# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 08:40:43 2020
#   Inital geometry file: a 116 line input string
#   Ligand name: 4-chloro-N-cyclopropyl-3-{[1-(2,6-difluorophenyl)-1H-pyrazolo[3,4-d]pyridazin-4-yl]amino}benzamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Fc1cccc(F)c1n2ncc3c(Nc4cc(ccc4Cl)C(=O)NC5CC5)nncc23
#
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
 P66  P66  4-chloro-N-cyclopropyl-3-{[1-(2,6-difluorophenyl)-1H-pyrazolo[3,4-d]pyridazin-4-yl]amino}benzamide  ligand  46  31  .  2022-09-22  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_P66
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
 P66  N1    N   N     0  -0.361  -0.0624  -0.9831  -0.0653
 P66  N3    N   NR5   0  -0.477   3.7591   0.3136  -0.0541
 P66  C4    C   CR6   0  -0.054   5.0260  -0.2909  -0.0711
 P66  C5    C   CR6   0   0.555   5.4525  -1.0207  -1.1724
 P66  C6    C   CR6   0   0.561   5.8882  -0.1821   1.0119
 P66  C7    C   CR6   0   0.487   0.2477   0.2978  -0.0456
 P66  C8    C   CR16  0  -0.425   6.6862  -1.6357  -1.2074
 P66  C10   C   CR16  0  -0.429   7.1359  -0.7688   1.0081
 P66  C13   C   CR16  0  -0.350  -2.8057  -0.0477   0.0043
 P66  C15   C   CR16  0  -0.325  -4.9146   1.1175   0.0850
 P66  C17   C   CR6   0  -0.167  -2.8550   2.3422   0.0378
 P66  C20   C   CH2   0  -0.512  -8.3144  -2.5649   0.5113
 P66  C21   C   CH2   0  -0.481  -7.4910  -3.1663  -0.5859
 P66  C19   C   CH1   0  -0.080  -6.8322  -2.6767   0.6633
 P66  N5    N   NH1   0  -0.658  -6.0761  -1.4687   0.6145
 P66  O1    O   O     0  -0.476  -4.3198  -2.3825  -0.4655
 P66  C14   C   CR6   0  -0.010  -4.1939  -0.0702   0.0580
 P66  C16   C   CR16  0  -0.192  -4.2357   2.3244   0.0712
 P66  CL1   CL  CL    0  -0.105  -2.0512   3.8787   0.0342
 P66  C12   C   CR6   0   0.483  -2.1017   1.1565   0.0053
 P66  N4    N   NH1   0  -0.780  -0.7204   1.2565  -0.0246
 P66  N6    N   N     0  -0.232   0.8799  -1.9255  -0.0782
 P66  C11   C   CR16  0  -0.108   2.1523  -1.6440  -0.0799
 P66  C1    C   CR56  0   0.424   2.5552  -0.2984  -0.0658
 P66  C2    C   CR56  0  -0.180   1.6024   0.7056  -0.0433
 P66  C3    C   CR15  0  -0.082   2.3500   1.9104  -0.0175
 P66  N2    N   N     0  -0.218   3.6304   1.6512  -0.0259
 P66  F1    F   F     0  -0.289   4.6223  -1.1233  -2.2097
 P66  C9    C   CR16  0  -0.220   7.5224  -1.4969  -0.1088
 P66  F2    F   F     0  -0.286   5.4771   0.5079   2.0727
 P66  H8    H   HCR6  0   0.299   6.9881  -2.2029  -2.0771
 P66  H10   H   HCR6  0   0.299   7.7890  -0.6663   1.8636
 P66  H13   H   HCR6  0   0.304  -2.2522  -0.9716  -0.0332
 P66  H15   H   HCR6  0   0.269  -5.9962   1.1282   0.0896
 P66  H20A  H   HCH2  0   0.260  -8.9324  -3.2148   1.1162
 P66  H21   H   HCH2  0   0.256  -7.5357  -4.2358  -0.7431
 P66  H21A  H   HCH2  0   0.256  -7.3496  -2.5828  -1.4864
 P66  H19   H   HCH1  0   0.269  -6.4583  -3.4294   1.3511
 P66  HN5   H   HNH1  0   0.408  -6.3923  -0.6951   1.1772
 P66  H16   H   HCR6  0   0.289  -4.7840   3.2561   0.0822
 P66  HN4   H   HNH1  0   0.408  -0.3686   2.2016  -0.0255
 P66  H11   H   HCR6  0   0.295   2.8469  -2.4740  -0.0851
 P66  H3    H   HCR5  0   0.289   2.0050   2.9328   0.0046
 P66  H9    H   HCR6  0   0.292   8.4949  -1.9688  -0.1213
 P66  C18   C   C     0   0.537  -4.8597  -1.4116   0.0419
 P66  H20   H   HCH2  0   0.258  -8.7281  -1.5776   0.3466

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
 P66  C7   N1    aromatic  1.318  0.020  1.318
 P66  N1   N6    aromatic  1.333  0.020  1.333
 P66  N2   N3    aromatic  1.344  0.020  1.344
 P66  N3   C1    aromatic  1.351  0.020  1.351
 P66  N3   C4    single    1.404  0.020  1.404
 P66  C5   C4    aromatic  1.388  0.020  1.388
 P66  C4   C6    aromatic  1.389  0.020  1.389
 P66  F1   C5    single    1.333  0.020  1.333
 P66  C5   C8    aromatic  1.379  0.020  1.379
 P66  C6   C10   aromatic  1.379  0.020  1.379
 P66  C6   F2    single    1.331  0.020  1.331
 P66  N4   C7    single    1.363  0.020  1.363
 P66  C7   C2    aromatic  1.415  0.020  1.415
 P66  C8   C9    aromatic  1.388  0.020  1.388
 P66  C8   H8    single    0.930  0.020  1.080
 P66  C9   C10   aromatic  1.388  0.020  1.388
 P66  C10  H10   single    0.930  0.020  1.080
 P66  C14  C13   aromatic  1.389  0.020  1.389
 P66  C13  C12   aromatic  1.395  0.020  1.395
 P66  C13  H13   single    0.930  0.020  1.080
 P66  C14  C15   aromatic  1.390  0.020  1.390
 P66  C15  C16   aromatic  1.385  0.020  1.385
 P66  C15  H15   single    0.930  0.020  1.080
 P66  C12  C17   aromatic  1.405  0.020  1.405
 P66  C16  C17   aromatic  1.381  0.020  1.381
 P66  C17  CL1   single    1.734  0.020  1.734
 P66  C20  C21   single    1.498  0.020  1.498
 P66  C20  C19   single    1.494  0.020  1.494
 P66  C20  H20   single    0.970  0.020  1.090
 P66  C20  H20A  single    0.970  0.020  1.090
 P66  C21  C19   single    1.495  0.020  1.495
 P66  C21  H21   single    0.970  0.020  1.090
 P66  C21  H21A  single    0.970  0.020  1.090
 P66  C19  N5    single    1.426  0.020  1.426
 P66  C19  H19   single    0.970  0.020  1.090
 P66  N5   C18   single    1.346  0.020  1.346
 P66  N5   HN5   single    0.860  0.020  1.020
 P66  O1   C18   double    1.221  0.020  1.221
 P66  C18  C14   single    1.498  0.020  1.498
 P66  C16  H16   single    0.930  0.020  1.080
 P66  C12  N4    single    1.385  0.020  1.385
 P66  N4   HN4   single    0.860  0.020  1.020
 P66  N6   C11   aromatic  1.303  0.020  1.303
 P66  C1   C11   aromatic  1.405  0.020  1.405
 P66  C11  H11   single    0.930  0.020  1.080
 P66  C2   C1    aromatic  1.384  0.020  1.384
 P66  C3   C2    aromatic  1.418  0.020  1.418
 P66  C3   N2    aromatic  1.306  0.020  1.306
 P66  C3   H3    single    0.930  0.020  1.080
 P66  C9   H9    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
 P66  N6    N1   C7   121.40  3.000
 P66  N2    N3   C1   111.46  3.000
 P66  C1    N3   C4   127.53  3.000
 P66  N2    N3   C4   121.01  3.000
 P66  C6    C4   C5   117.98  3.000
 P66  C6    C4   N3   121.14  3.000
 P66  C5    C4   N3   120.88  3.000
 P66  F1    C5   C8   120.22  3.000
 P66  C8    C5   C4   121.97  3.000
 P66  F1    C5   C4   117.81  3.000
 P66  F2    C6   C10  120.16  3.000
 P66  F2    C6   C4   118.07  3.000
 P66  C10   C6   C4   121.76  3.000
 P66  C2    C7   N4   118.52  3.000
 P66  C2    C7   N1   120.36  3.000
 P66  N4    C7   N1   121.11  3.000
 P66  H8    C8   C9   121.40  3.000
 P66  H8    C8   C5   120.27  3.000
 P66  C9    C8   C5   118.32  3.000
 P66  H10   C10  C9   121.21  3.000
 P66  H10   C10  C6   120.28  3.000
 P66  C9    C10  C6   118.51  3.000
 P66  H13   C13  C12  118.75  3.000
 P66  H13   C13  C14  120.04  3.000
 P66  C12   C13  C14  121.21  3.000
 P66  H15   C15  C16  118.79  3.000
 P66  H15   C15  C14  121.82  3.000
 P66  C16   C15  C14  119.37  3.000
 P66  C12   C17  CL1  119.94  3.000
 P66  CL1   C17  C16  118.35  3.000
 P66  C12   C17  C16  121.71  3.000
 P66  H20A  C20  H20  114.49  3.000
 P66  H20A  C20  C19  117.70  3.000
 P66  H20   C20  C19  117.55  3.000
 P66  H20A  C20  C21  118.85  3.000
 P66  H20   C20  C21  117.68  3.000
 P66  C19   C20  C21   59.94  3.000
 P66  H21A  C21  H21  114.68  3.000
 P66  H21A  C21  C19  117.46  3.000
 P66  H21   C21  C19  117.60  3.000
 P66  H21A  C21  C20  117.70  3.000
 P66  H21   C21  C20  118.72  3.000
 P66  C19   C21  C20   59.91  3.000
 P66  H19   C19  N5   115.23  3.000
 P66  H19   C19  C21  117.00  3.000
 P66  N5    C19  C21  118.85  3.000
 P66  H19   C19  C20  117.25  3.000
 P66  N5    C19  C20  117.33  3.000
 P66  C21   C19  C20   60.15  3.000
 P66  HN5   N5   C18  119.26  3.000
 P66  HN5   N5   C19  117.71  3.000
 P66  C18   N5   C19  122.00  3.000
 P66  C18   C14  C15  122.36  3.000
 P66  C18   C14  C13  117.28  3.000
 P66  C15   C14  C13  120.34  3.000
 P66  H16   C16  C17  119.75  3.000
 P66  H16   C16  C15  120.15  3.000
 P66  C17   C16  C15  120.10  3.000
 P66  N4    C12  C17  118.31  3.000
 P66  N4    C12  C13  124.44  3.000
 P66  C17   C12  C13  117.25  3.000
 P66  HN4   N4   C12  114.56  3.000
 P66  HN4   N4   C7   114.29  3.000
 P66  C12   N4   C7   131.15  3.000
 P66  C11   N6   N1   122.52  3.000
 P66  H11   C11  C1   123.41  3.000
 P66  H11   C11  N6   117.45  3.000
 P66  C1    C11  N6   119.14  3.000
 P66  C2    C1   C11  119.84  3.000
 P66  C2    C1   N3   106.54  3.000
 P66  C11   C1   N3   133.62  3.000
 P66  C3    C2   C1   104.70  3.000
 P66  C3    C2   C7   138.56  3.000
 P66  C1    C2   C7   116.74  3.000
 P66  H3    C3   N2   120.09  3.000
 P66  H3    C3   C2   129.54  3.000
 P66  N2    C3   C2   110.36  3.000
 P66  C3    N2   N3   106.94  3.000
 P66  H9    C9   C10  119.26  3.000
 P66  H9    C9   C8   119.30  3.000
 P66  C10   C9   C8   121.45  3.000
 P66  C14   C18  O1   121.33  3.000
 P66  C14   C18  N5   115.81  3.000
 P66  O1    C18  N5   122.86  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
 P66  CONST_01  C1   C2   C7   N1      0.00   0.0  0
 P66  CONST_02  C3   C2   C7   N1    180.00   0.0  0
 P66  CONST_03  C1   C11  N6   N1      0.00   0.0  0
 P66  CONST_04  C2   C3   N2   N3      0.00   0.0  0
 P66  CONST_05  N6   C11  C1   N3    180.00   0.0  0
 P66  CONST_06  C7   C2   C1   N3    180.00   0.0  0
 P66  CONST_07  C3   C2   C1   N3      0.00   0.0  0
 P66  CONST_08  C8   C5   C4   N3    180.00   0.0  0
 P66  CONST_09  C10  C6   C4   N3    180.00   0.0  0
 P66  CONST_10  C3   N2   N3   C4    180.00   0.0  0
 P66  CONST_11  C11  C1   N3   C4      0.00   0.0  0
 P66  CONST_12  C2   C1   N3   C4    180.00   0.0  0
 P66  CONST_13  C9   C8   C5   C4      0.00   0.0  0
 P66  CONST_14  C9   C10  C6   C4      0.00   0.0  0
 P66  CONST_17  C10  C6   C4   C5      0.00   0.0  0
 P66  CONST_18  C10  C9   C8   C5      0.00   0.0  0
 P66  CONST_21  C8   C5   C4   C6      0.00   0.0  0
 P66  CONST_22  C8   C9   C10  C6      0.00   0.0  0
 P66  CONST_23  C11  N6   N1   C7      0.00   0.0  0
 P66  CONST_24  C11  C1   C2   C7      0.00   0.0  0
 P66  CONST_25  N2   C3   C2   C7    180.00   0.0  0
 P66  CONST_26  C16  C15  C14  C13     0.00   0.0  0
 P66  CONST_27  C16  C17  C12  C13     0.00   0.0  0
 P66  CONST_28  C12  C13  C14  C15     0.00   0.0  0
 P66  CONST_29  C12  C17  C16  C15     0.00   0.0  0
 P66  CONST_30  C14  C13  C12  C17     0.00   0.0  0
 P66  CONST_31  C14  C15  C16  C17     0.00   0.0  0
 P66  CONST_32  C2   C7   N1   N6      0.00   0.0  0
 P66  CONST_33  C2   C1   C11  N6      0.00   0.0  0
 P66  CONST_34  N2   N3   C1   C11   180.00   0.0  0
 P66  CONST_35  C3   C2   C1   C11   180.00   0.0  0
 P66  CONST_36  C3   N2   N3   C1      0.00   0.0  0
 P66  CONST_37  N2   C3   C2   C1      0.00   0.0  0
 P66  CONST_38  N2   N3   C1   C2      0.00   0.0  0
 P66  CONST_39  F1   C5   C4   N3      0.00   0.0  0
 P66  CONST_40  F2   C6   C4   N3      0.00   0.0  0
 P66  CONST_41  F2   C6   C4   C5    180.00   0.0  0
 P66  CONST_42  F1   C5   C4   C6    180.00   0.0  0
 P66  CONST_43  CL1  C17  C12  C13   180.00   0.0  0
 P66  CONST_44  CL1  C17  C16  C15   180.00   0.0  0
 P66  CONST_45  C12  C13  C14  C18   180.00   0.0  0
 P66  CONST_46  C16  C15  C14  C18   180.00   0.0  0
 P66  CONST_47  N4   C12  C13  C14   180.00   0.0  0
 P66  CONST_48  N4   C12  C17  C16   180.00   0.0  0
 P66  CONST_49  N6   N1   C7   N4    180.00   0.0  0
 P66  CONST_50  C1   C2   C7   N4    180.00   0.0  0
 P66  CONST_51  C3   C2   C7   N4      0.00   0.0  0
 P66  CONST_52  C9   C8   C5   F1    180.00   0.0  0
 P66  CONST_53  F2   C6   C10  C9    180.00   0.0  0
 P66  CONST_54  H11  C11  N6   N1    180.00   0.0  0
 P66  CONST_55  H3   C3   N2   N3    180.00   0.0  0
 P66  CONST_56  H8   C8   C5   C4    180.00   0.0  0
 P66  CONST_57  H10  C10  C6   C4    180.00   0.0  0
 P66  CONST_58  H9   C9   C8   C5    180.00   0.0  0
 P66  CONST_59  H15  C15  C14  C13   180.00   0.0  0
 P66  CONST_60  H13  C13  C14  C15   180.00   0.0  0
 P66  CONST_61  H16  C16  C15  C14   180.00   0.0  0
 P66  CONST_62  C14  C18  N5   C19   180.00   0.0  0
 P66  CONST_63  O1   C18  N5   C19     0.00   0.0  0
 P66  CONST_64  HN5  N5   C18  C14     0.00   0.0  0
 P66  Var_01    C12  N4   C7   N1      1.34  30.0  2
 P66  Var_02    C13  C12  N4   C7     -0.80  30.0  2
 P66  Var_03    N5   C19  C21  C20  -106.75  30.0  1
 P66  Var_04    N5   C18  C14  C13   154.26  30.0  2
 P66  Var_05    C18  N5   C19  C20  -143.67  30.0  3

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
 P66  chir_01  C19  C20  C21  N5  both

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
 P66  plan-1  N3   0.020
 P66  plan-1  C4   0.020
 P66  plan-1  C5   0.020
 P66  plan-1  C6   0.020
 P66  plan-1  C8   0.020
 P66  plan-1  C10  0.020
 P66  plan-1  F1   0.020
 P66  plan-1  C9   0.020
 P66  plan-1  F2   0.020
 P66  plan-1  H8   0.020
 P66  plan-1  H10  0.020
 P66  plan-1  H9   0.020
 P66  plan-2  C13  0.020
 P66  plan-2  C15  0.020
 P66  plan-2  C17  0.020
 P66  plan-2  C14  0.020
 P66  plan-2  C16  0.020
 P66  plan-2  CL1  0.020
 P66  plan-2  C12  0.020
 P66  plan-2  N4   0.020
 P66  plan-2  H13  0.020
 P66  plan-2  H15  0.020
 P66  plan-2  H16  0.020
 P66  plan-2  C18  0.020
 P66  plan-3  N1   0.020
 P66  plan-3  N3   0.020
 P66  plan-3  C4   0.020
 P66  plan-3  C7   0.020
 P66  plan-3  N4   0.020
 P66  plan-3  N6   0.020
 P66  plan-3  C11  0.020
 P66  plan-3  C1   0.020
 P66  plan-3  C2   0.020
 P66  plan-3  C3   0.020
 P66  plan-3  N2   0.020
 P66  plan-3  H11  0.020
 P66  plan-3  H3   0.020
 P66  plan-4  C19  0.020
 P66  plan-4  N5   0.020
 P66  plan-4  O1   0.020
 P66  plan-4  C14  0.020
 P66  plan-4  HN5  0.020
 P66  plan-4  C18  0.020

