# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  2 22:08:34 2020
#   Inital geometry file: a 122 line input string
#   Ligand name: methyl 4-{[(2Z)-2-cyano-3-hydroxypent-2-enoyl]amino}-4'-fluorobiphenyl-2-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC(/O)=C(C#N)/C(=O)Nc1ccc(c2ccc(F)cc2)c(c1)C(=O)OC
#
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
 03U  03U  'methyl 4-{[(2Z)-2-cyano-3-hydroxypent-2-enoyl]amino}-4'-fluorobiphenyl-2-carboxylate'  ligand  44  27  .  2021-08-03  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_03U
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
 03U  C1    C  CR16  0  -0.280  -4.1938   1.7310  -0.5247
 03U  C2    C  CR6   0   0.054  -3.4639   0.7381   0.1245
 03U  C3    C  CR16  0  -0.400  -5.5700   1.8223  -0.3767
 03U  C4    C  CR16  0  -0.280  -4.1438  -0.1619   0.9436
 03U  C5    C  CR6   0   0.516  -6.2079   0.9079   0.4376
 03U  C6    C  CR16  0  -0.398  -5.5179  -0.0859   1.1056
 03U  C7    C  CR6   0   0.090  -1.9928   0.6859  -0.0083
 03U  C8    C  CR6   0  -0.058  -1.2926  -0.4705  -0.3675
 03U  C9    C  CR16  0  -0.286  -1.2456   1.8235   0.2884
 03U  C10   C  CR16  0  -0.312   0.0990  -0.4928  -0.4019
 03U  C11   C  CR16  0  -0.327   0.1345   1.8174   0.2371
 03U  C12   C  CR6   0   0.395   0.8263   0.6567  -0.1051
 03U  F13   F  F     0  -0.315  -7.5396   0.9907   0.5901
 03U  C14   C  C     0   0.502  -2.0217  -1.6812  -0.8428
 03U  O15   O  O2    0  -0.446  -1.4762  -2.7983  -0.3888
 03U  O16   O  O     0  -0.427  -2.9776  -1.6465  -1.5745
 03U  C17   C  CH3   0  -0.424  -2.0316  -4.0341  -0.8438
 03U  N18   N  NH1   0  -0.782   2.2190   0.7359  -0.1746
 03U  C19   C  C     0   0.598   3.1137  -0.2849  -0.0393
 03U  C20   C  C     0  -0.290   4.5315   0.1245  -0.2029
 03U  O21   O  O     0  -0.448   2.7833  -1.4330   0.1849
 03U  C22   C  C     0   0.446   5.5936  -0.6439   0.1920
 03U  C23   C  CSP   0   0.004   4.8060   1.3778  -0.8033
 03U  N24   N  NS    0  -0.254   4.9844   2.4107  -1.2897
 03U  O25   O  OH1   0  -0.539   5.3807  -1.7865   0.8003
 03U  C26   C  CH2   0  -0.589   7.0169  -0.2133   0.0303
 03U  C27   C  CH3   0  -0.659   7.5795   0.3480   1.3395
 03U  H1    H  HCR6  0   0.266  -3.6868   2.4384  -1.1689
 03U  H3    H  HCR6  0   0.281  -6.1333   2.5916  -0.8881
 03U  H4    H  HCR6  0   0.264  -3.5973  -0.9263   1.4819
 03U  H6    H  HCR6  0   0.281  -6.0408  -0.7823   1.7476
 03U  H9    H  HCR6  0   0.268  -1.7531   2.7295   0.5935
 03U  H10   H  HCR6  0   0.284   0.6068  -1.3941  -0.7039
 03U  H11   H  HCR6  0   0.281   0.6810   2.7211   0.4790
 03U  H17   H  HCH3  0   0.256  -1.4430  -4.8156  -0.3731
 03U  H17A  H  HCH3  0   0.242  -3.0739  -4.1343  -0.5429
 03U  H17B  H  HCH3  0   0.243  -1.9587  -4.1267  -1.9270
 03U  HN18  H  HNH1  0   0.424   2.5806   1.6778  -0.1979
 03U  H26   H  HCH2  0   0.292   7.6041  -1.0789  -0.2898
 03U  H26A  H  HCH2  0   0.286   7.1091   0.5286  -0.7603
 03U  H27   H  HCH3  0   0.245   7.0296   1.2339   1.6546
 03U  H27A  H  HCH3  0   0.239   7.5428  -0.3822   2.1474
 03U  H27B  H  HCH3  0   0.259   8.6208   0.6301   1.1953
 03U  H171  H  HOH1  0   0.500   6.2142  -2.2242   1.0199

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
 03U  C1   C3    aromatic  1.387  0.020  1.387
 03U  C1   H1    single    0.930  0.020  1.080
 03U  C2   C1    aromatic  1.393  0.020  1.393
 03U  C3   H3    single    0.930  0.020  1.080
 03U  C4   C2    aromatic  1.394  0.020  1.394
 03U  C4   C6    aromatic  1.386  0.020  1.386
 03U  C4   H4    single    0.930  0.020  1.080
 03U  C5   C3    aromatic  1.381  0.020  1.381
 03U  C5   F13   single    1.343  0.020  1.343
 03U  C6   C5    aromatic  1.382  0.020  1.382
 03U  C6   H6    single    0.930  0.020  1.080
 03U  C7   C2    single    1.478  0.020  1.478
 03U  C7   C8    aromatic  1.399  0.020  1.399
 03U  C8   C14   single    1.491  0.020  1.491
 03U  C9   C7    aromatic  1.393  0.020  1.393
 03U  C9   H9    single    0.930  0.020  1.080
 03U  C10  C8    aromatic  1.392  0.020  1.392
 03U  C10  H10   single    0.930  0.020  1.080
 03U  C11  C9    aromatic  1.381  0.020  1.381
 03U  C11  C12   aromatic  1.394  0.020  1.394
 03U  C11  H11   single    0.930  0.020  1.080
 03U  C12  C10   aromatic  1.392  0.020  1.392
 03U  C14  O16   double    1.204  0.020  1.204
 03U  C14  O15   single    1.324  0.020  1.324
 03U  O15  C17   single    1.429  0.020  1.429
 03U  C17  H17   single    0.970  0.020  1.090
 03U  C17  H17A  single    0.970  0.020  1.090
 03U  C17  H17B  single    0.970  0.020  1.090
 03U  N18  C12   single    1.397  0.020  1.397
 03U  N18  HN18  single    0.860  0.020  1.020
 03U  C19  N18   single    1.364  0.020  1.364
 03U  C19  C20   single    1.485  0.020  1.485
 03U  C20  C22   double    1.369  0.020  1.369
 03U  O21  C19   double    1.215  0.020  1.215
 03U  C22  C26   single    1.496  0.020  1.496
 03U  C22  O25   single    1.312  0.020  1.312
 03U  C23  C20   single    1.417  0.020  1.417
 03U  N24  C23   triple    1.156  0.020  1.156
 03U  C26  C27   single    1.532  0.020  1.532
 03U  C26  H26   single    0.970  0.020  1.090
 03U  C26  H26A  single    0.970  0.020  1.090
 03U  C27  H27   single    0.970  0.020  1.090
 03U  C27  H27A  single    0.970  0.020  1.090
 03U  C27  H27B  single    0.970  0.020  1.090
 03U  O25  H171  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
 03U  H1    C1   C3    119.01  3.000
 03U  H1    C1   C2    119.84  3.000
 03U  C3    C1   C2    121.14  3.000
 03U  C7    C2   C4    121.03  3.000
 03U  C7    C2   C1    120.32  3.000
 03U  C4    C2   C1    118.59  3.000
 03U  H3    C3   C5    120.61  3.000
 03U  C5    C3   C1    118.53  3.000
 03U  H3    C3   C1    120.86  3.000
 03U  H4    C4   C6    118.75  3.000
 03U  H4    C4   C2    120.11  3.000
 03U  C6    C4   C2    121.13  3.000
 03U  F13   C5   C6    118.98  3.000
 03U  C6    C5   C3    122.06  3.000
 03U  F13   C5   C3    118.96  3.000
 03U  H6    C6   C5    120.56  3.000
 03U  H6    C6   C4    120.89  3.000
 03U  C5    C6   C4    118.55  3.000
 03U  C9    C7   C8    117.48  3.000
 03U  C9    C7   C2    119.08  3.000
 03U  C8    C7   C2    123.40  3.000
 03U  C14   C8   C10   117.90  3.000
 03U  C10   C8   C7    121.32  3.000
 03U  C14   C8   C7    120.56  3.000
 03U  H9    C9   C11   118.86  3.000
 03U  C11   C9   C7    121.64  3.000
 03U  H9    C9   C7    119.48  3.000
 03U  H10   C10  C12   120.27  3.000
 03U  C12   C10  C8    120.25  3.000
 03U  H10   C10  C8    119.42  3.000
 03U  H11   C11  C12   119.94  3.000
 03U  H11   C11  C9    119.48  3.000
 03U  C12   C11  C9    120.58  3.000
 03U  N18   C12  C11   117.38  3.000
 03U  N18   C12  C10   123.85  3.000
 03U  C11   C12  C10   118.72  3.000
 03U  O16   C14  O15   124.05  3.000
 03U  O15   C14  C8    111.99  3.000
 03U  O16   C14  C8    123.94  3.000
 03U  C17   O15  C14   117.41  3.000
 03U  H17B  C17  H17A  109.31  3.000
 03U  H17B  C17  H17   109.48  3.000
 03U  H17A  C17  H17   109.44  3.000
 03U  H17B  C17  O15   111.34  3.000
 03U  H17A  C17  O15   111.31  3.000
 03U  H17   C17  O15   105.88  3.000
 03U  HN18  N18  C19   117.75  3.000
 03U  C19   N18  C12   127.35  3.000
 03U  HN18  N18  C12   114.29  3.000
 03U  O21   C19  C20   122.70  3.000
 03U  O21   C19  N18   123.15  3.000
 03U  C20   C19  N18   114.15  3.000
 03U  C23   C20  C22   117.93  3.000
 03U  C23   C20  C19   118.41  3.000
 03U  C22   C20  C19   123.66  3.000
 03U  C26   C22  O25   117.09  3.000
 03U  O25   C22  C20   119.78  3.000
 03U  C26   C22  C20   123.06  3.000
 03U  N24   C23  C20   180.00  3.000
 03U  H171  O25  C22   111.08  3.000
 03U  H26A  C26  H26   106.35  3.000
 03U  H26A  C26  C27   109.88  3.000
 03U  H26   C26  C27   110.06  3.000
 03U  H26A  C26  C22   110.82  3.000
 03U  H26   C26  C22   108.34  3.000
 03U  C27   C26  C22   111.26  3.000
 03U  H27B  C27  H27A  107.71  3.000
 03U  H27B  C27  H27   108.09  3.000
 03U  H27A  C27  H27   108.27  3.000
 03U  H27B  C27  C26   109.46  3.000
 03U  H27A  C27  C26   112.07  3.000
 03U  H27   C27  C26   111.09  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
 03U  CONST_01  C6   C5   C3   C1      0.00   0.0  0
 03U  CONST_02  C6   C4   C2   C1      0.00   0.0  0
 03U  CONST_05  C5   C3   C1   C2      0.00   0.0  0
 03U  CONST_06  C5   C6   C4   C2      0.00   0.0  0
 03U  CONST_07  C10  C8   C7   C2    180.00   0.0  0
 03U  CONST_08  C11  C9   C7   C2    180.00   0.0  0
 03U  CONST_09  C4   C2   C1   C3      0.00   0.0  0
 03U  CONST_10  C7   C2   C1   C3    180.00   0.0  0
 03U  CONST_11  C4   C6   C5   C3      0.00   0.0  0
 03U  CONST_14  C7   C2   C4   C6    180.00   0.0  0
 03U  CONST_15  C12  C10  C8   C7      0.00   0.0  0
 03U  CONST_16  C12  C11  C9   C7      0.00   0.0  0
 03U  CONST_17  C11  C9   C7   C8      0.00   0.0  0
 03U  CONST_18  C11  C12  C10  C8      0.00   0.0  0
 03U  CONST_19  C10  C8   C7   C9      0.00   0.0  0
 03U  CONST_20  C10  C12  C11  C9      0.00   0.0  0
 03U  CONST_21  F13  C5   C3   C1    180.00   0.0  0
 03U  CONST_22  C14  C8   C7   C2      0.00   0.0  0
 03U  CONST_23  F13  C5   C6   C4    180.00   0.0  0
 03U  CONST_24  N18  C12  C10  C8    180.00   0.0  0
 03U  CONST_25  C14  C8   C7   C9    180.00   0.0  0
 03U  CONST_26  N18  C12  C11  C9    180.00   0.0  0
 03U  CONST_27  C14  C8   C10  C12   180.00   0.0  0
 03U  CONST_28  H4   C4   C2   C1    180.00   0.0  0
 03U  CONST_29  H3   C3   C1   C2    180.00   0.0  0
 03U  CONST_30  H6   C6   C4   C2    180.00   0.0  0
 03U  CONST_31  H9   C9   C7   C2      0.00   0.0  0
 03U  CONST_32  H1   C1   C2   C4    180.00   0.0  0
 03U  CONST_33  H10  C10  C8   C7    180.00   0.0  0
 03U  CONST_34  H11  C11  C9   C7    180.00   0.0  0
 03U  CONST_38  C20  C19  N18  C12   180.00   0.0  0
 03U  CONST_39  O21  C19  N18  C12     0.00   0.0  0
 03U  Var_01    O16  C14  C8   C7     39.78  30.0  2
 03U  Var_02    C26  C22  C20  C19  -179.51   0.0  2
 03U  Var_03    C22  C20  C19  N18   164.16  30.0  2
 03U  Var_04    C27  C26  C22  C20    99.44  30.0  3
 03U  Var_05    H17  C17  O15  C14   179.24  30.0  3
 03U  Var_06    H27  C27  C26  C22   -62.01  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
 03U  plan-1  C1    0.020
 03U  plan-1  C2    0.020
 03U  plan-1  C3    0.020
 03U  plan-1  C4    0.020
 03U  plan-1  C5    0.020
 03U  plan-1  C6    0.020
 03U  plan-1  C7    0.020
 03U  plan-1  F13   0.020
 03U  plan-1  H1    0.020
 03U  plan-1  H3    0.020
 03U  plan-1  H4    0.020
 03U  plan-1  H6    0.020
 03U  plan-2  C2    0.020
 03U  plan-2  C7    0.020
 03U  plan-2  C8    0.020
 03U  plan-2  C9    0.020
 03U  plan-2  C10   0.020
 03U  plan-2  C11   0.020
 03U  plan-2  C12   0.020
 03U  plan-2  C14   0.020
 03U  plan-2  N18   0.020
 03U  plan-2  H9    0.020
 03U  plan-2  H10   0.020
 03U  plan-2  H11   0.020
 03U  plan-3  C12   0.020
 03U  plan-3  N18   0.020
 03U  plan-3  C19   0.020
 03U  plan-3  C20   0.020
 03U  plan-3  O21   0.020
 03U  plan-3  HN18  0.020
 03U  plan-4  C8    0.020
 03U  plan-4  C14   0.020
 03U  plan-4  O15   0.020
 03U  plan-4  O16   0.020
 03U  plan-5  C19   0.020
 03U  plan-5  C20   0.020
 03U  plan-5  C22   0.020
 03U  plan-5  C23   0.020
 03U  plan-5  O25   0.020
 03U  plan-5  C26   0.020

