# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  2 08:52:39 2020
#   Inital geometry file: a 104 line input string
#   Ligand name: (2E)-3-{3-[(5-ethyl-3-iodo-6-methyl-2-oxo-1,2-dihydropyridin-4-yl)oxy]phenyl}prop-2-enenitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC1=C(C)NC(=O)C(=C1Oc2cccc(\C=C\C#N)c2)I
#
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
 3AC  3AC  (2E)-3-{3-[(5-ethyl-3-iodo-6-methyl-2-oxo-1,2-dihydropyridin-4-yl)oxy]phenyl}prop-2-enenitrile  ligand  37  22  .  2022-07-22  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_3AC
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
 3AC  O11   O  O2    0  -0.494   0.0499   0.5567   0.7218
 3AC  C11   C  CR6   0   0.505  -1.1761   0.8918   0.2403
 3AC  C12   C  CR6   0  -0.549  -2.0057  -0.0924  -0.2178
 3AC  I12   I  I     0   0.096  -1.4270  -2.0883  -0.2659
 3AC  C13   C  CR6   0   0.563  -3.3325   0.2108  -0.6785
 3AC  O13   O  OC    0  -0.484  -4.1540  -0.5919  -1.1018
 3AC  N14   N  NR16  0  -0.709  -3.6308   1.5557  -0.6016
 3AC  C15   C  CR6   0   0.354  -2.8248   2.5475  -0.1533
 3AC  C51   C  CH3   0  -0.744  -3.3969   3.9275  -0.1819
 3AC  C16   C  CR6   0  -0.098  -1.5571   2.2561   0.2760
 3AC  C61   C  CH2   0  -0.520  -0.6334   3.3094   0.8252
 3AC  C62   C  CH3   0  -0.653  -0.6693   3.3873   2.3504
 3AC  C21   C  CR6   0   0.395   1.1303   0.5857  -0.1133
 3AC  C22   C  CR16  0  -0.329   1.0427   0.8565  -1.4705
 3AC  C23   C  CR16  0  -0.226   2.2070   0.8517  -2.2326
 3AC  C24   C  CR16  0  -0.319   3.4355   0.5833  -1.6620
 3AC  C25   C  CR6   0   0.152   3.5191   0.3115  -0.2923
 3AC  C26   C  CR16  0  -0.389   2.3576   0.3180   0.4766
 3AC  C27   C  C1    0  -0.204   4.7763   0.0202   0.3864
 3AC  C28   C  C1    0  -0.350   5.9804  -0.0746  -0.1953
 3AC  N29   N  NS    0  -0.267   8.0931  -0.6043   1.1739
 3AC  C29   C  CSP   0   0.088   7.1397  -0.3660   0.5697
 3AC  H14   H  HNR6  0   0.424  -4.5594   1.8077  -0.9167
 3AC  H511  H  HCH3  0   0.281  -2.9668   4.5027  -1.0036
 3AC  H512  H  HCH3  0   0.273  -4.4771   3.9113  -0.3173
 3AC  H513  H  HCH3  0   0.273  -3.1832   4.4627   0.7406
 3AC  H611  H  HCH2  0   0.259  -0.9023   4.2794   0.4058
 3AC  H612  H  HCH2  0   0.252   0.3902   3.1302   0.4924
 3AC  H621  H  HCH3  0   0.236   0.0125   4.1576   2.7111
 3AC  H622  H  HCH3  0   0.227  -1.6700   3.6320   2.7088
 3AC  H623  H  HCH3  0   0.231  -0.3752   2.4413   2.8049
 3AC  H22   H  HCR6  0   0.292   0.0940   1.0682  -1.9468
 3AC  H23   H  HCR6  0   0.275   2.1410   1.0615  -3.2915
 3AC  H24   H  HCR6  0   0.265   4.3198   0.5904  -2.2844
 3AC  H26   H  HCR6  0   0.282   2.4080   0.1137   1.5394
 3AC  H27   H  H     0   0.293   4.7064  -0.1337   1.4575
 3AC  H28   H  H     0   0.322   6.1397   0.0598  -1.2574

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
 3AC  O11  C11   single    1.359  0.020  1.359
 3AC  O11  C21   single    1.366  0.020  1.366
 3AC  C11  C12   aromatic  1.366  0.020  1.366
 3AC  C11  C16   aromatic  1.417  0.020  1.417
 3AC  C12  I12   single    2.079  0.020  2.079
 3AC  C12  C13   aromatic  1.437  0.020  1.437
 3AC  C13  O13   double    1.224  0.020  1.224
 3AC  C13  N14   aromatic  1.380  0.020  1.380
 3AC  N14  C15   aromatic  1.354  0.020  1.354
 3AC  N14  H14   single    0.860  0.020  1.020
 3AC  C15  C51   single    1.494  0.020  1.494
 3AC  C15  C16   aromatic  1.370  0.020  1.370
 3AC  C51  H511  single    0.970  0.020  1.090
 3AC  C51  H512  single    0.970  0.020  1.090
 3AC  C51  H513  single    0.970  0.020  1.090
 3AC  C16  C61   single    1.505  0.020  1.505
 3AC  C61  C62   single    1.528  0.020  1.528
 3AC  C61  H611  single    0.970  0.020  1.090
 3AC  C61  H612  single    0.970  0.020  1.090
 3AC  C62  H621  single    0.970  0.020  1.090
 3AC  C62  H622  single    0.970  0.020  1.090
 3AC  C62  H623  single    0.970  0.020  1.090
 3AC  C21  C22   aromatic  1.387  0.020  1.387
 3AC  C21  C26   aromatic  1.388  0.020  1.388
 3AC  C22  C23   aromatic  1.392  0.020  1.392
 3AC  C22  H22   single    0.930  0.020  1.080
 3AC  C23  C24   aromatic  1.381  0.020  1.381
 3AC  C23  H23   single    0.930  0.020  1.080
 3AC  C24  C25   aromatic  1.399  0.020  1.399
 3AC  C24  H24   single    0.930  0.020  1.080
 3AC  C25  C26   aromatic  1.393  0.020  1.393
 3AC  C25  C27   single    1.458  0.020  1.458
 3AC  C26  H26   single    0.930  0.020  1.080
 3AC  C27  C28   double    1.341  0.020  1.341
 3AC  C27  H27   single    0.930  0.020  1.080
 3AC  C28  C29   single    1.419  0.020  1.419
 3AC  C28  H28   single    0.930  0.020  1.080
 3AC  N29  C29   triple    1.154  0.020  1.154

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
 3AC  C21   O11  C11   119.45  3.000
 3AC  C16   C11  C12   122.60  3.000
 3AC  C16   C11  O11   118.10  3.000
 3AC  C12   C11  O11   119.27  3.000
 3AC  C13   C12  I12   116.89  3.000
 3AC  C13   C12  C11   121.08  3.000
 3AC  I12   C12  C11   122.03  3.000
 3AC  N14   C13  O13   120.89  3.000
 3AC  N14   C13  C12   112.80  3.000
 3AC  O13   C13  C12   126.31  3.000
 3AC  H14   N14  C15   117.81  3.000
 3AC  H14   N14  C13   115.06  3.000
 3AC  C15   N14  C13   127.13  3.000
 3AC  C16   C15  C51   123.84  3.000
 3AC  C16   C15  N14   119.91  3.000
 3AC  C51   C15  N14   116.25  3.000
 3AC  H513  C51  H512  107.92  3.000
 3AC  H513  C51  H511  107.57  3.000
 3AC  H512  C51  H511  107.77  3.000
 3AC  H513  C51  C15   111.28  3.000
 3AC  H512  C51  C15   111.63  3.000
 3AC  H511  C51  C15   110.51  3.000
 3AC  C61   C16  C15   122.25  3.000
 3AC  C61   C16  C11   121.21  3.000
 3AC  C15   C16  C11   116.47  3.000
 3AC  H612  C61  H611  105.08  3.000
 3AC  H612  C61  C62   109.57  3.000
 3AC  H611  C61  C62   109.45  3.000
 3AC  H612  C61  C16   110.46  3.000
 3AC  H611  C61  C16   109.32  3.000
 3AC  C62   C61  C16   112.69  3.000
 3AC  H623  C62  H622  107.77  3.000
 3AC  H623  C62  H621  107.85  3.000
 3AC  H622  C62  H621  107.85  3.000
 3AC  H623  C62  C61   111.45  3.000
 3AC  H622  C62  C61   111.17  3.000
 3AC  H621  C62  C61   110.59  3.000
 3AC  C26   C21  C22   120.64  3.000
 3AC  C26   C21  O11   115.82  3.000
 3AC  C22   C21  O11   123.55  3.000
 3AC  H22   C22  C23   119.54  3.000
 3AC  H22   C22  C21   121.61  3.000
 3AC  C23   C22  C21   118.85  3.000
 3AC  H23   C23  C24   119.78  3.000
 3AC  H23   C23  C22   118.98  3.000
 3AC  C24   C23  C22   121.25  3.000
 3AC  H24   C24  C25   121.06  3.000
 3AC  H24   C24  C23   119.24  3.000
 3AC  C25   C24  C23   119.70  3.000
 3AC  C27   C25  C26   117.58  3.000
 3AC  C27   C25  C24   123.10  3.000
 3AC  C26   C25  C24   119.33  3.000
 3AC  H26   C26  C25   120.12  3.000
 3AC  H26   C26  C21   119.64  3.000
 3AC  C25   C26  C21   120.24  3.000
 3AC  H27   C27  C28   118.46  3.000
 3AC  H27   C27  C25   115.63  3.000
 3AC  C28   C27  C25   125.92  3.000
 3AC  H28   C28  C29   115.74  3.000
 3AC  H28   C28  C27   123.31  3.000
 3AC  C29   C28  C27   120.95  3.000
 3AC  N29   C29  C28   180.00  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
 3AC  CONST_01  N14   C13  C12  C11     0.00   0.0  0
 3AC  CONST_02  N14   C15  C16  C11     0.00   0.0  0
 3AC  CONST_03  C15   C16  C11  C12     0.00   0.0  0
 3AC  CONST_04  C15   N14  C13  C12     0.00   0.0  0
 3AC  CONST_05  C16   C11  C12  C13     0.00   0.0  0
 3AC  CONST_06  C16   C15  N14  C13     0.00   0.0  0
 3AC  CONST_07  C24   C23  C22  C21     0.00   0.0  0
 3AC  CONST_08  C24   C25  C26  C21     0.00   0.0  0
 3AC  CONST_09  C25   C26  C21  C22     0.00   0.0  0
 3AC  CONST_10  C25   C24  C23  C22     0.00   0.0  0
 3AC  CONST_11  C26   C21  C22  C23     0.00   0.0  0
 3AC  CONST_12  C26   C25  C24  C23     0.00   0.0  0
 3AC  CONST_13  C13   C12  C11  O11   180.00   0.0  0
 3AC  CONST_14  C15   C16  C11  O11   180.00   0.0  0
 3AC  CONST_15  C23   C22  C21  O11   180.00   0.0  0
 3AC  CONST_16  C25   C26  C21  O11   180.00   0.0  0
 3AC  CONST_17  O13   C13  C12  C11   180.00   0.0  0
 3AC  CONST_18  C51   C15  C16  C11   180.00   0.0  0
 3AC  CONST_19  C61   C16  C11  C12   180.00   0.0  0
 3AC  CONST_20  C16   C11  C12  I12   180.00   0.0  0
 3AC  CONST_21  N14   C13  C12  I12   180.00   0.0  0
 3AC  CONST_22  C51   C15  N14  C13   180.00   0.0  0
 3AC  CONST_23  C15   N14  C13  O13   180.00   0.0  0
 3AC  CONST_24  C61   C16  C15  N14   180.00   0.0  0
 3AC  CONST_25  C27   C25  C26  C21   180.00   0.0  0
 3AC  CONST_26  C27   C25  C24  C23   180.00   0.0  0
 3AC  CONST_27  H14   N14  C13  C12   180.00   0.0  0
 3AC  CONST_28  H23   C23  C22  C21   180.00   0.0  0
 3AC  CONST_29  H26   C26  C21  C22   180.00   0.0  0
 3AC  CONST_30  H24   C24  C23  C22   180.00   0.0  0
 3AC  CONST_31  H22   C22  C23  C24   180.00   0.0  0
 3AC  Var_01    C22   C21  O11  C11    -4.44  30.0  2
 3AC  Var_02    C62   C61  C16  C11   -81.31  30.0  2
 3AC  Var_03    C28   C27  C25  C24    -2.60  30.0  2
 3AC  Var_04    H511  C51  C15  N14  -104.93  30.0  2
 3AC  Var_05    C29   C28  C27  C25  -179.91   0.0  2
 3AC  Var_06    H621  C62  C61  C16   179.86  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
 3AC  plan-1  O11  0.020
 3AC  plan-1  C11  0.020
 3AC  plan-1  C12  0.020
 3AC  plan-1  I12  0.020
 3AC  plan-1  C13  0.020
 3AC  plan-1  O13  0.020
 3AC  plan-1  N14  0.020
 3AC  plan-1  C15  0.020
 3AC  plan-1  C51  0.020
 3AC  plan-1  C16  0.020
 3AC  plan-1  C61  0.020
 3AC  plan-1  H14  0.020
 3AC  plan-2  O11  0.020
 3AC  plan-2  C21  0.020
 3AC  plan-2  C22  0.020
 3AC  plan-2  C23  0.020
 3AC  plan-2  C24  0.020
 3AC  plan-2  C25  0.020
 3AC  plan-2  C26  0.020
 3AC  plan-2  C27  0.020
 3AC  plan-2  H22  0.020
 3AC  plan-2  H23  0.020
 3AC  plan-2  H24  0.020
 3AC  plan-2  H26  0.020
 3AC  plan-3  C25  0.020
 3AC  plan-3  C27  0.020
 3AC  plan-3  C28  0.020
 3AC  plan-3  C29  0.020
 3AC  plan-3  H27  0.020
 3AC  plan-3  H28  0.020

