# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 16:41:35 2020
#   Inital geometry file: a 137 line input string
#   Ligand name: 6-(4-benzoylphenyl)-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(cc4)C(=O)c5ccccc5
#
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
 H90  H90  '6-(4-benzoylphenyl)-1-(pyridin-4-ylmethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid'  ligand  51  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_H90
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
 H90  C1    C  CR16  0  -0.056   5.8136   3.1350   1.3648
 H90  C2    C  CR16  0  -0.364   5.6416   2.3833   0.2118
 H90  C3    C  CR6   0   0.209   4.3548   2.1741  -0.2660
 H90  C4    C  CR16  0  -0.369   3.3012   2.7367   0.4435
 H90  C5    C  CR16  0  -0.056   3.5793   3.4718   1.5858
 H90  N6    N  N     0  -0.407   4.8087   3.6724   2.0463
 H90  C7    C  CH2   0  -0.413   4.1051   1.3233  -1.4837
 H90  N8    N  NR5   0  -0.379   3.9183  -0.0606  -1.1123
 H90  C9    C  CR56  0   0.607   2.7607  -0.6608  -0.7534
 H90  C10   C  CR56  0  -0.117   3.0942  -1.9548  -0.3164
 H90  C11   C  CR15  0  -0.123   4.5054  -2.0063  -0.4459
 H90  N12   N  N     0  -0.221   4.9618  -0.8683  -0.9082
 H90  N13   N  N     0  -0.453   1.5536  -0.1263  -0.8123
 H90  C14   C  CR6   0   0.251   0.5588  -0.9020  -0.4170
 H90  C15   C  CR16  0  -0.386   0.7640  -2.2188   0.0567
 H90  C16   C  CR6   0   0.003   2.0312  -2.7608   0.1089
 H90  C18   C  C     0   0.527   2.2992  -4.1374   0.6047
 H90  O19   O  OH1   0  -0.586   1.2075  -4.7703   0.9932
 H90  O20   O  O     0  -0.418   3.4076  -4.6094   0.6405
 H90  C21   C  CR6   0   0.072  -0.7985  -0.3198  -0.4722
 H90  C22   C  CR16  0  -0.278  -0.9597   1.0681  -0.4932
 H90  C23   C  CR16  0  -0.255  -2.2189   1.6318  -0.5495
 H90  C24   C  CR6   0  -0.046  -3.3567   0.8246  -0.5634
 H90  C25   C  CR16  0  -0.258  -3.2008  -0.5592  -0.5524
 H90  C26   C  CR16  0  -0.307  -1.9367  -1.1239  -0.5165
 H90  C27   C  C     0   0.365  -4.6963   1.4621  -0.6719
 H90  O27   O  O     0  -0.387  -4.8260   2.5119  -1.2698
 H90  C28   C  CR6   0  -0.037  -5.8691   0.8004  -0.0435
 H90  C29   C  CR16  0  -0.281  -5.7498   0.0693   1.1380
 H90  C30   C  CR16  0  -0.240  -6.8753  -0.4775   1.7375
 H90  C31   C  CR16  0  -0.246  -8.1231  -0.3144   1.1518
 H90  C32   C  CR16  0  -0.244  -8.2486   0.4121  -0.0271
 H90  C33   C  CR16  0  -0.269  -7.1303   0.9793  -0.6143
 H90  H1    H  HCR6  0   0.267   6.8110   3.3086   1.7530
 H90  H2    H  HCR6  0   0.271   6.5027   1.9736  -0.3002
 H90  H4    H  HCR6  0   0.280   2.2770   2.6069   0.1179
 H90  H5    H  HCR6  0   0.267   2.7695   3.9185   2.1519
 H90  H7    H  HCH2  0   0.295   3.2108   1.6526  -2.0105
 H90  H7A   H  HCH2  0   0.301   4.9418   1.3735  -2.1782
 H90  H11   H  HCR5  0   0.275   5.1814  -2.8151  -0.2247
 H90  H15   H  HCR6  0   0.286  -0.0836  -2.7923   0.3999
 H90  HO19  H  HOH1  0   0.496   1.4290  -5.6579   1.3139
 H90  H22   H  HCR6  0   0.277  -0.0904   1.7100  -0.4618
 H90  H23   H  HCR6  0   0.268  -2.3196   2.7092  -0.5629
 H90  H25   H  HCR6  0   0.277  -4.0640  -1.2098  -0.5987
 H90  H26   H  HCR6  0   0.265  -1.8529  -2.2019  -0.5438
 H90  H29   H  HCR6  0   0.272  -4.7841  -0.0555   1.6105
 H90  H30   H  HCR6  0   0.266  -6.7759  -1.0319   2.6611
 H90  H31   H  HCR6  0   0.268  -8.9990  -0.7508   1.6138
 H90  H32   H  HCR6  0   0.265  -9.2206   0.5391  -0.4850
 H90  H33   H  HCR6  0   0.265  -7.2325   1.5508  -1.5277

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
 H90  C2   C1    aromatic  1.387  0.020  1.387
 H90  C1   N6    aromatic  1.328  0.020  1.328
 H90  C1   H1    single    0.930  0.020  1.080
 H90  C3   C2    aromatic  1.389  0.020  1.389
 H90  C2   H2    single    0.930  0.020  1.080
 H90  C7   C3    single    1.506  0.020  1.506
 H90  C3   C4    aromatic  1.389  0.020  1.389
 H90  C4   C5    aromatic  1.387  0.020  1.387
 H90  C4   H4    single    0.930  0.020  1.080
 H90  C5   N6    aromatic  1.328  0.020  1.328
 H90  C5   H5    single    0.930  0.020  1.080
 H90  N8   C7    single    1.445  0.020  1.445
 H90  C7   H7    single    0.970  0.020  1.090
 H90  C7   H7A   single    0.970  0.020  1.090
 H90  C9   N8    aromatic  1.352  0.020  1.352
 H90  N12  N8    aromatic  1.335  0.020  1.335
 H90  C10  C9    aromatic  1.406  0.020  1.406
 H90  N13  C9    aromatic  1.321  0.020  1.321
 H90  C16  C10   aromatic  1.400  0.020  1.400
 H90  C10  C11   aromatic  1.418  0.020  1.418
 H90  C11  N12   aromatic  1.310  0.020  1.310
 H90  C11  H11   single    0.930  0.020  1.080
 H90  C14  N13   aromatic  1.322  0.020  1.322
 H90  C15  C14   aromatic  1.414  0.020  1.414
 H90  C21  C14   single    1.478  0.020  1.478
 H90  C15  C16   aromatic  1.379  0.020  1.379
 H90  C15  H15   single    0.930  0.020  1.080
 H90  C18  C16   single    1.488  0.020  1.488
 H90  O20  C18   double    1.205  0.020  1.205
 H90  C18  O19   single    1.320  0.020  1.320
 H90  O19  HO19  single    0.850  0.020  0.980
 H90  C26  C21   aromatic  1.394  0.020  1.394
 H90  C21  C22   aromatic  1.397  0.020  1.397
 H90  C23  C22   aromatic  1.381  0.020  1.381
 H90  C22  H22   single    0.930  0.020  1.080
 H90  C24  C23   aromatic  1.395  0.020  1.395
 H90  C23  H23   single    0.930  0.020  1.080
 H90  C25  C24   aromatic  1.393  0.020  1.393
 H90  C27  C24   single    1.488  0.020  1.488
 H90  C25  C26   aromatic  1.385  0.020  1.385
 H90  C25  H25   single    0.930  0.020  1.080
 H90  C26  H26   single    0.930  0.020  1.080
 H90  O27  C27   double    1.215  0.020  1.215
 H90  C27  C28   single    1.486  0.020  1.486
 H90  C29  C28   aromatic  1.395  0.020  1.395
 H90  C28  C33   aromatic  1.396  0.020  1.396
 H90  C29  C30   aromatic  1.387  0.020  1.387
 H90  C29  H29   single    0.930  0.020  1.080
 H90  C30  C31   aromatic  1.388  0.020  1.388
 H90  C30  H30   single    0.930  0.020  1.080
 H90  C31  C32   aromatic  1.390  0.020  1.390
 H90  C31  H31   single    0.930  0.020  1.080
 H90  C33  C32   aromatic  1.385  0.020  1.385
 H90  C32  H32   single    0.930  0.020  1.080
 H90  C33  H33   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
 H90  H1    C1   N6   116.59  3.000
 H90  H1    C1   C2   119.90  3.000
 H90  N6    C1   C2   123.51  3.000
 H90  H2    C2   C3   121.16  3.000
 H90  H2    C2   C1   119.98  3.000
 H90  C3    C2   C1   118.85  3.000
 H90  C7    C3   C4   121.06  3.000
 H90  C4    C3   C2   117.78  3.000
 H90  C7    C3   C2   121.13  3.000
 H90  H4    C4   C5   120.07  3.000
 H90  H4    C4   C3   121.02  3.000
 H90  C5    C4   C3   118.91  3.000
 H90  H5    C5   N6   116.62  3.000
 H90  H5    C5   C4   119.92  3.000
 H90  N6    C5   C4   123.46  3.000
 H90  C5    N6   C1   117.48  3.000
 H90  H7A   C7   H7   107.97  3.000
 H90  H7A   C7   N8   107.91  3.000
 H90  H7    C7   N8   107.93  3.000
 H90  H7A   C7   C3   111.24  3.000
 H90  H7    C7   C3   110.88  3.000
 H90  N8    C7   C3   110.77  3.000
 H90  N12   N8   C9   111.09  3.000
 H90  N12   N8   C7   121.17  3.000
 H90  C9    N8   C7   127.15  3.000
 H90  N13   C9   C10  127.07  3.000
 H90  N13   C9   N8   126.20  3.000
 H90  C10   C9   N8   106.73  3.000
 H90  C16   C10  C11  139.67  3.000
 H90  C11   C10  C9   103.95  3.000
 H90  C16   C10  C9   116.37  3.000
 H90  H11   C11  N12  120.40  3.000
 H90  H11   C11  C10  129.28  3.000
 H90  N12   C11  C10  110.32  3.000
 H90  C11   N12  N8   107.88  3.000
 H90  C14   N13  C9   115.90  3.000
 H90  C21   C14  C15  120.83  3.000
 H90  C21   C14  N13  116.67  3.000
 H90  C15   C14  N13  122.50  3.000
 H90  H15   C15  C16  120.05  3.000
 H90  H15   C15  C14  119.15  3.000
 H90  C16   C15  C14  120.79  3.000
 H90  C18   C16  C15  122.81  3.000
 H90  C18   C16  C10  119.81  3.000
 H90  C15   C16  C10  117.37  3.000
 H90  O20   C18  O19  124.33  3.000
 H90  O19   C18  C16  113.12  3.000
 H90  O20   C18  C16  122.55  3.000
 H90  HO19  O19  C18  110.32  3.000
 H90  C26   C21  C22  118.56  3.000
 H90  C22   C21  C14  119.85  3.000
 H90  C26   C21  C14  121.58  3.000
 H90  H22   C22  C23  119.47  3.000
 H90  H22   C22  C21  119.77  3.000
 H90  C23   C22  C21  120.75  3.000
 H90  H23   C23  C24  120.00  3.000
 H90  H23   C23  C22  119.46  3.000
 H90  C24   C23  C22  120.52  3.000
 H90  C27   C24  C25  121.82  3.000
 H90  C27   C24  C23  119.15  3.000
 H90  C25   C24  C23  118.92  3.000
 H90  H25   C25  C26  118.95  3.000
 H90  H25   C25  C24  120.52  3.000
 H90  C26   C25  C24  120.50  3.000
 H90  H26   C26  C25  118.45  3.000
 H90  H26   C26  C21  120.82  3.000
 H90  C25   C26  C21  120.71  3.000
 H90  C28   C27  O27  120.57  3.000
 H90  C28   C27  C24  119.28  3.000
 H90  O27   C27  C24  120.16  3.000
 H90  C33   C28  C29  119.41  3.000
 H90  C33   C28  C27  118.89  3.000
 H90  C29   C28  C27  121.61  3.000
 H90  H29   C29  C30  119.32  3.000
 H90  H29   C29  C28  120.44  3.000
 H90  C30   C29  C28  120.22  3.000
 H90  H30   C30  C31  120.21  3.000
 H90  H30   C30  C29  119.75  3.000
 H90  C31   C30  C29  120.04  3.000
 H90  H31   C31  C32  119.97  3.000
 H90  H31   C31  C30  120.01  3.000
 H90  C32   C31  C30  120.02  3.000
 H90  H32   C32  C33  119.87  3.000
 H90  H32   C32  C31  120.09  3.000
 H90  C33   C32  C31  120.04  3.000
 H90  H33   C33  C32  119.86  3.000
 H90  H33   C33  C28  119.88  3.000
 H90  C32   C33  C28  120.25  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
 H90  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 H90  CONST_02  C4    C5   N6   C1      0.00   0.0  0
 H90  CONST_03  C5    N6   C1   C2      0.00   0.0  0
 H90  CONST_04  C5    C4   C3   C2      0.00   0.0  0
 H90  CONST_05  N6    C1   C2   C3      0.00   0.0  0
 H90  CONST_06  N6    C5   C4   C3      0.00   0.0  0
 H90  CONST_07  C16   C10  C9   N8    180.00   0.0  0
 H90  CONST_08  C11   C10  C9   N8      0.00   0.0  0
 H90  CONST_09  C14   N13  C9   N8    180.00   0.0  0
 H90  CONST_10  C10   C11  N12  N8      0.00   0.0  0
 H90  CONST_11  C11   N12  N8   C9      0.00   0.0  0
 H90  CONST_12  C15   C16  C10  C9      0.00   0.0  0
 H90  CONST_13  N12   C11  C10  C9      0.00   0.0  0
 H90  CONST_14  C15   C14  N13  C9      0.00   0.0  0
 H90  CONST_15  C21   C14  N13  C9    180.00   0.0  0
 H90  CONST_16  N12   N8   C9   C10     0.00   0.0  0
 H90  CONST_17  C14   N13  C9   C10     0.00   0.0  0
 H90  CONST_18  C14   C15  C16  C10     0.00   0.0  0
 H90  CONST_19  N13   C9   C10  C11   180.00   0.0  0
 H90  CONST_20  C15   C16  C10  C11   180.00   0.0  0
 H90  CONST_21  N13   C9   N8   N12   180.00   0.0  0
 H90  CONST_22  C16   C10  C11  N12   180.00   0.0  0
 H90  CONST_23  C16   C10  C9   N13     0.00   0.0  0
 H90  CONST_24  C16   C15  C14  N13     0.00   0.0  0
 H90  CONST_27  C25   C26  C21  C14   180.00   0.0  0
 H90  CONST_28  C23   C22  C21  C14   180.00   0.0  0
 H90  CONST_31  C21   C14  C15  C16   180.00   0.0  0
 H90  CONST_32  C24   C25  C26  C21     0.00   0.0  0
 H90  CONST_33  C24   C23  C22  C21     0.00   0.0  0
 H90  CONST_34  C25   C26  C21  C22     0.00   0.0  0
 H90  CONST_35  C25   C24  C23  C22     0.00   0.0  0
 H90  CONST_36  C26   C21  C22  C23     0.00   0.0  0
 H90  CONST_37  C26   C25  C24  C23     0.00   0.0  0
 H90  CONST_38  C31   C30  C29  C28     0.00   0.0  0
 H90  CONST_39  C31   C32  C33  C28     0.00   0.0  0
 H90  CONST_40  C32   C33  C28  C29     0.00   0.0  0
 H90  CONST_41  C32   C31  C30  C29     0.00   0.0  0
 H90  CONST_42  C33   C28  C29  C30     0.00   0.0  0
 H90  CONST_43  C33   C32  C31  C30     0.00   0.0  0
 H90  CONST_44  C7    C3   C2   C1    180.00   0.0  0
 H90  CONST_45  C7    C3   C4   C5    180.00   0.0  0
 H90  CONST_46  C10   C9   N8   C7    180.00   0.0  0
 H90  CONST_47  N13   C9   N8   C7      0.00   0.0  0
 H90  CONST_48  C11   N12  N8   C7    180.00   0.0  0
 H90  CONST_49  C18   C16  C10  C9    180.00   0.0  0
 H90  CONST_50  C18   C16  C10  C11     0.00   0.0  0
 H90  CONST_51  C18   C16  C15  C14   180.00   0.0  0
 H90  CONST_52  C27   C24  C23  C22   180.00   0.0  0
 H90  CONST_53  C27   C24  C25  C26   180.00   0.0  0
 H90  CONST_54  C30   C29  C28  C27   180.00   0.0  0
 H90  CONST_55  C32   C33  C28  C27   180.00   0.0  0
 H90  CONST_56  H5    C5   N6   C1    180.00   0.0  0
 H90  CONST_57  H4    C4   C3   C2    180.00   0.0  0
 H90  CONST_58  H1    C1   C2   C3    180.00   0.0  0
 H90  CONST_59  H2    C2   C3   C4    180.00   0.0  0
 H90  CONST_60  H11   C11  N12  N8    180.00   0.0  0
 H90  CONST_61  H15   C15  C16  C10   180.00   0.0  0
 H90  CONST_62  H26   C26  C21  C14     0.00   0.0  0
 H90  CONST_63  H22   C22  C21  C14     0.00   0.0  0
 H90  CONST_64  H25   C25  C26  C21   180.00   0.0  0
 H90  CONST_65  H23   C23  C22  C21   180.00   0.0  0
 H90  CONST_66  H30   C30  C29  C28   180.00   0.0  0
 H90  CONST_67  H32   C32  C33  C28   180.00   0.0  0
 H90  CONST_68  H33   C33  C28  C29   180.00   0.0  0
 H90  CONST_69  H31   C31  C30  C29   180.00   0.0  0
 H90  CONST_70  H29   C29  C30  C31   180.00   0.0  0
 H90  CONST_71  HO19  O19  C18  C16   180.00   0.0  0
 H90  Var_01    N8    C7   C3   C2     89.45  30.0  3
 H90  Var_02    C9    N8   C7   C3     87.22  30.0  1
 H90  Var_03    C28   C27  C24  C23  -149.87  30.0  2
 H90  Var_04    C29   C28  C27  C24    33.43  30.0  2
 H90  Var_05    O20   C18  C16  C10    -1.14  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
 H90  plan-1  C1    0.020
 H90  plan-1  C2    0.020
 H90  plan-1  C3    0.020
 H90  plan-1  C4    0.020
 H90  plan-1  C5    0.020
 H90  plan-1  N6    0.020
 H90  plan-1  C7    0.020
 H90  plan-1  H1    0.020
 H90  plan-1  H2    0.020
 H90  plan-1  H4    0.020
 H90  plan-1  H5    0.020
 H90  plan-2  C14   0.020
 H90  plan-2  C21   0.020
 H90  plan-2  C22   0.020
 H90  plan-2  C23   0.020
 H90  plan-2  C24   0.020
 H90  plan-2  C25   0.020
 H90  plan-2  C26   0.020
 H90  plan-2  C27   0.020
 H90  plan-2  H22   0.020
 H90  plan-2  H23   0.020
 H90  plan-2  H25   0.020
 H90  plan-2  H26   0.020
 H90  plan-3  C27   0.020
 H90  plan-3  C28   0.020
 H90  plan-3  C29   0.020
 H90  plan-3  C30   0.020
 H90  plan-3  C31   0.020
 H90  plan-3  C32   0.020
 H90  plan-3  C33   0.020
 H90  plan-3  H29   0.020
 H90  plan-3  H30   0.020
 H90  plan-3  H31   0.020
 H90  plan-3  H32   0.020
 H90  plan-3  H33   0.020
 H90  plan-4  C7    0.020
 H90  plan-4  N8    0.020
 H90  plan-4  C9    0.020
 H90  plan-4  C10   0.020
 H90  plan-4  C11   0.020
 H90  plan-4  N12   0.020
 H90  plan-4  N13   0.020
 H90  plan-4  C14   0.020
 H90  plan-4  C15   0.020
 H90  plan-4  C16   0.020
 H90  plan-4  C18   0.020
 H90  plan-4  C21   0.020
 H90  plan-4  H11   0.020
 H90  plan-4  H15   0.020
 H90  plan-5  C24   0.020
 H90  plan-5  C27   0.020
 H90  plan-5  O27   0.020
 H90  plan-5  C28   0.020
 H90  plan-6  C16   0.020
 H90  plan-6  C18   0.020
 H90  plan-6  O19   0.020
 H90  plan-6  O20   0.020
 H90  plan-6  HO19  0.020

