# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 05:09:51 2020
#   Inital geometry file: a 142 line input string
#   Ligand name: (2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}-4-(piperidin-1-yl)but-2-enamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1NC(=O)\C=C\CN4CCCCC4
#
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
 1C9  1C9  (2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}-4-(piperidin-1-yl)but-2-enamide  ligand  58  33  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_1C9
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
 1C9  C1    C   CR6   0   0.323   0.3861   2.5222   0.0374
 1C9  C2    C   CR6   0   0.359   0.1942   3.9198   0.2805
 1C9  C3    C   CR16  0  -0.464  -1.0674   4.4418   0.3905
 1C9  C4    C   CR66  0   0.247  -2.1978   3.6109   0.2707
 1C9  C5    C   CR66  0  -0.015  -2.0173   2.2352   0.0436
 1C9  C6    C   CR16  0  -0.410  -0.7147   1.7092  -0.0765
 1C9  N7    N   N     0  -0.460  -3.4300   4.1724   0.3788
 1C9  C8    C   CR16  0   0.049  -4.4384   3.3588   0.2596
 1C9  N9    N   N     0  -0.483  -4.4026   2.0357   0.0553
 1C9  C10   C   CR6   0   0.541  -3.2229   1.4621  -0.0459
 1C9  N14   N   NH1   0  -0.789  -3.1410   0.1220  -0.2292
 1C9  C15   C   CR6   0   0.379  -4.1435  -0.8410  -0.3422
 1C9  C16   C   CR16  0  -0.327  -3.7293  -2.1707  -0.2230
 1C9  C17   C   CR6   0  -0.212  -4.6386  -3.2030  -0.3506
 1C9  C18   C   CR6   0   0.590  -5.9727  -2.9226  -0.5922
 1C9  C19   C   CR16  0  -0.407  -6.3947  -1.6171  -0.7124
 1C9  C20   C   CR16  0  -0.281  -5.4905  -0.5724  -0.5913
 1C9  F21   F   F     0  -0.297  -6.8456  -3.9275  -0.7081
 1C9  CL    CL  CL    0  -0.088  -4.1290  -4.8413  -0.2034
 1C9  O11   O   O2    0  -0.476   1.3238   4.6272   0.3817
 1C9  C12   C   CH3   0  -0.438   1.2433   6.0272   0.5935
 1C9  N13   N   NH1   0  -0.765   1.7074   2.0993  -0.0568
 1C9  C26   C   C     0   0.568   2.1878   0.8802  -0.4275
 1C9  C24   C   C1    0  -0.407   3.6651   0.8171  -0.4199
 1C9  C23   C   C1    0  -0.169   4.3200  -0.2694  -0.8226
 1C9  C25   C   CH2   0  -0.319   5.8078  -0.3795  -0.8833
 1C9  N33   N   NT    0  -0.424   6.2698  -1.6586  -0.3882
 1C9  O27   O   O     0  -0.470   1.4759  -0.0632  -0.7325
 1C9  C30   C   CH2   0  -0.277   7.6668  -1.8843  -0.7204
 1C9  C31   C   CH2   0  -0.437   8.1110  -3.2784  -0.3068
 1C9  C32   C   CH2   0  -0.440   7.8679  -3.5027   1.1803
 1C9  C33   C   CH2   0  -0.437   6.4168  -3.1921   1.5231
 1C9  C34   C   CH2   0  -0.279   6.0317  -1.8027   1.0396
 1C9  H6    H   HCR6  0   0.281  -0.5524   0.6602  -0.2639
 1C9  H8    H   HCR6  0   0.251  -5.4317   3.7889   0.3366
 1C9  H20   H   HCR6  0   0.299  -5.8389   0.4414  -0.6884
 1C9  H24   H   H     0   0.270   4.2137   1.6870  -0.0723
 1C9  H19   H   HCR6  0   0.293  -7.4385  -1.4073  -0.9054
 1C9  H3    H   HCR6  0   0.291  -1.2329   5.4954   0.5686
 1C9  H16   H   HCR6  0   0.301  -2.6899  -2.4040  -0.0277
 1C9  H12   H   HCH3  0   0.240   0.7063   6.5217  -0.2184
 1C9  H12A  H   HCH3  0   0.240   0.7552   6.2604   1.5421
 1C9  H12B  H   HCH3  0   0.271   2.2662   6.3912   0.6196
 1C9  H23   H   H     0   0.267   3.7637  -1.1380  -1.1635
 1C9  H25   H   HCH2  0   0.261   6.1013  -0.3000  -1.9365
 1C9  H25A  H   HCH2  0   0.215   6.2745   0.4751  -0.3647
 1C9  HN14  H   HNH1  0   0.434  -2.2127  -0.2661  -0.2130
 1C9  HN13  H   HNH1  0   0.423   2.3972   2.8071   0.1452
 1C9  H161  H   HCH2  0   0.235   7.7901  -1.7575  -1.7990
 1C9  H17   H   HCH2  0   0.185   8.3212  -1.1363  -0.2369
 1C9  H18   H   HCH2  0   0.215   7.5542  -4.0194  -0.8881
 1C9  H191  H   HCH2  0   0.231   9.1675  -3.4082  -0.5517
 1C9  H201  H   HCH2  0   0.232   8.1223  -4.5259   1.4645
 1C9  H21   H   HCH2  0   0.210   8.5258  -2.8437   1.7568
 1C9  H22   H   HCH2  0   0.216   5.7602  -3.9303   1.0526
 1C9  H231  H   HCH2  0   0.231   6.2498  -3.2571   2.6006
 1C9  H241  H   HCH2  0   0.186   6.5950  -1.0447   1.6143
 1C9  H251  H   HCH2  0   0.239   4.9730  -1.6226   1.2420

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
 1C9  C4   C5    aromatic  1.406  0.020  1.406
 1C9  C5   C6    aromatic  1.410  0.020  1.410
 1C9  C5   C10   aromatic  1.435  0.020  1.435
 1C9  C6   H6    single    0.930  0.020  1.080
 1C9  C8   N9    aromatic  1.339  0.020  1.339
 1C9  C8   H8    single    0.930  0.020  1.080
 1C9  C10  N14   single    1.355  0.020  1.355
 1C9  C15  C16   aromatic  1.398  0.020  1.398
 1C9  C15  C20   aromatic  1.396  0.020  1.396
 1C9  C17  CL    single    1.722  0.020  1.722
 1C9  C17  C18   aromatic  1.384  0.020  1.384
 1C9  C20  C19   aromatic  1.387  0.020  1.387
 1C9  C20  H20   single    0.930  0.020  1.080
 1C9  C24  C23   double    1.331  0.020  1.331
 1C9  C24  H24   single    0.930  0.020  1.080
 1C9  C26  C24   single    1.479  0.020  1.479
 1C9  C26  O27   double    1.221  0.020  1.221
 1C9  C19  C18   aromatic  1.377  0.020  1.377
 1C9  C19  H19   single    0.930  0.020  1.080
 1C9  C3   C4    aromatic  1.408  0.020  1.408
 1C9  C3   C2    aromatic  1.370  0.020  1.370
 1C9  C3   H3    single    0.930  0.020  1.080
 1C9  C16  C17   aromatic  1.382  0.020  1.382
 1C9  C16  H16   single    0.930  0.020  1.080
 1C9  C1   C6    aromatic  1.373  0.020  1.373
 1C9  C1   N13   single    1.390  0.020  1.390
 1C9  C2   C1    aromatic  1.432  0.020  1.432
 1C9  C18  F21   single    1.336  0.020  1.336
 1C9  C12  O11   single    1.418  0.020  1.418
 1C9  C12  H12   single    0.970  0.020  1.090
 1C9  C12  H12A  single    0.970  0.020  1.090
 1C9  C12  H12B  single    0.970  0.020  1.090
 1C9  C23  C25   single    1.493  0.020  1.493
 1C9  C23  H23   single    0.930  0.020  1.080
 1C9  C25  N33   single    1.447  0.020  1.447
 1C9  C25  H25   single    0.970  0.020  1.090
 1C9  C25  H25A  single    0.970  0.020  1.090
 1C9  N7   C4    aromatic  1.358  0.020  1.358
 1C9  N7   C8    aromatic  1.301  0.020  1.301
 1C9  N9   C10   aromatic  1.316  0.020  1.316
 1C9  N14  C15   single    1.395  0.020  1.395
 1C9  N14  HN14  single    0.860  0.020  1.020
 1C9  N13  C26   single    1.362  0.020  1.362
 1C9  N13  HN13  single    0.860  0.020  1.020
 1C9  O11  C2    single    1.337  0.020  1.337
 1C9  N33  C30   single    1.454  0.020  1.454
 1C9  N33  C34   single    1.455  0.020  1.455
 1C9  C30  C31   single    1.520  0.020  1.520
 1C9  C31  C32   single    1.523  0.020  1.523
 1C9  C32  C33   single    1.523  0.020  1.523
 1C9  C33  C34   single    1.521  0.020  1.521
 1C9  C30  H161  single    0.970  0.020  1.090
 1C9  C30  H17   single    0.970  0.020  1.090
 1C9  C31  H18   single    0.970  0.020  1.090
 1C9  C31  H191  single    0.970  0.020  1.090
 1C9  C32  H201  single    0.970  0.020  1.090
 1C9  C32  H21   single    0.970  0.020  1.090
 1C9  C33  H22   single    0.970  0.020  1.090
 1C9  C33  H231  single    0.970  0.020  1.090
 1C9  C34  H241  single    0.970  0.020  1.090
 1C9  C34  H251  single    0.970  0.020  1.090

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
 1C9  N13   C1   C6    125.17  3.000
 1C9  N13   C1   C2    115.84  3.000
 1C9  C6    C1   C2    118.99  3.000
 1C9  O11   C2   C3    124.79  3.000
 1C9  O11   C2   C1    114.60  3.000
 1C9  C3    C2   C1    120.61  3.000
 1C9  H3    C3   C4    117.78  3.000
 1C9  H3    C3   C2    121.71  3.000
 1C9  C4    C3   C2    120.51  3.000
 1C9  N7    C4   C5    122.26  3.000
 1C9  N7    C4   C3    118.53  3.000
 1C9  C5    C4   C3    119.22  3.000
 1C9  C10   C5   C6    124.74  3.000
 1C9  C10   C5   C4    115.43  3.000
 1C9  C6    C5   C4    119.83  3.000
 1C9  H6    C6   C5    121.13  3.000
 1C9  H6    C6   C1    118.03  3.000
 1C9  C5    C6   C1    120.84  3.000
 1C9  C8    N7   C4    115.93  3.000
 1C9  H8    C8   N9    115.27  3.000
 1C9  H8    C8   N7    117.07  3.000
 1C9  N9    C8   N7    127.67  3.000
 1C9  C10   N9   C8    117.80  3.000
 1C9  N14   C10  N9    119.72  3.000
 1C9  N9    C10  C5    120.91  3.000
 1C9  N14   C10  C5    119.37  3.000
 1C9  HN14  N14  C15   113.46  3.000
 1C9  HN14  N14  C10   115.78  3.000
 1C9  C15   N14  C10   130.57  3.000
 1C9  C20   C15  C16   118.96  3.000
 1C9  C20   C15  N14   125.11  3.000
 1C9  C16   C15  N14   115.91  3.000
 1C9  H16   C16  C17   119.17  3.000
 1C9  H16   C16  C15   120.31  3.000
 1C9  C17   C16  C15   120.53  3.000
 1C9  CL    C17  C18   119.52  3.000
 1C9  C18   C17  C16   119.93  3.000
 1C9  CL    C17  C16   120.54  3.000
 1C9  F21   C18  C19   120.34  3.000
 1C9  F21   C18  C17   119.49  3.000
 1C9  C19   C18  C17   120.16  3.000
 1C9  H19   C19  C20   119.90  3.000
 1C9  H19   C19  C18   119.66  3.000
 1C9  C20   C19  C18   120.44  3.000
 1C9  H20   C20  C19   119.38  3.000
 1C9  H20   C20  C15   120.64  3.000
 1C9  C19   C20  C15   119.98  3.000
 1C9  C12   O11  C2    119.06  3.000
 1C9  H12B  C12  H12A  109.18  3.000
 1C9  H12B  C12  H12   109.22  3.000
 1C9  H12A  C12  H12   109.23  3.000
 1C9  H12B  C12  O11   106.32  3.000
 1C9  H12A  C12  O11   111.47  3.000
 1C9  H12   C12  O11   111.34  3.000
 1C9  HN13  N13  C26   116.19  3.000
 1C9  HN13  N13  C1    115.01  3.000
 1C9  C26   N13  C1    128.75  3.000
 1C9  O27   C26  C24   123.43  3.000
 1C9  O27   C26  N13   123.66  3.000
 1C9  C24   C26  N13   112.91  3.000
 1C9  H24   C24  C23   120.16  3.000
 1C9  H24   C24  C26   118.18  3.000
 1C9  C23   C24  C26   121.66  3.000
 1C9  H23   C23  C25   116.01  3.000
 1C9  H23   C23  C24   119.72  3.000
 1C9  C25   C23  C24   124.24  3.000
 1C9  H25A  C25  H25   106.39  3.000
 1C9  H25A  C25  N33   112.88  3.000
 1C9  H25   C25  N33   107.90  3.000
 1C9  H25A  C25  C23   110.21  3.000
 1C9  H25   C25  C23   107.48  3.000
 1C9  N33   C25  C23   111.67  3.000
 1C9  C34   N33  C30   111.49  3.000
 1C9  C34   N33  C25   111.78  3.000
 1C9  C30   N33  C25   111.46  3.000
 1C9  H17   C30  H161  106.64  3.000
 1C9  H17   C30  C31   109.18  3.000
 1C9  H161  C30  C31   109.99  3.000
 1C9  H17   C30  N33   111.34  3.000
 1C9  H161  C30  N33   108.42  3.000
 1C9  C31   C30  N33   111.16  3.000
 1C9  H191  C31  H18   107.02  3.000
 1C9  H191  C31  C32   110.83  3.000
 1C9  H18   C31  C32   109.74  3.000
 1C9  H191  C31  C30   109.30  3.000
 1C9  H18   C31  C30   109.14  3.000
 1C9  C32   C31  C30   110.73  3.000
 1C9  H21   C32  H201  106.67  3.000
 1C9  H21   C32  C33   109.33  3.000
 1C9  H201  C32  C33   110.76  3.000
 1C9  H21   C32  C31   109.24  3.000
 1C9  H201  C32  C31   110.78  3.000
 1C9  C33   C32  C31   109.98  3.000
 1C9  H231  C33  H22   106.99  3.000
 1C9  H231  C33  C34   109.23  3.000
 1C9  H22   C33  C34   109.13  3.000
 1C9  H231  C33  C32   110.83  3.000
 1C9  H22   C33  C32   109.72  3.000
 1C9  C34   C33  C32   110.86  3.000
 1C9  H251  C34  H241  106.52  3.000
 1C9  H251  C34  C33   109.70  3.000
 1C9  H241  C34  C33   109.40  3.000
 1C9  H251  C34  N33   108.91  3.000
 1C9  H241  C34  N33   111.03  3.000
 1C9  C33   C34  N33   111.17  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
 1C9  CONST_01  C4    C5   C6   C1      0.00   0.0  0
 1C9  CONST_02  C10   C5   C6   C1    180.00   0.0  0
 1C9  CONST_03  C4    C3   C2   C1      0.00   0.0  0
 1C9  CONST_04  C5    C4   C3   C2      0.00   0.0  0
 1C9  CONST_05  N7    C4   C3   C2    180.00   0.0  0
 1C9  CONST_06  C5    C6   C1   C2      0.00   0.0  0
 1C9  CONST_07  C6    C5   C4   C3      0.00   0.0  0
 1C9  CONST_08  C10   C5   C4   C3    180.00   0.0  0
 1C9  CONST_09  C8    N7   C4   C3    180.00   0.0  0
 1C9  CONST_10  C6    C1   C2   C3      0.00   0.0  0
 1C9  CONST_11  N9    C10  C5   C4      0.00   0.0  0
 1C9  CONST_12  N9    C8   N7   C4      0.00   0.0  0
 1C9  CONST_13  C8    N7   C4   C5      0.00   0.0  0
 1C9  CONST_14  C8    N9   C10  C5      0.00   0.0  0
 1C9  CONST_15  N7    C4   C5   C6    180.00   0.0  0
 1C9  CONST_16  N9    C10  C5   C6    180.00   0.0  0
 1C9  CONST_17  C10   C5   C4   N7      0.00   0.0  0
 1C9  CONST_18  C10   N9   C8   N7      0.00   0.0  0
 1C9  CONST_19  C18   C17  C16  C15     0.00   0.0  0
 1C9  CONST_20  C18   C19  C20  C15     0.00   0.0  0
 1C9  CONST_21  C19   C20  C15  C16     0.00   0.0  0
 1C9  CONST_22  C19   C18  C17  C16     0.00   0.0  0
 1C9  CONST_23  C20   C19  C18  C17     0.00   0.0  0
 1C9  CONST_24  C20   C15  C16  C17     0.00   0.0  0
 1C9  CONST_25  N13   C1   C2   C3    180.00   0.0  0
 1C9  CONST_26  N14   C10  C5   C4    180.00   0.0  0
 1C9  CONST_27  O11   C2   C3   C4    180.00   0.0  0
 1C9  CONST_28  N13   C1   C6   C5    180.00   0.0  0
 1C9  CONST_29  N14   C10  C5   C6      0.00   0.0  0
 1C9  CONST_30  O11   C2   C1   C6    180.00   0.0  0
 1C9  CONST_31  N14   C10  N9   C8    180.00   0.0  0
 1C9  CONST_32  C17   C16  C15  N14   180.00   0.0  0
 1C9  CONST_33  C19   C20  C15  N14   180.00   0.0  0
 1C9  CONST_34  CL    C17  C16  C15   180.00   0.0  0
 1C9  CONST_35  F21   C18  C17  C16   180.00   0.0  0
 1C9  CONST_36  CL    C17  C18  C19   180.00   0.0  0
 1C9  CONST_37  F21   C18  C19  C20   180.00   0.0  0
 1C9  CONST_38  H3    C3   C2   C1    180.00   0.0  0
 1C9  CONST_39  H6    C6   C1   C2    180.00   0.0  0
 1C9  CONST_40  H8    C8   N7   C4    180.00   0.0  0
 1C9  CONST_41  H19   C19  C20  C15   180.00   0.0  0
 1C9  CONST_42  H20   C20  C15  C16   180.00   0.0  0
 1C9  CONST_43  H16   C16  C17  C18   180.00   0.0  0
 1C9  CONST_44  C26   N13  C1   C2    180.00   0.0  0
 1C9  CONST_45  C26   N13  C1   C6      0.00   0.0  0
 1C9  CONST_46  HN13  N13  C1   C2      0.00   0.0  0
 1C9  CONST_47  C24   C26  N13  C1    180.00   0.0  0
 1C9  CONST_48  O27   C26  N13  C1      0.00   0.0  0
 1C9  Var_01    C32   C31  C30  N33   -56.51  30.0  1
 1C9  Var_02    C32   C33  C34  N33    56.16  30.0  1
 1C9  Var_03    C33   C34  N33  C30   -59.15  30.0  1
 1C9  Var_04    C33   C32  C31  C30    53.32  30.0  1
 1C9  Var_05    C34   N33  C30  C31    59.36  30.0  1
 1C9  Var_06    C34   C33  C32  C31   -53.19  30.0  1
 1C9  Var_07    C15   N14  C10  C5    179.74  30.0  2
 1C9  Var_08    C16   C15  N14  C10  -166.00  30.0  2
 1C9  Var_09    C30   N33  C25  C23   167.17  30.0  3
 1C9  Var_10    N33   C25  C23  C24   137.59  30.0  3
 1C9  Var_11    H12   C12  O11  C2    -59.84  30.0  3
 1C9  Var_12    C25   C23  C24  C26   177.81   0.0  2
 1C9  Var_13    C23   C24  C26  N13  -176.31  30.0  2

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
 1C9  plan-1  N14   0.020
 1C9  plan-1  C15   0.020
 1C9  plan-1  C16   0.020
 1C9  plan-1  C17   0.020
 1C9  plan-1  C18   0.020
 1C9  plan-1  C19   0.020
 1C9  plan-1  C20   0.020
 1C9  plan-1  F21   0.020
 1C9  plan-1  CL    0.020
 1C9  plan-1  H20   0.020
 1C9  plan-1  H19   0.020
 1C9  plan-1  H16   0.020
 1C9  plan-2  C1    0.020
 1C9  plan-2  C2    0.020
 1C9  plan-2  C3    0.020
 1C9  plan-2  C4    0.020
 1C9  plan-2  C5    0.020
 1C9  plan-2  C6    0.020
 1C9  plan-2  N7    0.020
 1C9  plan-2  C8    0.020
 1C9  plan-2  N9    0.020
 1C9  plan-2  C10   0.020
 1C9  plan-2  N14   0.020
 1C9  plan-2  O11   0.020
 1C9  plan-2  N13   0.020
 1C9  plan-2  H6    0.020
 1C9  plan-2  H8    0.020
 1C9  plan-2  H3    0.020
 1C9  plan-3  C1    0.020
 1C9  plan-3  N13   0.020
 1C9  plan-3  C26   0.020
 1C9  plan-3  C24   0.020
 1C9  plan-3  O27   0.020
 1C9  plan-3  HN13  0.020
 1C9  plan-4  C26   0.020
 1C9  plan-4  C24   0.020
 1C9  plan-4  C23   0.020
 1C9  plan-4  C25   0.020
 1C9  plan-4  H24   0.020
 1C9  plan-4  H23   0.020

