# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 05:17:15 2021
#   Inital geometry file: a 143 line input string
#   Ligand name: [4-[[6-(3,5-dimethyl-4-oxidanyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]-morpholin-4-yl-methanone
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1cc(cc(C)c1O)c2ccc3nc(Nc4ccc(cc4)C(=O)N5CCOCC5)nn3c2
#
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
 NN5  NN5  '[4-[[6-(3,5-dimethyl-4-oxidanyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]-morpholin-4-yl-methanone'  ligand  58  33  .  2022-07-22  2022-07-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_NN5
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
 NN5  N1   N  N     0  -0.351  45.1758  33.3909  37.1970
 NN5  C5   C  CR56  0   0.576  45.7893  32.1717  37.1210
 NN5  C6   C  CR16  0  -0.415  45.0998  31.0543  37.6172
 NN5  C7   C  CR16  0  -0.180  43.8554  31.2403  38.1514
 NN5  C8   C  CR6   0  -0.073  43.2489  32.5226  38.2114
 NN5  C10  C  CR6   0   0.103  41.9072  32.7112  38.7905
 NN5  C13  C  CR6   0   0.270  39.3558  33.0725  39.8601
 NN5  C15  C  CR16  0  -0.383  41.5914  33.8565  39.5163
 NN5  C20  C  CR6   0   0.367  48.4212  35.4714  35.3571
 NN5  C21  C  CR16  0  -0.317  47.5594  36.5521  35.5713
 NN5  C22  C  CR16  0  -0.262  47.9355  37.8234  35.1712
 NN5  C24  C  CR16  0  -0.249  50.0248  36.9881  34.3698
 NN5  C29  C  C     0  -0.350  51.6954  39.3755  35.2852
 NN5  C30  C  C     0  -0.170  52.3870  40.5173  36.0058
 NN5  O31  O  O     0  -0.492  53.1129  41.3594  35.1334
 NN5  C32  C  C     0  -0.192  52.5914  41.4136  33.8204
 NN5  C33  C  C     0  -0.326  51.0895  41.2189  33.7658
 NN5  N28  N  NR6   0  -0.465  50.7438  39.9159  34.3203
 NN5  O27  O  O     0  -0.496  48.6383  40.1238  33.5572
 NN5  C23  C  CR6   0  -0.081  49.1731  38.0708  34.5870
 NN5  C25  C  CR16  0  -0.351  49.6560  35.7114  34.7399
 NN5  C3   C  CR5   0   0.581  47.0310  33.6410  36.3060
 NN5  N4   N  N     0  -0.540  46.9791  32.3213  36.5537
 NN5  N2   N  N     0  -0.360  45.9678  34.3416  36.6725
 NN5  C9   C  CR16  0   0.016  43.9451  33.5913  37.7114
 NN5  C11  C  CR16  0  -0.370  40.9152  31.7465  38.6217
 NN5  C12  C  CR6   0   0.029  39.6406  31.9046  39.1455
 NN5  C18  C  CH3   0  -0.714  38.5831  30.8596  38.9482
 NN5  O17  O  OH1   0  -0.618  38.1044  33.1907  40.3517
 NN5  C14  C  CR6   0   0.021  40.3274  34.0589  40.0544
 NN5  C16  C  CH3   0  -0.776  40.0099  35.3007  40.8378
 NN5  H1   H  HCR6  0   0.286  45.5621  30.0789  37.5749
 NN5  H2   H  HCR6  0   0.275  43.3245  30.3878  38.5538
 NN5  H3   H  HCR6  0   0.250  42.3507  34.6105  39.6897
 NN5  H4   H  HCR6  0   0.288  46.5992  36.4065  36.0401
 NN5  H5   H  HCR6  0   0.259  47.2452  38.6411  35.3355
 NN5  H6   H  HCR6  0   0.268  50.9835  37.1297  33.8867
 NN5  H8   H  H     0   0.253  52.4362  38.7345  34.7986
 NN5  H9   H  H     0   0.214  51.6399  41.0936  36.5658
 NN5  H10  H  H     0   0.246  53.0878  40.1005  36.7320
 NN5  H11  H  H     0   0.214  53.0757  40.6652  33.1804
 NN5  H12  H  H     0   0.249  52.8339  42.3942  33.4075
 NN5  H13  H  H     0   0.265  50.7720  41.2780  32.7241
 NN5  H14  H  H     0   0.246  50.5791  42.0237  34.3049
 NN5  H15  H  HCR6  0   0.271  50.3306  34.8855  34.5474
 NN5  H17  H  HCR6  0   0.314  43.5743  34.6051  37.6804
 NN5  H18  H  HCR6  0   0.248  41.1289  30.8512  38.0493
 NN5  H19  H  HCH3  0   0.244  38.2050  30.4823  39.8998
 NN5  H20  H  HCH3  0   0.245  37.7252  31.2494  38.3974
 NN5  H21  H  HCH3  0   0.244  38.9761  30.0123  38.3881
 NN5  H22  H  HOH1  0   0.482  37.9960  34.0177  40.8335
 NN5  H23  H  HCH3  0   0.255  39.2214  35.8931  40.3663
 NN5  H24  H  HCH3  0   0.253  39.6854  35.0752  41.8570
 NN5  H25  H  HCH3  0   0.268  40.8856  35.9417  40.9163
 NN5  N19  N  NH1   0  -0.789  48.1365  34.1675  35.7111
 NN5  C26  C  C     0   0.525  49.4922  39.4496  34.1230
 NN5  H7   H  H     0   0.281  51.1777  38.7694  36.0267
 NN5  H16  H  HNH1  0   0.415  48.8445  33.4822  35.4970

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
 NN5  O27  C26  double    1.226  0.020  1.226
 NN5  C26  C23  single    1.489  0.020  1.489
 NN5  C26  N28  single    1.350  0.020  1.350
 NN5  C22  C23  aromatic  1.391  0.020  1.391
 NN5  C22  C21  aromatic  1.385  0.020  1.385
 NN5  C23  C24  aromatic  1.395  0.020  1.395
 NN5  C33  N28  single    1.458  0.020  1.458
 NN5  C33  C32  single    1.516  0.020  1.516
 NN5  C21  C20  aromatic  1.399  0.020  1.399
 NN5  C24  C25  aromatic  1.380  0.020  1.380
 NN5  N28  C29  single    1.459  0.020  1.459
 NN5  C20  C25  aromatic  1.401  0.020  1.401
 NN5  C20  N19  single    1.381  0.020  1.381
 NN5  N19  C3   single    1.361  0.020  1.361
 NN5  C32  O31  single    1.414  0.020  1.414
 NN5  C3   N4   aromatic  1.344  0.020  1.344
 NN5  C3   N2   aromatic  1.325  0.020  1.325
 NN5  N4   C5   aromatic  1.327  0.020  1.327
 NN5  C29  C30  single    1.517  0.020  1.517
 NN5  O31  C30  single    1.413  0.020  1.413
 NN5  N2   N1   aromatic  1.344  0.020  1.344
 NN5  C5   N1   aromatic  1.367  0.020  1.367
 NN5  C5   C6   aromatic  1.404  0.020  1.404
 NN5  N1   C9   aromatic  1.349  0.020  1.349
 NN5  C6   C7   aromatic  1.367  0.020  1.367
 NN5  C9   C8   aromatic  1.370  0.020  1.370
 NN5  C7   C8   aromatic  1.420  0.020  1.420
 NN5  C8   C10  single    1.473  0.020  1.473
 NN5  C11  C10  aromatic  1.394  0.020  1.394
 NN5  C11  C12  aromatic  1.387  0.020  1.387
 NN5  C10  C15  aromatic  1.392  0.020  1.392
 NN5  C18  C12  single    1.500  0.020  1.500
 NN5  C12  C13  aromatic  1.398  0.020  1.398
 NN5  C15  C14  aromatic  1.389  0.020  1.389
 NN5  C13  C14  aromatic  1.398  0.020  1.398
 NN5  C13  O17  single    1.350  0.020  1.350
 NN5  C14  C16  single    1.502  0.020  1.502
 NN5  C6   H1   single    0.930  0.020  1.080
 NN5  C7   H2   single    0.930  0.020  1.080
 NN5  C15  H3   single    0.930  0.020  1.080
 NN5  C21  H4   single    0.930  0.020  1.080
 NN5  C22  H5   single    0.930  0.020  1.080
 NN5  C24  H6   single    0.930  0.020  1.080
 NN5  C29  H7   single    0.970  0.020  1.090
 NN5  C29  H8   single    0.970  0.020  1.090
 NN5  C30  H9   single    0.970  0.020  1.090
 NN5  C30  H10  single    0.970  0.020  1.090
 NN5  C32  H11  single    0.970  0.020  1.090
 NN5  C32  H12  single    0.970  0.020  1.090
 NN5  C33  H13  single    0.970  0.020  1.090
 NN5  C33  H14  single    0.970  0.020  1.090
 NN5  C25  H15  single    0.930  0.020  1.080
 NN5  N19  H16  single    0.860  0.020  1.020
 NN5  C9   H17  single    0.930  0.020  1.080
 NN5  C11  H18  single    0.930  0.020  1.080
 NN5  C18  H19  single    0.970  0.020  1.090
 NN5  C18  H20  single    0.970  0.020  1.090
 NN5  C18  H21  single    0.970  0.020  1.090
 NN5  O17  H22  single    0.850  0.020  0.980
 NN5  C16  H23  single    0.970  0.020  1.090
 NN5  C16  H24  single    0.970  0.020  1.090
 NN5  C16  H25  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
 NN5  C9   N1   N2   125.55  3.000
 NN5  C9   N1   C5   124.28  3.000
 NN5  N2   N1   C5   110.17  3.000
 NN5  N4   C5   C6   132.96  3.000
 NN5  C6   C5   N1   118.03  3.000
 NN5  N4   C5   N1   109.01  3.000
 NN5  H1   C6   C7   121.86  3.000
 NN5  H1   C6   C5   119.65  3.000
 NN5  C7   C6   C5   118.49  3.000
 NN5  H2   C7   C8   119.09  3.000
 NN5  H2   C7   C6   119.00  3.000
 NN5  C8   C7   C6   121.89  3.000
 NN5  C9   C8   C10  120.42  3.000
 NN5  C10  C8   C7   121.41  3.000
 NN5  C9   C8   C7   118.16  3.000
 NN5  C11  C10  C15  118.10  3.000
 NN5  C15  C10  C8   121.11  3.000
 NN5  C11  C10  C8   120.79  3.000
 NN5  C14  C13  O17  122.14  3.000
 NN5  O17  C13  C12  116.62  3.000
 NN5  C14  C13  C12  121.24  3.000
 NN5  H3   C15  C14  118.31  3.000
 NN5  H3   C15  C10  119.78  3.000
 NN5  C14  C15  C10  121.90  3.000
 NN5  N19  C20  C25  117.16  3.000
 NN5  N19  C20  C21  124.28  3.000
 NN5  C25  C20  C21  118.56  3.000
 NN5  H4   C21  C22  119.42  3.000
 NN5  H4   C21  C20  120.72  3.000
 NN5  C22  C21  C20  119.85  3.000
 NN5  H5   C22  C23  119.78  3.000
 NN5  H5   C22  C21  118.45  3.000
 NN5  C23  C22  C21  121.76  3.000
 NN5  H6   C24  C25  118.51  3.000
 NN5  H6   C24  C23  120.58  3.000
 NN5  C25  C24  C23  120.90  3.000
 NN5  H8   C29  H7   107.38  3.000
 NN5  H8   C29  N28  111.38  3.000
 NN5  H7   C29  N28  110.28  3.000
 NN5  H8   C29  C30  110.10  3.000
 NN5  H7   C29  C30  108.20  3.000
 NN5  N28  C29  C30  109.43  3.000
 NN5  H10  C30  H9   107.35  3.000
 NN5  H10  C30  O31  107.95  3.000
 NN5  H9   C30  O31  110.60  3.000
 NN5  H10  C30  C29  108.74  3.000
 NN5  H9   C30  C29  109.11  3.000
 NN5  O31  C30  C29  112.92  3.000
 NN5  C32  O31  C30  113.99  3.000
 NN5  H12  C32  H11  107.11  3.000
 NN5  H12  C32  C33  108.78  3.000
 NN5  H11  C32  C33  109.19  3.000
 NN5  H12  C32  O31  107.69  3.000
 NN5  H11  C32  O31  110.65  3.000
 NN5  C33  C32  O31  113.21  3.000
 NN5  H14  C33  H13  107.15  3.000
 NN5  H14  C33  N28  111.05  3.000
 NN5  H13  C33  N28  110.04  3.000
 NN5  H14  C33  C32  110.47  3.000
 NN5  H13  C33  C32  108.42  3.000
 NN5  N28  C33  C32  109.64  3.000
 NN5  C33  N28  C29  115.35  3.000
 NN5  C29  N28  C26  124.98  3.000
 NN5  C33  N28  C26  118.23  3.000
 NN5  C26  C23  C24  122.64  3.000
 NN5  C24  C23  C22  118.08  3.000
 NN5  C26  C23  C22  119.09  3.000
 NN5  H15  C25  C24  119.43  3.000
 NN5  H15  C25  C20  119.76  3.000
 NN5  C24  C25  C20  120.82  3.000
 NN5  N2   C3   N4   115.93  3.000
 NN5  N2   C3   N19  124.61  3.000
 NN5  N4   C3   N19  119.45  3.000
 NN5  C3   N4   C5   102.95  3.000
 NN5  C3   N2   N1   101.93  3.000
 NN5  H17  C9   C8   124.63  3.000
 NN5  H17  C9   N1   116.22  3.000
 NN5  C8   C9   N1   119.15  3.000
 NN5  H18  C11  C12  118.34  3.000
 NN5  H18  C11  C10  119.68  3.000
 NN5  C12  C11  C10  121.96  3.000
 NN5  C18  C12  C11  121.25  3.000
 NN5  C18  C12  C13  120.37  3.000
 NN5  C11  C12  C13  118.38  3.000
 NN5  H21  C18  H20  107.57  3.000
 NN5  H21  C18  H19  107.73  3.000
 NN5  H20  C18  H19  106.93  3.000
 NN5  H21  C18  C12  110.82  3.000
 NN5  H20  C18  C12  111.82  3.000
 NN5  H19  C18  C12  111.74  3.000
 NN5  H22  O17  C13  111.21  3.000
 NN5  C16  C14  C15  121.00  3.000
 NN5  C16  C14  C13  120.58  3.000
 NN5  C15  C14  C13  118.42  3.000
 NN5  H25  C16  H24  107.05  3.000
 NN5  H25  C16  H23  107.00  3.000
 NN5  H24  C16  H23  107.45  3.000
 NN5  H25  C16  C14  110.76  3.000
 NN5  H24  C16  C14  112.24  3.000
 NN5  H23  C16  C14  112.05  3.000
 NN5  H16  N19  C3   113.59  3.000
 NN5  H16  N19  C20  116.27  3.000
 NN5  C3   N19  C20  130.14  3.000
 NN5  C23  C26  O27  120.24  3.000
 NN5  C23  C26  N28  118.22  3.000
 NN5  O27  C26  N28  121.53  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
 NN5  CONST_01  N4   C3   N2   N1     0.00   0.0  0
 NN5  CONST_02  C3   N4   C5   N1     0.00   0.0  0
 NN5  CONST_03  C7   C6   C5   N1     0.00   0.0  0
 NN5  CONST_04  C7   C8   C9   N1     0.00   0.0  0
 NN5  CONST_05  C10  C8   C9   N1   180.00   0.0  0
 NN5  CONST_06  N2   C3   N4   C5     0.00   0.0  0
 NN5  CONST_07  C3   N2   N1   C5     0.00   0.0  0
 NN5  CONST_08  C8   C9   N1   C5     0.00   0.0  0
 NN5  CONST_09  C8   C7   C6   C5     0.00   0.0  0
 NN5  CONST_10  C3   N4   C5   C6   180.00   0.0  0
 NN5  CONST_11  N2   N1   C5   C6   180.00   0.0  0
 NN5  CONST_12  C9   N1   C5   C6     0.00   0.0  0
 NN5  CONST_13  C9   C8   C7   C6     0.00   0.0  0
 NN5  CONST_14  C10  C8   C7   C6   180.00   0.0  0
 NN5  CONST_15  N4   C5   C6   C7   180.00   0.0  0
 NN5  CONST_18  N2   N1   C9   C8   180.00   0.0  0
 NN5  CONST_19  C12  C11  C10  C8   180.00   0.0  0
 NN5  CONST_20  C14  C15  C10  C8   180.00   0.0  0
 NN5  CONST_21  C13  C12  C11  C10    0.00   0.0  0
 NN5  CONST_22  C13  C14  C15  C10    0.00   0.0  0
 NN5  CONST_24  C12  C11  C10  C15    0.00   0.0  0
 NN5  CONST_25  C12  C13  C14  C15    0.00   0.0  0
 NN5  CONST_26  C23  C22  C21  C20    0.00   0.0  0
 NN5  CONST_27  C23  C24  C25  C20    0.00   0.0  0
 NN5  CONST_28  C24  C23  C22  C21    0.00   0.0  0
 NN5  CONST_29  C24  C25  C20  C21    0.00   0.0  0
 NN5  CONST_30  C25  C24  C23  C22    0.00   0.0  0
 NN5  CONST_31  C25  C20  C21  C22    0.00   0.0  0
 NN5  CONST_32  C9   N1   N2   C3   180.00   0.0  0
 NN5  CONST_33  N2   N1   C5   N4     0.00   0.0  0
 NN5  CONST_34  C9   N1   C5   N4   180.00   0.0  0
 NN5  CONST_36  C14  C15  C10  C11    0.00   0.0  0
 NN5  CONST_37  C14  C13  C12  C11    0.00   0.0  0
 NN5  CONST_38  N19  C3   N2   N1   180.00   0.0  0
 NN5  CONST_39  N19  C3   N4   C5   180.00   0.0  0
 NN5  CONST_40  C18  C12  C11  C10  180.00   0.0  0
 NN5  CONST_41  C16  C14  C15  C10  180.00   0.0  0
 NN5  CONST_42  O17  C13  C14  C15  180.00   0.0  0
 NN5  CONST_43  C26  C23  C22  C21  180.00   0.0  0
 NN5  CONST_44  N19  C20  C21  C22  180.00   0.0  0
 NN5  CONST_45  N19  C20  C25  C24  180.00   0.0  0
 NN5  CONST_46  C25  C24  C23  C26  180.00   0.0  0
 NN5  CONST_47  O17  C13  C12  C11  180.00   0.0  0
 NN5  CONST_48  C16  C14  C13  C12  180.00   0.0  0
 NN5  CONST_49  C14  C13  C12  C18  180.00   0.0  0
 NN5  CONST_51  C23  C26  N28  C33  180.00   0.0  0
 NN5  CONST_52  H1   C6   C5   N1   180.00   0.0  0
 NN5  CONST_53  H17  C9   N1   C5   180.00   0.0  0
 NN5  CONST_54  H2   C7   C6   C5   180.00   0.0  0
 NN5  CONST_55  H18  C11  C10  C8     0.00   0.0  0
 NN5  CONST_56  H3   C15  C10  C8     0.00   0.0  0
 NN5  CONST_57  H5   C22  C21  C20  180.00   0.0  0
 NN5  CONST_58  H6   C24  C25  C20  180.00   0.0  0
 NN5  CONST_59  H15  C25  C20  C21  180.00   0.0  0
 NN5  CONST_60  H4   C21  C22  C23  180.00   0.0  0
 NN5  CONST_62  O27  C26  N28  C33    0.00   0.0  0
 NN5  Var_01    C32  C33  N28  C29   25.77  30.0  1
 NN5  Var_02    C33  N28  C29  C30   29.38  30.0  1
 NN5  Var_03    C33  C32  O31  C30   30.47  30.0  1
 NN5  Var_04    N28  C33  C32  O31  -60.02  30.0  1
 NN5  Var_05    N28  C29  C30  O31  -60.82  30.0  1
 NN5  Var_06    N4   C3   N19  C20  179.88  30.0  2
 NN5  Var_07    C3   N19  C20  C21    0.29  30.0  2
 NN5  Var_08    N28  C26  C23  C22  140.61  30.0  2
 NN5  Var_09    H9   C30  O31  C32  -94.00  30.0  1
 NN5  Var_10    H19  C18  C12  C13  -58.84  30.0  2
 NN5  Var_11    H23  C16  C14  C13  -62.39  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
 NN5  plan-1  C20  0.020
 NN5  plan-1  C21  0.020
 NN5  plan-1  C22  0.020
 NN5  plan-1  C24  0.020
 NN5  plan-1  C23  0.020
 NN5  plan-1  C25  0.020
 NN5  plan-1  H4   0.020
 NN5  plan-1  H5   0.020
 NN5  plan-1  H6   0.020
 NN5  plan-1  H15  0.020
 NN5  plan-1  N19  0.020
 NN5  plan-1  C26  0.020
 NN5  plan-2  C8   0.020
 NN5  plan-2  C10  0.020
 NN5  plan-2  C13  0.020
 NN5  plan-2  C15  0.020
 NN5  plan-2  C11  0.020
 NN5  plan-2  C12  0.020
 NN5  plan-2  C18  0.020
 NN5  plan-2  O17  0.020
 NN5  plan-2  C14  0.020
 NN5  plan-2  C16  0.020
 NN5  plan-2  H3   0.020
 NN5  plan-2  H18  0.020
 NN5  plan-3  N1   0.020
 NN5  plan-3  C5   0.020
 NN5  plan-3  C6   0.020
 NN5  plan-3  C7   0.020
 NN5  plan-3  C8   0.020
 NN5  plan-3  C10  0.020
 NN5  plan-3  C3   0.020
 NN5  plan-3  N4   0.020
 NN5  plan-3  N2   0.020
 NN5  plan-3  C9   0.020
 NN5  plan-3  H1   0.020
 NN5  plan-3  H2   0.020
 NN5  plan-3  H17  0.020
 NN5  plan-3  N19  0.020
 NN5  plan-4  C29  0.020
 NN5  plan-4  C33  0.020
 NN5  plan-4  N28  0.020
 NN5  plan-4  O27  0.020
 NN5  plan-4  C23  0.020
 NN5  plan-4  C26  0.020

