# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 08:27:53 2020
#   Inital geometry file: a 100 line input string
#   Ligand name: 4-[(4-amino-5-cyano-6-ethoxypyridin-2-yl)amino]benzamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCOc1nc(Nc2ccc(cc2)C(N)=O)cc(N)c1C#N
#
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
 O22  O22  4-[(4-amino-5-cyano-6-ethoxypyridin-2-yl)amino]benzamide  ligand  37  22  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_O22
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
 O22  O2   O  O     0  -0.487   5.7858  -1.2104   0.3549
 O22  C15  C  C     0   0.485   5.5198  -0.0761  -0.0246
 O22  N4   N  NH2   0  -0.818   6.4665   0.7816  -0.4430
 O22  C12  C  CR6   0  -0.062   4.1169   0.4247  -0.0340
 O22  C11  C  CR16  0  -0.268   3.7825   1.7790  -0.0640
 O22  C10  C  CR16  0  -0.353   2.4643   2.1839  -0.0538
 O22  C13  C  CR16  0  -0.260   3.0766  -0.4977   0.0217
 O22  C14  C  CR16  0  -0.309   1.7485  -0.1089   0.0197
 O22  C9   C  CR6   0   0.372   1.4183   1.2505  -0.0203
 O22  N3   N  NH1   0  -0.782   0.1359   1.7712  -0.0232
 O22  C8   C  CR6   0   0.583  -1.0944   1.1774  -0.0365
 O22  C7   C  CR16  0  -0.549  -2.2148   2.0021  -0.0588
 O22  C6   C  CR6   0   0.523  -3.4849   1.4221  -0.0798
 O22  N2   N  NH2   0  -0.861  -4.5928   2.1712  -0.1007
 O22  C4   C  CR6   0  -0.301  -3.5524   0.0062  -0.0770
 O22  C5   C  CSP   0   0.036  -4.7882  -0.6690  -0.0945
 O22  N1   N  NS    0  -0.271  -5.8191  -1.1919  -0.1092
 O22  N5   N  N     0  -0.548  -1.1602  -0.1581  -0.0293
 O22  C3   C  CR6   0   0.577  -2.3468  -0.7129  -0.0501
 O22  O1   O  O2    0  -0.458  -2.4599  -2.0305  -0.0465
 O22  C2   C  CH2   0  -0.181  -1.2756  -2.8337   0.0345
 O22  C1   C  CH3   0  -0.682  -1.7060  -4.2800   0.0437
 O22  H1   H  HNH2  0   0.403   7.4239   0.4731  -0.4897
 O22  H2   H  HNH2  0   0.410   6.2476   1.6388  -0.9189
 O22  H3   H  HCR6  0   0.259   4.5456   2.5466  -0.0724
 O22  H4   H  HCR6  0   0.274   2.2393   3.2439  -0.0668
 O22  H5   H  HCR6  0   0.259   3.3006  -1.5557   0.0582
 O22  H6   H  HCR6  0   0.307   0.9759  -0.8572   0.0509
 O22  H7   H  HNH1  0   0.420   0.1037   2.7795  -0.0390
 O22  H8   H  HCR6  0   0.283  -2.1113   3.0794  -0.0620
 O22  H9   H  HNH2  0   0.412  -4.5326   3.1741  -0.1049
 O22  H10  H  HNH2  0   0.408  -5.5141   1.7700  -0.1171
 O22  H11  H  HCH2  0   0.234  -0.6262  -2.6255  -0.8186
 O22  H12  H  HCH2  0   0.234  -0.7242  -2.5830   0.9433
 O22  H13  H  HCH3  0   0.240  -0.8214  -4.9122   0.1124
 O22  H14  H  HCH3  0   0.236  -2.3449  -4.5044   0.8979
 O22  H15  H  HCH3  0   0.236  -2.2378  -4.5465  -0.8696

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
 O22  N1   C5   triple    1.156  0.020  1.156
 O22  C5   C4   single    1.408  0.020  1.408
 O22  C4   C3   aromatic  1.404  0.020  1.404
 O22  C4   C6   aromatic  1.417  0.020  1.417
 O22  O1   C3   single    1.322  0.020  1.322
 O22  O1   C2   single    1.433  0.020  1.433
 O22  C1   C2   single    1.509  0.020  1.509
 O22  N2   C6   single    1.338  0.020  1.338
 O22  C3   N5   aromatic  1.310  0.020  1.310
 O22  C6   C7   aromatic  1.396  0.020  1.396
 O22  N5   C8   aromatic  1.337  0.020  1.337
 O22  C7   C8   aromatic  1.391  0.020  1.391
 O22  C8   N3   single    1.366  0.020  1.366
 O22  N3   C9   single    1.384  0.020  1.384
 O22  C10  C9   aromatic  1.402  0.020  1.402
 O22  C10  C11  aromatic  1.379  0.020  1.379
 O22  C9   C14  aromatic  1.400  0.020  1.400
 O22  C11  C12  aromatic  1.395  0.020  1.395
 O22  C14  C13  aromatic  1.384  0.020  1.384
 O22  C12  C13  aromatic  1.391  0.020  1.391
 O22  C12  C15  single    1.490  0.020  1.490
 O22  N4   C15  single    1.344  0.020  1.344
 O22  C15  O2   double    1.225  0.020  1.225
 O22  N4   H1   single    0.860  0.020  1.020
 O22  N4   H2   single    0.860  0.020  1.020
 O22  C11  H3   single    0.930  0.020  1.080
 O22  C10  H4   single    0.930  0.020  1.080
 O22  C13  H5   single    0.930  0.020  1.080
 O22  C14  H6   single    0.930  0.020  1.080
 O22  N3   H7   single    0.860  0.020  1.020
 O22  C7   H8   single    0.930  0.020  1.080
 O22  N2   H9   single    0.860  0.020  1.020
 O22  N2   H10  single    0.860  0.020  1.020
 O22  C2   H11  single    0.970  0.020  1.090
 O22  C2   H12  single    0.970  0.020  1.090
 O22  C1   H13  single    0.970  0.020  1.090
 O22  C1   H14  single    0.970  0.020  1.090
 O22  C1   H15  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
 O22  C12  C15  N4   116.54  3.000
 O22  N4   C15  O2   122.29  3.000
 O22  C12  C15  O2   121.17  3.000
 O22  H2   N4   H1   116.53  3.000
 O22  H2   N4   C15  122.58  3.000
 O22  H1   N4   C15  119.25  3.000
 O22  C13  C12  C11  117.72  3.000
 O22  C13  C12  C15  118.75  3.000
 O22  C11  C12  C15  123.51  3.000
 O22  H3   C11  C10  117.76  3.000
 O22  H3   C11  C12  121.30  3.000
 O22  C10  C11  C12  120.93  3.000
 O22  H4   C10  C9   119.77  3.000
 O22  H4   C10  C11  119.05  3.000
 O22  C9   C10  C11  121.18  3.000
 O22  H5   C13  C14  118.26  3.000
 O22  H5   C13  C12  119.65  3.000
 O22  C14  C13  C12  122.09  3.000
 O22  H6   C14  C9   120.46  3.000
 O22  H6   C14  C13  119.58  3.000
 O22  C9   C14  C13  119.96  3.000
 O22  N3   C9   C14  125.73  3.000
 O22  C14  C9   C10  118.12  3.000
 O22  N3   C9   C10  116.15  3.000
 O22  H7   N3   C8   113.92  3.000
 O22  H7   N3   C9   113.92  3.000
 O22  C8   N3   C9   132.14  3.000
 O22  N5   C8   C7   123.53  3.000
 O22  C7   C8   N3   117.89  3.000
 O22  N5   C8   N3   118.58  3.000
 O22  H8   C7   C6   120.03  3.000
 O22  H8   C7   C8   120.86  3.000
 O22  C6   C7   C8   119.11  3.000
 O22  C4   C6   N2   121.33  3.000
 O22  N2   C6   C7   121.40  3.000
 O22  C4   C6   C7   117.27  3.000
 O22  H10  N2   H9   116.96  3.000
 O22  H10  N2   C6   122.41  3.000
 O22  H9   N2   C6   120.63  3.000
 O22  C3   C4   C5   120.54  3.000
 O22  C3   C4   C6   118.08  3.000
 O22  C5   C4   C6   121.38  3.000
 O22  N1   C5   C4   180.00  3.000
 O22  C3   N5   C8   117.87  3.000
 O22  O1   C3   N5   119.96  3.000
 O22  N5   C3   C4   124.13  3.000
 O22  O1   C3   C4   115.91  3.000
 O22  C2   O1   C3   119.20  3.000
 O22  H12  C2   H11  107.82  3.000
 O22  H12  C2   C1   111.03  3.000
 O22  H11  C2   C1   110.92  3.000
 O22  H12  C2   O1   109.61  3.000
 O22  H11  C2   O1   109.90  3.000
 O22  C1   C2   O1   107.56  3.000
 O22  H15  C1   H14  108.69  3.000
 O22  H15  C1   H13  107.88  3.000
 O22  H14  C1   H13  107.88  3.000
 O22  H15  C1   C2   111.62  3.000
 O22  H14  C1   C2   111.67  3.000
 O22  H13  C1   C2   108.97  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
 O22  CONST_01  C9   C10  C11  C12     0.00   0.0  0
 O22  CONST_02  C9   C14  C13  C12     0.00   0.0  0
 O22  CONST_03  C14  C9   C10  C11     0.00   0.0  0
 O22  CONST_04  C14  C13  C12  C11     0.00   0.0  0
 O22  CONST_05  C13  C14  C9   C10     0.00   0.0  0
 O22  CONST_06  C13  C12  C11  C10     0.00   0.0  0
 O22  CONST_07  C4   C3   N5   C8      0.00   0.0  0
 O22  CONST_08  C4   C6   C7   C8      0.00   0.0  0
 O22  CONST_09  C3   C4   C6   C7      0.00   0.0  0
 O22  CONST_10  C3   N5   C8   C7      0.00   0.0  0
 O22  CONST_11  N5   C3   C4   C6      0.00   0.0  0
 O22  CONST_12  N5   C8   C7   C6      0.00   0.0  0
 O22  CONST_13  C10  C11  C12  C15   180.00   0.0  0
 O22  CONST_14  C14  C13  C12  C15   180.00   0.0  0
 O22  CONST_15  N3   C9   C10  C11   180.00   0.0  0
 O22  CONST_16  N3   C9   C14  C13   180.00   0.0  0
 O22  CONST_17  C3   N5   C8   N3    180.00   0.0  0
 O22  CONST_18  C6   C7   C8   N3    180.00   0.0  0
 O22  CONST_19  O1   C3   N5   C8    180.00   0.0  0
 O22  CONST_20  N2   C6   C7   C8    180.00   0.0  0
 O22  CONST_21  C5   C4   C6   C7    180.00   0.0  0
 O22  CONST_22  O1   C3   C4   C6    180.00   0.0  0
 O22  CONST_23  C3   C4   C6   N2    180.00   0.0  0
 O22  CONST_24  N5   C3   C4   C5    180.00   0.0  0
 O22  CONST_25  H4   C10  C11  C12   180.00   0.0  0
 O22  CONST_26  H6   C14  C13  C12   180.00   0.0  0
 O22  CONST_27  H5   C13  C12  C11   180.00   0.0  0
 O22  CONST_28  H3   C11  C12  C13   180.00   0.0  0
 O22  CONST_29  H8   C7   C6   C4    180.00   0.0  0
 O22  CONST_30  H9   N2   C6   C7      0.00   0.0  0
 O22  CONST_31  H10  N2   C6   C7    180.00   0.0  0
 O22  CONST_32  H1   N4   C15  C12   180.00   0.0  0
 O22  CONST_33  H2   N4   C15  C12     0.00   0.0  0
 O22  Var_01    C8   N3   C9   C10   177.78  30.0  2
 O22  Var_02    N5   C8   N3   C9      0.99  30.0  3
 O22  Var_03    C11  C12  C15  O2    160.25  30.0  3
 O22  Var_04    C1   C2   O1   C3    179.03  30.0  3
 O22  Var_05    H13  C1   C2   O1   -179.58  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
 O22  plan-1  C15  0.020
 O22  plan-1  C12  0.020
 O22  plan-1  C11  0.020
 O22  plan-1  C10  0.020
 O22  plan-1  C13  0.020
 O22  plan-1  C14  0.020
 O22  plan-1  C9   0.020
 O22  plan-1  N3   0.020
 O22  plan-1  H3   0.020
 O22  plan-1  H4   0.020
 O22  plan-1  H5   0.020
 O22  plan-1  H6   0.020
 O22  plan-2  N3   0.020
 O22  plan-2  C8   0.020
 O22  plan-2  C7   0.020
 O22  plan-2  C6   0.020
 O22  plan-2  N2   0.020
 O22  plan-2  C4   0.020
 O22  plan-2  C5   0.020
 O22  plan-2  N1   0.020
 O22  plan-2  N5   0.020
 O22  plan-2  C3   0.020
 O22  plan-2  O1   0.020
 O22  plan-2  H8   0.020
 O22  plan-3  O2   0.020
 O22  plan-3  C15  0.020
 O22  plan-3  N4   0.020
 O22  plan-3  C12  0.020
 O22  plan-3  H1   0.020
 O22  plan-3  H2   0.020
 O22  plan-4  C6   0.020
 O22  plan-4  N2   0.020
 O22  plan-4  H9   0.020
 O22  plan-4  H10  0.020

