# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar 22 21:12:35 2022
#   Inital geometry file: a 73 line input string
#   Ligand name: (1R,3S,5S,8R)-8-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@@H]1C=C[C@@]2(C[C@H]1O[C@@H](C2)C(O)=O)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
 TSA  TSA  '(1R,3S,5S,8R)-8-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid'  ligand  26  16  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_TSA
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
 TSA  C1   C  CT     0  -0.285  27.4605  17.7335  49.9039
 TSA  C2   C  C1     0  -0.170  27.3781  18.4049  51.2461
 TSA  C3   C  C1     0  -0.251  26.5690  17.9990  52.2206
 TSA  C4   C  CH1    0  -0.009  25.6719  16.8067  52.0990
 TSA  O5   O  OH1    0  -0.675  24.3324  17.2851  52.1048
 TSA  C5   C  CH1    0  -0.014  25.9571  16.0097  50.8158
 TSA  C6   C  CH2    0  -0.431  26.1713  16.9626  49.6537
 TSA  O7   O  O2     0  -0.494  27.0261  15.0936  50.9455
 TSA  C8   C  CH1    0  -0.102  28.3567  15.5826  50.9587
 TSA  C9   C  CH2    0  -0.426  28.5922  16.6887  49.9279
 TSA  C10  C  C      0   0.437  27.7880  18.7670  48.7882
 TSA  O1   O  O      0  -0.588  27.1298  18.6931  47.7331
 TSA  O2   O  OC    -1  -0.603  28.7145  19.5660  49.0333
 TSA  C11  C  C      0   0.403  28.9129  15.8833  52.3795
 TSA  O3   O  O      0  -0.610  30.0368  16.4278  52.4004
 TSA  O4   O  OC    -1  -0.600  28.2650  15.4775  53.3611
 TSA  H2   H  H      0   0.224  28.0405  19.2463  51.4151
 TSA  H3   H  H      0   0.223  26.5569  18.5280  53.1688
 TSA  H4   H  HCH1   0   0.215  25.8443  16.1481  52.9576
 TSA  HO5  H  HOH1   0   0.442  23.7486  16.5269  52.2101
 TSA  H5   H  HCH1   0   0.218  25.0834  15.3749  50.6237
 TSA  H61  H  HCH2   0   0.218  25.3151  17.6370  49.5741
 TSA  H62  H  HCH2   0   0.218  26.2294  16.4082  48.7143
 TSA  H8   H  HCH1   0   0.219  28.9567  14.7235  50.6272
 TSA  H91  H  HCH2   0   0.213  28.6571  16.2451  48.9278
 TSA  H92  H  HCH2   0   0.228  29.5540  17.1546  50.1334

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
 TSA  C1   C2   single  1.503  0.020  1.503
 TSA  C1   C6   single  1.523  0.020  1.523
 TSA  C1   C9   single  1.540  0.020  1.540
 TSA  C1   C10  single  1.556  0.020  1.556
 TSA  C2   C3   double  1.330  0.020  1.330
 TSA  C2   H2   single  0.930  0.020  1.080
 TSA  C3   C4   single  1.497  0.020  1.497
 TSA  C3   H3   single  0.930  0.020  1.080
 TSA  C4   O5   single  1.422  0.020  1.422
 TSA  C4   C5   single  1.537  0.020  1.537
 TSA  C4   H4   single  0.970  0.020  1.090
 TSA  O5   HO5  single  0.850  0.020  0.980
 TSA  C5   C6   single  1.518  0.020  1.518
 TSA  C5   O7   single  1.414  0.020  1.414
 TSA  C5   H5   single  0.970  0.020  1.090
 TSA  C6   H61  single  0.970  0.020  1.090
 TSA  C6   H62  single  0.970  0.020  1.090
 TSA  O7   C8   single  1.418  0.020  1.418
 TSA  C8   C9   single  1.530  0.020  1.530
 TSA  C8   C11  single  1.555  0.020  1.555
 TSA  C8   H8   single  0.970  0.020  1.090
 TSA  C9   H91  single  0.970  0.020  1.090
 TSA  C9   H92  single  0.970  0.020  1.090
 TSA  C10  O1   deloc   1.246  0.020  1.246
 TSA  C10  O2   deloc   1.248  0.020  1.248
 TSA  C11  O3   deloc   1.249  0.020  1.249
 TSA  C11  O4   deloc   1.244  0.020  1.244

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
 TSA  C10  C1   C9   107.88  3.000
 TSA  C10  C1   C6   113.37  3.000
 TSA  C9   C1   C6   106.33  3.000
 TSA  C10  C1   C2   110.80  3.000
 TSA  C9   C1   C2   109.23  3.000
 TSA  C6   C1   C2   109.06  3.000
 TSA  H2   C2   C3   119.63  3.000
 TSA  H2   C2   C1   116.90  3.000
 TSA  C3   C2   C1   123.45  3.000
 TSA  H3   C3   C4   116.89  3.000
 TSA  H3   C3   C2   119.86  3.000
 TSA  C4   C3   C2   123.24  3.000
 TSA  H4   C4   C5   108.25  3.000
 TSA  H4   C4   O5   110.31  3.000
 TSA  C5   C4   O5   110.64  3.000
 TSA  H4   C4   C3   108.71  3.000
 TSA  C5   C4   C3   111.69  3.000
 TSA  O5   C4   C3   107.23  3.000
 TSA  HO5  O5   C4   107.86  3.000
 TSA  H5   C5   O7   104.08  3.000
 TSA  H5   C5   C6   109.98  3.000
 TSA  O7   C5   C6   111.73  3.000
 TSA  H5   C5   C4   107.37  3.000
 TSA  O7   C5   C4   113.56  3.000
 TSA  C6   C5   C4   109.86  3.000
 TSA  H62  C6   H61  106.99  3.000
 TSA  H62  C6   C5   110.32  3.000
 TSA  H61  C6   C5   109.42  3.000
 TSA  H62  C6   C1   110.69  3.000
 TSA  H61  C6   C1   111.28  3.000
 TSA  C5   C6   C1   108.15  3.000
 TSA  C8   O7   C5   119.14  3.000
 TSA  H8   C8   C11  103.38  3.000
 TSA  H8   C8   C9   106.13  3.000
 TSA  C11  C8   C9   114.87  3.000
 TSA  H8   C8   O7   103.88  3.000
 TSA  C11  C8   O7   114.26  3.000
 TSA  C9   C8   O7   112.80  3.000
 TSA  H92  C9   H91  107.05  3.000
 TSA  H92  C9   C8   108.56  3.000
 TSA  H91  C9   C8   109.34  3.000
 TSA  H92  C9   C1   111.22  3.000
 TSA  H91  C9   C1   107.69  3.000
 TSA  C8   C9   C1   112.81  3.000
 TSA  O2   C10  O1   126.64  3.000
 TSA  O2   C10  C1   116.15  3.000
 TSA  O1   C10  C1   117.18  3.000
 TSA  O4   C11  O3   126.69  3.000
 TSA  O4   C11  C8   118.13  3.000
 TSA  O3   C11  C8   114.93  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
 TSA  Var_01  C4  C3  C2  C1  1.46  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
 TSA  chir_01  C1  C6  C2  C10  positiv
 TSA  chir_02  C4  O5  C5  C3   negativ
 TSA  chir_03  C5  O7  C6  C4   positiv
 TSA  chir_04  C8  O7  C9  C11  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
 TSA  plan-1  C1   0.020
 TSA  plan-1  C10  0.020
 TSA  plan-1  O1   0.020
 TSA  plan-1  O2   0.020
 TSA  plan-2  C8   0.020
 TSA  plan-2  C11  0.020
 TSA  plan-2  O3   0.020
 TSA  plan-2  O4   0.020

