# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 12:55:27 2020
#   Inital geometry file: a 127 line input string
#   Ligand name: (2E,4E,7R,12R,13R)-13-formyl-12,14-dihydroxy-3,5,7-trimethyltetradeca-2,4-dienoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](CCCC[C@@H](O)[C@@H](CO)C=O)CC(/C)=C/C(C)=C/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
 F24  F24  '(2E,4E,7R,12R,13R)-13-formyl-12,14-dihydroxy-3,5,7-trimethyltetradeca-2,4-dienoic acid'  ligand  53  23  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_F24
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
 F24  C1    C  CH1   0  -0.407   6.6640  -0.1202   0.4441
 F24  O1    O  O     0  -0.458  -8.4681   1.1175   0.0110
 F24  C2    C  CH1   0   0.024   5.4170  -0.6677  -0.2872
 F24  O2    O  O     0  -0.376   6.6080   2.2384   0.9221
 F24  C3    C  C     0   0.521  -7.9515   0.0947   0.4063
 F24  C4    C  CH2   0  -0.140   7.9152  -0.8806   0.0342
 F24  O4    O  OH1   0  -0.611  -8.6036  -0.7763   1.1823
 F24  C5    C  CH2   0  -0.469   4.1224  -0.0780   0.2575
 F24  O5    O  OH1   0  -0.670   9.0026  -0.3192   0.7357
 F24  C6    C  C1    0  -0.456  -6.5875  -0.3598   0.1391
 F24  O6    O  OH1   0  -0.664   5.5249  -0.5365  -1.6894
 F24  C7    C  CH3   0  -0.748  -3.8047  -0.7227   1.5667
 F24  C8    C  C1    0   0.191   6.8707   1.3412   0.1597
 F24  C9    C  C     0   0.154  -5.7171   0.2464  -0.6942
 F24  C10   C  CH2   0  -0.410   2.8719  -0.7233  -0.3272
 F24  C11   C  CH2   0  -0.424   1.5865  -0.1375   0.2439
 F24  C12   C  C1    0  -0.340  -4.3539  -0.2623  -0.8504
 F24  C13   C  CH3   0  -0.657  -1.2223   1.2104  -0.2244
 F24  C16   C  CH2   0  -0.482  -2.1296  -1.1451  -0.2959
 F24  C18   C  CH1   0  -0.235  -0.9843  -0.2382   0.1870
 F24  C20   C  CH2   0  -0.403   0.3407  -0.7805  -0.3529
 F24  C21   C  CH3   0  -0.720  -6.0389   1.4426  -1.5446
 F24  H1    H  HCH1  0   0.266   6.4927  -0.2459   1.5177
 F24  H2    H  HCH1  0   0.239   5.4029  -1.7466  -0.0933
 F24  H4    H  HCH2  0   0.216   7.7807  -1.9444   0.2671
 F24  H4A   H  HCH2  0   0.207   8.0530  -0.8020  -1.0508
 F24  HO4   H  HOH1  0   0.476  -9.4994  -0.4516   1.3539
 F24  H5    H  HCH2  0   0.236   4.1217  -0.2007   1.3447
 F24  H5A   H  HCH2  0   0.227   4.0932   1.0040   0.0793
 F24  HO5   H  HOH1  0   0.459   9.8148  -0.7144   0.4055
 F24  H6    H  H     0   0.270  -6.2818  -1.2644   0.6489
 F24  HO6   H  HOH1  0   0.449   5.2107   0.3346  -1.9530
 F24  H7    H  HCH3  0   0.251  -4.0438  -1.7395   1.8890
 F24  H7A   H  HCH3  0   0.249  -2.9317  -0.4133   2.1434
 F24  H7B   H  HCH3  0   0.252  -4.6404  -0.0842   1.8464
 F24  H8    H  H     0   0.187   7.2835   1.5632  -0.8426
 F24  H10   H  HCH2  0   0.216   2.8632  -0.6053  -1.4146
 F24  H10A  H  HCH2  0   0.215   2.8987  -1.8021  -0.1387
 F24  H11   H  HCH2  0   0.211   1.5754  -0.2650   1.3320
 F24  H11A  H  HCH2  0   0.217   1.5793   0.9424   0.0660
 F24  H12   H  H     0   0.245  -3.9731  -0.2158  -1.8677
 F24  H13   H  HCH3  0   0.231  -2.1269   1.6145   0.2315
 F24  H13A  H  HCH3  0   0.231  -0.3940   1.8551   0.0701
 F24  H13B  H  HCH3  0   0.213  -1.3392   1.2908  -1.3085
 F24  H16   H  HCH2  0   0.241  -1.9622  -2.1530   0.1016
 F24  H16A  H  HCH2  0   0.233  -2.0712  -1.2244  -1.3855
 F24  H18   H  HCH1  0   0.215  -0.9370  -0.2863   1.2817
 F24  H20   H  HCH2  0   0.208   0.3577  -0.6627  -1.4431
 F24  H20A  H  HCH2  0   0.218   0.3834  -1.8597  -0.1672
 F24  H21   H  HCH3  0   0.257  -6.0369   2.3510  -0.9395
 F24  H21A  H  HCH3  0   0.243  -5.2840   1.5681  -2.3193
 F24  H21B  H  HCH3  0   0.252  -7.0149   1.3751  -2.0184
 F24  C14   C  C     0   0.149  -3.5068  -0.6904   0.0998

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
 F24  C1   C2    single  1.546  0.020  1.546
 F24  O1   C3    double  1.212  0.020  1.212
 F24  C2   O6    single  1.413  0.020  1.413
 F24  C2   C5    single  1.523  0.020  1.523
 F24  O2   C8    double  1.206  0.020  1.206
 F24  C3   O4    single  1.336  0.020  1.336
 F24  C4   C1    single  1.520  0.020  1.520
 F24  O5   C4    single  1.411  0.020  1.411
 F24  C6   C3    single  1.462  0.020  1.462
 F24  C6   C9    double  1.349  0.020  1.349
 F24  C7   C14   single  1.497  0.020  1.497
 F24  C8   C1    single  1.503  0.020  1.503
 F24  C9   C21   single  1.503  0.020  1.503
 F24  C10  C5    single  1.524  0.020  1.524
 F24  C10  C11   single  1.524  0.020  1.524
 F24  C11  C20   single  1.524  0.020  1.524
 F24  C12  C9    single  1.463  0.020  1.463
 F24  C14  C12   double  1.343  0.020  1.343
 F24  C16  C14   single  1.503  0.020  1.503
 F24  C18  C13   single  1.525  0.020  1.525
 F24  C18  C16   single  1.539  0.020  1.539
 F24  C20  C18   single  1.530  0.020  1.530
 F24  C1   H1    single  0.970  0.020  1.090
 F24  C2   H2    single  0.970  0.020  1.090
 F24  C4   H4    single  0.970  0.020  1.090
 F24  C4   H4A   single  0.970  0.020  1.090
 F24  O4   HO4   single  0.850  0.020  0.980
 F24  C5   H5    single  0.970  0.020  1.090
 F24  C5   H5A   single  0.970  0.020  1.090
 F24  O5   HO5   single  0.850  0.020  0.980
 F24  C6   H6    single  0.930  0.020  1.080
 F24  O6   HO6   single  0.850  0.020  0.980
 F24  C7   H7    single  0.970  0.020  1.090
 F24  C7   H7A   single  0.970  0.020  1.090
 F24  C7   H7B   single  0.970  0.020  1.090
 F24  C8   H8    single  0.930  0.020  1.080
 F24  C10  H10   single  0.970  0.020  1.090
 F24  C10  H10A  single  0.970  0.020  1.090
 F24  C11  H11   single  0.970  0.020  1.090
 F24  C11  H11A  single  0.970  0.020  1.090
 F24  C12  H12   single  0.930  0.020  1.080
 F24  C13  H13   single  0.970  0.020  1.090
 F24  C13  H13A  single  0.970  0.020  1.090
 F24  C13  H13B  single  0.970  0.020  1.090
 F24  C16  H16   single  0.970  0.020  1.090
 F24  C16  H16A  single  0.970  0.020  1.090
 F24  C18  H18   single  0.970  0.020  1.090
 F24  C20  H20   single  0.970  0.020  1.090
 F24  C20  H20A  single  0.970  0.020  1.090
 F24  C21  H21   single  0.970  0.020  1.090
 F24  C21  H21A  single  0.970  0.020  1.090
 F24  C21  H21B  single  0.970  0.020  1.090

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
 F24  H1    C1   C8    108.59  3.000
 F24  H1    C1   C4    109.62  3.000
 F24  C8    C1   C4    108.79  3.000
 F24  H1    C1   C2    107.28  3.000
 F24  C8    C1   C2    111.46  3.000
 F24  C4    C1   C2    111.05  3.000
 F24  H2    C2   O6    105.55  3.000
 F24  H2    C2   C5    107.87  3.000
 F24  O6    C2   C5    112.58  3.000
 F24  H2    C2   C1    105.98  3.000
 F24  C5    C2   C1    112.29  3.000
 F24  O6    C2   C1    112.03  3.000
 F24  C6    C3   O4    111.02  3.000
 F24  C6    C3   O1    126.89  3.000
 F24  O4    C3   O1    122.10  3.000
 F24  H4A   C4   H4    107.15  3.000
 F24  H4A   C4   O5    111.51  3.000
 F24  H4    C4   O5    112.01  3.000
 F24  H4A   C4   C1    109.53  3.000
 F24  H4    C4   C1    109.08  3.000
 F24  O5    C4   C1    107.53  3.000
 F24  HO4   O4   C3    109.62  3.000
 F24  H5A   C5   H5    105.78  3.000
 F24  H5A   C5   C10   109.48  3.000
 F24  H5    C5   C10   109.47  3.000
 F24  H5A   C5   C2    110.27  3.000
 F24  H5    C5   C2    108.21  3.000
 F24  C10   C5   C2    113.35  3.000
 F24  HO5   O5   C4    108.47  3.000
 F24  H6    C6   C9    118.97  3.000
 F24  H6    C6   C3    115.92  3.000
 F24  C9    C6   C3    125.10  3.000
 F24  HO6   O6   C2    109.32  3.000
 F24  H7B   C7   H7A   108.20  3.000
 F24  H7B   C7   H7    107.58  3.000
 F24  H7A   C7   H7    106.43  3.000
 F24  H7B   C7   C14   113.08  3.000
 F24  H7A   C7   C14   110.64  3.000
 F24  H7    C7   C14   110.63  3.000
 F24  H8    C8   O2    120.31  3.000
 F24  H8    C8   C1    114.69  3.000
 F24  O2    C8   C1    125.00  3.000
 F24  C21   C9   C12   114.57  3.000
 F24  C12   C9   C6    120.72  3.000
 F24  C21   C9   C6    124.70  3.000
 F24  H10A  C10  H10   106.11  3.000
 F24  H10A  C10  C11   109.56  3.000
 F24  H10   C10  C11   108.93  3.000
 F24  H10A  C10  C5    109.32  3.000
 F24  H10   C10  C5    110.02  3.000
 F24  C11   C10  C5    112.68  3.000
 F24  H11A  C11  H11   106.03  3.000
 F24  H11A  C11  C20   110.33  3.000
 F24  H11   C11  C20   109.37  3.000
 F24  H11A  C11  C10   108.90  3.000
 F24  H11   C11  C10   109.63  3.000
 F24  C20   C11  C10   112.37  3.000
 F24  H12   C12  C14   117.04  3.000
 F24  H12   C12  C9    114.28  3.000
 F24  C14   C12  C9    128.53  3.000
 F24  H13B  C13  H13A  107.79  3.000
 F24  H13B  C13  H13   107.37  3.000
 F24  H13A  C13  H13   107.34  3.000
 F24  H13B  C13  C18   110.74  3.000
 F24  H13A  C13  C18   111.74  3.000
 F24  H13   C13  C18   111.64  3.000
 F24  H16A  C16  H16   106.64  3.000
 F24  H16A  C16  C18   108.39  3.000
 F24  H16   C16  C18   108.33  3.000
 F24  H16A  C16  C14   109.44  3.000
 F24  H16   C16  C14   108.82  3.000
 F24  C18   C16  C14   114.90  3.000
 F24  H18   C18  C20   107.41  3.000
 F24  H18   C18  C16   108.64  3.000
 F24  C20   C18  C16   108.96  3.000
 F24  H18   C18  C13   108.52  3.000
 F24  C20   C18  C13   112.13  3.000
 F24  C16   C18  C13   111.05  3.000
 F24  H20A  C20  H20   105.88  3.000
 F24  H20A  C20  C18   108.84  3.000
 F24  H20   C20  C18   109.04  3.000
 F24  H20A  C20  C11   108.50  3.000
 F24  H20   C20  C11   109.35  3.000
 F24  C18   C20  C11   114.85  3.000
 F24  H21B  C21  H21A  108.63  3.000
 F24  H21B  C21  H21   107.15  3.000
 F24  H21A  C21  H21   107.29  3.000
 F24  H21B  C21  C9    112.92  3.000
 F24  H21A  C21  C9    110.24  3.000
 F24  H21   C21  C9    110.39  3.000
 F24  C16   C14  C12   119.22  3.000
 F24  C16   C14  C7    115.70  3.000
 F24  C12   C14  C7    125.07  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
 F24  CONST_01  HO4  O4   C3   O1     0.00   0.0  0
 F24  Var_01    C21  C9   C6   C3    -3.80   0.0  2
 F24  Var_02    C9   C12  C14  C7    -0.42   0.0  2
 F24  Var_03    C9   C6   C3   O1    -5.95  30.0  1
 F24  Var_04    C11  C10  C5   C2   179.10  30.0  1
 F24  Var_05    C20  C11  C10  C5   179.58  30.0  3
 F24  Var_06    C14  C12  C9   C6   -43.05  30.0  2
 F24  Var_07    C18  C16  C14  C7   -66.25  30.0  2
 F24  Var_08    C18  C20  C11  C10  179.71  30.0  3
 F24  Var_09    H21  C21  C9   C6    77.59  30.0  3
 F24  Var_10    H7   C7   C14  C12  102.41  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
 F24  chir_01  C1   C2   C4   C8   negativ
 F24  chir_02  C2   O6   C1   C5   negativ
 F24  chir_03  C18  C13  C16  C20  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
 F24  plan-1  O1   0.020
 F24  plan-1  C3   0.020
 F24  plan-1  O4   0.020
 F24  plan-1  C6   0.020
 F24  plan-1  HO4  0.020
 F24  plan-2  C1   0.020
 F24  plan-2  O2   0.020
 F24  plan-2  C8   0.020
 F24  plan-2  H8   0.020
 F24  plan-3  C3   0.020
 F24  plan-3  C6   0.020
 F24  plan-3  C9   0.020
 F24  plan-3  C12  0.020
 F24  plan-3  C21  0.020
 F24  plan-3  H6   0.020
 F24  plan-4  C7   0.020
 F24  plan-4  C9   0.020
 F24  plan-4  C12  0.020
 F24  plan-4  C16  0.020
 F24  plan-4  H12  0.020
 F24  plan-4  C14  0.020

