# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Jul 21 01:50:01 2021
#   Inital geometry file: a 92 line input string
#   Ligand name: (1S,3aS,5aR,8aS)-1,7,7-trimethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene-4-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H]1CC[C@@H]2C(=C[C@H]3CC(C)(C)C[C@@]123)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
 1PL  1PL  '(1S,3aS,5aR,8aS)-1,7,7-trimethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene-4-carboxylic acid'  ligand  39  17  .  2022-07-22  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_1PL
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
 1PL  C10   C  CH3   0  -0.668  24.5455  30.9345  -0.5094
 1PL  C9    C  CH1   0  -0.251  24.5978  31.5280   0.8974
 1PL  C11   C  CH2   0  -0.433  23.5495  32.6311   1.0518
 1PL  C12   C  CH2   0  -0.441  22.2588  31.8559   1.2919
 1PL  C5    C  CR15  0  -0.286  22.6883  30.7081   2.2269
 1PL  C4    C  C     0   0.002  24.2326  30.5288   2.0224
 1PL  C3    C  CH2   0  -0.424  24.7117  29.0891   1.7717
 1PL  C2    C  CR5   0  -0.068  25.1234  28.4783   3.1199
 1PL  C14   C  CH3   0  -0.649  26.1737  27.3845   2.9460
 1PL  C15   C  CH3   0  -0.650  23.9288  27.8788   3.8671
 1PL  C1    C  CH2   0  -0.413  25.7120  29.6989   3.8434
 1PL  C8    C  C     0  -0.278  24.8771  30.9105   3.3949
 1PL  C7    C  CR15  0  -0.181  23.7264  31.2156   4.2891
 1PL  C6    C  CR5   0  -0.047  22.5506  31.0883   3.6736
 1PL  C13   C  C     0   0.504  21.2332  31.2607   4.2964
 1PL  O1    O  OH1   0  -0.598  21.2889  31.6829   5.5569
 1PL  O2    O  O     0  -0.449  20.1890  31.0342   3.7266
 1PL  H101  H  HCH3  0   0.229  24.7256  31.7155  -1.2508
 1PL  H102  H  HCH3  0   0.229  25.3042  30.1672  -0.6619
 1PL  H103  H  HCH3  0   0.221  23.5773  30.4853  -0.7380
 1PL  H9    H  HCH1  0   0.226  25.6099  31.9136   1.0585
 1PL  H111  H  HCH2  0   0.228  23.7757  33.2626   1.9162
 1PL  H112  H  HCH2  0   0.229  23.5002  33.2904   0.1826
 1PL  H121  H  HCH2  0   0.235  21.4635  32.4684   1.7182
 1PL  H122  H  HCH2  0   0.230  21.8743  31.4551   0.3519
 1PL  H5    H  HCR5  0   0.244  22.1342  29.7926   2.0011
 1PL  H31   H  HCH2  0   0.230  23.9706  28.4836   1.2425
 1PL  H32   H  HCH2  0   0.227  25.6013  29.1132   1.1341
 1PL  H141  H  HCH3  0   0.220  27.0517  27.7555   2.4122
 1PL  H142  H  HCH3  0   0.222  26.5093  27.0046   3.9138
 1PL  H143  H  HCH3  0   0.221  25.7770  26.5374   2.3813
 1PL  H151  H  HCH3  0   0.220  24.2240  27.5444   4.8642
 1PL  H152  H  HCH3  0   0.239  23.1046  28.5788   3.9888
 1PL  H153  H  HCH3  0   0.220  23.5455  27.0101   3.3272
 1PL  H11   H  HCH2  0   0.233  25.7353  29.5782   4.9296
 1PL  H12   H  HCH2  0   0.232  26.7467  29.8424   3.5189
 1PL  H8    H  H     0   0.254  25.5240  31.7922   3.3227
 1PL  H7    H  HCR5  0   0.262  23.8665  31.4912   5.3274
 1PL  HO1   H  HOH1  0   0.481  20.3924  31.7635   5.9136

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
 1PL  C10  C9    single  1.528  0.020  1.528
 1PL  C9   C11   single  1.530  0.020  1.530
 1PL  C9   C4    single  1.548  0.020  1.548
 1PL  C11  C12   single  1.525  0.020  1.525
 1PL  C12  C5    single  1.541  0.020  1.541
 1PL  C3   C4    single  1.538  0.020  1.538
 1PL  C3   C2    single  1.536  0.020  1.536
 1PL  C4   C5    single  1.568  0.020  1.568
 1PL  C4   C8    single  1.564  0.020  1.564
 1PL  C5   C6    single  1.502  0.020  1.502
 1PL  C14  C2    single  1.526  0.020  1.526
 1PL  C2   C15   single  1.531  0.020  1.531
 1PL  C2   C1    single  1.536  0.020  1.536
 1PL  C8   C1    single  1.538  0.020  1.538
 1PL  C8   C7    single  1.489  0.020  1.489
 1PL  O2   C13   double  1.211  0.020  1.211
 1PL  C6   C7    double  1.333  0.020  1.333
 1PL  C6   C13   single  1.467  0.020  1.467
 1PL  C13  O1    single  1.330  0.020  1.330
 1PL  C10  H101  single  0.970  0.020  1.090
 1PL  C10  H102  single  0.970  0.020  1.090
 1PL  C10  H103  single  0.970  0.020  1.090
 1PL  C9   H9    single  0.970  0.020  1.090
 1PL  C11  H111  single  0.970  0.020  1.090
 1PL  C11  H112  single  0.970  0.020  1.090
 1PL  C12  H121  single  0.970  0.020  1.090
 1PL  C12  H122  single  0.970  0.020  1.090
 1PL  C5   H5    single  0.970  0.020  1.090
 1PL  C3   H31   single  0.970  0.020  1.090
 1PL  C3   H32   single  0.970  0.020  1.090
 1PL  C14  H141  single  0.970  0.020  1.090
 1PL  C14  H142  single  0.970  0.020  1.090
 1PL  C14  H143  single  0.970  0.020  1.090
 1PL  C15  H151  single  0.970  0.020  1.090
 1PL  C15  H152  single  0.970  0.020  1.090
 1PL  C15  H153  single  0.970  0.020  1.090
 1PL  C1   H11   single  0.970  0.020  1.090
 1PL  C1   H12   single  0.970  0.020  1.090
 1PL  C8   H8    single  0.970  0.020  1.090
 1PL  C7   H7    single  0.930  0.020  1.080
 1PL  O1   HO1   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
 1PL  H103  C10  H102  107.36  3.000
 1PL  H103  C10  H101  107.37  3.000
 1PL  H102  C10  H101  107.09  3.000
 1PL  H103  C10  C9    112.52  3.000
 1PL  H102  C10  C9    112.24  3.000
 1PL  H101  C10  C9    109.99  3.000
 1PL  H9    C9   C4    109.78  3.000
 1PL  H9    C9   C11   111.39  3.000
 1PL  C4    C9   C11   103.32  3.000
 1PL  H9    C9   C10   107.70  3.000
 1PL  C4    C9   C10   114.22  3.000
 1PL  C11   C9   C10   110.46  3.000
 1PL  H112  C11  H111  106.84  3.000
 1PL  H112  C11  C12   113.21  3.000
 1PL  H111  C11  C12   110.12  3.000
 1PL  H112  C11  C9    112.71  3.000
 1PL  H111  C11  C9    110.75  3.000
 1PL  C12   C11  C9    103.26  3.000
 1PL  H122  C12  H121  106.62  3.000
 1PL  H122  C12  C5    110.30  3.000
 1PL  H121  C12  C5    112.60  3.000
 1PL  H122  C12  C11   110.44  3.000
 1PL  H121  C12  C11   113.16  3.000
 1PL  C5    C12  C11   103.78  3.000
 1PL  H5    C5   C6    111.36  3.000
 1PL  H5    C5   C4    112.10  3.000
 1PL  C6    C5   C4    104.17  3.000
 1PL  H5    C5   C12   110.91  3.000
 1PL  C6    C5   C12   111.73  3.000
 1PL  C4    C5   C12   106.29  3.000
 1PL  C8    C4   C3    104.08  3.000
 1PL  C8    C4   C5    105.28  3.000
 1PL  C3    C4   C5    115.79  3.000
 1PL  C8    C4   C9    112.52  3.000
 1PL  C5    C4   C9    104.67  3.000
 1PL  C3    C4   C9    114.34  3.000
 1PL  H32   C3   H31   106.33  3.000
 1PL  H32   C3   C2    107.58  3.000
 1PL  H31   C3   C2    112.71  3.000
 1PL  H32   C3   C4    109.11  3.000
 1PL  H31   C3   C4    112.71  3.000
 1PL  C2    C3   C4    108.21  3.000
 1PL  C1    C2   C15   112.35  3.000
 1PL  C1    C2   C14   111.07  3.000
 1PL  C15   C2   C14   108.17  3.000
 1PL  C1    C2   C3    101.54  3.000
 1PL  C15   C2   C3    112.01  3.000
 1PL  C14   C2   C3    111.67  3.000
 1PL  H143  C14  H142  107.45  3.000
 1PL  H143  C14  H141  107.61  3.000
 1PL  H142  C14  H141  107.70  3.000
 1PL  H143  C14  C2    111.39  3.000
 1PL  H142  C14  C2    111.08  3.000
 1PL  H141  C14  C2    111.42  3.000
 1PL  H153  C15  H152  107.53  3.000
 1PL  H153  C15  H151  107.61  3.000
 1PL  H152  C15  H151  107.42  3.000
 1PL  H153  C15  C2    110.12  3.000
 1PL  H152  C15  C2    113.18  3.000
 1PL  H151  C15  C2    110.76  3.000
 1PL  H12   C1   H11   106.81  3.000
 1PL  H12   C1   C8    108.88  3.000
 1PL  H11   C1   C8    112.85  3.000
 1PL  H12   C1   C2    109.09  3.000
 1PL  H11   C1   C2    112.85  3.000
 1PL  C8    C1   C2    106.29  3.000
 1PL  H8    C8   C7    109.33  3.000
 1PL  H8    C8   C1    109.42  3.000
 1PL  C7    C8   C1    113.94  3.000
 1PL  H8    C8   C4    112.45  3.000
 1PL  C7    C8   C4    104.99  3.000
 1PL  C1    C8   C4    106.70  3.000
 1PL  H7    C7   C6    125.50  3.000
 1PL  H7    C7   C8    121.86  3.000
 1PL  C6    C7   C8    112.63  3.000
 1PL  C13   C6   C7    125.78  3.000
 1PL  C13   C6   C5    121.39  3.000
 1PL  C7    C6   C5    112.82  3.000
 1PL  O2    C13  O1    122.77  3.000
 1PL  O1    C13  C6    113.69  3.000
 1PL  O2    C13  C6    123.54  3.000
 1PL  HO1   O1   C13   109.68  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
 1PL  CONST_01  HO1   O1   C13  C6   180.00   0.0  0
 1PL  Var_01    C5    C12  C11  C9    40.26  30.0  1
 1PL  Var_02    C8    C7   C6   C5    -1.62  30.0  1
 1PL  Var_03    C1    C2   C3   C4   -34.84  30.0  1
 1PL  Var_04    C8    C1   C2   C3    34.97  30.0  1
 1PL  Var_05    O2    C13  C6   C5     4.65  30.0  2
 1PL  Var_06    H141  C14  C2   C3    56.04  30.0  3
 1PL  Var_07    H151  C15  C2   C3  -174.12  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
 1PL  chir_01  C9  C10  C11  C4   negativ
 1PL  chir_02  C5  C6   C4   C12  positiv
 1PL  chir_03  C4  C3   C5   C8   negativ
 1PL  chir_04  C8  C7   C1   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
 1PL  plan-1  C6   0.020
 1PL  plan-1  C13  0.020
 1PL  plan-1  O1   0.020
 1PL  plan-1  O2   0.020
 1PL  plan-1  HO1  0.020

