# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar 22 19:10:35 2022
#   Inital geometry file: a 99 line input string
#   Ligand name: 1-(4-chlorophenyl)-6-methyl-3-propan-2-yl-pyrazolo[3,4-b]pyridine-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)c1nn(c2ccc(Cl)cc2)c3nc(C)cc(C(O)=O)c13
#
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
 T02  T02  '1-(4-chlorophenyl)-6-methyl-3-propan-2-yl-pyrazolo[3,4-b]pyridine-4-carboxylic acid'  ligand  38  23  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_T02
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
 T02  C01  C   CR6    0   0.254  11.5752  -11.9412  -29.3131
 T02  C02  C   CR16   0  -0.407  12.0246  -11.7334  -27.9965
 T02  C03  C   CR6    0   0.015  13.3592  -11.8573  -27.6552
 T02  C04  C   CR56   0  -0.155  14.2325  -12.1704  -28.7078
 T02  C06  C   CR56   0   0.554  13.6737  -12.3317  -29.9836
 T02  C07  C   CR5    0   0.275  15.6411  -12.3391  -28.9082
 T02  C09  C   CH3    0  -0.734  10.1144  -11.8292  -29.6260
 T02  C10  C   C      0   0.345  13.7856  -11.6832  -26.2046
 T02  C11  C   CH1    0  -0.335  16.7487  -12.2286  -27.9069
 T02  C13  C   CH3    0  -0.650  18.0609  -12.8131  -28.4163
 T02  C14  C   CH3    0  -0.658  16.9354  -10.7649  -27.4950
 T02  C17  C   CR16   0  -0.304  13.5960  -13.2804  -32.8840
 T02  C18  C   CR16   0  -0.206  13.6133  -13.4315  -34.2619
 T02  C19  C   CR6    0  -0.051  14.7430  -13.0747  -34.9793
 T02  C21  C   CR16   0  -0.204  15.8580  -12.5654  -34.3327
 T02  C22  C   CR16   0  -0.310  15.8363  -12.4018  -32.9580
 T02  C23  C   CR6    0   0.356  14.7057  -12.7569  -32.2249
 T02  N05  N   N      0  -0.471  12.3925  -12.2377  -30.3119
 T02  N08  N   N      0  -0.282  15.8849  -12.5818  -30.1667
 T02  N12  N   NR5    0  -0.498  14.7107  -12.5902  -30.8334
 T02  O15  O   OC    -1  -0.572  14.3474  -12.6646  -25.6896
 T02  O16  O   O      0  -0.579  13.5022  -10.5902  -25.6886
 T02  H1   H   HCR6   0   0.254  11.2945  -11.4824  -27.2371
 T02  H2   H   HCH3   0   0.249   9.9289  -12.0038  -30.6833
 T02  H3   H   HCH3   0   0.252   9.5367  -12.5537  -29.0499
 T02  H4   H   HCH3   0   0.251   9.7331  -10.8405  -29.3657
 T02  H5   H   HCH1   0   0.252  16.4372  -12.7851  -27.0209
 T02  H6   H   HCH3   0   0.229  18.8177  -12.7564  -27.6334
 T02  H7   H   HCH3   0   0.229  17.9558  -13.8591  -28.7052
 T02  H8   H   HCH3   0   0.218  18.4352  -12.2629  -29.2802
 T02  H9   H   HCH3   0   0.231  17.6834  -10.6852  -26.7049
 T02  H10  H   HCH3   0   0.222  17.2767  -10.1668  -28.3421
 T02  H11  H   HCH3   0   0.235  16.0136  -10.3194  -27.1216
 T02  H12  H   HCR6   0   0.284  12.7155  -13.5748  -32.3340
 T02  H13  H   HCR6   0   0.281  12.7469  -13.8383  -34.7654
 T02  H14  H   HCR6   0   0.281  16.7398  -12.2849  -34.8926
 T02  H15  H   HCR6   0   0.280  16.7037  -11.9962  -32.4575
 T02  CL   CL  CL     0  -0.130  14.7638  -13.2677  -36.7012

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
 T02  CL   C19  single    1.733  0.020  1.733
 T02  C19  C21  aromatic  1.386  0.020  1.386
 T02  C19  C18  aromatic  1.385  0.020  1.385
 T02  C21  C22  aromatic  1.385  0.020  1.385
 T02  C18  C17  aromatic  1.386  0.020  1.386
 T02  C22  C23  aromatic  1.393  0.020  1.393
 T02  C17  C23  aromatic  1.393  0.020  1.393
 T02  C23  N12  single    1.401  0.020  1.401
 T02  N12  N08  aromatic  1.350  0.020  1.350
 T02  N12  C06  aromatic  1.365  0.020  1.365
 T02  N05  C06  aromatic  1.326  0.020  1.326
 T02  N05  C01  aromatic  1.324  0.020  1.324
 T02  N08  C07  aromatic  1.305  0.020  1.305
 T02  C06  C04  aromatic  1.402  0.020  1.402
 T02  C09  C01  single    1.498  0.020  1.498
 T02  C01  C02  aromatic  1.407  0.020  1.407
 T02  C07  C04  aromatic  1.433  0.020  1.433
 T02  C07  C11  single    1.497  0.020  1.497
 T02  C04  C03  aromatic  1.403  0.020  1.403
 T02  C13  C11  single    1.524  0.020  1.524
 T02  C02  C03  aromatic  1.383  0.020  1.383
 T02  C11  C14  single    1.532  0.020  1.532
 T02  C03  C10  single    1.522  0.020  1.522
 T02  C10  O16  deloc     1.241  0.020  1.241
 T02  C10  O15  deloc     1.243  0.020  1.243
 T02  C02  H1   single    0.930  0.020  1.080
 T02  C09  H2   single    0.970  0.020  1.090
 T02  C09  H3   single    0.970  0.020  1.090
 T02  C09  H4   single    0.970  0.020  1.090
 T02  C11  H5   single    0.970  0.020  1.090
 T02  C13  H6   single    0.970  0.020  1.090
 T02  C13  H7   single    0.970  0.020  1.090
 T02  C13  H8   single    0.970  0.020  1.090
 T02  C14  H9   single    0.970  0.020  1.090
 T02  C14  H10  single    0.970  0.020  1.090
 T02  C14  H11  single    0.970  0.020  1.090
 T02  C17  H12  single    0.930  0.020  1.080
 T02  C18  H13  single    0.930  0.020  1.080
 T02  C21  H14  single    0.930  0.020  1.080
 T02  C22  H15  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
 T02  N05  C01  C09  117.45  3.000
 T02  C09  C01  C02  119.74  3.000
 T02  N05  C01  C02  122.81  3.000
 T02  H1   C02  C03  119.89  3.000
 T02  H1   C02  C01  118.37  3.000
 T02  C03  C02  C01  121.74  3.000
 T02  C10  C03  C04  124.49  3.000
 T02  C10  C03  C02  119.68  3.000
 T02  C04  C03  C02  115.82  3.000
 T02  C07  C04  C06  104.53  3.000
 T02  C07  C04  C03  138.00  3.000
 T02  C06  C04  C03  117.40  3.000
 T02  N12  C06  N05  126.38  3.000
 T02  N05  C06  C04  127.03  3.000
 T02  N12  C06  C04  106.59  3.000
 T02  N08  C07  C11  121.37  3.000
 T02  C11  C07  C04  128.69  3.000
 T02  N08  C07  C04  109.91  3.000
 T02  H4   C09  H3   106.90  3.000
 T02  H4   C09  H2   108.52  3.000
 T02  H3   C09  H2   108.45  3.000
 T02  H4   C09  C01  111.02  3.000
 T02  H3   C09  C01  110.87  3.000
 T02  H2   C09  C01  110.94  3.000
 T02  O16  C10  O15  128.78  3.000
 T02  O15  C10  C03  115.55  3.000
 T02  O16  C10  C03  115.65  3.000
 T02  H5   C11  C14  107.67  3.000
 T02  H5   C11  C13  108.75  3.000
 T02  C14  C11  C13  110.57  3.000
 T02  H5   C11  C07  107.10  3.000
 T02  C14  C11  C07  109.91  3.000
 T02  C13  C11  C07  112.65  3.000
 T02  H8   C13  H7   107.89  3.000
 T02  H8   C13  H6   107.72  3.000
 T02  H7   C13  H6   107.88  3.000
 T02  H8   C13  C11  111.51  3.000
 T02  H7   C13  C11  111.93  3.000
 T02  H6   C13  C11  109.73  3.000
 T02  H11  C14  H10  107.84  3.000
 T02  H11  C14  H9   107.57  3.000
 T02  H10  C14  H9   107.92  3.000
 T02  H11  C14  C11  112.31  3.000
 T02  H10  C14  C11  110.66  3.000
 T02  H9   C14  C11  110.37  3.000
 T02  H12  C17  C23  120.76  3.000
 T02  H12  C17  C18  119.15  3.000
 T02  C23  C17  C18  120.09  3.000
 T02  H13  C18  C19  120.61  3.000
 T02  H13  C18  C17  119.58  3.000
 T02  C19  C18  C17  119.80  3.000
 T02  CL   C19  C21  119.67  3.000
 T02  C21  C19  C18  120.61  3.000
 T02  CL   C19  C18  119.72  3.000
 T02  H14  C21  C22  119.75  3.000
 T02  H14  C21  C19  120.64  3.000
 T02  C22  C21  C19  119.61  3.000
 T02  H15  C22  C23  120.22  3.000
 T02  H15  C22  C21  119.45  3.000
 T02  C23  C22  C21  120.33  3.000
 T02  N12  C23  C22  119.29  3.000
 T02  N12  C23  C17  121.16  3.000
 T02  C22  C23  C17  119.55  3.000
 T02  C06  N05  C01  115.18  3.000
 T02  N12  N08  C07  108.36  3.000
 T02  N08  N12  C23  119.61  3.000
 T02  N08  N12  C06  110.61  3.000
 T02  C23  N12  C06  129.63  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
 T02  CONST_01  N12  C06  N05  C01   180.00   0.0  0
 T02  CONST_02  C04  C06  N05  C01     0.00   0.0  0
 T02  CONST_03  C04  C03  C02  C01     0.00   0.0  0
 T02  CONST_04  C06  N05  C01  C02     0.00   0.0  0
 T02  CONST_05  C06  C04  C03  C02     0.00   0.0  0
 T02  CONST_06  C07  C04  C03  C02   180.00   0.0  0
 T02  CONST_07  N12  C06  C04  C03   180.00   0.0  0
 T02  CONST_08  N05  C06  C04  C03     0.00   0.0  0
 T02  CONST_09  N08  C07  C04  C03   180.00   0.0  0
 T02  CONST_10  N05  C01  C02  C03     0.00   0.0  0
 T02  CONST_11  C23  N12  C06  C04   180.00   0.0  0
 T02  CONST_12  N08  N12  C06  C04     0.00   0.0  0
 T02  CONST_13  N12  N08  C07  C04     0.00   0.0  0
 T02  CONST_16  C07  N08  N12  C06     0.00   0.0  0
 T02  CONST_17  N08  C07  C04  C06     0.00   0.0  0
 T02  CONST_18  C23  N12  N08  C07   180.00   0.0  0
 T02  CONST_19  N12  C06  C04  C07     0.00   0.0  0
 T02  CONST_20  N05  C06  C04  C07   180.00   0.0  0
 T02  CONST_21  C21  C19  C18  C17     0.00   0.0  0
 T02  CONST_22  C21  C22  C23  C17     0.00   0.0  0
 T02  CONST_24  C22  C21  C19  C18     0.00   0.0  0
 T02  CONST_25  C22  C23  C17  C18     0.00   0.0  0
 T02  CONST_26  N12  C23  C17  C18   180.00   0.0  0
 T02  CONST_27  C23  C22  C21  C19     0.00   0.0  0
 T02  CONST_28  C23  C17  C18  C19     0.00   0.0  0
 T02  CONST_29  N12  C23  C22  C21   180.00   0.0  0
 T02  CONST_31  N05  C06  N12  C23     0.00   0.0  0
 T02  CONST_32  N08  N12  C06  N05   180.00   0.0  0
 T02  CONST_33  C10  C03  C02  C01   180.00   0.0  0
 T02  CONST_34  C11  C07  C04  C03     0.00   0.0  0
 T02  CONST_35  C09  C01  C02  C03   180.00   0.0  0
 T02  CONST_36  C09  C01  N05  C06   180.00   0.0  0
 T02  CONST_37  C11  C07  C04  C06   180.00   0.0  0
 T02  CONST_38  C10  C03  C04  C06   180.00   0.0  0
 T02  CONST_39  C10  C03  C04  C07     0.00   0.0  0
 T02  CONST_40  N12  N08  C07  C11   180.00   0.0  0
 T02  CONST_41  CL   C19  C18  C17   180.00   0.0  0
 T02  CONST_42  CL   C19  C21  C22   180.00   0.0  0
 T02  CONST_43  H1   C02  C03  C04   180.00   0.0  0
 T02  CONST_44  H15  C22  C23  C17   180.00   0.0  0
 T02  CONST_45  H14  C21  C19  C18   180.00   0.0  0
 T02  CONST_46  H12  C17  C18  C19   180.00   0.0  0
 T02  CONST_47  H13  C18  C19  C21   180.00   0.0  0
 T02  Var_01    O16  C10  C03  C02   -58.35  30.0  2
 T02  Var_02    C13  C11  C07  C04   165.57  30.0  2
 T02  Var_03    H2   C09  C01  C02   179.27  30.0  2
 T02  Var_04    H6   C13  C11  C07  -176.98  30.0  3
 T02  Var_05    H9   C14  C11  C07   175.29  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
 T02  plan-1  C17  0.020
 T02  plan-1  C18  0.020
 T02  plan-1  C19  0.020
 T02  plan-1  C21  0.020
 T02  plan-1  C22  0.020
 T02  plan-1  C23  0.020
 T02  plan-1  N12  0.020
 T02  plan-1  H12  0.020
 T02  plan-1  H13  0.020
 T02  plan-1  H14  0.020
 T02  plan-1  H15  0.020
 T02  plan-1  CL   0.020
 T02  plan-2  C01  0.020
 T02  plan-2  C02  0.020
 T02  plan-2  C03  0.020
 T02  plan-2  C04  0.020
 T02  plan-2  C06  0.020
 T02  plan-2  C07  0.020
 T02  plan-2  C09  0.020
 T02  plan-2  C10  0.020
 T02  plan-2  C11  0.020
 T02  plan-2  C23  0.020
 T02  plan-2  N05  0.020
 T02  plan-2  N08  0.020
 T02  plan-2  N12  0.020
 T02  plan-2  H1   0.020
 T02  plan-3  C03  0.020
 T02  plan-3  C10  0.020
 T02  plan-3  O15  0.020
 T02  plan-3  O16  0.020

