# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May 23 16:32:36 2020
#   Inital geometry file: a 76 line input string
#   Ligand name: cis-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@H]1C=C[C@](CC(=O)C(O)=O)(C=C1)C(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
 PRE  PRE  'cis-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid'  ligand  26  16  .  2021-08-20  2021-08-20  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_PRE
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
 PRE  C1    C  CT    0  -0.371  -0.3078   0.2133   0.5690
 PRE  C2    C  C1    0  -0.159  -0.0461   1.2628   1.6233
 PRE  C3    C  C1    0  -0.247   0.5482   1.0201   2.7829
 PRE  C4    C  CH1   0  -0.032   1.0164  -0.3303   3.2161
 PRE  O4    O  OH1   0  -0.669   2.3707  -0.2078   3.6211
 PRE  C5    C  C1    0  -0.266   0.8641  -1.3462   2.1264
 PRE  C6    C  C1    0  -0.140   0.2649  -1.1184   0.9658
 PRE  C7    C  C     0   0.594  -1.8280   0.1788   0.4186
 PRE  O71   O  O     0  -0.441  -2.4474   0.9967  -0.2136
 PRE  O72   O  OH1   0  -0.573  -2.3894  -0.7896   1.1199
 PRE  C8    C  CH2   0  -0.535   0.3188   0.7092  -0.7426
 PRE  C1'   C  C     0   0.290  -0.0545  -0.0971  -1.9464
 PRE  O1'   O  O     0  -0.341  -0.8509  -0.9972  -1.9501
 PRE  C2'   C  C     0   0.494   0.6531   0.3037  -3.2508
 PRE  O'L   O  O     0  -0.399   1.4725   1.1816  -3.2921
 PRE  O'M   O  OH1   0  -0.568   0.2473  -0.4253  -4.2637
 PRE  H2    H  H     0   0.273  -0.3661   2.2704   1.3805
 PRE  H3    H  H     0   0.262   0.7045   1.8350   3.4812
 PRE  H4    H  HCH1  0   0.237   0.4035  -0.6452   4.0735
 PRE  HO4   H  HOH1  0   0.457   2.5807  -0.9518   4.1939
 PRE  H5    H  H     0   0.259   1.2634  -2.3344   2.3312
 PRE  H6    H  H     0   0.268   0.1926  -1.9216   0.2429
 PRE  HO72  H  HOH1  0   0.484  -3.3544  -0.7371   1.0406
 PRE  H81   H  HCH2  0   0.314   0.0346   1.7484  -0.9392
 PRE  H82   H  HCH2  0   0.313   1.4069   0.7243  -0.6398
 PRE  HO2'  H  HOH1  0   0.496   0.7043  -0.1615  -5.0779

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
 PRE  C1   C2    single  1.510  0.020  1.510
 PRE  C1   C6    single  1.503  0.020  1.503
 PRE  C1   C7    single  1.528  0.020  1.528
 PRE  C1   C8    single  1.536  0.020  1.536
 PRE  C2   C3    double  1.325  0.020  1.325
 PRE  C2   H2    single  0.930  0.020  1.080
 PRE  C3   C4    single  1.493  0.020  1.493
 PRE  C3   H3    single  0.930  0.020  1.080
 PRE  C4   O4    single  1.419  0.020  1.419
 PRE  C4   C5    single  1.498  0.020  1.498
 PRE  C4   H4    single  0.970  0.020  1.090
 PRE  O4   HO4   single  0.850  0.020  0.980
 PRE  C5   C6    double  1.326  0.020  1.326
 PRE  C5   H5    single  0.930  0.020  1.080
 PRE  C6   H6    single  0.930  0.020  1.080
 PRE  C7   O71   double  1.205  0.020  1.205
 PRE  C7   O72   single  1.321  0.020  1.321
 PRE  O72  HO72  single  0.850  0.020  0.980
 PRE  C8   C1'   single  1.496  0.020  1.496
 PRE  C8   H81   single  0.970  0.020  1.090
 PRE  C8   H82   single  0.970  0.020  1.090
 PRE  C1'  O1'   double  1.202  0.020  1.202
 PRE  C1'  C2'   single  1.537  0.020  1.537
 PRE  C2'  O'L   double  1.202  0.020  1.202
 PRE  C2'  O'M   single  1.312  0.020  1.312
 PRE  O'M  HO2'  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
 PRE  C8    C1   C7   109.22  3.000
 PRE  C8    C1   C6   110.86  3.000
 PRE  C7    C1   C6   112.65  3.000
 PRE  C8    C1   C2   107.52  3.000
 PRE  C7    C1   C2   104.88  3.000
 PRE  C6    C1   C2   111.43  3.000
 PRE  H2    C2   C3   119.89  3.000
 PRE  H2    C2   C1   115.98  3.000
 PRE  C3    C2   C1   124.13  3.000
 PRE  H3    C3   C4   116.58  3.000
 PRE  H3    C3   C2   119.36  3.000
 PRE  C4    C3   C2   124.05  3.000
 PRE  H4    C4   C5   108.44  3.000
 PRE  H4    C4   O4   109.51  3.000
 PRE  C5    C4   O4   111.31  3.000
 PRE  H4    C4   C3   108.08  3.000
 PRE  C5    C4   C3   111.74  3.000
 PRE  O4    C4   C3   107.70  3.000
 PRE  HO4   O4   C4   108.15  3.000
 PRE  H5    C5   C6   119.20  3.000
 PRE  H5    C5   C4   116.29  3.000
 PRE  C6    C5   C4   124.50  3.000
 PRE  H6    C6   C5   119.15  3.000
 PRE  H6    C6   C1   117.10  3.000
 PRE  C5    C6   C1   123.74  3.000
 PRE  O72   C7   O71  123.90  3.000
 PRE  O72   C7   C1   112.77  3.000
 PRE  O71   C7   C1   123.20  3.000
 PRE  HO72  O72  C7   109.87  3.000
 PRE  H82   C8   H81  105.20  3.000
 PRE  H82   C8   C1'  109.36  3.000
 PRE  H81   C8   C1'  107.59  3.000
 PRE  H82   C8   C1   109.29  3.000
 PRE  H81   C8   C1   110.72  3.000
 PRE  C1'   C8   C1   114.29  3.000
 PRE  C2'   C1'  O1'  119.85  3.000
 PRE  C2'   C1'  C8   115.30  3.000
 PRE  O1'   C1'  C8   124.85  3.000
 PRE  O'M   C2'  O'L  126.17  3.000
 PRE  O'M   C2'  C1'  111.58  3.000
 PRE  O'L   C2'  C1'  122.26  3.000
 PRE  HO2'  O'M  C2'  110.55  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
 PRE  CONST_01  HO72  O72  C7   C1   180.00   0.0  0
 PRE  CONST_02  HO2'  O'M  C2'  C1'  180.00   0.0  0
 PRE  Var_01    C4    C3   C2   C1    -1.24  30.0  1
 PRE  Var_02    C4    C5   C6   C1     2.02  30.0  1
 PRE  Var_03    O1'   C1'  C8   C1     5.54  30.0  3
 PRE  Var_04    O'L   C2'  C1'  C8     1.75  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
 PRE  chir_01  C1  C6  C2  C8  negativ
 PRE  chir_02  C4  O4  C3  C5  negativ

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
 PRE  plan-1  C8    0.020
 PRE  plan-1  C1'   0.020
 PRE  plan-1  O1'   0.020
 PRE  plan-1  C2'   0.020
 PRE  plan-2  C1    0.020
 PRE  plan-2  C7    0.020
 PRE  plan-2  O71   0.020
 PRE  plan-2  O72   0.020
 PRE  plan-2  HO72  0.020
 PRE  plan-3  C1'   0.020
 PRE  plan-3  C2'   0.020
 PRE  plan-3  O'L   0.020
 PRE  plan-3  O'M   0.020
 PRE  plan-3  HO2'  0.020

