# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Jul 31 22:39:03 2022
#   Inital geometry file: a 113 line input string
#   Ligand name: 4-[(~{Z})-1-cyano-2-[4-[2-hydroxyethyl(methyl)amino]phenyl]ethenyl]benzenecarbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN(CCO)c1ccc(cc1)\C=C(C#N)\c2ccc(cc2)C#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
 J8F  J8F  "4-[(~{Z})-1-cyano-2-[4-[2-hydroxyethyl(methyl)amino]phenyl]ethenyl]benzenecarbonitrile"
  ligand  40  23  .  2022-08-10  2022-08-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_J8F
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
 J8F  C10  C  C1    0  -0.283  31.3444  14.1540   2.3285
 J8F  N12  N  NS    0  -0.254  33.6009  13.2322   4.8497
 J8F  C13  C  CR6   0   0.126  31.0996  12.8056   1.9011
 J8F  C15  C  CR16  0  -0.334  31.1559  10.3856   2.1003
 J8F  C17  C  CR16  0  -0.335  30.0814  11.3901   0.1944
 J8F  C20  C  CH3   0  -0.539  30.5445   7.8062   1.1784
 J8F  C21  C  CH2   0  -0.151  27.8563   8.9367  -0.4766
 J8F  C01  C  CR16  0  -0.220  31.1110  18.3084   3.5514
 J8F  C02  C  CR16  0  -0.318  31.0641  16.9523   3.2982
 J8F  C03  C  CR6   0   0.160  32.1404  16.1194   3.6237
 J8F  C04  C  CR16  0  -0.297  33.2585  16.6917   4.2393
 J8F  C05  C  CR16  0  -0.218  33.3135  18.0463   4.5029
 J8F  C06  C  CR6   0  -0.012  32.2388  18.8641   4.1560
 J8F  C07  C  CSP   0   0.052  32.2864  20.2626   4.4285
 J8F  C09  C  C     0  -0.007  32.0935  14.6743   3.3385
 J8F  C11  C  CSP   0  -0.016  32.9137  13.8578   4.1643
 J8F  C14  C  CR16  0  -0.297  31.4630  11.6335   2.5860
 J8F  C16  C  CR6   0   0.407  30.4609  10.2122   0.8789
 J8F  C18  C  CR16  0  -0.286  30.3940  12.6290   0.6973
 J8F  C19  C  CH2   0  -0.367  29.3396   8.7843  -0.7604
 J8F  N08  N  NS    0  -0.249  32.3231  21.3935   4.6483
 J8F  N22  N  NT    0  -0.488  30.1817   8.9751   0.4049
 J8F  O23  O  OH1   0  -0.660  27.4746   7.9678   0.4704
 J8F  H1   H  H     0   0.276  30.8431  14.8924   1.7108
 J8F  H2   H  HCR6  0   0.276  31.4532   9.5292   2.6877
 J8F  H3   H  HCR6  0   0.269  29.5353  11.3454  -0.7364
 J8F  H4   H  HCH3  0   0.239  30.0268   7.7666   2.1396
 J8F  H5   H  HCH3  0   0.261  30.2797   6.9135   0.6205
 J8F  H6   H  HCH3  0   0.241  31.6193   7.7714   1.3658
 J8F  H7   H  HCH2  0   0.205  27.6508   9.9529  -0.1176
 J8F  H8   H  HCH2  0   0.204  27.3184   8.8207  -1.4271
 J8F  H9   H  HCR6  0   0.283  30.2660  18.9337   3.2965
 J8F  H10  H  HCR6  0   0.271  30.1618  16.5409   2.8662
 J8F  H11  H  HCR6  0   0.271  34.1092  16.0791   4.5088
 J8F  H12  H  HCR6  0   0.283  34.1911  18.4692   4.9729
 J8F  H13  H  HCR6  0   0.262  31.9769  11.6795   3.5346
 J8F  H14  H  HCR6  0   0.262  30.0774  13.5027   0.1395
 J8F  H15  H  HCH2  0   0.268  29.5365   7.7863  -1.1530
 J8F  H16  H  HCH2  0   0.260  29.6239   9.4761  -1.5551
 J8F  H17  H  HOH1  0   0.455  26.5692   8.1464   0.7395

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
 J8F  C19  C21  single    1.518  0.020  1.518
 J8F  C19  N22  single    1.450  0.020  1.450
 J8F  C21  O23  single    1.408  0.020  1.408
 J8F  C17  C18  aromatic  1.373  0.020  1.373
 J8F  C17  C16  aromatic  1.414  0.020  1.414
 J8F  N22  C16  single    1.354  0.020  1.354
 J8F  N22  C20  single    1.448  0.020  1.448
 J8F  C18  C13  aromatic  1.406  0.020  1.406
 J8F  C16  C15  aromatic  1.416  0.020  1.416
 J8F  C13  C10  single    1.436  0.020  1.436
 J8F  C13  C14  aromatic  1.405  0.020  1.405
 J8F  C15  C14  aromatic  1.374  0.020  1.374
 J8F  C10  C09  double    1.361  0.020  1.361
 J8F  C02  C01  aromatic  1.380  0.020  1.380
 J8F  C02  C03  aromatic  1.399  0.020  1.399
 J8F  C01  C06  aromatic  1.395  0.020  1.395
 J8F  C09  C03  single    1.474  0.020  1.474
 J8F  C09  C11  single    1.422  0.020  1.422
 J8F  C03  C04  aromatic  1.399  0.020  1.399
 J8F  C06  C07  single    1.426  0.020  1.426
 J8F  C06  C05  aromatic  1.394  0.020  1.394
 J8F  C11  N12  triple    1.155  0.020  1.155
 J8F  C07  N08  triple    1.153  0.020  1.153
 J8F  C04  C05  aromatic  1.381  0.020  1.381
 J8F  C10  H1   single    0.930  0.020  1.080
 J8F  C15  H2   single    0.930  0.020  1.080
 J8F  C17  H3   single    0.930  0.020  1.080
 J8F  C20  H4   single    0.970  0.020  1.090
 J8F  C20  H5   single    0.970  0.020  1.090
 J8F  C20  H6   single    0.970  0.020  1.090
 J8F  C21  H7   single    0.970  0.020  1.090
 J8F  C21  H8   single    0.970  0.020  1.090
 J8F  C01  H9   single    0.930  0.020  1.080
 J8F  C02  H10  single    0.930  0.020  1.080
 J8F  C04  H11  single    0.930  0.020  1.080
 J8F  C05  H12  single    0.930  0.020  1.080
 J8F  C14  H13  single    0.930  0.020  1.080
 J8F  C18  H14  single    0.930  0.020  1.080
 J8F  C19  H15  single    0.970  0.020  1.090
 J8F  C19  H16  single    0.970  0.020  1.090
 J8F  O23  H17  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
 J8F  H1   C10  C09  114.62  3.000
 J8F  H1   C10  C13  113.00  3.000
 J8F  C09  C10  C13  132.37  3.000
 J8F  C18  C13  C14  116.24  3.000
 J8F  C14  C13  C10  126.46  3.000
 J8F  C18  C13  C10  117.28  3.000
 J8F  H2   C15  C16  120.46  3.000
 J8F  H2   C15  C14  117.80  3.000
 J8F  C16  C15  C14  121.73  3.000
 J8F  H3   C17  C18  117.91  3.000
 J8F  H3   C17  C16  121.22  3.000
 J8F  C18  C17  C16  120.87  3.000
 J8F  H6   C20  H5   107.59  3.000
 J8F  H6   C20  H4   108.33  3.000
 J8F  H5   C20  H4   107.87  3.000
 J8F  H6   C20  N22  111.36  3.000
 J8F  H5   C20  N22  109.16  3.000
 J8F  H4   C20  N22  112.37  3.000
 J8F  H8   C21  H7   106.82  3.000
 J8F  H8   C21  O23  112.13  3.000
 J8F  H7   C21  O23  111.51  3.000
 J8F  H8   C21  C19  107.83  3.000
 J8F  H7   C21  C19  109.71  3.000
 J8F  O23  C21  C19  108.76  3.000
 J8F  H9   C01  C06  120.23  3.000
 J8F  H9   C01  C02  119.88  3.000
 J8F  C06  C01  C02  119.89  3.000
 J8F  H10  C02  C03  120.54  3.000
 J8F  H10  C02  C01  118.38  3.000
 J8F  C03  C02  C01  121.06  3.000
 J8F  C09  C03  C04  120.78  3.000
 J8F  C04  C03  C02  118.27  3.000
 J8F  C09  C03  C02  120.94  3.000
 J8F  H11  C04  C05  118.44  3.000
 J8F  H11  C04  C03  120.42  3.000
 J8F  C05  C04  C03  121.14  3.000
 J8F  H12  C05  C06  120.28  3.000
 J8F  H12  C05  C04  119.91  3.000
 J8F  C06  C05  C04  119.81  3.000
 J8F  C07  C06  C05  120.14  3.000
 J8F  C05  C06  C01  119.82  3.000
 J8F  C07  C06  C01  120.04  3.000
 J8F  N08  C07  C06  180.00  3.000
 J8F  C11  C09  C03  115.62  3.000
 J8F  C11  C09  C10  121.95  3.000
 J8F  C03  C09  C10  122.41  3.000
 J8F  C09  C11  N12  180.00  3.000
 J8F  H13  C14  C15  117.11  3.000
 J8F  H13  C14  C13  121.04  3.000
 J8F  C15  C14  C13  121.84  3.000
 J8F  N22  C16  C17  122.43  3.000
 J8F  N22  C16  C15  121.01  3.000
 J8F  C17  C16  C15  116.56  3.000
 J8F  H14  C18  C17  118.18  3.000
 J8F  H14  C18  C13  119.06  3.000
 J8F  C17  C18  C13  122.75  3.000
 J8F  H16  C19  H15  105.72  3.000
 J8F  H16  C19  N22  110.51  3.000
 J8F  H15  C19  N22  107.75  3.000
 J8F  H16  C19  C21  109.09  3.000
 J8F  H15  C19  C21  109.62  3.000
 J8F  N22  C19  C21  113.83  3.000
 J8F  C19  N22  C16  121.42  3.000
 J8F  C16  N22  C20  119.93  3.000
 J8F  C19  N22  C20  117.94  3.000
 J8F  H17  O23  C21  108.42  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
 J8F  CONST_01  C16  C17  C18  C13     0.00   0.0  0
 J8F  CONST_02  C16  C15  C14  C13     0.00   0.0  0
 J8F  CONST_03  C18  C17  C16  C15     0.00   0.0  0
 J8F  CONST_04  C18  C13  C14  C15     0.00   0.0  0
 J8F  CONST_05  C14  C13  C18  C17     0.00   0.0  0
 J8F  CONST_06  C14  C15  C16  C17     0.00   0.0  0
 J8F  CONST_07  C04  C03  C02  C01     0.00   0.0  0
 J8F  CONST_08  C04  C05  C06  C01     0.00   0.0  0
 J8F  CONST_09  C05  C06  C01  C02     0.00   0.0  0
 J8F  CONST_10  C05  C04  C03  C02     0.00   0.0  0
 J8F  CONST_11  C06  C01  C02  C03     0.00   0.0  0
 J8F  CONST_12  C06  C05  C04  C03     0.00   0.0  0
 J8F  CONST_13  C17  C18  C13  C10   180.00   0.0  0
 J8F  CONST_14  C15  C14  C13  C10   180.00   0.0  0
 J8F  CONST_15  C09  C03  C02  C01   180.00   0.0  0
 J8F  CONST_16  C07  C06  C01  C02   180.00   0.0  0
 J8F  CONST_17  C07  C06  C05  C04   180.00   0.0  0
 J8F  CONST_18  C09  C03  C04  C05   180.00   0.0  0
 J8F  CONST_19  N22  C16  C15  C14   180.00   0.0  0
 J8F  CONST_20  N22  C16  C17  C18   180.00   0.0  0
 J8F  CONST_21  H3   C17  C18  C13   180.00   0.0  0
 J8F  CONST_22  H2   C15  C14  C13   180.00   0.0  0
 J8F  CONST_23  H3   C17  C16  C15   180.00   0.0  0
 J8F  CONST_24  H2   C15  C16  C17   180.00   0.0  0
 J8F  CONST_25  H12  C05  C06  C01   180.00   0.0  0
 J8F  CONST_26  H11  C04  C03  C02   180.00   0.0  0
 J8F  CONST_27  H9   C01  C02  C03   180.00   0.0  0
 J8F  CONST_28  H12  C05  C04  C03   180.00   0.0  0
 J8F  CONST_29  H10  C02  C03  C04   180.00   0.0  0
 J8F  CONST_30  H9   C01  C06  C05   180.00   0.0  0
 J8F  CONST_31  H10  C02  C01  C06   180.00   0.0  0
 J8F  CONST_32  H11  C04  C05  C06   180.00   0.0  0
 J8F  CONST_33  H14  C18  C13  C14   180.00   0.0  0
 J8F  CONST_34  H14  C18  C17  C16   180.00   0.0  0
 J8F  CONST_35  H13  C14  C15  C16   180.00   0.0  0
 J8F  CONST_36  H13  C14  C13  C18   180.00   0.0  0
 J8F  CONST_37  C19  N22  C16  C15   180.00   0.0  0
 J8F  CONST_38  C20  N22  C16  C15     0.00   0.0  0
 J8F  CONST_39  C19  N22  C16  C17     0.00   0.0  0
 J8F  CONST_40  C20  N22  C16  C17   180.00   0.0  0
 J8F  Var_01    C03  C09  C10  C13  -177.03   0.0  2
 J8F  Var_02    C02  C03  C09  C10    27.18  30.0  2
 J8F  Var_03    C04  C03  C09  C10  -153.44  30.0  2
 J8F  Var_04    C11  C09  C03  C02  -154.55  30.0  3
 J8F  Var_05    C11  C09  C03  C04    24.83  30.0  3
 J8F  Var_06    C18  C13  C10  C09  -172.17  30.0  3
 J8F  Var_07    C14  C13  C10  C09     9.74  30.0  3
 J8F  Var_08    H1   C10  C13  C14  -171.37  30.0  2
 J8F  Var_09    H1   C10  C13  C18     6.72  30.0  2
 J8F  Var_10    C11  C09  C10  C13     4.81   0.0  2
 J8F  Var_11    C03  C09  C11  N12   -13.12  30.0  1
 J8F  Var_12    C16  N22  C19  C21   -77.70  30.0  3
 J8F  Var_13    H1   C10  C09  C03     4.09   0.0  2
 J8F  Var_14    H15  C19  N22  C16   160.52  30.0  2
 J8F  Var_15    H16  C19  N22  C16    45.46  30.0  2
 J8F  Var_16    H4   C20  N22  C16    62.74  30.0  3
 J8F  Var_17    H5   C20  N22  C16  -177.65  30.0  3
 J8F  Var_18    H6   C20  N22  C16   -59.00  30.0  3
 J8F  Var_19    N12  C11  C09  C10   165.15  30.0  3
 J8F  Var_20    C21  C19  N22  C20    92.61  30.0  2
 J8F  Var_21    O23  C21  C19  N22   -60.81  30.0  3
 J8F  Var_22    H1   C10  C09  C11  -174.07   0.0  2
 J8F  Var_23    H15  C19  N22  C20   -29.17  30.0  2
 J8F  Var_24    H16  C19  N22  C20  -144.23  30.0  2
 J8F  Var_25    H4   C20  N22  C19  -107.72  30.0  3
 J8F  Var_26    H5   C20  N22  C19    11.90  30.0  3
 J8F  Var_27    H6   C20  N22  C19   130.54  30.0  3
 J8F  Var_28    H7   C21  C19  N22    61.40  30.0  3
 J8F  Var_29    H8   C21  C19  N22   177.38  30.0  3
 J8F  Var_30    H15  C19  C21  O23    59.94  30.0  1
 J8F  Var_31    H16  C19  C21  O23   175.26  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
 J8F  plan-1  C10  0.020
 J8F  plan-1  C13  0.020
 J8F  plan-1  C15  0.020
 J8F  plan-1  C17  0.020
 J8F  plan-1  C14  0.020
 J8F  plan-1  C16  0.020
 J8F  plan-1  C18  0.020
 J8F  plan-1  N22  0.020
 J8F  plan-1  H2   0.020
 J8F  plan-1  H3   0.020
 J8F  plan-1  H13  0.020
 J8F  plan-1  H14  0.020
 J8F  plan-2  C01  0.020
 J8F  plan-2  C02  0.020
 J8F  plan-2  C03  0.020
 J8F  plan-2  C04  0.020
 J8F  plan-2  C05  0.020
 J8F  plan-2  C06  0.020
 J8F  plan-2  C07  0.020
 J8F  plan-2  C09  0.020
 J8F  plan-2  N08  0.020
 J8F  plan-2  H9   0.020
 J8F  plan-2  H10  0.020
 J8F  plan-2  H11  0.020
 J8F  plan-2  H12  0.020
 J8F  plan-3  C20  0.020
 J8F  plan-3  C16  0.020
 J8F  plan-3  C19  0.020
 J8F  plan-3  N22  0.020
 J8F  plan-4  C10  0.020
 J8F  plan-4  C13  0.020
 J8F  plan-4  C03  0.020
 J8F  plan-4  C09  0.020
 J8F  plan-4  C11  0.020
 J8F  plan-4  H1   0.020

