# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 30 03:39:45 2022
#   Inital geometry file: a 121 line input string
#   Ligand name: 4-[5-(2-chloro-6-fluoroanilino)-6-methyl-1H-pyrazolo[3,4-b]pyridin-1-yl]-N-(oxetan-3-yl)thiophene-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1nc2n(ncc2cc1Nc3c(F)cccc3Cl)c4csc(c4)C(=O)NC5COC5
#
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
 86C  86C  "4-[5-(2-chloro-6-fluoroanilino)-6-methyl-1H-pyrazolo[3,4-b]pyridin-1-yl]-N-(oxetan-3-yl)thiophene-2-carboxamide"  ligand  48  31  .  2023-02-15  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_86C
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
 86C  C21  C   CH3   0  -0.755  -3.4974  24.3663  -31.6938
 86C  C12  C   CR16  0  -0.409  -7.2500  23.0022  -36.6059
 86C  C13  C   CR6   0   0.531  -6.3689  23.4485  -35.6469
 86C  C14  C   CR15  0  -0.261  -2.6056  31.0170  -32.5901
 86C  C15  C   CR5   0  -0.290  -1.5088  31.4399  -31.8961
 86C  C16  C   CR15  0  -0.521  -1.8033  29.0027  -31.7557
 86C  C17  C   C     0   0.561  -0.9268  32.7804  -31.6828
 86C  C18  C   C     0  -0.201  -1.0981  35.1667  -32.1783
 86C  C19  C   C     0  -0.134  -2.1525  36.2791  -32.1393
 86C  C1   C   CR5   0   0.428  -2.7721  29.6090  -32.5090
 86C  N1   N   NR5   0  -0.497  -3.8217  28.9483  -33.1471
 86C  S1   S   S2    0   0.280  -0.6861  30.1350  -31.1447
 86C  C2   C   CR56  0   0.557  -4.1793  27.6305  -33.0867
 86C  C3   C   CR56  0  -0.139  -5.2856  27.4779  -33.9238
 86C  C4   C   CR15  0  -0.089  -5.5179  28.7801  -34.4386
 86C  C5   C   CR6   0   0.217  -4.1306  25.4660  -32.4846
 86C  C6   C   CR6   0   0.222  -5.2615  25.1872  -33.3103
 86C  C7   C   CR16  0  -0.260  -5.8515  26.2079  -34.0302
 86C  C10  C   CR16  0  -0.235  -8.8004  22.4327  -34.8560
 86C  C11  C   CR16  0  -0.257  -8.4726  22.4842  -36.2005
 86C  C20  C   C     0  -0.129  -0.6330  35.8697  -33.4625
 86C  C8   C   CR6   0   0.203  -6.6574  23.4353  -34.2818
 86C  C9   C   CR6   0  -0.110  -7.9033  22.9203  -33.9175
 86C  N2   N   N     0  -0.240  -4.6432  29.6273  -33.9667
 86C  N3   N   N     0  -0.455  -3.6077  26.6716  -32.3742
 86C  N4   N   NH1   0  -0.763  -5.7147  23.8693  -33.3576
 86C  N5   N   NH1   0  -0.660  -1.5613  33.8161  -32.2613
 86C  O1   O   O     0  -0.479   0.0825  32.8930  -31.0006
 86C  O2   O   O     0  -0.505  -1.4939  36.9828  -33.1977
 86C  CL1  CL  CL    0  -0.105  -8.3322  22.8849  -32.2424
 86C  H16  H   HCH3  0   0.266  -2.6179  24.7373  -31.1736
 86C  H17  H   HCH3  0   0.257  -4.1816  23.9604  -30.9437
 86C  H15  H   HCH3  0   0.259  -3.1999  23.5354  -32.3363
 86C  H6   H   HCR6  0   0.287  -6.9746  23.0409  -37.6516
 86C  H7   H   HCR5  0   0.288  -3.2770  31.6592  -33.1410
 86C  H8   H   HCR5  0   0.317  -1.7014  27.9531  -31.5355
 86C  H10  H   H     0   0.286  -0.3738  35.2417  -31.3709
 86C  H11  H   H     0   0.234  -2.2177  36.8605  -31.2170
 86C  H12  H   H     0   0.217  -3.1569  35.9415  -32.4193
 86C  H1   H   HCR5  0   0.277  -6.2832  29.1094  -35.1247
 86C  H2   H   HCR6  0   0.281  -6.7273  26.0398  -34.6441
 86C  H4   H   HCR6  0   0.285  -9.7516  22.0308  -34.5359
 86C  H5   H   HCR6  0   0.278  -9.1721  22.1173  -36.9385
 86C  H13  H   H     0   0.215  -0.9067  35.3334  -34.3775
 86C  H14  H   H     0   0.231   0.4213  36.1513  -33.5146
 86C  H3   H   HNH1  0   0.399  -5.7320  23.3837  -32.4728
 86C  H9   H   HNH1  0   0.415  -2.3562  33.6394  -32.8564
 86C  F1   F   F     0  -0.299  -5.1756  23.9216  -36.0235

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
 86C  C12  C11  aromatic  1.388  0.020  1.388
 86C  C12  C13  aromatic  1.377  0.020  1.377
 86C  C11  C10  aromatic  1.385  0.020  1.385
 86C  F1   C13  single    1.338  0.020  1.338
 86C  C13  C8   aromatic  1.395  0.020  1.395
 86C  C10  C9   aromatic  1.387  0.020  1.387
 86C  C8   C9   aromatic  1.396  0.020  1.396
 86C  C8   N4   single    1.390  0.020  1.390
 86C  C9   CL1  single    1.730  0.020  1.730
 86C  O2   C20  single    1.432  0.020  1.432
 86C  O2   C19  single    1.432  0.020  1.432
 86C  C20  C18  single    1.536  0.020  1.536
 86C  N4   C6   single    1.394  0.020  1.394
 86C  C7   C3   aromatic  1.394  0.020  1.394
 86C  C7   C6   aromatic  1.381  0.020  1.381
 86C  C19  C18  single    1.533  0.020  1.533
 86C  C4   C3   aromatic  1.419  0.020  1.419
 86C  C4   N2   aromatic  1.306  0.020  1.306
 86C  C3   C2   aromatic  1.396  0.020  1.396
 86C  C6   C5   aromatic  1.428  0.020  1.428
 86C  C18  N5   single    1.430  0.020  1.430
 86C  N2   N1   aromatic  1.344  0.020  1.344
 86C  N5   C17  single    1.345  0.020  1.345
 86C  C2   N1   aromatic  1.367  0.020  1.367
 86C  C2   N3   aromatic  1.324  0.020  1.324
 86C  C5   N3   aromatic  1.319  0.020  1.319
 86C  C5   C21  single    1.495  0.020  1.495
 86C  N1   C1   single    1.395  0.020  1.395
 86C  C14  C1   aromatic  1.420  0.020  1.420
 86C  C14  C15  aromatic  1.365  0.020  1.365
 86C  C17  C15  single    1.477  0.020  1.477
 86C  C17  O1   double    1.223  0.020  1.223
 86C  C1   C16  aromatic  1.369  0.020  1.369
 86C  C15  S1   aromatic  1.716  0.020  1.716
 86C  C16  S1   aromatic  1.704  0.020  1.704
 86C  C21  H16  single    0.970  0.020  1.090
 86C  C21  H17  single    0.970  0.020  1.090
 86C  C21  H15  single    0.970  0.020  1.090
 86C  C12  H6   single    0.930  0.020  1.080
 86C  C14  H7   single    0.930  0.020  1.080
 86C  C16  H8   single    0.930  0.020  1.080
 86C  C18  H10  single    0.970  0.020  1.090
 86C  C19  H11  single    0.970  0.020  1.090
 86C  C19  H12  single    0.970  0.020  1.090
 86C  C4   H1   single    0.930  0.020  1.080
 86C  C7   H2   single    0.930  0.020  1.080
 86C  C10  H4   single    0.930  0.020  1.080
 86C  C11  H5   single    0.930  0.020  1.080
 86C  C20  H13  single    0.970  0.020  1.090
 86C  C20  H14  single    0.970  0.020  1.090
 86C  N4   H3   single    0.890  0.020  1.040
 86C  N5   H9   single    0.860  0.020  1.020

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
 86C  H15  C21  H17  106.97  3.000
 86C  H15  C21  H16  108.72  3.000
 86C  H17  C21  H16  107.74  3.000
 86C  H15  C21  C5   111.34  3.000
 86C  H17  C21  C5   111.77  3.000
 86C  H16  C21  C5   110.16  3.000
 86C  H6   C12  C11  121.31  3.000
 86C  H6   C12  C13  119.92  3.000
 86C  C11  C12  C13  118.76  3.000
 86C  F1   C13  C8   117.59  3.000
 86C  C8   C13  C12  123.11  3.000
 86C  F1   C13  C12  119.30  3.000
 86C  H7   C14  C1   123.07  3.000
 86C  H7   C14  C15  125.07  3.000
 86C  C1   C14  C15  111.86  3.000
 86C  S1   C15  C17  115.98  3.000
 86C  S1   C15  C14  111.85  3.000
 86C  C17  C15  C14  132.16  3.000
 86C  H8   C16  S1   120.80  3.000
 86C  H8   C16  C1   127.66  3.000
 86C  S1   C16  C1   111.54  3.000
 86C  O1   C17  N5   123.92  3.000
 86C  O1   C17  C15  119.28  3.000
 86C  N5   C17  C15  116.80  3.000
 86C  H10  C18  N5   108.90  3.000
 86C  H10  C18  C20  112.80  3.000
 86C  N5   C18  C20  118.79  3.000
 86C  H10  C18  C19  112.91  3.000
 86C  N5   C18  C19  117.64  3.000
 86C  C20  C18  C19   84.11  3.000
 86C  H12  C19  H11  108.96  3.000
 86C  H12  C19  O2   112.59  3.000
 86C  H11  C19  O2   112.96  3.000
 86C  H12  C19  C18  113.60  3.000
 86C  H11  C19  C18  116.66  3.000
 86C  O2   C19  C18   91.23  3.000
 86C  N1   C1   C16  125.07  3.000
 86C  C16  C1   C14  112.80  3.000
 86C  N1   C1   C14  122.13  3.000
 86C  N2   N1   C2   110.73  3.000
 86C  C2   N1   C1   129.30  3.000
 86C  N2   N1   C1   119.96  3.000
 86C  C16  S1   C15   91.95  3.000
 86C  N3   C2   C3   125.85  3.000
 86C  N3   C2   N1   127.51  3.000
 86C  C3   C2   N1   106.64  3.000
 86C  C7   C3   C4   137.86  3.000
 86C  C4   C3   C2   104.29  3.000
 86C  C7   C3   C2   117.84  3.000
 86C  H1   C4   N2   120.45  3.000
 86C  H1   C4   C3   128.79  3.000
 86C  N2   C4   C3   110.76  3.000
 86C  N3   C5   C6   122.75  3.000
 86C  N3   C5   C21  117.40  3.000
 86C  C6   C5   C21  119.84  3.000
 86C  N4   C6   C7   122.81  3.000
 86C  C7   C6   C5   119.69  3.000
 86C  N4   C6   C5   117.49  3.000
 86C  H2   C7   C6   121.75  3.000
 86C  H2   C7   C3   120.86  3.000
 86C  C6   C7   C3   117.38  3.000
 86C  H4   C10  C9   119.97  3.000
 86C  H4   C10  C11  120.63  3.000
 86C  C9   C10  C11  119.40  3.000
 86C  H5   C11  C10  119.80  3.000
 86C  H5   C11  C12  119.81  3.000
 86C  C10  C11  C12  120.39  3.000
 86C  H14  C20  H13  109.12  3.000
 86C  H14  C20  O2   112.87  3.000
 86C  H13  C20  O2   112.63  3.000
 86C  H14  C20  C18  116.75  3.000
 86C  H13  C20  C18  113.50  3.000
 86C  O2   C20  C18   91.10  3.000
 86C  N4   C8   C9   123.15  3.000
 86C  N4   C8   C13  120.50  3.000
 86C  C9   C8   C13  116.31  3.000
 86C  CL1  C9   C8   118.78  3.000
 86C  CL1  C9   C10  119.20  3.000
 86C  C8   C9   C10  122.02  3.000
 86C  C4   N2   N1   107.57  3.000
 86C  C5   N3   C2   116.47  3.000
 86C  H3   N4   C8   114.90  3.000
 86C  H3   N4   C6   115.50  3.000
 86C  C8   N4   C6   122.56  3.000
 86C  H9   N5   C18  117.06  3.000
 86C  H9   N5   C17  119.37  3.000
 86C  C18  N5   C17  123.32  3.000
 86C  C20  O2   C19   91.78  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
 86C  CONST_01  C9   C10  C11  C12     0.00   0.0  0
 86C  CONST_02  C9   C8   C13  C12     0.00   0.0  0
 86C  CONST_03  C10  C11  C12  C13     0.00   0.0  0
 86C  CONST_04  C10  C9   C8   C13     0.00   0.0  0
 86C  CONST_05  N2   N1   C1   C14     0.00   0.0  0
 86C  CONST_06  C2   N1   C1   C14   180.00   0.0  0
 86C  CONST_07  S1   C16  C1   C14     0.00   0.0  0
 86C  CONST_08  C16  S1   C15  C14     0.00   0.0  0
 86C  CONST_09  N1   C1   C14  C15   180.00   0.0  0
 86C  CONST_10  C16  C1   C14  C15     0.00   0.0  0
 86C  CONST_11  C1   C16  S1   C15     0.00   0.0  0
 86C  CONST_12  N2   N1   C1   C16   180.00   0.0  0
 86C  CONST_13  C2   N1   C1   C16     0.00   0.0  0
 86C  CONST_14  C4   N2   N1   C1    180.00   0.0  0
 86C  CONST_15  C3   C2   N1   C1    180.00   0.0  0
 86C  CONST_16  N3   C2   N1   C1      0.00   0.0  0
 86C  CONST_17  S1   C15  C14  C1      0.00   0.0  0
 86C  CONST_18  C3   C4   N2   N1      0.00   0.0  0
 86C  CONST_19  C7   C3   C2   N1    180.00   0.0  0
 86C  CONST_20  C4   C3   C2   N1      0.00   0.0  0
 86C  CONST_21  C5   N3   C2   N1    180.00   0.0  0
 86C  CONST_22  S1   C16  C1   N1    180.00   0.0  0
 86C  CONST_23  C6   C7   C3   C2      0.00   0.0  0
 86C  CONST_24  N2   C4   C3   C2      0.00   0.0  0
 86C  CONST_25  C4   N2   N1   C2      0.00   0.0  0
 86C  CONST_26  C6   C5   N3   C2      0.00   0.0  0
 86C  CONST_27  C5   C6   C7   C3      0.00   0.0  0
 86C  CONST_28  N2   N1   C2   C3      0.00   0.0  0
 86C  CONST_29  C5   N3   C2   C3      0.00   0.0  0
 86C  CONST_30  C6   C7   C3   C4    180.00   0.0  0
 86C  CONST_31  N3   C2   C3   C4    180.00   0.0  0
 86C  CONST_32  N2   C4   C3   C7    180.00   0.0  0
 86C  CONST_33  N3   C2   C3   C7      0.00   0.0  0
 86C  CONST_34  N3   C5   C6   C7      0.00   0.0  0
 86C  CONST_35  C8   C13  C12  C11     0.00   0.0  0
 86C  CONST_36  C8   C9   C10  C11     0.00   0.0  0
 86C  CONST_37  N3   C2   N1   N2    180.00   0.0  0
 86C  CONST_38  C7   C6   C5   C21   180.00   0.0  0
 86C  CONST_39  C2   N3   C5   C21   180.00   0.0  0
 86C  CONST_40  N4   C8   C13  C12   180.00   0.0  0
 86C  CONST_41  CL1  C9   C8   C13   180.00   0.0  0
 86C  CONST_42  C17  C15  S1   C16   180.00   0.0  0
 86C  CONST_43  C1   C14  C15  C17   180.00   0.0  0
 86C  CONST_44  N4   C6   C7   C3    180.00   0.0  0
 86C  CONST_45  N4   C8   C9   C10   180.00   0.0  0
 86C  CONST_46  F1   C13  C12  C11   180.00   0.0  0
 86C  CONST_47  CL1  C9   C10  C11   180.00   0.0  0
 86C  CONST_48  F1   C13  C8   C9    180.00   0.0  0
 86C  CONST_49  N4   C6   C5   N3    180.00   0.0  0
 86C  CONST_50  H4   C10  C11  C12   180.00   0.0  0
 86C  CONST_51  H5   C11  C12  C13   180.00   0.0  0
 86C  CONST_52  H8   C16  C1   C14   180.00   0.0  0
 86C  CONST_53  H8   C16  S1   C15   180.00   0.0  0
 86C  CONST_54  H7   C14  C1   C16   180.00   0.0  0
 86C  CONST_55  H1   C4   N2   N1    180.00   0.0  0
 86C  CONST_56  H7   C14  C1   N1      0.00   0.0  0
 86C  CONST_57  H8   C16  C1   N1      0.00   0.0  0
 86C  CONST_58  H7   C14  C15  S1    180.00   0.0  0
 86C  CONST_59  H2   C7   C3   C2    180.00   0.0  0
 86C  CONST_60  H1   C4   C3   C2    180.00   0.0  0
 86C  CONST_61  H2   C7   C3   C4      0.00   0.0  0
 86C  CONST_62  H2   C7   C6   C5    180.00   0.0  0
 86C  CONST_63  H1   C4   C3   C7      0.00   0.0  0
 86C  CONST_64  H6   C12  C11  C10   180.00   0.0  0
 86C  CONST_65  H6   C12  C13  C8    180.00   0.0  0
 86C  CONST_66  H4   C10  C9   C8    180.00   0.0  0
 86C  CONST_67  H5   C11  C10  C9    180.00   0.0  0
 86C  CONST_68  C18  N5   C17  C15   180.00   0.0  0
 86C  CONST_69  O1   C17  N5   C18     0.00   0.0  0
 86C  CONST_70  H9   N5   C17  C15     0.00   0.0  0
 86C  CONST_71  H9   N5   C17  O1    180.00   0.0  0
 86C  Var_01    C19  O2   C20  C18   -10.38  30.0  1
 86C  Var_02    C6   N4   C8   C13    64.20  30.0  2
 86C  Var_03    C8   N4   C6   C5   -169.23  30.0  1
 86C  Var_04    C9   C8   N4   C6   -118.38  30.0  3
 86C  Var_05    C8   N4   C6   C7     10.20  30.0  1
 86C  Var_06    H13  C20  O2   C19   105.73  30.0  1
 86C  Var_07    H14  C20  O2   C19  -130.16  30.0  1
 86C  Var_08    H11  C19  O2   C20   130.17  30.0  1
 86C  Var_09    H12  C19  O2   C20  -105.87  30.0  1
 86C  Var_10    N5   C17  C15  C14     0.02  30.0  2
 86C  Var_11    O1   C17  C15  C14   179.77  30.0  2
 86C  Var_12    N5   C17  C15  S1   -179.80  30.0  2
 86C  Var_13    O1   C17  C15  S1     -0.05  30.0  2
 86C  Var_14    H3   N4   C8   C13  -146.53  30.0  2
 86C  Var_15    H3   N4   C6   C5     41.66  30.0  1
 86C  Var_16    H16  C21  C5   C6    176.48  30.0  2
 86C  Var_17    H17  C21  C5   C6    -63.78  30.0  2
 86C  Var_18    H15  C21  C5   C6     55.78  30.0  2
 86C  Var_19    H3   N4   C6   C7   -138.90  30.0  1
 86C  Var_20    H3   N4   C8   C9     30.89  30.0  2
 86C  Var_21    H16  C21  C5   N3     -3.90  30.0  2
 86C  Var_22    H17  C21  C5   N3    115.84  30.0  2
 86C  Var_23    H15  C21  C5   N3   -124.60  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 86C  chir_01  C18  C20  C19  N5  negativ

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
 86C  plan-1  C14  0.020
 86C  plan-1  C15  0.020
 86C  plan-1  C16  0.020
 86C  plan-1  C17  0.020
 86C  plan-1  C1   0.020
 86C  plan-1  N1   0.020
 86C  plan-1  S1   0.020
 86C  plan-1  H7   0.020
 86C  plan-1  H8   0.020
 86C  plan-2  C12  0.020
 86C  plan-2  C13  0.020
 86C  plan-2  C10  0.020
 86C  plan-2  C11  0.020
 86C  plan-2  C8   0.020
 86C  plan-2  C9   0.020
 86C  plan-2  N4   0.020
 86C  plan-2  CL1  0.020
 86C  plan-2  H6   0.020
 86C  plan-2  H4   0.020
 86C  plan-2  H5   0.020
 86C  plan-2  F1   0.020
 86C  plan-3  C21  0.020
 86C  plan-3  C1   0.020
 86C  plan-3  N1   0.020
 86C  plan-3  C2   0.020
 86C  plan-3  C3   0.020
 86C  plan-3  C4   0.020
 86C  plan-3  C5   0.020
 86C  plan-3  C6   0.020
 86C  plan-3  C7   0.020
 86C  plan-3  N2   0.020
 86C  plan-3  N3   0.020
 86C  plan-3  N4   0.020
 86C  plan-3  H1   0.020
 86C  plan-3  H2   0.020
 86C  plan-4  C15  0.020
 86C  plan-4  C17  0.020
 86C  plan-4  C18  0.020
 86C  plan-4  N5   0.020
 86C  plan-4  O1   0.020
 86C  plan-4  H9   0.020

