# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 10:33:55 2020
#   Inital geometry file: a 167 line input string
#   Ligand name: (2~{S})-~{N}-[(1~{R},2~{S})-1-cyano-1-oxidanyl-3-[(3~{S})-2-oxidanylidenepiperidin-3-yl]propan-2-yl]-3-phenyl-2-[[(~{E})-3-phenylprop-2-enoyl]amino]propanamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@@H](C#N)[C@H](C[C@@H]1CCCNC1=O)NC(=O)[C@H](Cc2ccccc2)NC(=O)\C=C\c3ccccc3
#
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
 E22  E22  (2~{S})-~{N}-[(1~{R},2~{S})-1-cyano-1-oxidanyl-3-[(3~{S})-2-oxidanylidenepiperidin-3-yl]propan-2-yl]-3-phenyl-2-[[(~{E})-3-phenylprop-2-enoyl]amino]propanamide  ligand  65  35  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_E22
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
 E22  C5   C  C     0   0.591  -2.0995  -0.0855   0.5361
 E22  O2   O  O     0  -0.489  -1.9585  -0.6464   1.6142
 E22  C9   C  C1    0  -0.424  -3.2602   0.7768   0.2173
 E22  C16  C  C1    0  -0.230  -4.2396   0.9678   1.1052
 E22  C21  C  CR6   0   0.148  -5.4383   1.7827   0.9237
 E22  C14  C  CR16  0  -0.317  -5.7387   2.4444  -0.2721
 E22  C8   C  CR16  0  -0.233  -6.8865   3.2092  -0.3853
 E22  C4   C  CR16  0  -0.261  -7.7598   3.3293   0.6916
 E22  C10  C  CR16  0  -0.240  -7.4759   2.6769   1.8829
 E22  C26  C  CR16  0  -0.306  -6.3260   1.9091   1.9951
 E22  N1   N  NH1   0  -0.658  -1.2085  -0.1860  -0.4729
 E22  C1   C  CH1   0  -0.220  -0.0580  -1.0421  -0.4425
 E22  C3   C  C     0   0.582   1.1681  -0.2809  -0.9341
 E22  O1   O  O     0  -0.478   1.0763   0.6056  -1.7651
 E22  C2   C  CH2   0  -0.520  -0.2538  -2.2838  -1.3401
 E22  C7   C  CR6   0   0.148  -1.4422  -3.0899  -0.9059
 E22  C12  C  CR16  0  -0.305  -2.6930  -2.8819  -1.4795
 E22  C18  C  CR16  0  -0.296  -1.3227  -4.0298   0.1151
 E22  C22  C  CR16  0  -0.239  -3.8017  -3.5962  -1.0444
 E22  C23  C  CR16  0  -0.242  -2.4264  -4.7479   0.5514
 E22  C20  C  CR16  0  -0.271  -3.6711  -4.5316  -0.0272
 E22  C6   C  CH2   0  -0.468   3.7344   3.5006   1.4220
 E22  C11  C  CH1   0  -0.144   3.6281  -0.3425  -0.9035
 E22  C13  C  CH2   0  -0.453   3.8967   2.3536   0.4414
 E22  C15  C  C     0   0.565   5.1163   1.1549   2.3397
 E22  C17  C  CH2   0  -0.450   4.5987  -0.0824   0.2441
 E22  C19  C  CSP   0   0.098   5.4292  -1.1033  -2.4175
 E22  C24  C  CH1   0   0.009   4.1347  -1.4801  -1.8144
 E22  C25  C  CH1   0  -0.374   4.1368   1.0377   1.1782
 E22  C27  C  CH2   0  -0.262   4.9963   3.6577   2.2414
 E22  N2   N  NS    0  -0.256   6.4273  -0.8154  -2.9107
 E22  N3   N  NH1   0  -0.630   2.3285  -0.7059  -0.4027
 E22  N4   N  NH1   0  -0.629   5.4161   2.3822   2.7904
 E22  O3   O  OH1   0  -0.634   3.1975  -1.7206  -2.8166
 E22  H1   H  H     0   0.270  -3.2862   1.2431  -0.7615
 E22  H3   H  H     0   0.259  -4.1537   0.4773   2.0702
 E22  H5   H  HCR6  0   0.257  -5.0754   2.3636  -1.1240
 E22  H6   H  HCR6  0   0.262  -7.1039   3.7149  -1.3171
 E22  H7   H  HCR6  0   0.262  -8.6560   3.9289   0.5992
 E22  H8   H  HCR6  0   0.261  -8.1487   2.7650   2.7258
 E22  H9   H  HCR6  0   0.259  -6.1088   1.4011   2.9272
 E22  H10  H  HNH1  0   0.399  -1.3915   0.3065  -1.3335
 E22  H11  H  HCH1  0   0.291   0.0879  -1.3689   0.5883
 E22  H12  H  HCH2  0   0.264  -0.3747  -1.9528  -2.3746
 E22  H13  H  HCH2  0   0.264   0.6526  -2.8918  -1.3045
 E22  H14  H  HCR6  0   0.245  -2.8006  -2.1574  -2.2780
 E22  H15  H  HCR6  0   0.244  -0.3545  -4.2031   0.5715
 E22  H16  H  HCR6  0   0.251  -4.7670  -3.4248  -1.5034
 E22  H17  H  HCR6  0   0.252  -2.3168  -5.4790   1.3422
 E22  H18  H  HCR6  0   0.252  -4.5324  -5.0941   0.3101
 E22  H19  H  HCH2  0   0.252   3.5318   4.4354   0.8979
 E22  H20  H  HCH2  0   0.235   2.8830   3.3107   2.0818
 E22  H21  H  HCH1  0   0.288   3.5150   0.5531  -1.5158
 E22  H22  H  HCH2  0   0.254   3.0059   2.2716  -0.1838
 E22  H23  H  HCH2  0   0.232   4.7346   2.5575  -0.2347
 E22  H24  H  HCH2  0   0.257   4.7348  -1.0052   0.8120
 E22  H25  H  HCH2  0   0.262   5.5765   0.1819  -0.1681
 E22  H26  H  HCH1  0   0.292   4.3199  -2.3663  -1.1944
 E22  H27  H  HCH1  0   0.279   3.1901   0.7321   1.6404
 E22  H28  H  HCH2  0   0.233   5.7942   4.0796   1.6218
 E22  H29  H  HCH2  0   0.253   4.8371   4.3490   3.0695
 E22  H30  H  HNH1  0   0.406   2.2959  -1.4409   0.2884
 E22  H31  H  HNH1  0   0.393   6.0738   2.4122   3.5559
 E22  H32  H  HOH1  0   0.474   3.2869  -2.6298  -3.1204
 E22  O4   O  O     0  -0.512   5.5855   0.1509   2.8669

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
 E22  N2   C19  triple    1.150  0.020  1.150
 E22  C19  C24  single    1.477  0.020  1.477
 E22  O3   C24  single    1.393  0.020  1.393
 E22  C24  C11  single    1.543  0.020  1.543
 E22  C11  N3   single    1.439  0.020  1.439
 E22  C11  C17  single    1.525  0.020  1.525
 E22  N3   C3   single    1.345  0.020  1.345
 E22  O1   C3   double    1.219  0.020  1.219
 E22  C2   C7   single    1.500  0.020  1.500
 E22  C2   C1   single    1.545  0.020  1.545
 E22  C17  C25  single    1.530  0.020  1.530
 E22  C3   C1   single    1.525  0.020  1.525
 E22  C7   C12  aromatic  1.392  0.020  1.392
 E22  C7   C18  aromatic  1.393  0.020  1.393
 E22  C12  C22  aromatic  1.389  0.020  1.389
 E22  C18  C23  aromatic  1.387  0.020  1.387
 E22  C1   N1   single    1.434  0.020  1.434
 E22  C22  C20  aromatic  1.388  0.020  1.388
 E22  C23  C20  aromatic  1.390  0.020  1.390
 E22  C25  C13  single    1.527  0.020  1.527
 E22  C25  C15  single    1.524  0.020  1.524
 E22  C13  C6   single    1.518  0.020  1.518
 E22  O4   C15  double    1.227  0.020  1.227
 E22  N1   C5   single    1.350  0.020  1.350
 E22  C15  N4   single    1.341  0.020  1.341
 E22  C6   C27  single    1.513  0.020  1.513
 E22  O2   C5   double    1.223  0.020  1.223
 E22  C5   C9   single    1.481  0.020  1.481
 E22  N4   C27  single    1.451  0.020  1.451
 E22  C9   C16  double    1.336  0.020  1.336
 E22  C16  C21  single    1.461  0.020  1.461
 E22  C21  C26  aromatic  1.397  0.020  1.397
 E22  C21  C14  aromatic  1.399  0.020  1.399
 E22  C26  C10  aromatic  1.387  0.020  1.387
 E22  C14  C8   aromatic  1.384  0.020  1.384
 E22  C10  C4   aromatic  1.388  0.020  1.388
 E22  C8   C4   aromatic  1.392  0.020  1.392
 E22  C9   H1   single    0.930  0.020  1.080
 E22  C16  H3   single    0.930  0.020  1.080
 E22  C14  H5   single    0.930  0.020  1.080
 E22  C8   H6   single    0.930  0.020  1.080
 E22  C4   H7   single    0.930  0.020  1.080
 E22  C10  H8   single    0.930  0.020  1.080
 E22  C26  H9   single    0.930  0.020  1.080
 E22  N1   H10  single    0.860  0.020  1.020
 E22  C1   H11  single    0.970  0.020  1.090
 E22  C2   H12  single    0.970  0.020  1.090
 E22  C2   H13  single    0.970  0.020  1.090
 E22  C12  H14  single    0.930  0.020  1.080
 E22  C18  H15  single    0.930  0.020  1.080
 E22  C22  H16  single    0.930  0.020  1.080
 E22  C23  H17  single    0.930  0.020  1.080
 E22  C20  H18  single    0.930  0.020  1.080
 E22  C6   H19  single    0.970  0.020  1.090
 E22  C6   H20  single    0.970  0.020  1.090
 E22  C11  H21  single    0.970  0.020  1.090
 E22  C13  H22  single    0.970  0.020  1.090
 E22  C13  H23  single    0.970  0.020  1.090
 E22  C17  H24  single    0.970  0.020  1.090
 E22  C17  H25  single    0.970  0.020  1.090
 E22  C24  H26  single    0.970  0.020  1.090
 E22  C25  H27  single    0.970  0.020  1.090
 E22  C27  H28  single    0.970  0.020  1.090
 E22  C27  H29  single    0.970  0.020  1.090
 E22  N3   H30  single    0.860  0.020  1.020
 E22  N4   H31  single    0.860  0.020  1.020
 E22  O3   H32  single    0.850  0.020  0.980

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
 E22  N1   C5   C9   113.57  3.000
 E22  C9   C5   O2   123.17  3.000
 E22  N1   C5   O2   123.26  3.000
 E22  H1   C9   C16  121.39  3.000
 E22  H1   C9   C5   117.62  3.000
 E22  C16  C9   C5   120.99  3.000
 E22  H3   C16  C21  115.29  3.000
 E22  H3   C16  C9   117.91  3.000
 E22  C21  C16  C9   126.79  3.000
 E22  C26  C21  C14  118.43  3.000
 E22  C14  C21  C16  123.10  3.000
 E22  C26  C21  C16  118.47  3.000
 E22  H5   C14  C8   119.01  3.000
 E22  H5   C14  C21  120.37  3.000
 E22  C8   C14  C21  120.61  3.000
 E22  H6   C8   C4   119.99  3.000
 E22  H6   C8   C14  119.69  3.000
 E22  C4   C8   C14  120.32  3.000
 E22  H7   C4   C10  120.21  3.000
 E22  H7   C4   C8   120.09  3.000
 E22  C10  C4   C8   119.69  3.000
 E22  H8   C10  C26  119.83  3.000
 E22  H8   C10  C4   120.22  3.000
 E22  C26  C10  C4   119.95  3.000
 E22  H9   C26  C10  119.69  3.000
 E22  H9   C26  C21  119.33  3.000
 E22  C10  C26  C21  120.98  3.000
 E22  H10  N1   C1   117.08  3.000
 E22  H10  N1   C5   118.80  3.000
 E22  C1   N1   C5   123.92  3.000
 E22  H11  C1   C2   108.97  3.000
 E22  H11  C1   C3   110.28  3.000
 E22  C2   C1   C3   108.42  3.000
 E22  H11  C1   N1   107.82  3.000
 E22  C3   C1   N1   109.89  3.000
 E22  C2   C1   N1   111.46  3.000
 E22  N3   C3   O1   124.35  3.000
 E22  O1   C3   C1   121.50  3.000
 E22  N3   C3   C1   114.12  3.000
 E22  H13  C2   H12  106.94  3.000
 E22  H13  C2   C7   110.42  3.000
 E22  H12  C2   C7   110.43  3.000
 E22  H13  C2   C1   108.87  3.000
 E22  H12  C2   C1   108.70  3.000
 E22  C7   C2   C1   111.35  3.000
 E22  C18  C7   C12  118.69  3.000
 E22  C18  C7   C2   120.45  3.000
 E22  C12  C7   C2   120.82  3.000
 E22  H14  C12  C22  119.70  3.000
 E22  H14  C12  C7   119.53  3.000
 E22  C22  C12  C7   120.76  3.000
 E22  H15  C18  C23  119.69  3.000
 E22  H15  C18  C7   119.54  3.000
 E22  C23  C18  C7   120.78  3.000
 E22  H16  C22  C20  120.08  3.000
 E22  H16  C22  C12  119.84  3.000
 E22  C20  C22  C12  120.08  3.000
 E22  H17  C23  C20  120.00  3.000
 E22  H17  C23  C18  119.93  3.000
 E22  C20  C23  C18  120.08  3.000
 E22  H18  C20  C23  120.14  3.000
 E22  H18  C20  C22  120.24  3.000
 E22  C23  C20  C22  119.62  3.000
 E22  H20  C6   H19  107.11  3.000
 E22  H20  C6   C27  109.91  3.000
 E22  H19  C6   C27  109.04  3.000
 E22  H20  C6   C13  109.98  3.000
 E22  H19  C6   C13  110.92  3.000
 E22  C27  C6   C13  109.83  3.000
 E22  H21  C11  N3   108.00  3.000
 E22  H21  C11  C24  107.94  3.000
 E22  N3   C11  C24  108.41  3.000
 E22  H21  C11  C17  110.38  3.000
 E22  N3   C11  C17  110.84  3.000
 E22  C24  C11  C17  111.16  3.000
 E22  H23  C13  H22  106.54  3.000
 E22  H23  C13  C25  109.74  3.000
 E22  H22  C13  C25  109.87  3.000
 E22  H23  C13  C6   109.87  3.000
 E22  H22  C13  C6   109.85  3.000
 E22  C25  C13  C6   110.88  3.000
 E22  O4   C15  N4   121.24  3.000
 E22  N4   C15  C25  118.05  3.000
 E22  O4   C15  C25  120.68  3.000
 E22  H25  C17  H24  106.78  3.000
 E22  H25  C17  C25  108.85  3.000
 E22  H24  C17  C25  109.80  3.000
 E22  H25  C17  C11  109.07  3.000
 E22  H24  C17  C11  109.05  3.000
 E22  C25  C17  C11  113.09  3.000
 E22  N2   C19  C24  180.00  3.000
 E22  H26  C24  O3   112.37  3.000
 E22  H26  C24  C19  106.79  3.000
 E22  O3   C24  C19  109.87  3.000
 E22  H26  C24  C11  108.50  3.000
 E22  O3   C24  C11  109.34  3.000
 E22  C19  C24  C11  109.92  3.000
 E22  H27  C25  C17  108.30  3.000
 E22  H27  C25  C15  104.77  3.000
 E22  C17  C25  C15  109.13  3.000
 E22  H27  C25  C13  107.92  3.000
 E22  C15  C25  C13  113.73  3.000
 E22  C17  C25  C13  112.57  3.000
 E22  H29  C27  H28  106.98  3.000
 E22  H29  C27  N4   108.19  3.000
 E22  H28  C27  N4   110.00  3.000
 E22  H29  C27  C6   110.82  3.000
 E22  H28  C27  C6   109.96  3.000
 E22  N4   C27  C6   110.80  3.000
 E22  H30  N3   C11  116.82  3.000
 E22  H30  N3   C3   118.21  3.000
 E22  C11  N3   C3   124.17  3.000
 E22  H31  N4   C27  116.70  3.000
 E22  H31  N4   C15  115.32  3.000
 E22  C27  N4   C15  127.78  3.000
 E22  H32  O3   C24  109.12  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
 E22  CONST_01  C4   C10  C26  C21     0.00   0.0  0
 E22  CONST_02  C4   C8   C14  C21     0.00   0.0  0
 E22  CONST_03  C10  C26  C21  C14     0.00   0.0  0
 E22  CONST_04  C10  C4   C8   C14     0.00   0.0  0
 E22  CONST_05  C26  C21  C14  C8      0.00   0.0  0
 E22  CONST_06  C26  C10  C4   C8      0.00   0.0  0
 E22  CONST_07  C20  C22  C12  C7      0.00   0.0  0
 E22  CONST_08  C20  C23  C18  C7      0.00   0.0  0
 E22  CONST_09  C23  C18  C7   C12     0.00   0.0  0
 E22  CONST_10  C23  C20  C22  C12     0.00   0.0  0
 E22  CONST_11  C22  C12  C7   C18     0.00   0.0  0
 E22  CONST_12  C22  C20  C23  C18     0.00   0.0  0
 E22  CONST_13  C27  N4   C15  C25     0.00   0.0  0
 E22  CONST_14  C10  C26  C21  C16   180.00   0.0  0
 E22  CONST_15  C8   C14  C21  C16   180.00   0.0  0
 E22  CONST_16  C22  C12  C7   C2    180.00   0.0  0
 E22  CONST_17  C23  C18  C7   C2    180.00   0.0  0
 E22  CONST_18  O4   C15  N4   C27   180.00   0.0  0
 E22  CONST_19  H8   C10  C26  C21   180.00   0.0  0
 E22  CONST_20  H6   C8   C14  C21   180.00   0.0  0
 E22  CONST_21  H9   C26  C21  C14   180.00   0.0  0
 E22  CONST_22  H7   C4   C8   C14   180.00   0.0  0
 E22  CONST_23  H5   C14  C8   C4    180.00   0.0  0
 E22  CONST_24  H16  C22  C12  C7    180.00   0.0  0
 E22  CONST_25  H17  C23  C18  C7    180.00   0.0  0
 E22  CONST_26  H15  C18  C7   C12   180.00   0.0  0
 E22  CONST_27  H18  C20  C22  C12   180.00   0.0  0
 E22  CONST_28  H14  C12  C7   C18   180.00   0.0  0
 E22  CONST_29  H31  N4   C15  C25   180.00   0.0  0
 E22  CONST_30  C1   N1   C5   O2      0.00   0.0  0
 E22  CONST_31  C1   N1   C5   C9    180.00   0.0  0
 E22  CONST_32  C11  N3   C3   C1    180.00   0.0  0
 E22  CONST_33  C11  N3   C3   O1      0.00   0.0  0
 E22  CONST_34  H10  N1   C5   O2    180.00   0.0  0
 E22  CONST_35  H30  N3   C3   C1      0.00   0.0  0
 E22  Var_01    C15  N4   C27  C6     22.83  30.0  1
 E22  Var_02    N4   C27  C6   C13   -49.48  30.0  1
 E22  Var_03    C27  C6   C13  C25    61.17  30.0  1
 E22  Var_04    C26  C21  C16  C9   -177.20  30.0  2
 E22  Var_05    C12  C7   C2   C1     93.35  30.0  2
 E22  Var_06    C21  C16  C9   C5   -179.72   0.0  2
 E22  Var_07    C16  C9   C5   O2     -1.16  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
 E22  chir_01  C1   C2   C3   N1   negativ
 E22  chir_02  C11  N3   C24  C17  positiv
 E22  chir_03  C24  O3   C11  C19  positiv
 E22  chir_04  C25  C17  C13  C15  positiv

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
 E22  plan-1  C16  0.020
 E22  plan-1  C21  0.020
 E22  plan-1  C14  0.020
 E22  plan-1  C8   0.020
 E22  plan-1  C4   0.020
 E22  plan-1  C10  0.020
 E22  plan-1  C26  0.020
 E22  plan-1  H5   0.020
 E22  plan-1  H6   0.020
 E22  plan-1  H7   0.020
 E22  plan-1  H8   0.020
 E22  plan-1  H9   0.020
 E22  plan-2  C5   0.020
 E22  plan-2  C9   0.020
 E22  plan-2  C16  0.020
 E22  plan-2  C21  0.020
 E22  plan-2  H1   0.020
 E22  plan-2  H3   0.020
 E22  plan-3  C2   0.020
 E22  plan-3  C7   0.020
 E22  plan-3  C12  0.020
 E22  plan-3  C18  0.020
 E22  plan-3  C22  0.020
 E22  plan-3  C23  0.020
 E22  plan-3  C20  0.020
 E22  plan-3  H14  0.020
 E22  plan-3  H15  0.020
 E22  plan-3  H16  0.020
 E22  plan-3  H17  0.020
 E22  plan-3  H18  0.020
 E22  plan-4  C5   0.020
 E22  plan-4  O2   0.020
 E22  plan-4  C9   0.020
 E22  plan-4  N1   0.020
 E22  plan-4  C1   0.020
 E22  plan-4  H10  0.020
 E22  plan-5  C1   0.020
 E22  plan-5  C3   0.020
 E22  plan-5  O1   0.020
 E22  plan-5  C11  0.020
 E22  plan-5  N3   0.020
 E22  plan-5  H30  0.020
 E22  plan-6  C15  0.020
 E22  plan-6  C25  0.020
 E22  plan-6  C27  0.020
 E22  plan-6  N4   0.020
 E22  plan-6  H31  0.020
 E22  plan-6  O4   0.020

