# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 21:46:16 2020
#   Inital geometry file: a 138 line input string
#   Ligand name: 6-[4-(benzyloxy)phenyl]-1-(pyridin-4-ylmethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1cc(nc2n(Cc3ccncc3)ncc12)c4ccc(OCc5ccccc5)cc4
#
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
 H89  H89  '6-[4-(benzyloxy)phenyl]-1-(pyridin-4-ylmethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid'  ligand  52  33  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_H89
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
 H89  C1    C  CR16   0  -0.059  -3.0391  -3.9395  -1.4626
 H89  C2    C  CR16   0  -0.359  -2.8375  -3.0730  -0.3994
 H89  C3    C  CR6    0   0.212  -3.8916  -2.8208   0.4702
 H89  C4    C  CR16   0  -0.368  -5.1010  -3.4554   0.2210
 H89  C5    C  CR16   0  -0.057  -5.1998  -4.3064  -0.8703
 H89  N6    N  N      0  -0.407  -4.1944  -4.5503  -1.7024
 H89  C7    C  CH2    0  -0.409  -3.7368  -1.8579   1.6181
 H89  N8    N  N      0  -0.383  -3.9624  -0.4985   1.1928
 H89  C9    C  CR6    0   0.591  -3.0430   0.3745   0.7155
 H89  C10   C  CR6    0  -0.156  -3.7471   1.5144   0.2935
 H89  C11   C  C1     0  -0.130  -5.1047   1.1904   0.5542
 H89  N12   N  N      0  -0.240  -5.2039  -0.0076   1.0749
 H89  N13   N  N      0  -0.483  -1.7361   0.1775   0.6661
 H89  C14   C  CR6    0   0.269  -1.0227   1.1774   0.1661
 H89  C15   C  CR16   0  -0.427  -1.6249   2.3754  -0.2837
 H89  C16   C  CR6    0  -0.019  -2.9896   2.5705  -0.2303
 H89  C18   C  C      0   0.397  -3.6264   3.8675  -0.7198
 H89  O19   O  O      0  -0.575  -4.8655   3.9248  -0.6305
 H89  O20   O  OC    -1  -0.580  -2.8528   4.7368  -1.1569
 H89  C21   C  CR6    0   0.032   0.4400   0.9726   0.1035
 H89  C22   C  CR16   0  -0.328   1.3177   1.9481  -0.3822
 H89  C23   C  CR16   0  -0.323   2.6806   1.7346  -0.4287
 H89  C24   C  CR6    0   0.380   3.2224   0.5257   0.0125
 H89  C25   C  CR16   0  -0.362   2.3651  -0.4595   0.4988
 H89  C26   C  CR16   0  -0.268   0.9992  -0.2281   0.5387
 H89  O27   O  O2     0  -0.464   4.5589   0.4034  -0.0685
 H89  C28   C  CR6    0   0.102   6.6419  -0.6587   0.2102
 H89  C29   C  CR16   0  -0.291   7.4156  -0.0820   1.2132
 H89  C30   C  CR16   0  -0.242   8.7841   0.0773   1.0446
 H89  C31   C  CR16   0  -0.261   9.3918  -0.3372  -0.1339
 H89  C32   C  CR16   0  -0.242   8.6264  -0.9117  -1.1404
 H89  C33   C  CR16   0  -0.293   7.2579  -1.0696  -0.9679
 H89  C34   C  CH2    0  -0.273   5.1611  -0.8043   0.3846
 H89  H1    H  HCR6   0   0.265  -2.2267  -4.1517  -2.1488
 H89  H2    H  HCR6   0   0.270  -1.8721  -2.6054  -0.2549
 H89  H4    H  HCR6   0   0.270  -5.9567  -3.2985   0.8651
 H89  H5    H  HCR6   0   0.265  -6.1352  -4.8147  -1.0769
 H89  H7    H  HCH2   0   0.293  -4.4420  -2.0857   2.4162
 H89  H7A   H  HCH2   0   0.289  -2.7304  -1.9137   2.0318
 H89  H11   H  H      0   0.263  -5.9830   1.7892   0.3808
 H89  H15   H  HCR6   0   0.258  -1.0200   3.1732  -0.6880
 H89  H22   H  HCR6   0   0.258   0.9505   2.9013  -0.7369
 H89  H23   H  HCR6   0   0.265   3.3370   2.5074  -0.8087
 H89  H25   H  HCR6   0   0.283   2.7373  -1.4110   0.8525
 H89  H26   H  HCR6   0   0.263   0.3536  -1.0069   0.9213
 H89  H29   H  HCR6   0   0.255   6.9466   0.2398   2.1355
 H89  H30   H  HCR6   0   0.258   9.3757   0.5217   1.8344
 H89  H31   H  HCR6   0   0.259  10.4592  -0.2166  -0.2661
 H89  H32   H  HCR6   0   0.259   9.0948  -1.2409  -2.0588
 H89  H33   H  HCR6   0   0.255   6.6668  -1.5233  -1.7547
 H89  H34   H  HCH2   0   0.244   4.9125  -0.9806   1.4362
 H89  H34A  H  HCH2   0   0.244   4.7882  -1.6550  -0.1951

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
 H89  N6   C1    aromatic  1.329  0.020  1.329
 H89  C1   C2    aromatic  1.386  0.020  1.386
 H89  C1   H1    single    0.930  0.020  1.080
 H89  C2   C3    aromatic  1.390  0.020  1.390
 H89  C2   H2    single    0.930  0.020  1.080
 H89  C4   C3    aromatic  1.388  0.020  1.388
 H89  C3   C7    single    1.506  0.020  1.506
 H89  C5   C4    aromatic  1.387  0.020  1.387
 H89  C4   H4    single    0.930  0.020  1.080
 H89  N6   C5    aromatic  1.328  0.020  1.328
 H89  C5   H5    single    0.930  0.020  1.080
 H89  C7   N8    single    1.442  0.020  1.442
 H89  C7   H7    single    0.970  0.020  1.090
 H89  C7   H7A   single    0.970  0.020  1.090
 H89  N8   N12   aromatic  1.340  0.020  1.340
 H89  N8   C9    aromatic  1.355  0.020  1.355
 H89  C9   N13   aromatic  1.322  0.020  1.322
 H89  C9   C10   aromatic  1.405  0.020  1.405
 H89  C11  C10   aromatic  1.420  0.020  1.420
 H89  C10  C16   aromatic  1.401  0.020  1.401
 H89  N12  C11   aromatic  1.310  0.020  1.310
 H89  C11  H11   single    0.930  0.020  1.080
 H89  N13  C14   aromatic  1.326  0.020  1.326
 H89  C14  C21   single    1.478  0.020  1.478
 H89  C14  C15   aromatic  1.414  0.020  1.414
 H89  C16  C15   aromatic  1.380  0.020  1.380
 H89  C15  H15   single    0.930  0.020  1.080
 H89  C16  C18   single    1.526  0.020  1.526
 H89  O19  C18   deloc     1.244  0.020  1.244
 H89  C18  O20   deloc     1.243  0.020  1.243
 H89  C22  C21   aromatic  1.399  0.020  1.399
 H89  C21  C26   aromatic  1.394  0.020  1.394
 H89  C22  C23   aromatic  1.380  0.020  1.380
 H89  C22  H22   single    0.930  0.020  1.080
 H89  C23  C24   aromatic  1.396  0.020  1.396
 H89  C23  H23   single    0.930  0.020  1.080
 H89  C24  O27   single    1.344  0.020  1.344
 H89  C24  C25   aromatic  1.394  0.020  1.394
 H89  C26  C25   aromatic  1.386  0.020  1.386
 H89  C25  H25   single    0.930  0.020  1.080
 H89  C26  H26   single    0.930  0.020  1.080
 H89  O27  C34   single    1.424  0.020  1.424
 H89  C34  C28   single    1.498  0.020  1.498
 H89  C33  C28   aromatic  1.391  0.020  1.391
 H89  C28  C29   aromatic  1.392  0.020  1.392
 H89  C29  C30   aromatic  1.388  0.020  1.388
 H89  C29  H29   single    0.930  0.020  1.080
 H89  C31  C30   aromatic  1.389  0.020  1.389
 H89  C30  H30   single    0.930  0.020  1.080
 H89  C32  C31   aromatic  1.389  0.020  1.389
 H89  C31  H31   single    0.930  0.020  1.080
 H89  C33  C32   aromatic  1.388  0.020  1.388
 H89  C32  H32   single    0.930  0.020  1.080
 H89  C33  H33   single    0.930  0.020  1.080
 H89  C34  H34   single    0.970  0.020  1.090
 H89  C34  H34A  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
 H89  H1    C1   N6   116.57  3.000
 H89  H1    C1   C2   119.92  3.000
 H89  N6    C1   C2   123.51  3.000
 H89  H2    C2   C3   120.97  3.000
 H89  H2    C2   C1   120.14  3.000
 H89  C3    C2   C1   118.89  3.000
 H89  C7    C3   C4   121.23  3.000
 H89  C7    C3   C2   121.00  3.000
 H89  C4    C3   C2   117.74  3.000
 H89  H4    C4   C5   120.04  3.000
 H89  H4    C4   C3   121.04  3.000
 H89  C5    C4   C3   118.92  3.000
 H89  H5    C5   N6   116.59  3.000
 H89  H5    C5   C4   119.92  3.000
 H89  N6    C5   C4   123.49  3.000
 H89  C5    N6   C1   117.44  3.000
 H89  H7A   C7   H7   108.00  3.000
 H89  H7A   C7   N8   107.74  3.000
 H89  H7    C7   N8   108.18  3.000
 H89  H7A   C7   C3   110.59  3.000
 H89  H7    C7   C3   111.00  3.000
 H89  N8    C7   C3   111.21  3.000
 H89  N12   N8   C9   111.21  3.000
 H89  C9    N8   C7   127.24  3.000
 H89  N12   N8   C7   121.07  3.000
 H89  N13   C9   C10  127.23  3.000
 H89  C10   C9   N8   106.77  3.000
 H89  N13   C9   N8   126.00  3.000
 H89  C16   C10  C11  139.24  3.000
 H89  C16   C10  C9   116.93  3.000
 H89  C11   C10  C9   103.83  3.000
 H89  H11   C11  N12  120.71  3.000
 H89  H11   C11  C10  128.56  3.000
 H89  N12   C11  C10  110.73  3.000
 H89  C11   N12  N8   107.44  3.000
 H89  C14   N13  C9   115.68  3.000
 H89  C21   C14  C15  121.68  3.000
 H89  C15   C14  N13  121.97  3.000
 H89  C21   C14  N13  116.35  3.000
 H89  H15   C15  C16  117.66  3.000
 H89  H15   C15  C14  120.42  3.000
 H89  C16   C15  C14  121.92  3.000
 H89  C18   C16  C15  121.38  3.000
 H89  C18   C16  C10  122.35  3.000
 H89  C15   C16  C10  116.27  3.000
 H89  O20   C18  O19  127.82  3.000
 H89  O20   C18  C16  116.59  3.000
 H89  O19   C18  C16  115.59  3.000
 H89  C26   C21  C22  117.20  3.000
 H89  C26   C21  C14  120.19  3.000
 H89  C22   C21  C14  122.60  3.000
 H89  H22   C22  C23  117.43  3.000
 H89  H22   C22  C21  121.02  3.000
 H89  C23   C22  C21  121.55  3.000
 H89  H23   C23  C24  119.57  3.000
 H89  H23   C23  C22  120.00  3.000
 H89  C24   C23  C22  120.43  3.000
 H89  O27   C24  C25  124.62  3.000
 H89  C25   C24  C23  118.92  3.000
 H89  O27   C24  C23  116.46  3.000
 H89  H25   C25  C26  118.48  3.000
 H89  H25   C25  C24  121.64  3.000
 H89  C26   C25  C24  119.89  3.000
 H89  H26   C26  C25  118.57  3.000
 H89  H26   C26  C21  119.41  3.000
 H89  C25   C26  C21  122.01  3.000
 H89  C34   O27  C24  118.59  3.000
 H89  C34   C28  C33  120.49  3.000
 H89  C33   C28  C29  119.10  3.000
 H89  C34   C28  C29  120.39  3.000
 H89  H29   C29  C30  119.74  3.000
 H89  H29   C29  C28  119.72  3.000
 H89  C30   C29  C28  120.54  3.000
 H89  H30   C30  C31  120.17  3.000
 H89  H30   C30  C29  119.83  3.000
 H89  C31   C30  C29  120.00  3.000
 H89  H31   C31  C32  120.07  3.000
 H89  H31   C31  C30  120.11  3.000
 H89  C32   C31  C30  119.81  3.000
 H89  H32   C32  C33  119.84  3.000
 H89  H32   C32  C31  120.15  3.000
 H89  C33   C32  C31  120.01  3.000
 H89  H33   C33  C32  119.67  3.000
 H89  H33   C33  C28  119.80  3.000
 H89  C32   C33  C28  120.53  3.000
 H89  H34A  C34  H34  107.83  3.000
 H89  H34A  C34  C28  110.52  3.000
 H89  H34   C34  C28  110.60  3.000
 H89  H34A  C34  O27  110.28  3.000
 H89  H34   C34  O27  110.26  3.000
 H89  C28   C34  O27  107.38  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
 H89  CONST_01  C4   C5   N6   C1      0.00   0.0  0
 H89  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 H89  CONST_03  C5   N6   C1   C2      0.00   0.0  0
 H89  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 H89  CONST_05  N6   C1   C2   C3      0.00   0.0  0
 H89  CONST_06  N6   C5   C4   C3      0.00   0.0  0
 H89  CONST_07  C10  C11  N12  N8      0.00   0.0  0
 H89  CONST_08  C14  N13  C9   N8    180.00   0.0  0
 H89  CONST_09  C11  C10  C9   N8      0.00   0.0  0
 H89  CONST_10  C16  C10  C9   N8    180.00   0.0  0
 H89  CONST_11  C11  N12  N8   C9      0.00   0.0  0
 H89  CONST_12  C21  C14  N13  C9    180.00   0.0  0
 H89  CONST_13  C15  C14  N13  C9      0.00   0.0  0
 H89  CONST_14  N12  C11  C10  C9      0.00   0.0  0
 H89  CONST_15  C15  C16  C10  C9      0.00   0.0  0
 H89  CONST_16  N12  N8   C9   C10     0.00   0.0  0
 H89  CONST_17  C14  N13  C9   C10     0.00   0.0  0
 H89  CONST_18  C14  C15  C16  C10     0.00   0.0  0
 H89  CONST_19  N13  C9   C10  C11   180.00   0.0  0
 H89  CONST_20  C15  C16  C10  C11   180.00   0.0  0
 H89  CONST_21  N13  C9   N8   N12   180.00   0.0  0
 H89  CONST_22  C16  C10  C11  N12   180.00   0.0  0
 H89  CONST_23  C16  C10  C9   N13     0.00   0.0  0
 H89  CONST_24  C22  C21  C14  N13   180.00   0.0  0
 H89  CONST_25  C26  C21  C14  N13     0.00   0.0  0
 H89  CONST_26  C16  C15  C14  N13     0.00   0.0  0
 H89  CONST_27  C23  C22  C21  C14   180.00   0.0  0
 H89  CONST_28  C25  C26  C21  C14   180.00   0.0  0
 H89  CONST_29  C22  C21  C14  C15     0.00   0.0  0
 H89  CONST_30  C26  C21  C14  C15   180.00   0.0  0
 H89  CONST_31  C21  C14  C15  C16   180.00   0.0  0
 H89  CONST_32  C24  C23  C22  C21     0.00   0.0  0
 H89  CONST_33  C24  C25  C26  C21     0.00   0.0  0
 H89  CONST_34  C25  C26  C21  C22     0.00   0.0  0
 H89  CONST_35  C25  C24  C23  C22     0.00   0.0  0
 H89  CONST_36  C26  C21  C22  C23     0.00   0.0  0
 H89  CONST_37  C26  C25  C24  C23     0.00   0.0  0
 H89  CONST_38  C31  C32  C33  C28     0.00   0.0  0
 H89  CONST_39  C31  C30  C29  C28     0.00   0.0  0
 H89  CONST_40  C32  C33  C28  C29     0.00   0.0  0
 H89  CONST_41  C32  C31  C30  C29     0.00   0.0  0
 H89  CONST_42  C33  C28  C29  C30     0.00   0.0  0
 H89  CONST_43  C33  C32  C31  C30     0.00   0.0  0
 H89  CONST_44  C7   C3   C2   C1    180.00   0.0  0
 H89  CONST_45  C7   C3   C4   C5    180.00   0.0  0
 H89  CONST_46  C11  N12  N8   C7    180.00   0.0  0
 H89  CONST_47  N13  C9   N8   C7      0.00   0.0  0
 H89  CONST_48  C10  C9   N8   C7    180.00   0.0  0
 H89  CONST_49  C18  C16  C10  C9    180.00   0.0  0
 H89  CONST_50  C18  C16  C10  C11     0.00   0.0  0
 H89  CONST_51  C18  C16  C15  C14   180.00   0.0  0
 H89  CONST_52  O27  C24  C23  C22   180.00   0.0  0
 H89  CONST_53  O27  C24  C25  C26   180.00   0.0  0
 H89  CONST_54  C34  C28  C29  C30   180.00   0.0  0
 H89  CONST_55  C34  C28  C33  C32   180.00   0.0  0
 H89  CONST_56  H5   C5   N6   C1    180.00   0.0  0
 H89  CONST_57  H4   C4   C3   C2    180.00   0.0  0
 H89  CONST_58  H1   C1   C2   C3    180.00   0.0  0
 H89  CONST_59  H2   C2   C3   C4    180.00   0.0  0
 H89  CONST_60  H11  C11  N12  N8    180.00   0.0  0
 H89  CONST_61  H15  C15  C16  C10   180.00   0.0  0
 H89  CONST_62  H22  C22  C21  C14     0.00   0.0  0
 H89  CONST_63  H26  C26  C21  C14     0.00   0.0  0
 H89  CONST_64  H23  C23  C22  C21   180.00   0.0  0
 H89  CONST_65  H25  C25  C26  C21   180.00   0.0  0
 H89  CONST_66  H32  C32  C33  C28   180.00   0.0  0
 H89  CONST_67  H30  C30  C29  C28   180.00   0.0  0
 H89  CONST_68  H33  C33  C28  C29   180.00   0.0  0
 H89  CONST_69  H31  C31  C30  C29   180.00   0.0  0
 H89  CONST_70  H29  C29  C30  C31   180.00   0.0  0
 H89  Var_01    N8   C7   C3   C2     84.18  30.0  2
 H89  Var_02    N12  N8   C7   C3     81.73  30.0  2
 H89  Var_03    O19  C18  C16  C10    -0.37  30.0  2
 H89  Var_04    C28  C34  O27  C24  -178.72  30.0  3
 H89  Var_05    C33  C28  C34  O27   -91.17  30.0  2

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
 H89  plan-1  C1   0.020
 H89  plan-1  C2   0.020
 H89  plan-1  C3   0.020
 H89  plan-1  C4   0.020
 H89  plan-1  C5   0.020
 H89  plan-1  N6   0.020
 H89  plan-1  C7   0.020
 H89  plan-1  H1   0.020
 H89  plan-1  H2   0.020
 H89  plan-1  H4   0.020
 H89  plan-1  H5   0.020
 H89  plan-2  C14  0.020
 H89  plan-2  C21  0.020
 H89  plan-2  C22  0.020
 H89  plan-2  C23  0.020
 H89  plan-2  C24  0.020
 H89  plan-2  C25  0.020
 H89  plan-2  C26  0.020
 H89  plan-2  O27  0.020
 H89  plan-2  H22  0.020
 H89  plan-2  H23  0.020
 H89  plan-2  H25  0.020
 H89  plan-2  H26  0.020
 H89  plan-3  C28  0.020
 H89  plan-3  C29  0.020
 H89  plan-3  C30  0.020
 H89  plan-3  C31  0.020
 H89  plan-3  C32  0.020
 H89  plan-3  C33  0.020
 H89  plan-3  C34  0.020
 H89  plan-3  H29  0.020
 H89  plan-3  H30  0.020
 H89  plan-3  H31  0.020
 H89  plan-3  H32  0.020
 H89  plan-3  H33  0.020
 H89  plan-4  C7   0.020
 H89  plan-4  N8   0.020
 H89  plan-4  C9   0.020
 H89  plan-4  C10  0.020
 H89  plan-4  C11  0.020
 H89  plan-4  N12  0.020
 H89  plan-4  N13  0.020
 H89  plan-4  C14  0.020
 H89  plan-4  C15  0.020
 H89  plan-4  C16  0.020
 H89  plan-4  C18  0.020
 H89  plan-4  C21  0.020
 H89  plan-4  H11  0.020
 H89  plan-4  H15  0.020
 H89  plan-5  C16  0.020
 H89  plan-5  C18  0.020
 H89  plan-5  O19  0.020
 H89  plan-5  O20  0.020

