# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Jun  1 00:05:36 2020
#   Inital geometry file: a 85 line input string
#   Ligand name: 3-{[(E)-1-carboxy-2-cyclopropylethenyl]oxy}-2-hydroxybenzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)C(\Oc1cccc(C(O)=O)c1O)=C/C2CC2
#
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
 VCE  VCE  '3-{[(E)-1-carboxy-2-cyclopropylethenyl]oxy}-2-hydroxybenzoic acid'  ligand  31  19  .  2022-09-22  2022-11-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_VCE
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
 VCE  OA'   O  OH1   0  -0.587   1.0655  -1.0040  -2.3090
 VCE  OA    O  O     0  -0.484  -4.3105   1.3092  -0.6361
 VCE  OB'   O  O     0  -0.437   3.1701  -1.4356  -1.7032
 VCE  OB    O  OH1   0  -0.580  -5.0995  -0.4189   0.5208
 VCE  C8    C  C1    0  -0.180   2.8223   0.6398   0.3658
 VCE  C5    C  CR16  0  -0.264  -1.3163  -1.8642   1.3061
 VCE  C4    C  CR16  0  -0.332  -0.2073  -1.1728   0.8133
 VCE  C6    C  CR16  0  -0.283  -2.5858  -1.4022   1.0533
 VCE  C10   C  CH2   0  -0.473   4.8524   0.3473   1.8632
 VCE  C11   C  CH2   0  -0.473   5.1653   1.4457   0.9174
 VCE  O3    O  O2    0  -0.490   0.6385   0.7202  -0.4442
 VCE  C'    C  C     0   0.493   2.1340  -0.8342  -1.5441
 VCE  C7    C  C     0   0.147   1.9008   0.1742  -0.4864
 VCE  C2    C  CR6   0   0.287  -1.6663   0.4604  -0.2072
 VCE  C3    C  CR6   0   0.325  -0.3759  -0.0291   0.0639
 VCE  C1    C  CR6   0  -0.224  -2.7744  -0.2346   0.2987
 VCE  C9    C  CH1   0  -0.346   4.2430   0.3284   0.4769
 VCE  HOA'  H  HOH1  0   0.489   1.2511  -1.6735  -2.9846
 VCE  HOB   H  HOH1  0   0.494  -5.9537  -0.0175   0.3000
 VCE  HO2   H  HOH1  0   0.481  -2.7023   1.7965  -1.0254
 VCE  H8    H  H     0   0.278   2.4611   1.3821   1.0735
 VCE  H5    H  HCR6  0   0.267  -1.1671  -2.7613   1.8902
 VCE  H4    H  HCR6  0   0.288   0.7869  -1.5405   1.0335
 VCE  H6    H  HCR6  0   0.271  -3.4388  -1.9410   1.4404
 VCE  H10   H  HCH2  0   0.268   5.6095  -0.3994   2.0631
 VCE  H10A  H  HCH2  0   0.261   4.1975   0.5574   2.6993
 VCE  H11   H  HCH2  0   0.261   4.7275   2.4195   1.0962
 VCE  H11A  H  HCH2  0   0.268   6.1427   1.4715   0.4542
 VCE  H9    H  HCH1  0   0.286   4.6597  -0.3879  -0.2130
 VCE  O2    O  OH1   0  -0.612  -1.7520   1.5714  -0.9337
 VCE  C     C  C     0   0.599  -4.1153   0.2937   0.0139

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
 VCE  OA'  C'    single    1.325  0.020  1.325
 VCE  OA   C     double    1.221  0.020  1.221
 VCE  OB'  C'    double    1.208  0.020  1.208
 VCE  OB   C     single    1.317  0.020  1.317
 VCE  O2   C2    single    1.330  0.020  1.330
 VCE  C8   C7    double    1.339  0.020  1.339
 VCE  C8   C9    single    1.459  0.020  1.459
 VCE  C5   C4    aromatic  1.397  0.020  1.397
 VCE  C5   C6    aromatic  1.374  0.020  1.374
 VCE  C4   C3    aromatic  1.378  0.020  1.378
 VCE  C6   C1    aromatic  1.403  0.020  1.403
 VCE  C10  C11   single    1.483  0.020  1.483
 VCE  C10  C9    single    1.514  0.020  1.514
 VCE  C11  C9    single    1.514  0.020  1.514
 VCE  O3   C7    single    1.376  0.020  1.376
 VCE  O3   C3    single    1.360  0.020  1.360
 VCE  C'   C7    single    1.480  0.020  1.480
 VCE  C    C1    single    1.469  0.020  1.469
 VCE  C2   C3    aromatic  1.407  0.020  1.407
 VCE  C2   C1    aromatic  1.402  0.020  1.402
 VCE  OA'  HOA'  single    0.850  0.020  0.980
 VCE  OB   HOB   single    0.850  0.020  0.980
 VCE  O2   HO2   single    0.850  0.020  0.980
 VCE  C8   H8    single    0.930  0.020  1.080
 VCE  C5   H5    single    0.930  0.020  1.080
 VCE  C4   H4    single    0.930  0.020  1.080
 VCE  C6   H6    single    0.930  0.020  1.080
 VCE  C10  H10   single    0.970  0.020  1.090
 VCE  C10  H10A  single    0.970  0.020  1.090
 VCE  C11  H11   single    0.970  0.020  1.090
 VCE  C11  H11A  single    0.970  0.020  1.090
 VCE  C9   H9    single    0.970  0.020  1.090

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
 VCE  HOA'  OA'  C'   109.66  3.000
 VCE  HOB   OB   C    110.30  3.000
 VCE  H8    C8   C9   114.81  3.000
 VCE  H8    C8   C7   115.03  3.000
 VCE  C9    C8   C7   130.15  3.000
 VCE  H5    C5   C6   120.39  3.000
 VCE  H5    C5   C4   119.46  3.000
 VCE  C6    C5   C4   120.15  3.000
 VCE  H4    C4   C3   120.33  3.000
 VCE  H4    C4   C5   119.30  3.000
 VCE  C3    C4   C5   120.37  3.000
 VCE  H6    C6   C1   120.10  3.000
 VCE  H6    C6   C5   119.71  3.000
 VCE  C1    C6   C5   120.19  3.000
 VCE  H10A  C10  H10  114.49  3.000
 VCE  H10A  C10  C9   117.77  3.000
 VCE  H10   C10  C9   116.24  3.000
 VCE  H10A  C10  C11  118.46  3.000
 VCE  H10   C10  C11  118.77  3.000
 VCE  C9    C10  C11   60.68  3.000
 VCE  H11A  C11  H11  114.50  3.000
 VCE  H11A  C11  C9   116.32  3.000
 VCE  H11   C11  C9   117.73  3.000
 VCE  H11A  C11  C10  118.78  3.000
 VCE  H11   C11  C10  118.39  3.000
 VCE  C9    C11  C10   60.69  3.000
 VCE  C3    O3   C7   118.51  3.000
 VCE  C7    C'   OB'  124.63  3.000
 VCE  C7    C'   OA'  111.89  3.000
 VCE  OB'   C'   OA'  123.48  3.000
 VCE  C'    C7   O3   115.91  3.000
 VCE  C'    C7   C8   125.69  3.000
 VCE  O3    C7   C8   118.29  3.000
 VCE  C1    C2   C3   118.88  3.000
 VCE  C1    C2   O2   124.06  3.000
 VCE  C3    C2   O2   117.07  3.000
 VCE  C2    C3   O3   114.88  3.000
 VCE  C2    C3   C4   120.40  3.000
 VCE  O3    C3   C4   124.71  3.000
 VCE  C2    C1   C    118.23  3.000
 VCE  C2    C1   C6   120.02  3.000
 VCE  C     C1   C6   121.75  3.000
 VCE  H9    C9   C11  116.16  3.000
 VCE  H9    C9   C10  116.01  3.000
 VCE  C11   C9   C10   58.63  3.000
 VCE  H9    C9   C8   118.00  3.000
 VCE  C11   C9   C8   117.25  3.000
 VCE  C10   C9   C8   117.32  3.000
 VCE  HO2   O2   C2   107.77  3.000
 VCE  C1    C    OB   114.40  3.000
 VCE  C1    C    OA   123.23  3.000
 VCE  OB    C    OA   122.37  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
 VCE  CONST_01  C2    C3   C4  C5      0.00   0.0  0
 VCE  CONST_02  C2    C1   C6  C5      0.00   0.0  0
 VCE  CONST_03  C1    C6   C5  C4      0.00   0.0  0
 VCE  CONST_04  C1    C2   C3  C4      0.00   0.0  0
 VCE  CONST_05  C3    C4   C5  C6      0.00   0.0  0
 VCE  CONST_06  C3    C2   C1  C6      0.00   0.0  0
 VCE  CONST_07  C4    C3   C2  O2    180.00   0.0  0
 VCE  CONST_08  C6    C1   C2  O2    180.00   0.0  0
 VCE  CONST_09  O3    C3   C4  C5    180.00   0.0  0
 VCE  CONST_10  C     C1   C6  C5    180.00   0.0  0
 VCE  CONST_11  C1    C2   C3  O3    180.00   0.0  0
 VCE  CONST_12  C3    C2   C1  C     180.00   0.0  0
 VCE  CONST_13  H6    C6   C5  C4    180.00   0.0  0
 VCE  CONST_14  H4    C4   C5  C6    180.00   0.0  0
 VCE  CONST_15  H5    C5   C4  C3    180.00   0.0  0
 VCE  CONST_16  HOB   OB   C   C1    180.00   0.0  0
 VCE  CONST_17  HOA'  OA'  C'  OB'     0.00   0.0  0
 VCE  Var_01    C11   C10  C9  C8   -106.78  30.0  1
 VCE  Var_02    C6    C1   C   OA    179.76  30.0  2
 VCE  Var_03    C7    C8   C9  C10  -146.77  30.0  1
 VCE  Var_04    C2    C3   O3  C7   -165.86  30.0  2
 VCE  Var_05    C9    C8   C7  O3   -174.77   0.0  2
 VCE  Var_06    C8    C7   C'  OA'  -174.12  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
 VCE  chir_01  C9  C8  C10  C11  both

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
 VCE  plan-1  C5    0.020
 VCE  plan-1  C4    0.020
 VCE  plan-1  C6    0.020
 VCE  plan-1  O3    0.020
 VCE  plan-1  C2    0.020
 VCE  plan-1  C3    0.020
 VCE  plan-1  C1    0.020
 VCE  plan-1  H5    0.020
 VCE  plan-1  H4    0.020
 VCE  plan-1  H6    0.020
 VCE  plan-1  O2    0.020
 VCE  plan-1  C     0.020
 VCE  plan-2  OA    0.020
 VCE  plan-2  OB    0.020
 VCE  plan-2  C1    0.020
 VCE  plan-2  HOB   0.020
 VCE  plan-2  C     0.020
 VCE  plan-3  OA'   0.020
 VCE  plan-3  OB'   0.020
 VCE  plan-3  C'    0.020
 VCE  plan-3  C7    0.020
 VCE  plan-3  HOA'  0.020
 VCE  plan-4  C8    0.020
 VCE  plan-4  O3    0.020
 VCE  plan-4  C'    0.020
 VCE  plan-4  C7    0.020
 VCE  plan-4  C9    0.020
 VCE  plan-4  H8    0.020

