# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 19:12:25 2022
#   Inital geometry file: a 122 line input string
#   Ligand name: 6-(4-carboxyphenyl)-3-(4-ethylphenyl)-2~{H}-pyrazolo[3,4-b]pyridine-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1ccc(cc1)c2[nH]nc3nc(cc(C(O)=O)c23)c4ccc(cc4)C(O)=O
#
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
 LKW  LKW  '6-(4-carboxyphenyl)-3-(4-ethylphenyl)-2~{H}-pyrazolo[3,4-b]pyridine-4-carboxylic acid'  ligand  44  29  .  2022-03-22  2022-03-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_LKW
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
 LKW  C6   C  CR56   0   0.342  -3.0575  -11.1511  58.7164
 LKW  C8   C  CR6    0   0.220  -1.0453  -10.1468  58.8676
 LKW  C10  C  CR16   0  -0.315   1.2078   -9.0533  58.6054
 LKW  C1   C  CR16   0  -0.272  -3.5985  -14.6234  61.4582
 LKW  C3   C  CR5    0   0.388  -3.7782  -13.1037  59.5133
 LKW  C2   C  CR6    0   0.032  -4.0763  -14.3721  60.1720
 LKW  C12  C  CR6    0  -0.106   1.4115   -6.7104  58.0329
 LKW  C11  C  CR16   0  -0.272   1.9886   -7.9404  58.3336
 LKW  C9   C  CR6    0   0.058  -0.1856   -8.9752  58.5813
 LKW  C28  C  CH3    0  -0.653  -3.8747  -19.1014  61.9511
 LKW  C26  C  CR6    0   0.123  -4.7029  -16.7767  61.4947
 LKW  C29  C  CR16   0  -0.296  -3.9065  -15.8077  62.1040
 LKW  C25  C  CR16   0  -0.301  -5.1819  -16.5190  60.2136
 LKW  C24  C  CR16   0  -0.283  -4.8751  -15.3361  59.5576
 LKW  N4   N  NR15   0  -0.473  -4.7187  -12.4086  58.8556
 LKW  N5   N  N      0  -0.302  -4.3393  -11.2381  58.3626
 LKW  N7   N  N      0  -0.469  -2.2790  -10.0964  58.4227
 LKW  C23  C  CR56   0  -0.185  -2.6313  -12.3056  59.4325
 LKW  C19  C  CR6    0   0.004  -1.2882  -12.3655  59.8648
 LKW  C20  C  C      0   0.339  -0.6497  -13.5912  60.5018
 LKW  O22  O  OC    -1  -0.581  -0.0136  -13.4023  61.5514
 LKW  O21  O  O      0  -0.572  -0.8136  -14.6463  59.8683
 LKW  C18  C  CR16   0  -0.414  -0.5285  -11.2548  59.5999
 LKW  O15  O  O      0  -0.585   1.6601   -4.4267  57.4963
 LKW  O14  O  OC    -1  -0.586   3.5063   -5.6491  57.7775
 LKW  C16  C  CR16   0  -0.275   0.0200   -6.6347  58.0049
 LKW  C17  C  CR16   0  -0.272  -0.7652   -7.7432  58.2691
 LKW  H1   H  HCR6   0   0.244   1.7035   -9.9917  58.8179
 LKW  H2   H  HCR6   0   0.251  -2.9951  -13.8819  61.9658
 LKW  H3   H  HCR6   0   0.241   3.0663   -8.0328  58.3531
 LKW  H4   H  HCH3   0   0.231  -4.0963  -20.0409  62.4584
 LKW  H5   H  HCH3   0   0.226  -3.7541  -19.3142  60.8883
 LKW  H6   H  HCH3   0   0.226  -2.9194  -18.7342  62.3278
 LKW  H7   H  HCH2   0   0.240  -5.1073  -17.9127  63.2564
 LKW  H8   H  HCH2   0   0.240  -5.9351  -18.4900  61.8243
 LKW  H9   H  HCR6   0   0.248  -3.5280  -15.9800  63.1051
 LKW  H10  H  HCR6   0   0.248  -5.8014  -17.2556  59.7154
 LKW  H11  H  HCR6   0   0.254  -5.2487  -15.1739  58.5535
 LKW  H12  H  HNR5   0   0.427  -5.6848  -12.6868  58.7525
 LKW  H14  H  HCR6   0   0.254   0.4950  -11.2297  59.9466
 LKW  H16  H  HCR6   0   0.240  -0.4544   -5.6900  57.7743
 LKW  H17  H  HCR6   0   0.241  -1.8433   -7.6562  58.2440
 LKW  C27  C  CH2    0  -0.502  -4.9881  -18.0809  62.1836
 LKW  C13  C  C      0   0.394   2.2719   -5.4833  57.7422

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
 LKW  O15  C13  deloc     1.246  0.020  1.246
 LKW  C13  C12  single    1.527  0.020  1.527
 LKW  C13  O14  deloc     1.246  0.020  1.246
 LKW  C12  C16  aromatic  1.394  0.020  1.394
 LKW  C12  C11  aromatic  1.392  0.020  1.392
 LKW  C16  C17  aromatic  1.384  0.020  1.384
 LKW  C11  C10  aromatic  1.386  0.020  1.386
 LKW  C17  C9   aromatic  1.397  0.020  1.397
 LKW  C10  C9   aromatic  1.396  0.020  1.396
 LKW  C9   C8   single    1.481  0.020  1.481
 LKW  N7   C8   aromatic  1.312  0.020  1.312
 LKW  N7   C6   aromatic  1.343  0.020  1.343
 LKW  N5   C6   aromatic  1.333  0.020  1.333
 LKW  N5   N4   aromatic  1.326  0.020  1.326
 LKW  C8   C18  aromatic  1.425  0.020  1.425
 LKW  C6   C23  aromatic  1.424  0.020  1.424
 LKW  N4   C3   aromatic  1.342  0.020  1.342
 LKW  C24  C25  aromatic  1.387  0.020  1.387
 LKW  C24  C2   aromatic  1.395  0.020  1.395
 LKW  C18  C19  aromatic  1.371  0.020  1.371
 LKW  C23  C3   aromatic  1.400  0.020  1.400
 LKW  C23  C19  aromatic  1.412  0.020  1.412
 LKW  C3   C2   single    1.460  0.020  1.460
 LKW  C19  C20  single    1.522  0.020  1.522
 LKW  O21  C20  deloc     1.242  0.020  1.242
 LKW  C25  C26  aromatic  1.392  0.020  1.392
 LKW  C2   C1   aromatic  1.395  0.020  1.395
 LKW  C20  O22  deloc     1.242  0.020  1.242
 LKW  C26  C27  single    1.502  0.020  1.502
 LKW  C26  C29  aromatic  1.395  0.020  1.395
 LKW  C1   C29  aromatic  1.384  0.020  1.384
 LKW  C28  C27  single    1.528  0.020  1.528
 LKW  C10  H1   single    0.930  0.020  1.080
 LKW  C1   H2   single    0.930  0.020  1.080
 LKW  C11  H3   single    0.930  0.020  1.080
 LKW  C28  H4   single    0.970  0.020  1.090
 LKW  C28  H5   single    0.970  0.020  1.090
 LKW  C28  H6   single    0.970  0.020  1.090
 LKW  C27  H7   single    0.970  0.020  1.090
 LKW  C27  H8   single    0.970  0.020  1.090
 LKW  C29  H9   single    0.930  0.020  1.080
 LKW  C25  H10  single    0.930  0.020  1.080
 LKW  C24  H11  single    0.930  0.020  1.080
 LKW  N4   H12  single    0.860  0.020  1.020
 LKW  C18  H14  single    0.930  0.020  1.080
 LKW  C16  H16  single    0.930  0.020  1.080
 LKW  C17  H17  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
 LKW  C23  C6   N7   124.96  3.000
 LKW  C23  C6   N5   111.63  3.000
 LKW  N7   C6   N5   123.41  3.000
 LKW  C18  C8   N7   123.02  3.000
 LKW  C18  C8   C9   120.25  3.000
 LKW  N7   C8   C9   116.72  3.000
 LKW  H1   C10  C9   120.61  3.000
 LKW  H1   C10  C11  118.46  3.000
 LKW  C9   C10  C11  120.92  3.000
 LKW  H2   C1   C29  119.44  3.000
 LKW  H2   C1   C2   120.00  3.000
 LKW  C29  C1   C2   120.55  3.000
 LKW  C23  C3   N4   104.52  3.000
 LKW  C23  C3   C2   133.53  3.000
 LKW  N4   C3   C2   121.88  3.000
 LKW  C24  C2   C3   121.25  3.000
 LKW  C3   C2   C1   120.17  3.000
 LKW  C24  C2   C1   118.55  3.000
 LKW  C16  C12  C13  121.01  3.000
 LKW  C16  C12  C11  117.80  3.000
 LKW  C13  C12  C11  121.19  3.000
 LKW  H3   C11  C12  119.51  3.000
 LKW  H3   C11  C10  119.27  3.000
 LKW  C12  C11  C10  121.22  3.000
 LKW  C17  C9   C10  117.87  3.000
 LKW  C10  C9   C8   122.13  3.000
 LKW  C17  C9   C8   120.00  3.000
 LKW  H6   C28  H5   107.79  3.000
 LKW  H6   C28  H4   107.90  3.000
 LKW  H5   C28  H4   107.93  3.000
 LKW  H6   C28  C27  111.15  3.000
 LKW  H5   C28  C27  111.05  3.000
 LKW  H4   C28  C27  110.88  3.000
 LKW  C25  C26  C29  118.04  3.000
 LKW  C29  C26  C27  120.75  3.000
 LKW  C25  C26  C27  121.16  3.000
 LKW  H9   C29  C26  119.50  3.000
 LKW  H9   C29  C1   119.30  3.000
 LKW  C26  C29  C1   121.20  3.000
 LKW  H10  C25  C24  119.26  3.000
 LKW  H10  C25  C26  119.61  3.000
 LKW  C24  C25  C26  121.14  3.000
 LKW  H11  C24  C25  119.31  3.000
 LKW  H11  C24  C2   120.15  3.000
 LKW  C25  C24  C2   120.53  3.000
 LKW  H12  N4   N5   118.60  3.000
 LKW  H12  N4   C3   125.27  3.000
 LKW  N5   N4   C3   116.05  3.000
 LKW  N4   N5   C6   103.54  3.000
 LKW  C8   N7   C6   116.13  3.000
 LKW  C19  C23  C3   137.51  3.000
 LKW  C19  C23  C6   118.23  3.000
 LKW  C3   C23  C6   104.25  3.000
 LKW  C18  C19  C20  120.05  3.000
 LKW  C20  C19  C23  124.15  3.000
 LKW  C18  C19  C23  115.68  3.000
 LKW  O21  C20  O22  128.92  3.000
 LKW  O22  C20  C19  116.50  3.000
 LKW  O21  C20  C19  114.55  3.000
 LKW  H14  C18  C19  118.77  3.000
 LKW  H14  C18  C8   119.35  3.000
 LKW  C19  C18  C8   121.87  3.000
 LKW  H16  C16  C17  119.43  3.000
 LKW  H16  C16  C12  119.30  3.000
 LKW  C17  C16  C12  121.27  3.000
 LKW  H17  C17  C16  119.77  3.000
 LKW  H17  C17  C9   119.32  3.000
 LKW  C16  C17  C9   120.91  3.000
 LKW  H8   C27  H7   106.63  3.000
 LKW  H8   C27  C26  109.81  3.000
 LKW  H7   C27  C26  109.72  3.000
 LKW  H8   C27  C28  109.36  3.000
 LKW  H7   C27  C28  109.37  3.000
 LKW  C26  C27  C28  111.82  3.000
 LKW  O14  C13  O15  127.24  3.000
 LKW  O14  C13  C12  116.49  3.000
 LKW  O15  C13  C12  116.27  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
 LKW  CONST_01  C9   C8   N7   C6    180.00   0.0  0
 LKW  CONST_02  C18  C8   N7   C6      0.00   0.0  0
 LKW  CONST_03  C3   N4   N5   C6      0.00   0.0  0
 LKW  CONST_04  N4   C3   C23  C6      0.00   0.0  0
 LKW  CONST_05  C2   C3   C23  C6    180.00   0.0  0
 LKW  CONST_06  C18  C19  C23  C6      0.00   0.0  0
 LKW  CONST_07  C16  C17  C9   C8    180.00   0.0  0
 LKW  CONST_08  C11  C10  C9   C8    180.00   0.0  0
 LKW  CONST_09  N5   C6   N7   C8    180.00   0.0  0
 LKW  CONST_10  C23  C6   N7   C8      0.00   0.0  0
 LKW  CONST_11  C23  C19  C18  C8      0.00   0.0  0
 LKW  CONST_12  C16  C12  C11  C10     0.00   0.0  0
 LKW  CONST_13  C16  C17  C9   C10     0.00   0.0  0
 LKW  CONST_16  C25  C24  C2   C1      0.00   0.0  0
 LKW  CONST_19  C25  C26  C29  C1      0.00   0.0  0
 LKW  CONST_20  N7   C6   C23  C3    180.00   0.0  0
 LKW  CONST_21  N5   C6   C23  C3      0.00   0.0  0
 LKW  CONST_22  C18  C19  C23  C3    180.00   0.0  0
 LKW  CONST_23  C25  C24  C2   C3    180.00   0.0  0
 LKW  CONST_24  C29  C1   C2   C3    180.00   0.0  0
 LKW  CONST_25  C26  C25  C24  C2      0.00   0.0  0
 LKW  CONST_26  N5   N4   C3   C2    180.00   0.0  0
 LKW  CONST_27  C19  C23  C3   C2      0.00   0.0  0
 LKW  CONST_28  C26  C29  C1   C2      0.00   0.0  0
 LKW  CONST_29  C9   C17  C16  C12     0.00   0.0  0
 LKW  CONST_30  C9   C10  C11  C12     0.00   0.0  0
 LKW  CONST_31  C17  C16  C12  C11     0.00   0.0  0
 LKW  CONST_32  C17  C9   C10  C11     0.00   0.0  0
 LKW  CONST_33  C19  C18  C8   C9    180.00   0.0  0
 LKW  CONST_34  C24  C25  C26  C29     0.00   0.0  0
 LKW  CONST_35  C24  C2   C1   C29     0.00   0.0  0
 LKW  CONST_38  N7   C6   N5   N4    180.00   0.0  0
 LKW  CONST_39  C23  C6   N5   N4      0.00   0.0  0
 LKW  CONST_40  C19  C23  C3   N4    180.00   0.0  0
 LKW  CONST_41  C19  C23  C6   N5    180.00   0.0  0
 LKW  CONST_42  C23  C3   N4   N5      0.00   0.0  0
 LKW  CONST_44  C19  C18  C8   N7      0.00   0.0  0
 LKW  CONST_45  C19  C23  C6   N7      0.00   0.0  0
 LKW  CONST_47  C20  C19  C23  C6    180.00   0.0  0
 LKW  CONST_48  C20  C19  C18  C8    180.00   0.0  0
 LKW  CONST_49  C13  C12  C11  C10   180.00   0.0  0
 LKW  CONST_50  C27  C26  C29  C1    180.00   0.0  0
 LKW  CONST_51  C20  C19  C23  C3      0.00   0.0  0
 LKW  CONST_52  C24  C25  C26  C27   180.00   0.0  0
 LKW  CONST_53  C17  C16  C12  C13   180.00   0.0  0
 LKW  CONST_54  H12  N4   N5   C6    180.00   0.0  0
 LKW  CONST_55  H17  C17  C9   C8      0.00   0.0  0
 LKW  CONST_56  H1   C10  C9   C8      0.00   0.0  0
 LKW  CONST_57  H11  C24  C2   C1    180.00   0.0  0
 LKW  CONST_58  H2   C1   C2   C3      0.00   0.0  0
 LKW  CONST_59  H10  C25  C24  C2    180.00   0.0  0
 LKW  CONST_60  H9   C29  C1   C2    180.00   0.0  0
 LKW  CONST_61  H16  C16  C12  C11   180.00   0.0  0
 LKW  CONST_62  H3   C11  C10  C9    180.00   0.0  0
 LKW  CONST_63  H14  C18  C8   C9      0.00   0.0  0
 LKW  Var_01    O15  C13  C12  C11  -179.35  30.0  2
 LKW  Var_02    C25  C26  C27  C28    93.03  30.0  2
 LKW  Var_03    O21  C20  C19  C23    50.49  30.0  2
 LKW  Var_04    H4   C28  C27  C26   179.92  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
 LKW  plan-1  C8   0.020
 LKW  plan-1  C10  0.020
 LKW  plan-1  C12  0.020
 LKW  plan-1  C11  0.020
 LKW  plan-1  C9   0.020
 LKW  plan-1  C16  0.020
 LKW  plan-1  C17  0.020
 LKW  plan-1  H1   0.020
 LKW  plan-1  H3   0.020
 LKW  plan-1  H16  0.020
 LKW  plan-1  H17  0.020
 LKW  plan-1  C13  0.020
 LKW  plan-2  C1   0.020
 LKW  plan-2  C3   0.020
 LKW  plan-2  C2   0.020
 LKW  plan-2  C26  0.020
 LKW  plan-2  C29  0.020
 LKW  plan-2  C25  0.020
 LKW  plan-2  C24  0.020
 LKW  plan-2  H2   0.020
 LKW  plan-2  H9   0.020
 LKW  plan-2  H10  0.020
 LKW  plan-2  H11  0.020
 LKW  plan-2  C27  0.020
 LKW  plan-3  C6   0.020
 LKW  plan-3  C8   0.020
 LKW  plan-3  C3   0.020
 LKW  plan-3  C2   0.020
 LKW  plan-3  C9   0.020
 LKW  plan-3  N4   0.020
 LKW  plan-3  N5   0.020
 LKW  plan-3  N7   0.020
 LKW  plan-3  C23  0.020
 LKW  plan-3  C19  0.020
 LKW  plan-3  C20  0.020
 LKW  plan-3  C18  0.020
 LKW  plan-3  H12  0.020
 LKW  plan-3  H14  0.020
 LKW  plan-4  C19  0.020
 LKW  plan-4  C20  0.020
 LKW  plan-4  O22  0.020
 LKW  plan-4  O21  0.020
 LKW  plan-5  C12  0.020
 LKW  plan-5  O15  0.020
 LKW  plan-5  O14  0.020
 LKW  plan-5  C13  0.020

