plan-4  H1   0.020
 C9O  plan-4  H5   0.020
 C9O  plan-4  H11  0.020
 C9O  plan-4  O23  0.020
 C9O  plan-5  N06  0.020
 C9O  plan-5  C07  0.020
 C9O  plan-5  H7   0.020
 C9O  plan-5  S05  0.020

