# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 05:20:00 2020
#   Inital geometry file: a 124 line input string
#   Ligand name: [4-({4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]quinazolin-2-yl}amino)phenyl]acetonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: N#CCc1ccc(Nc2nc(Nc3cc([nH]n3)C4CC4)c5ccccc5n2)cc1
#
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
 IHH  IHH  '[4-({4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]quinazolin-2-yl}amino)phenyl]acetonitrile'  ligand  48  29  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_IHH
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
 IHH  C1    C  CR16  0  -0.263   0.8681  -5.2748   0.1625
 IHH  C2    C  CR16  0  -0.244  -0.5331  -5.2563   0.2393
 IHH  C3    C  CR16  0  -0.320  -1.2170  -4.0667   0.2626
 IHH  C4    C  CR16  0  -0.309   1.5644  -4.0918   0.1105
 IHH  C5    C  CR66  0  -0.056   0.8843  -2.8629   0.1328
 IHH  C6    C  CR66  0   0.287  -0.5233  -2.8411   0.2108
 IHH  C8    C  CR6   0   0.595  -0.5422  -0.5798   0.1898
 IHH  C10   C  CR6   0   0.548   1.5122  -1.5637   0.0809
 IHH  C12   C  CR6   0   0.357  -2.5013   0.9836   0.2784
 IHH  C13   C  CR16  0  -0.344  -2.7930   2.3540   0.3182
 IHH  C14   C  CR16  0  -0.270  -4.0976   2.8022   0.3791
 IHH  C15   C  CR6   0   0.090  -5.1596   1.9029   0.4022
 IHH  C28   C  CH2   0  -0.475   5.8635   3.7009  -1.0486
 IHH  C29   C  CH2   0  -0.475   6.0794   3.6755   0.4269
 IHH  C27   C  CH1   0  -0.371   4.8026   3.1235  -0.1490
 IHH  C24   C  CR5   0   0.493   4.5177   1.6833  -0.1351
 IHH  C23   C  CR15  0  -0.538   3.3041   1.0339  -0.0193
 IHH  N25   N  NR15  0  -0.520   5.4471   0.7200  -0.2446
 IHH  N26   N  N     0  -0.325   4.9381  -0.5139  -0.2108
 IHH  C22   C  CR5   0   0.456   3.6384  -0.3334  -0.0743
 IHH  N21   N  NH1   0  -0.756   2.8533  -1.4764  -0.0017
 IHH  N9    N  N     0  -0.531   0.8020  -0.4660   0.1123
 IHH  N7    N  N     0  -0.531  -1.2341  -1.6850   0.2379
 IHH  N11   N  NH1   0  -0.777  -1.1605   0.6368   0.2164
 IHH  C17   C  CR16  0  -0.303  -3.5650   0.0785   0.3025
 IHH  C16   C  CR16  0  -0.279  -4.8702   0.5471   0.3617
 IHH  C18   C  CH2   0  -0.628  -6.5868   2.3915   0.4558
 IHH  C19   C  CSP   0   0.138  -7.0724   2.7666  -0.8660
 IHH  N20   N  NS    0  -0.277  -7.4439   3.0581  -1.9152
 IHH  H1    H  HCR6  0   0.265   1.3993  -6.2165   0.1445
 IHH  H2    H  HCR6  0   0.266  -1.0793  -6.1898   0.2814
 IHH  H3    H  HCR6  0   0.261  -2.2974  -4.0456   0.3213
 IHH  H4    H  HCR6  0   0.256   2.6447  -4.1383   0.0538
 IHH  H13   H  HCR6  0   0.271  -1.9848   3.0759   0.3057
 IHH  H14   H  HCR6  0   0.261  -4.2844   3.8689   0.4124
 IHH  H28A  H  HCH2  0   0.258   6.4342   3.0157  -1.6633
 IHH  H29   H  HCH2  0   0.257   6.8001   2.9744   0.8295
 IHH  H29A  H  HCH2  0   0.267   6.0139   4.6054   0.9762
 IHH  H27   H  HCH1  0   0.277   3.9151   3.7283  -0.0120
 IHH  H23   H  HCR5  0   0.275   2.3351   1.4828   0.0886
 IHH  HN11  H  HNH1  0   0.409  -0.5137   1.4095   0.1815
 IHH  H17   H  HCR6  0   0.290  -3.3778  -0.9823   0.2780
 IHH  H16   H  HCR6  0   0.258  -5.6772  -0.1756   0.3784
 IHH  H18   H  HCH2  0   0.328  -7.2518   1.6217   0.8511
 IHH  H18A  H  HCH2  0   0.328  -6.6858   3.2605   1.1095
 IHH  H181  H  HNR5  0   0.419   6.4436   0.8294  -0.3431
 IHH  H19   H  HNH1  0   0.419   3.3833  -2.3324  -0.0392
 IHH  H28   H  HCH2  0   0.266   5.6462   4.6488  -1.5226

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
 IHH  C1   C2    aromatic  1.403  0.020  1.403
 IHH  C1   C4    aromatic  1.374  0.020  1.374
 IHH  C1   H1    single    0.930  0.020  1.080
 IHH  C2   C3    aromatic  1.372  0.020  1.372
 IHH  C2   H2    single    0.930  0.020  1.080
 IHH  C3   C6    aromatic  1.409  0.020  1.409
 IHH  C3   H3    single    0.930  0.020  1.080
 IHH  C4   C5    aromatic  1.405  0.020  1.405
 IHH  C4   H4    single    0.930  0.020  1.080
 IHH  C5   C6    aromatic  1.410  0.020  1.410
 IHH  C5   C10   aromatic  1.444  0.020  1.444
 IHH  C6   N7    aromatic  1.357  0.020  1.357
 IHH  C8   N9    aromatic  1.351  0.020  1.351
 IHH  C8   N7    aromatic  1.305  0.020  1.305
 IHH  C8   N11   single    1.365  0.020  1.365
 IHH  C10  N21   single    1.347  0.020  1.347
 IHH  C10  N9    aromatic  1.308  0.020  1.308
 IHH  C12  C13   aromatic  1.402  0.020  1.402
 IHH  C12  N11   single    1.386  0.020  1.386
 IHH  C12  C17   aromatic  1.397  0.020  1.397
 IHH  C13  C14   aromatic  1.381  0.020  1.381
 IHH  C13  H13   single    0.930  0.020  1.080
 IHH  C14  C15   aromatic  1.392  0.020  1.392
 IHH  C14  H14   single    0.930  0.020  1.080
 IHH  C15  C16   aromatic  1.387  0.020  1.387
 IHH  C15  C18   single    1.509  0.020  1.509
 IHH  C28  C29   single    1.491  0.020  1.491
 IHH  C28  C27   single    1.506  0.020  1.506
 IHH  C28  H28   single    0.970  0.020  1.090
 IHH  C28  H28A  single    0.970  0.020  1.090
 IHH  C29  C27   single    1.505  0.020  1.505
 IHH  C29  H29   single    0.970  0.020  1.090
 IHH  C29  H29A  single    0.970  0.020  1.090
 IHH  C27  C24   single    1.468  0.020  1.468
 IHH  C27  H27   single    0.970  0.020  1.090
 IHH  C24  C23   aromatic  1.381  0.020  1.381
 IHH  C24  N25   aromatic  1.343  0.020  1.343
 IHH  C23  C22   aromatic  1.409  0.020  1.409
 IHH  C23  H23   single    0.930  0.020  1.080
 IHH  N25  N26   aromatic  1.335  0.020  1.335
 IHH  N26  C22   aromatic  1.319  0.020  1.319
 IHH  C22  N21   single    1.388  0.020  1.388
 IHH  N11  HN11  single    0.860  0.020  1.020
 IHH  C17  C16   aromatic  1.388  0.020  1.388
 IHH  C17  H17   single    0.930  0.020  1.080
 IHH  C16  H16   single    0.930  0.020  1.080
 IHH  C18  C19   single    1.457  0.020  1.457
 IHH  C18  H18   single    0.970  0.020  1.090
 IHH  C18  H18A  single    0.970  0.020  1.090
 IHH  C19  N20   triple    1.151  0.020  1.151
 IHH  N25  H181  single    0.860  0.020  1.020
 IHH  N21  H19   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
 IHH  H1    C1   C4   120.03  3.000
 IHH  H1    C1   C2   120.19  3.000
 IHH  C4    C1   C2   119.79  3.000
 IHH  H2    C2   C3   119.70  3.000
 IHH  H2    C2   C1   119.64  3.000
 IHH  C3    C2   C1   120.66  3.000
 IHH  H3    C3   C6   118.45  3.000
 IHH  H3    C3   C2   121.02  3.000
 IHH  C6    C3   C2   120.53  3.000
 IHH  H4    C4   C5   121.42  3.000
 IHH  H4    C4   C1   118.08  3.000
 IHH  C5    C4   C1   120.49  3.000
 IHH  C10   C5   C6   114.98  3.000
 IHH  C10   C5   C4   125.18  3.000
 IHH  C6    C5   C4   119.85  3.000
 IHH  N7    C6   C5   122.48  3.000
 IHH  N7    C6   C3   118.83  3.000
 IHH  C5    C6   C3   118.69  3.000
 IHH  N11   C8   N7   120.93  3.000
 IHH  N11   C8   N9   112.13  3.000
 IHH  N7    C8   N9   126.94  3.000
 IHH  N9    C10  N21  119.21  3.000
 IHH  N9    C10  C5   121.21  3.000
 IHH  N21   C10  C5   119.58  3.000
 IHH  C17   C12  N11  125.11  3.000
 IHH  C17   C12  C13  118.33  3.000
 IHH  N11   C12  C13  116.56  3.000
 IHH  H13   C13  C14  119.27  3.000
 IHH  H13   C13  C12  119.72  3.000
 IHH  C14   C13  C12  121.01  3.000
 IHH  H14   C14  C15  120.26  3.000
 IHH  H14   C14  C13  118.94  3.000
 IHH  C15   C14  C13  120.80  3.000
 IHH  C18   C15  C16  120.98  3.000
 IHH  C18   C15  C14  120.85  3.000
 IHH  C16   C15  C14  118.16  3.000
 IHH  H28A  C28  H28  114.30  3.000
 IHH  H28A  C28  C27  117.88  3.000
 IHH  H28   C28  C27  117.13  3.000
 IHH  H28A  C28  C29  118.33  3.000
 IHH  H28   C28  C29  118.51  3.000
 IHH  C27   C28  C29   60.29  3.000
 IHH  H29A  C29  H29  114.07  3.000
 IHH  H29A  C29  C27  117.25  3.000
 IHH  H29   C29  C27  117.98  3.000
 IHH  H29A  C29  C28  118.61  3.000
 IHH  H29   C29  C28  118.36  3.000
 IHH  C27   C29  C28   60.34  3.000
 IHH  H27   C27  C24  112.81  3.000
 IHH  H27   C27  C29  116.23  3.000
 IHH  C24   C27  C29  121.37  3.000
 IHH  H27   C27  C28  116.03  3.000
 IHH  C24   C27  C28  121.22  3.000
 IHH  C29   C27  C28   59.37  3.000
 IHH  N25   C24  C23  106.12  3.000
 IHH  N25   C24  C27  124.65  3.000
 IHH  C23   C24  C27  129.23  3.000
 IHH  H23   C23  C22  128.62  3.000
 IHH  H23   C23  C24  127.23  3.000
 IHH  C22   C23  C24  104.15  3.000
 IHH  H181  N25  N26  118.68  3.000
 IHH  H181  N25  C24  127.92  3.000
 IHH  N26   N25  C24  113.39  3.000
 IHH  C22   N26  N25  104.58  3.000
 IHH  N21   C22  N26  116.73  3.000
 IHH  N21   C22  C23  131.51  3.000
 IHH  N26   C22  C23  111.76  3.000
 IHH  H19   N21  C22  113.58  3.000
 IHH  H19   N21  C10  118.10  3.000
 IHH  C22   N21  C10  128.30  3.000
 IHH  C10   N9   C8   118.10  3.000
 IHH  C8    N7   C6   116.29  3.000
 IHH  HN11  N11  C12  115.48  3.000
 IHH  HN11  N11  C8   113.07  3.000
 IHH  C12   N11  C8   131.45  3.000
 IHH  H17   C17  C16  119.78  3.000
 IHH  H17   C17  C12  120.35  3.000
 IHH  C16   C17  C12  119.87  3.000
 IHH  H16   C16  C17  118.41  3.000
 IHH  H16   C16  C15  119.75  3.000
 IHH  C17   C16  C15  121.84  3.000
 IHH  H18A  C18  H18  106.82  3.000
 IHH  H18A  C18  C19  107.93  3.000
 IHH  H18   C18  C19  107.88  3.000
 IHH  H18A  C18  C15  111.39  3.000
 IHH  H18   C18  C15  111.14  3.000
 IHH  C19   C18  C15  111.48  3.000
 IHH  N20   C19  C18  180.00  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
 IHH  CONST_01  C6    C3   C2   C1      0.00   0.0  0
 IHH  CONST_02  C6    C5   C4   C1      0.00   0.0  0
 IHH  CONST_03  C10   C5   C4   C1    180.00   0.0  0
 IHH  CONST_04  C5    C4   C1   C2      0.00   0.0  0
 IHH  CONST_05  C5    C6   C3   C2      0.00   0.0  0
 IHH  CONST_06  N7    C6   C3   C2    180.00   0.0  0
 IHH  CONST_07  C4    C1   C2   C3      0.00   0.0  0
 IHH  CONST_08  C4    C5   C6   C3      0.00   0.0  0
 IHH  CONST_09  C10   C5   C6   C3    180.00   0.0  0
 IHH  CONST_10  C8    N7   C6   C3    180.00   0.0  0
 IHH  CONST_11  N7    C6   C5   C4    180.00   0.0  0
 IHH  CONST_12  N9    C10  C5   C4    180.00   0.0  0
 IHH  CONST_13  C8    N7   C6   C5      0.00   0.0  0
 IHH  CONST_14  C8    N9   C10  C5      0.00   0.0  0
 IHH  CONST_15  N9    C10  C5   C6      0.00   0.0  0
 IHH  CONST_16  N9    C8   N7   C6      0.00   0.0  0
 IHH  CONST_17  N7    C6   C5   C10     0.00   0.0  0
 IHH  CONST_18  N7    C8   N9   C10     0.00   0.0  0
 IHH  CONST_19  C15   C14  C13  C12     0.00   0.0  0
 IHH  CONST_20  C15   C16  C17  C12     0.00   0.0  0
 IHH  CONST_21  C16   C17  C12  C13     0.00   0.0  0
 IHH  CONST_22  C16   C15  C14  C13     0.00   0.0  0
 IHH  CONST_23  C17   C12  C13  C14     0.00   0.0  0
 IHH  CONST_24  C17   C16  C15  C14     0.00   0.0  0
 IHH  CONST_25  N26   C22  C23  C24     0.00   0.0  0
 IHH  CONST_26  C22   N26  N25  C24     0.00   0.0  0
 IHH  CONST_27  N26   N25  C24  C23     0.00   0.0  0
 IHH  CONST_28  N25   N26  C22  C23     0.00   0.0  0
 IHH  CONST_29  C22   C23  C24  N25     0.00   0.0  0
 IHH  CONST_30  C22   C23  C24  C27   180.00   0.0  0
 IHH  CONST_31  N26   N25  C24  C27   180.00   0.0  0
 IHH  CONST_32  N21   C10  C5   C4      0.00   0.0  0
 IHH  CONST_33  N21   C10  C5   C6    180.00   0.0  0
 IHH  CONST_34  N11   C8   N7   C6    180.00   0.0  0
 IHH  CONST_35  N21   C10  N9   C8    180.00   0.0  0
 IHH  CONST_36  N11   C8   N9   C10   180.00   0.0  0
 IHH  CONST_37  C18   C15  C14  C13   180.00   0.0  0
 IHH  CONST_38  N11   C12  C13  C14   180.00   0.0  0
 IHH  CONST_39  N21   C22  C23  C24   180.00   0.0  0
 IHH  CONST_40  N21   C22  N26  N25   180.00   0.0  0
 IHH  CONST_41  C16   C17  C12  N11   180.00   0.0  0
 IHH  CONST_42  C18   C15  C16  C17   180.00   0.0  0
 IHH  CONST_43  H3    C3   C2   C1    180.00   0.0  0
 IHH  CONST_44  H4    C4   C1   C2    180.00   0.0  0
 IHH  CONST_45  H1    C1   C2   C3    180.00   0.0  0
 IHH  CONST_46  H2    C2   C1   C4    180.00   0.0  0
 IHH  CONST_47  H14   C14  C13  C12   180.00   0.0  0
 IHH  CONST_48  H16   C16  C17  C12   180.00   0.0  0
 IHH  CONST_49  H17   C17  C12  C13   180.00   0.0  0
 IHH  CONST_50  H13   C13  C14  C15   180.00   0.0  0
 IHH  CONST_51  H23   C23  C24  C27     0.00   0.0  0
 IHH  CONST_52  H181  N25  C24  C27     0.00   0.0  0
 IHH  Var_01    C24   C27  C29  C28   110.15  30.0  1
 IHH  Var_02    C23   C24  C27  C28  -141.92  30.0  2
 IHH  Var_03    C22   N21  C10  C5    179.33  30.0  2
 IHH  Var_04    C13   C12  N11  C8    178.69  30.0  3
 IHH  Var_05    C23   C22  N21  C10     3.54  30.0  2
 IHH  Var_06    N9    C8   N11  C12   179.34  30.0  2
 IHH  Var_07    C19   C18  C15  C14    81.73  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
 IHH  chir_01  C27  C28  C29  C24  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
 IHH  plan-1  C27   0.020
 IHH  plan-1  C24   0.020
 IHH  plan-1  C23   0.020
 IHH  plan-1  N25   0.020
 IHH  plan-1  N26   0.020
 IHH  plan-1  C22   0.020
 IHH  plan-1  N21   0.020
 IHH  plan-1  H23   0.020
 IHH  plan-1  H181  0.020
 IHH  plan-2  C12   0.020
 IHH  plan-2  C13   0.020
 IHH  plan-2  C14   0.020
 IHH  plan-2  C15   0.020
 IHH  plan-2  N11   0.020
 IHH  plan-2  C17   0.020
 IHH  plan-2  C16   0.020
 IHH  plan-2  C18   0.020
 IHH  plan-2  H13   0.020
 IHH  plan-2  H14   0.020
 IHH  plan-2  H17   0.020
 IHH  plan-2  H16   0.020
 IHH  plan-3  C1    0.020
 IHH  plan-3  C2    0.020
 IHH  plan-3  C3    0.020
 IHH  plan-3  C4    0.020
 IHH  plan-3  C5    0.020
 IHH  plan-3  C6    0.020
 IHH  plan-3  C8    0.020
 IHH  plan-3  C10   0.020
 IHH  plan-3  N21   0.020
 IHH  plan-3  N9    0.020
 IHH  plan-3  N7    0.020
 IHH  plan-3  N11   0.020
 IHH  plan-3  H1    0.020
 IHH  plan-3  H2    0.020
 IHH  plan-3  H3    0.020
 IHH  plan-3  H4    0.020

