# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 11 00:57:49 2020
#   Inital geometry file: a 161 line input string
#   Ligand name: 2-methoxyethyl (2E)-3-phenylprop-2-en-1-yl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COCCOC(=O)c1c(C)nc(C)c(C(=O)OC/C=C/c2ccccc2)c1c3cccc(c3)[N+]([O-])=O
#
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
 93O  93O  '2-methoxyethyl (2E)-3-phenylprop-2-en-1-yl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate'  ligand  62  36  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_93O
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
 93O  C1   C  CR6    0   0.262  -3.3493  -0.3148   1.7630
 93O  C2   C  CR6    0  -0.139  -2.3739  -0.2498   0.7656
 93O  C3   C  CR6    0   0.315  -1.0658   0.0693   1.1107
 93O  C4   C  CR6    0  -0.153  -0.7792   0.3211   2.4503
 93O  C5   C  CR6    0   0.259  -1.8122   0.2496   3.3902
 93O  C6   C  CH3    0  -0.738  -1.5855   0.4979   4.8504
 93O  C8   C  CH2    0  -0.244   2.8824  -0.0280   2.5976
 93O  C9   C  C1     0  -0.235   3.5118  -0.4418   1.3139
 93O  C11  C  CR6    0   0.144   4.8244   0.1237  -0.7388
 93O  C14  C  CR16   0  -0.270   5.9592  -0.2990  -3.2648
 93O  C15  C  CR16   0  -0.233   5.4512  -1.3690  -2.5340
 93O  C16  C  CR16   0  -0.315   4.8915  -1.1618  -1.2853
 93O  C17  C  CR6    0  -0.014  -0.0279   0.1401   0.0550
 93O  C18  C  CR16   0  -0.298   0.5580   1.3535  -0.2670
 93O  C19  C  CR6    0   0.266   1.4779   1.3962  -1.3036
 93O  C20  C  CR16   0  -0.244   1.8397   0.2675  -2.0197
 93O  O4   O  O      0  -0.415  -2.6713   0.4448  -1.4924
 93O  C23  C  C      0   0.466  -2.7434  -0.4297  -0.6687
 93O  O5   O  O2     0  -0.439  -3.1647  -1.6561  -0.9056
 93O  C24  C  CH2    0  -0.214  -3.6729  -1.9608  -2.2120
 93O  C25  C  CH2    0  -0.169  -4.2104  -3.3650  -2.1758
 93O  O6   O  O2     0  -0.477  -5.2961  -3.4253  -1.2909
 93O  C26  C  CH3    0  -0.396  -5.8541  -4.7124  -1.2105
 93O  C22  C  CR16   0  -0.254   0.3420  -1.0095  -0.6387
 93O  C21  C  CR16   0  -0.232   1.2701  -0.9438  -1.6653
 93O  N1   N  N      1   0.320   2.0883   2.6715  -1.6431
 93O  O3   O  O     -1  -0.377   2.0042   3.5716  -0.8400
 93O  O2   O  O      0  -0.368   2.6542   2.7644  -2.7064
 93O  N    N  N      0  -0.453  -3.0510  -0.0668   3.0322
 93O  C    C  CH3    0  -0.749  -4.7804  -0.6341   1.4535
 93O  C7   C  C      0   0.464   0.6079   0.6607   2.8769
 93O  O    O  O      0  -0.424   0.8904   1.6449   3.5115
 93O  O1   O  O2     0  -0.439   1.4627  -0.2575   2.4711
 93O  C10  C  C1     0  -0.272   4.1892   0.4127   0.5478
 93O  C13  C  CR16   0  -0.235   5.9087   0.9796  -2.7299
 93O  C12  C  CR16   0  -0.313   5.3487   1.1854  -1.4769
 93O  H1   H  HCH3   0   0.265  -1.3934   1.5534   5.0429
 93O  H2   H  HCH3   0   0.259  -2.4683   0.2030   5.4121
 93O  H3   H  HCH3   0   0.254  -0.7313  -0.0616   5.2319
 93O  H4   H  HCH2   0   0.260   3.2322  -0.6335   3.4362
 93O  H5   H  HCH2   0   0.259   3.0890   1.0188   2.8204
 93O  H6   H  H      0   0.257   3.3867  -1.4803   1.0253
 93O  H7   H  HCR6   0   0.258   6.3945  -0.4666  -4.2413
 93O  H8   H  HCR6   0   0.258   5.4936  -2.3707  -2.9417
 93O  H9   H  HCR6   0   0.248   4.5006  -2.0106  -0.7390
 93O  H10  H  HCR6   0   0.299   0.2738   2.2533   0.2614
 93O  H11  H  HCR6   0   0.303   2.5645   0.3174  -2.8189
 93O  H12  H  HCH2   0   0.250  -4.4559  -1.2497  -2.4844
 93O  H13  H  HCH2   0   0.253  -2.8732  -1.8921  -2.9519
 93O  H14  H  HCH2   0   0.218  -4.5088  -3.6310  -3.1995
 93O  H15  H  HCH2   0   0.214  -3.4165  -4.0677  -1.8846
 93O  H16  H  HCH3   0   0.206  -6.2359  -5.0571  -2.1789
 93O  H17  H  HCH3   0   0.206  -5.1293  -5.4529  -0.8520
 93O  H18  H  HCH3   0   0.235  -6.6846  -4.6745  -0.5070
 93O  H19  H  HCR6   0   0.280  -0.0911  -1.9645  -0.3692
 93O  H20  H  HCR6   0   0.280   1.5567  -1.8433  -2.1921
 93O  H21  H  HCH3   0   0.256  -5.1704   0.0005   0.6562
 93O  H22  H  HCH3   0   0.268  -4.8990  -1.6680   1.1278
 93O  H23  H  HCH3   0   0.263  -5.3919  -0.4805   2.3390
 93O  H24  H  H      0   0.252   4.2707   1.4447   0.8796
 93O  H25  H  HCR6   0   0.257   6.3030   1.8196  -3.2869
 93O  H26  H  HCR6   0   0.254   5.3123   2.1878  -1.0665

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
 93O  C20  C21  aromatic  1.385  0.020  1.385
 93O  C20  C19  aromatic  1.385  0.020  1.385
 93O  C21  C22  aromatic  1.386  0.020  1.386
 93O  C26  O6   single    1.405  0.020  1.405
 93O  C15  C16  aromatic  1.384  0.020  1.384
 93O  C15  C14  aromatic  1.392  0.020  1.392
 93O  C16  C11  aromatic  1.398  0.020  1.398
 93O  O2   N1   double    1.208  0.020  1.208
 93O  O3   N1   single    1.209  0.020  1.209
 93O  C14  C13  aromatic  1.387  0.020  1.387
 93O  N1   C19  single    1.454  0.020  1.454
 93O  C19  C18  aromatic  1.387  0.020  1.387
 93O  C11  C12  aromatic  1.395  0.020  1.395
 93O  C11  C10  single    1.464  0.020  1.464
 93O  C13  C12  aromatic  1.388  0.020  1.388
 93O  C22  C17  aromatic  1.393  0.020  1.393
 93O  O6   C25  single    1.402  0.020  1.402
 93O  C10  C9   double    1.333  0.020  1.333
 93O  C24  C25  single    1.504  0.020  1.504
 93O  C24  O5   single    1.435  0.020  1.435
 93O  C18  C17  aromatic  1.385  0.020  1.385
 93O  O4   C23  double    1.204  0.020  1.204
 93O  C17  C3   single    1.482  0.020  1.482
 93O  O5   C23  single    1.318  0.020  1.318
 93O  C9   C8   single    1.488  0.020  1.488
 93O  C23  C2   single    1.492  0.020  1.492
 93O  C8   O1   single    1.444  0.020  1.444
 93O  C3   C2   aromatic  1.390  0.020  1.390
 93O  C3   C4   aromatic  1.393  0.020  1.393
 93O  C2   C1   aromatic  1.397  0.020  1.397
 93O  O1   C7   single    1.319  0.020  1.319
 93O  C7   C4   single    1.490  0.020  1.490
 93O  C7   O    double    1.205  0.020  1.205
 93O  C4   C5   aromatic  1.398  0.020  1.398
 93O  C    C1   single    1.499  0.020  1.499
 93O  C1   N    aromatic  1.327  0.020  1.327
 93O  C5   N    aromatic  1.328  0.020  1.328
 93O  C5   C6   single    1.498  0.020  1.498
 93O  C6   H1   single    0.970  0.020  1.090
 93O  C6   H2   single    0.970  0.020  1.090
 93O  C6   H3   single    0.970  0.020  1.090
 93O  C8   H4   single    0.970  0.020  1.090
 93O  C8   H5   single    0.970  0.020  1.090
 93O  C9   H6   single    0.930  0.020  1.080
 93O  C14  H7   single    0.930  0.020  1.080
 93O  C15  H8   single    0.930  0.020  1.080
 93O  C16  H9   single    0.930  0.020  1.080
 93O  C18  H10  single    0.930  0.020  1.080
 93O  C20  H11  single    0.930  0.020  1.080
 93O  C24  H12  single    0.970  0.020  1.090
 93O  C24  H13  single    0.970  0.020  1.090
 93O  C25  H14  single    0.970  0.020  1.090
 93O  C25  H15  single    0.970  0.020  1.090
 93O  C26  H16  single    0.970  0.020  1.090
 93O  C26  H17  single    0.970  0.020  1.090
 93O  C26  H18  single    0.970  0.020  1.090
 93O  C22  H19  single    0.930  0.020  1.080
 93O  C21  H20  single    0.930  0.020  1.080
 93O  C    H21  single    0.970  0.020  1.090
 93O  C    H22  single    0.970  0.020  1.090
 93O  C    H23  single    0.970  0.020  1.090
 93O  C10  H24  single    0.930  0.020  1.080
 93O  C13  H25  single    0.930  0.020  1.080
 93O  C12  H26  single    0.930  0.020  1.080

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
 93O  C    C1   N    116.87  3.000
 93O  N    C1   C2   121.15  3.000
 93O  C    C1   C2   121.96  3.000
 93O  C23  C2   C3   119.96  3.000
 93O  C3   C2   C1   119.38  3.000
 93O  C23  C2   C1   120.53  3.000
 93O  C17  C3   C4   122.16  3.000
 93O  C4   C3   C2   118.29  3.000
 93O  C17  C3   C2   119.54  3.000
 93O  C7   C4   C5   120.44  3.000
 93O  C5   C4   C3   119.03  3.000
 93O  C7   C4   C3   120.53  3.000
 93O  N    C5   C6   116.32  3.000
 93O  C6   C5   C4   122.33  3.000
 93O  N    C5   C4   121.34  3.000
 93O  H3   C6   H2   108.44  3.000
 93O  H3   C6   H1   107.29  3.000
 93O  H2   C6   H1   108.34  3.000
 93O  H3   C6   C5   112.00  3.000
 93O  H2   C6   C5   109.62  3.000
 93O  H1   C6   C5   111.05  3.000
 93O  H5   C8   H4   108.35  3.000
 93O  H5   C8   O1   110.92  3.000
 93O  H4   C8   O1   107.11  3.000
 93O  H5   C8   C9   111.29  3.000
 93O  H4   C8   C9   111.88  3.000
 93O  O1   C8   C9   107.22  3.000
 93O  H6   C9   C10  121.29  3.000
 93O  H6   C9   C8   116.54  3.000
 93O  C10  C9   C8   122.17  3.000
 93O  C12  C11  C10  118.55  3.000
 93O  C10  C11  C16  123.08  3.000
 93O  C12  C11  C16  118.34  3.000
 93O  H7   C14  C13  120.36  3.000
 93O  H7   C14  C15  120.10  3.000
 93O  C13  C14  C15  119.54  3.000
 93O  H8   C15  C16  119.62  3.000
 93O  H8   C15  C14  119.97  3.000
 93O  C16  C15  C14  120.41  3.000
 93O  H9   C16  C15  118.94  3.000
 93O  H9   C16  C11  120.41  3.000
 93O  C15  C16  C11  120.64  3.000
 93O  C22  C17  C18  119.66  3.000
 93O  C18  C17  C3   120.24  3.000
 93O  C22  C17  C3   120.09  3.000
 93O  H10  C18  C19  120.93  3.000
 93O  H10  C18  C17  120.26  3.000
 93O  C19  C18  C17  118.77  3.000
 93O  N1   C19  C20  118.98  3.000
 93O  N1   C19  C18  118.69  3.000
 93O  C20  C19  C18  122.33  3.000
 93O  H11  C20  C21  120.39  3.000
 93O  H11  C20  C19  121.35  3.000
 93O  C21  C20  C19  118.25  3.000
 93O  O5   C23  O4   124.91  3.000
 93O  O5   C23  C2   111.35  3.000
 93O  O4   C23  C2   123.74  3.000
 93O  C24  O5   C23  118.33  3.000
 93O  H13  C24  H12  108.37  3.000
 93O  H13  C24  C25  109.69  3.000
 93O  H12  C24  C25  110.95  3.000
 93O  H13  C24  O5   110.15  3.000
 93O  H12  C24  O5   110.04  3.000
 93O  C25  C24  O5   107.64  3.000
 93O  H15  C25  H14  106.74  3.000
 93O  H15  C25  O6   111.38  3.000
 93O  H14  C25  O6   111.55  3.000
 93O  H15  C25  C24  110.18  3.000
 93O  H14  C25  C24  107.49  3.000
 93O  O6   C25  C24  109.40  3.000
 93O  C26  O6   C25  112.53  3.000
 93O  H18  C26  H17  108.45  3.000
 93O  H18  C26  H16  108.42  3.000
 93O  H17  C26  H16  107.86  3.000
 93O  H18  C26  O6   107.93  3.000
 93O  H17  C26  O6   112.01  3.000
 93O  H16  C26  O6   112.07  3.000
 93O  H19  C22  C21  119.62  3.000
 93O  H19  C22  C17  119.86  3.000
 93O  C21  C22  C17  120.52  3.000
 93O  H20  C21  C22  119.94  3.000
 93O  H20  C21  C20  119.61  3.000
 93O  C22  C21  C20  120.44  3.000
 93O  O2   N1   O3   124.05  3.000
 93O  O3   N1   C19  117.94  3.000
 93O  O2   N1   C19  118.01  3.000
 93O  C5   N    C1   120.80  3.000
 93O  H23  C    H22  108.42  3.000
 93O  H23  C    H21  108.18  3.000
 93O  H22  C    H21  107.12  3.000
 93O  H23  C    C1   109.81  3.000
 93O  H22  C    C1   111.57  3.000
 93O  H21  C    C1   111.62  3.000
 93O  O1   C7   O    125.38  3.000
 93O  O    C7   C4   123.72  3.000
 93O  O1   C7   C4   110.89  3.000
 93O  C7   O1   C8   119.99  3.000
 93O  H24  C10  C11  115.04  3.000
 93O  H24  C10  C9   118.12  3.000
 93O  C11  C10  C9   126.82  3.000
 93O  H25  C13  C12  119.77  3.000
 93O  H25  C13  C14  120.25  3.000
 93O  C12  C13  C14  119.97  3.000
 93O  H26  C12  C13  119.51  3.000
 93O  H26  C12  C11  119.40  3.000
 93O  C13  C12  C11  121.09  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
 93O  CONST_01  C17  C3   C2   C1    180.00   0.0  0
 93O  CONST_02  C4   C3   C2   C1      0.00   0.0  0
 93O  CONST_03  C4   C5   N    C1      0.00   0.0  0
 93O  CONST_06  C5   C4   C3   C2      0.00   0.0  0
 93O  CONST_07  C5   N    C1   C2      0.00   0.0  0
 93O  CONST_08  C21  C22  C17  C3    180.00   0.0  0
 93O  CONST_09  C19  C18  C17  C3    180.00   0.0  0
 93O  CONST_10  N    C1   C2   C3      0.00   0.0  0
 93O  CONST_11  N    C5   C4   C3      0.00   0.0  0
 93O  CONST_14  C17  C3   C4   C5    180.00   0.0  0
 93O  CONST_15  C14  C15  C16  C11     0.00   0.0  0
 93O  CONST_16  C14  C13  C12  C11     0.00   0.0  0
 93O  CONST_17  C12  C11  C16  C15     0.00   0.0  0
 93O  CONST_18  C12  C13  C14  C15     0.00   0.0  0
 93O  CONST_19  C13  C14  C15  C16     0.00   0.0  0
 93O  CONST_20  C13  C12  C11  C16     0.00   0.0  0
 93O  CONST_21  C20  C21  C22  C17     0.00   0.0  0
 93O  CONST_22  C20  C19  C18  C17     0.00   0.0  0
 93O  CONST_23  C21  C20  C19  C18     0.00   0.0  0
 93O  CONST_24  C21  C22  C17  C18     0.00   0.0  0
 93O  CONST_25  C22  C21  C20  C19     0.00   0.0  0
 93O  CONST_26  C22  C17  C18  C19     0.00   0.0  0
 93O  CONST_27  C6   C5   N    C1    180.00   0.0  0
 93O  CONST_28  C7   C4   C3   C2    180.00   0.0  0
 93O  CONST_29  C    C1   C2   C3    180.00   0.0  0
 93O  CONST_30  C6   C5   C4   C3    180.00   0.0  0
 93O  CONST_31  C23  C2   C3   C4    180.00   0.0  0
 93O  CONST_32  C    C1   N    C5    180.00   0.0  0
 93O  CONST_33  C10  C11  C16  C15   180.00   0.0  0
 93O  CONST_34  N1   C19  C18  C17   180.00   0.0  0
 93O  CONST_35  C23  C2   C3   C17     0.00   0.0  0
 93O  CONST_36  C7   C4   C3   C17     0.00   0.0  0
 93O  CONST_37  N    C1   C2   C23   180.00   0.0  0
 93O  CONST_38  N1   C19  C20  C21   180.00   0.0  0
 93O  CONST_39  C7   C4   C5   N     180.00   0.0  0
 93O  CONST_40  C13  C12  C11  C10   180.00   0.0  0
 93O  CONST_41  H19  C22  C17  C3      0.00   0.0  0
 93O  CONST_42  H10  C18  C17  C3      0.00   0.0  0
 93O  CONST_43  H8   C15  C16  C11   180.00   0.0  0
 93O  CONST_44  H25  C13  C12  C11   180.00   0.0  0
 93O  CONST_45  H9   C16  C15  C14   180.00   0.0  0
 93O  CONST_46  H26  C12  C13  C14   180.00   0.0  0
 93O  CONST_47  H7   C14  C15  C16   180.00   0.0  0
 93O  CONST_48  H20  C21  C22  C17   180.00   0.0  0
 93O  CONST_49  H11  C20  C19  C18   180.00   0.0  0
 93O  Var_01    O4   C23  C2   C1    113.20  30.0  2
 93O  Var_02    O1   C7   C4   C3    -54.29  30.0  2
 93O  Var_03    C16  C11  C10  C9     -5.64  30.0  2
 93O  Var_04    H21  C    C1   C2    -51.19  30.0  2
 93O  Var_05    H1   C6   C5   C4     71.28  30.0  2
 93O  Var_06    C11  C10  C9   C8   -178.76   0.0  2
 93O  Var_07    C25  C24  O5   C23  -174.31  30.0  1
 93O  Var_08    O6   C25  C24  O5     64.14  30.0  3
 93O  Var_09    C10  C9   C8   O1    119.15  30.0  2
 93O  Var_10    H16  C26  O6   C25   -60.75  30.0  3
 93O  Var_11    H4   C8   O1   C7    104.72  30.0  1

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
 93O  plan-1  C1   0.020
 93O  plan-1  C2   0.020
 93O  plan-1  C3   0.020
 93O  plan-1  C4   0.020
 93O  plan-1  C5   0.020
 93O  plan-1  C6   0.020
 93O  plan-1  C17  0.020
 93O  plan-1  C23  0.020
 93O  plan-1  N    0.020
 93O  plan-1  C    0.020
 93O  plan-1  C7   0.020
 93O  plan-2  C11  0.020
 93O  plan-2  C14  0.020
 93O  plan-2  C15  0.020
 93O  plan-2  C16  0.020
 93O  plan-2  C10  0.020
 93O  plan-2  C13  0.020
 93O  plan-2  C12  0.020
 93O  plan-2  H7   0.020
 93O  plan-2  H8   0.020
 93O  plan-2  H9   0.020
 93O  plan-2  H25  0.020
 93O  plan-2  H26  0.020
 93O  plan-3  C3   0.020
 93O  plan-3  C17  0.020
 93O  plan-3  C18  0.020
 93O  plan-3  C19  0.020
 93O  plan-3  C20  0.020
 93O  plan-3  C22  0.020
 93O  plan-3  C21  0.020
 93O  plan-3  N1   0.020
 93O  plan-3  H10  0.020
 93O  plan-3  H11  0.020
 93O  plan-3  H19  0.020
 93O  plan-3  H20  0.020
 93O  plan-4  C19  0.020
 93O  plan-4  N1   0.020
 93O  plan-4  O3   0.020
 93O  plan-4  O2   0.020
 93O  plan-5  C8   0.020
 93O  plan-5  C9   0.020
 93O  plan-5  C11  0.020
 93O  plan-5  C10  0.020
 93O  plan-5  H6   0.020
 93O  plan-5  H24  0.020
 93O  plan-6  C2   0.020
 93O  plan-6  O4   0.020
 93O  plan-6  C23  0.020
 93O  plan-6  O5   0.020
 93O  plan-7  C4   0.020
 93O  plan-7  C7   0.020
 93O  plan-7  O    0.020
 93O  plan-7  O1   0.020

