# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 11 07:25:05 2020
#   Inital geometry file: a 105 line input string
#   Ligand name: (3~{R},4~{S},5~{R})-3-[(~{E})-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-4,5-bis(oxidanyl)cyclohexene-1-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@@H]1CC(=C[C@@H](OC(=O)/C=C/c2ccc(O)cc2)[C@H]1O)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
 6TO  6TO  '(3~{R},4~{S},5~{R})-3-[(~{E})-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-4,5-bis(oxidanyl)cyclohexene-1-carboxylic acid'  ligand  38  23  .  2021-08-05  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_6TO
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
 6TO  C10  C  CH1    0  -0.001   4.2052   1.7696   0.1750
 6TO  C13  C  C1     0  -0.292   2.7006  -0.5846  -0.3250
 6TO  C15  C  CH2    0  -0.512   4.7608   0.4181   0.6080
 6TO  C01  C  CR6    0   0.359  -6.7117  -0.3335   0.4990
 6TO  C02  C  CR16   0  -0.327  -6.4066  -0.5080  -0.8500
 6TO  C03  C  CR16   0  -0.287  -5.0943  -0.4166  -1.2729
 6TO  C04  C  CR6    0   0.121  -4.0512  -0.1479  -0.3807
 6TO  C05  C  CR16   0  -0.295  -4.3785   0.0225   0.9691
 6TO  C06  C  CR16   0  -0.360  -5.6837  -0.0685   1.4075
 6TO  C07  C  C1     0  -0.211  -2.6930  -0.0639  -0.8886
 6TO  C08  C  C1     0  -0.447  -1.5892   0.2439  -0.1932
 6TO  C09  C  C      0   0.606  -0.2788   0.2772  -0.8528
 6TO  O02  O  O      0  -0.461  -0.0651  -0.0050  -2.0099
 6TO  O03  O  O2     0  -0.497   0.6699   0.6631  -0.0002
 6TO  C11  C  CH1    0  -0.021   2.6985   1.8274   0.3971
 6TO  C12  C  CH1    0   0.016   2.0322   0.7465  -0.4532
 6TO  C14  C  C      0  -0.080   3.9426  -0.7449   0.1297
 6TO  O04  O  OH1    0  -0.668   2.4844   1.6333   1.7723
 6TO  O05  O  OH1    0  -0.674   4.4101   2.0151  -1.2013
 6TO  C16  C  C      0   0.390   4.5574  -2.1374   0.2171
 6TO  O06  O  O      0  -0.596   3.8763  -3.0973  -0.1937
 6TO  O07  O  OC    -1  -0.597   5.7033  -2.1956   0.7065
 6TO  H1   H  HCH1   0   0.229   4.6737   2.5592   0.7795
 6TO  H2   H  H      0   0.245   2.1473  -1.4544  -0.6624
 6TO  H4   H  HCH2   0   0.244   5.7944   0.3217   0.2635
 6TO  H5   H  HCH2   0   0.241   4.8300   0.3874   1.6994
 6TO  H7   H  HCR6   0   0.263  -4.8736  -0.5549  -2.3245
 6TO  H8   H  HCR6   0   0.263  -3.6044   0.2237   1.6985
 6TO  H9   H  HCR6   0   0.279  -5.9062   0.0638   2.4599
 6TO  H10  H  HOH1   0   0.479  -8.0891  -0.3009   1.8218
 6TO  H11  H  H      0   0.267  -2.5823  -0.2727  -1.9487
 6TO  H12  H  H      0   0.274  -1.6208   0.4762   0.8643
 6TO  H13  H  HCH1   0   0.236   2.3191   2.8083   0.0768
 6TO  H14  H  HCH1   0   0.257   2.0404   1.0671  -1.4984
 6TO  H16  H  HOH1   0   0.453   1.5432   1.7203   1.9503
 6TO  H17  H  HOH1   0   0.453   5.3488   1.9162  -1.3871
 6TO  O01  O  OH1    0  -0.620  -7.9965  -0.4310   0.8708
 6TO  H6   H  HCR6   0   0.270  -7.1983  -0.7144  -1.5589

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
 6TO  O06  C16  deloc     1.247  0.020  1.247
 6TO  O02  C09  double    1.210  0.020  1.210
 6TO  C07  C04  single    1.452  0.020  1.452
 6TO  C07  C08  double    1.340  0.020  1.340
 6TO  C05  C04  aromatic  1.399  0.020  1.399
 6TO  C05  C06  aromatic  1.380  0.020  1.380
 6TO  C04  C03  aromatic  1.399  0.020  1.399
 6TO  C09  C08  single    1.467  0.020  1.467
 6TO  C09  O03  single    1.333  0.020  1.333
 6TO  C06  C01  aromatic  1.397  0.020  1.397
 6TO  C03  C02  aromatic  1.382  0.020  1.382
 6TO  C01  C02  aromatic  1.394  0.020  1.394
 6TO  C01  O01  single    1.341  0.020  1.341
 6TO  C16  O07  deloc     1.247  0.020  1.247
 6TO  C16  C14  single    1.525  0.020  1.525
 6TO  O03  C12  single    1.438  0.020  1.438
 6TO  C13  C12  single    1.495  0.020  1.495
 6TO  C13  C14  double    1.332  0.020  1.332
 6TO  C12  C11  single    1.528  0.020  1.528
 6TO  C14  C15  single    1.500  0.020  1.500
 6TO  C15  C10  single    1.524  0.020  1.524
 6TO  C11  C10  single    1.524  0.020  1.524
 6TO  C11  O04  single    1.405  0.020  1.405
 6TO  C10  O05  single    1.413  0.020  1.413
 6TO  C10  H1   single    0.970  0.020  1.090
 6TO  C13  H2   single    0.930  0.020  1.080
 6TO  C15  H4   single    0.970  0.020  1.090
 6TO  C15  H5   single    0.970  0.020  1.090
 6TO  C02  H6   single    0.930  0.020  1.080
 6TO  C03  H7   single    0.930  0.020  1.080
 6TO  C05  H8   single    0.930  0.020  1.080
 6TO  C06  H9   single    0.930  0.020  1.080
 6TO  O01  H10  single    0.850  0.020  0.980
 6TO  C07  H11  single    0.930  0.020  1.080
 6TO  C08  H12  single    0.930  0.020  1.080
 6TO  C11  H13  single    0.970  0.020  1.090
 6TO  C12  H14  single    0.970  0.020  1.090
 6TO  O04  H16  single    0.850  0.020  0.980
 6TO  O05  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
 6TO  H1   C10  O05  110.43  3.000
 6TO  H1   C10  C11  108.30  3.000
 6TO  O05  C10  C11  106.19  3.000
 6TO  H1   C10  C15  108.98  3.000
 6TO  O05  C10  C15  112.21  3.000
 6TO  C11  C10  C15  110.65  3.000
 6TO  H2   C13  C14  119.03  3.000
 6TO  H2   C13  C12  117.34  3.000
 6TO  C14  C13  C12  123.59  3.000
 6TO  H5   C15  H4   104.59  3.000
 6TO  H5   C15  C14  109.32  3.000
 6TO  H4   C15  C14  110.28  3.000
 6TO  H5   C15  C10  109.36  3.000
 6TO  H4   C15  C10  109.46  3.000
 6TO  C14  C15  C10  113.45  3.000
 6TO  O01  C01  C06  122.57  3.000
 6TO  O01  C01  C02  117.96  3.000
 6TO  C06  C01  C02  119.46  3.000
 6TO  H6   C02  C03  120.45  3.000
 6TO  H6   C02  C01  119.83  3.000
 6TO  C03  C02  C01  119.72  3.000
 6TO  H7   C03  C04  119.46  3.000
 6TO  H7   C03  C02  118.83  3.000
 6TO  C04  C03  C02  121.72  3.000
 6TO  C07  C04  C05  123.30  3.000
 6TO  C05  C04  C03  117.66  3.000
 6TO  C07  C04  C03  119.04  3.000
 6TO  H8   C05  C06  118.33  3.000
 6TO  H8   C05  C04  120.35  3.000
 6TO  C06  C05  C04  121.31  3.000
 6TO  H9   C06  C05  119.64  3.000
 6TO  H9   C06  C01  120.23  3.000
 6TO  C05  C06  C01  120.12  3.000
 6TO  H11  C07  C08  117.81  3.000
 6TO  H11  C07  C04  115.18  3.000
 6TO  C08  C07  C04  127.01  3.000
 6TO  H12  C08  C09  117.39  3.000
 6TO  H12  C08  C07  122.12  3.000
 6TO  C09  C08  C07  120.49  3.000
 6TO  O03  C09  O02  123.62  3.000
 6TO  O03  C09  C08  110.78  3.000
 6TO  O02  C09  C08  125.61  3.000
 6TO  C12  O03  C09  119.32  3.000
 6TO  H13  C11  O04  110.84  3.000
 6TO  H13  C11  C12  108.57  3.000
 6TO  O04  C11  C12  112.36  3.000
 6TO  H13  C11  C10  109.43  3.000
 6TO  O04  C11  C10  106.74  3.000
 6TO  C12  C11  C10  108.85  3.000
 6TO  H14  C12  C11  108.74  3.000
 6TO  H14  C12  O03  108.98  3.000
 6TO  C11  C12  O03  106.19  3.000
 6TO  H14  C12  C13  109.86  3.000
 6TO  C11  C12  C13  112.77  3.000
 6TO  O03  C12  C13  110.17  3.000
 6TO  C16  C14  C15  118.02  3.000
 6TO  C15  C14  C13  121.60  3.000
 6TO  C16  C14  C13  120.36  3.000
 6TO  H16  O04  C11  108.53  3.000
 6TO  H17  O05  C10  108.17  3.000
 6TO  O07  C16  O06  126.53  3.000
 6TO  O07  C16  C14  115.82  3.000
 6TO  O06  C16  C14  117.65  3.000
 6TO  H10  O01  C01  110.83  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
 6TO  CONST_01  C04  C05  C06  C01    0.00   0.0  0
 6TO  CONST_02  C04  C03  C02  C01    0.00   0.0  0
 6TO  CONST_03  C05  C04  C03  C02    0.00   0.0  0
 6TO  CONST_04  C05  C06  C01  C02    0.00   0.0  0
 6TO  CONST_05  C06  C05  C04  C03    0.00   0.0  0
 6TO  CONST_06  C06  C01  C02  C03    0.00   0.0  0
 6TO  CONST_07  C07  C04  C03  C02  180.00   0.0  0
 6TO  CONST_08  O01  C01  C02  C03  180.00   0.0  0
 6TO  CONST_09  O01  C01  C06  C05  180.00   0.0  0
 6TO  CONST_10  C07  C04  C05  C06  180.00   0.0  0
 6TO  CONST_11  H8   C05  C06  C01  180.00   0.0  0
 6TO  CONST_12  H7   C03  C02  C01  180.00   0.0  0
 6TO  CONST_13  H9   C06  C01  C02  180.00   0.0  0
 6TO  CONST_14  H6   C02  C03  C04  180.00   0.0  0
 6TO  Var_01    C13  C14  C15  C10  -15.75  30.0  1
 6TO  Var_02    C12  C13  C14  C15    2.51  30.0  1
 6TO  Var_03    O06  C16  C14  C13    2.49  30.0  2
 6TO  Var_04    C08  C07  C04  C03  176.69  30.0  2
 6TO  Var_05    C09  C08  C07  C04  179.51   0.0  2
 6TO  Var_06    O02  C09  C08  C07   -2.98  30.0  1

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
 6TO  chir_01  C10  C15  C11  O05  positiv
 6TO  chir_02  C11  O04  C10  C12  negativ
 6TO  chir_03  C12  O03  C13  C11  positiv

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
 6TO  plan-1  C01  0.020
 6TO  plan-1  C02  0.020
 6TO  plan-1  C03  0.020
 6TO  plan-1  C04  0.020
 6TO  plan-1  C05  0.020
 6TO  plan-1  C06  0.020
 6TO  plan-1  C07  0.020
 6TO  plan-1  H7   0.020
 6TO  plan-1  H8   0.020
 6TO  plan-1  H9   0.020
 6TO  plan-1  O01  0.020
 6TO  plan-1  H6   0.020
 6TO  plan-2  C14  0.020
 6TO  plan-2  C16  0.020
 6TO  plan-2  O06  0.020
 6TO  plan-2  O07  0.020
 6TO  plan-3  C08  0.020
 6TO  plan-3  C09  0.020
 6TO  plan-3  O02  0.020
 6TO  plan-3  O03  0.020
 6TO  plan-4  C04  0.020
 6TO  plan-4  C07  0.020
 6TO  plan-4  C08  0.020
 6TO  plan-4  C09  0.020
 6TO  plan-4  H11  0.020
 6TO  plan-4  H12  0.020

