# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 23 23:25:27 2020
#   Inital geometry file: a 82 line input string
#   Ligand name: (1R,6R)-2-(3-carboxypropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@@H]1C=CC=C([C@H]1C(O)=O)C(=O)CCC(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
 164  164  '(1R,6R)-2-(3-carboxypropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid'  ligand  29  17  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_164
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
 164  O1    O  O     0  -0.427   2.5693   0.4008   2.3462
 164  C7    C  C     0   0.597   1.7006   0.5662   1.5296
 164  O2    O  OH1   0  -0.585   1.6882   1.5762   0.6728
 164  C2    C  CH1   0  -0.566   0.5165  -0.3690   1.3181
 164  C3    C  CH1   0   0.041   0.2625  -1.1993   2.5723
 164  C4    C  C1    0  -0.262  -0.4649  -0.3853   3.6095
 164  C5    C  C1    0  -0.215  -1.3179   0.5743   3.2402
 164  C6    C  C1    0  -0.231  -1.5327   0.8670   1.8346
 164  O9    O  OH1   0  -0.658  -0.5142  -2.3168   2.1880
 164  C1    C  C     0   0.028  -0.7028   0.4076   0.8842
 164  C8    C  C     0   0.379  -0.9863   0.7036  -0.5422
 164  O3    O  O     0  -0.408  -1.8337   1.5160  -0.8553
 164  C9    C  CH2   0  -0.586  -0.2146  -0.0653  -1.5851
 164  C10   C  CH2   0  -0.581  -0.6132   0.2940  -3.0032
 164  C11   C  C     0   0.557   0.1665  -0.4759  -4.0331
 164  O5    O  OH1   0  -0.596  -0.1826  -0.1299  -5.2679
 164  O4    O  O     0  -0.444   1.0068  -1.3074  -3.7953
 164  HO2   H  HOH1  0   0.487   2.4779   2.1265   0.7902
 164  H2    H  HCH1  0   0.333   0.8346  -1.0674   0.5350
 164  H3    H  HCH1  0   0.243   1.2269  -1.5242   2.9729
 164  H4    H  H     0   0.274  -0.3412  -0.6480   4.6533
 164  H5    H  H     0   0.270  -1.8982   1.1193   3.9734
 164  H6    H  H     0   0.272  -2.3979   1.4581   1.5610
 164  HO9   H  HOH1  0   0.457  -0.5944  -2.9020   2.9483
 164  H91   H  HCH2  0   0.280   0.8535   0.1103  -1.4343
 164  H92   H  HCH2  0   0.285  -0.3624  -1.1341  -1.4005
 164  H101  H  HCH2  0   0.289  -1.6767   0.1061  -3.1716
 164  H102  H  HCH2  0   0.288  -0.4675   1.3608  -3.1910
 164  HO5   H  HOH1  0   0.480   0.3312  -0.6393  -5.9123

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
 164  O1   C7    double  1.204  0.020  1.204
 164  C7   O2    single  1.324  0.020  1.324
 164  C7   C2    single  1.524  0.020  1.524
 164  O2   HO2   single  0.850  0.020  0.980
 164  C2   C3    single  1.525  0.020  1.525
 164  C2   C1    single  1.509  0.020  1.509
 164  C2   H2    single  0.970  0.020  1.090
 164  C3   C4    single  1.506  0.020  1.506
 164  C3   O9    single  1.414  0.020  1.414
 164  C3   H3    single  0.970  0.020  1.090
 164  C4   C5    double  1.336  0.020  1.336
 164  C4   H4    single  0.930  0.020  1.080
 164  C5   C6    single  1.452  0.020  1.452
 164  C5   H5    single  0.930  0.020  1.080
 164  C6   C1    double  1.343  0.020  1.343
 164  C6   H6    single  0.930  0.020  1.080
 164  O9   HO9   single  0.850  0.020  0.980
 164  C1   C8    single  1.484  0.020  1.484
 164  C8   O3    double  1.215  0.020  1.215
 164  C8   C9    single  1.508  0.020  1.508
 164  C9   C10   single  1.516  0.020  1.516
 164  C9   H91   single  0.970  0.020  1.090
 164  C9   H92   single  0.970  0.020  1.090
 164  C10  C11   single  1.504  0.020  1.504
 164  C10  H101  single  0.970  0.020  1.090
 164  C10  H102  single  0.970  0.020  1.090
 164  C11  O5    single  1.329  0.020  1.329
 164  C11  O4    double  1.206  0.020  1.206
 164  O5   HO5   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
 164  C2    C7   O2    111.78  3.000
 164  C2    C7   O1    124.80  3.000
 164  O2    C7   O1    123.39  3.000
 164  HO2   O2   C7    110.29  3.000
 164  H2    C2   C1    110.90  3.000
 164  H2    C2   C3    106.79  3.000
 164  C1    C2   C3    112.45  3.000
 164  H2    C2   C7    105.35  3.000
 164  C1    C2   C7    110.61  3.000
 164  C3    C2   C7    110.45  3.000
 164  H3    C3   O9    110.43  3.000
 164  H3    C3   C4    109.53  3.000
 164  O9    C3   C4    110.43  3.000
 164  H3    C3   C2    108.42  3.000
 164  O9    C3   C2    107.35  3.000
 164  C4    C3   C2    110.64  3.000
 164  H4    C4   C5    120.89  3.000
 164  H4    C4   C3    118.52  3.000
 164  C5    C4   C3    120.42  3.000
 164  H5    C5   C6    118.36  3.000
 164  H5    C5   C4    121.12  3.000
 164  C6    C5   C4    120.46  3.000
 164  H6    C6   C1    120.11  3.000
 164  H6    C6   C5    118.22  3.000
 164  C1    C6   C5    121.66  3.000
 164  HO9   O9   C3    108.14  3.000
 164  C8    C1   C6    119.60  3.000
 164  C8    C1   C2    122.23  3.000
 164  C6    C1   C2    118.15  3.000
 164  C9    C8   O3    121.30  3.000
 164  C9    C8   C1    117.72  3.000
 164  O3    C8   C1    120.96  3.000
 164  H92   C9   H91   105.40  3.000
 164  H92   C9   C10   110.71  3.000
 164  H91   C9   C10   110.36  3.000
 164  H92   C9   C8    108.19  3.000
 164  H91   C9   C8    108.82  3.000
 164  C10   C9   C8    113.04  3.000
 164  H102  C10  H101  105.72  3.000
 164  H102  C10  C11   108.23  3.000
 164  H101  C10  C11   108.12  3.000
 164  H102  C10  C9    110.92  3.000
 164  H101  C10  C9    111.05  3.000
 164  C11   C10  C9    112.52  3.000
 164  O4    C11  O5    123.08  3.000
 164  O4    C11  C10   125.40  3.000
 164  O5    C11  C10   111.52  3.000
 164  HO5   O5   C11   109.99  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
 164  CONST_01  HO2  O2   C7   C2    180.00   0.0  0
 164  CONST_02  HO5  O5   C11  C10   180.00   0.0  0
 164  Var_01    C5   C6   C1   C2     -3.24  30.0  1
 164  Var_02    C1   C6   C5   C4    -14.37  30.0  1
 164  Var_03    O3   C8   C1   C2   -167.15  30.0  2
 164  Var_04    C10  C9   C8   C1    178.48  30.0  3
 164  Var_05    C11  C10  C9   C8    179.81  30.0  3
 164  Var_06    O5   C11  C10  C9   -178.96  30.0  3

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
 164  chir_01  C2  C7  C3  C1  negativ
 164  chir_02  C3  O9  C2  C4  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
 164  plan-1  C1   0.020
 164  plan-1  C8   0.020
 164  plan-1  O3   0.020
 164  plan-1  C9   0.020
 164  plan-2  O1   0.020
 164  plan-2  C7   0.020
 164  plan-2  O2   0.020
 164  plan-2  C2   0.020
 164  plan-2  HO2  0.020
 164  plan-3  C10  0.020
 164  plan-3  C11  0.020
 164  plan-3  O5   0.020
 164  plan-3  O4   0.020
 164  plan-3  HO5  0.020

