# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 20:03:35 2020
#   Inital geometry file: a 71 line input string
#   Ligand name: 5-[(1E)-3,3-dihydroxyprop-1-en-1-yl]-3-methoxybenzene-1,2-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(\C=C\C(O)O)cc(O)c1O
#
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
 HFL  HFL  5-[(1E)-3,3-dihydroxyprop-1-en-1-yl]-3-methoxybenzene-1,2-diol  ligand  27  15  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_HFL
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
 HFL  C1    C  CR6   0   0.167  -0.6428  -0.1296   2.4627
 HFL  C2    C  CR6   0   0.355   0.7113  -0.1066   2.1159
 HFL  C3    C  CR16  0  -0.399   1.0953   0.0049   0.7867
 HFL  C4    C  CR6   0   0.047   0.1310   0.0758  -0.2203
 HFL  C5    C  CR16  0  -0.337  -1.2177   0.0530   0.1270
 HFL  C6    C  CR6   0   0.305  -1.6037  -0.0469   1.4560
 HFL  O7    O  OH1   0  -0.656  -1.0619  -0.2312   3.7413
 HFL  O8    O  OH1   0  -0.703  -2.8958  -0.0560   1.8489
 HFL  O9    O  O2    0  -0.511   1.5549  -0.1995   3.1658
 HFL  C10   C  C1    0  -0.304   0.5772   0.1775  -1.6103
 HFL  C11   C  C1    0  -0.275  -0.1422  -0.0976  -2.6970
 HFL  C12   C  CH1   0   0.202   0.3946   0.0661  -4.0871
 HFL  O13   O  OH1   0  -0.724   0.5281  -1.2133  -4.6346
 HFL  O14   O  OH1   0  -0.673  -0.4306   0.8900  -4.8634
 HFL  C15   C  CH3   0  -0.455   2.9457  -0.2544   2.9175
 HFL  H3    H  HCR6  0   0.301   2.1429   0.0263   0.5147
 HFL  H5    H  HCR6  0   0.272  -1.9821   0.1330  -0.6372
 HFL  H7    H  HOH1  0   0.475  -0.3006  -0.2984   4.3301
 HFL  H8    H  HOH1  0   0.470  -3.4686  -0.1797   1.0846
 HFL  H10   H  H     0   0.255   1.6096   0.4919  -1.7431
 HFL  H11   H  H     0   0.283  -1.1664  -0.4562  -2.6138
 HFL  H12   H  HCH1  0   0.284   1.3589   0.5881  -4.0547
 HFL  H13   H  HOH1  0   0.439   0.9882  -1.1430  -5.4792
 HFL  H14   H  HOH1  0   0.459  -1.3141   0.5023  -4.8966
 HFL  H151  H  HCH3  0   0.252   3.4289  -0.3493   3.8865
 HFL  H152  H  HCH3  0   0.218   3.2137  -1.1182   2.3036
 HFL  H153  H  HCH3  0   0.253   3.3065   0.6544   2.4298

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
 HFL  C1   C2    aromatic  1.398  0.020  1.398
 HFL  C1   C6    aromatic  1.394  0.020  1.394
 HFL  C1   O7    single    1.349  0.020  1.349
 HFL  C2   C3    aromatic  1.388  0.020  1.388
 HFL  C2   O9    single    1.350  0.020  1.350
 HFL  C3   C4    aromatic  1.396  0.020  1.396
 HFL  C3   H3    single    0.930  0.020  1.080
 HFL  C4   C5    aromatic  1.393  0.020  1.393
 HFL  C4   C10   single    1.463  0.020  1.463
 HFL  C5   C6    aromatic  1.388  0.020  1.388
 HFL  C5   H5    single    0.930  0.020  1.080
 HFL  C6   O8    single    1.351  0.020  1.351
 HFL  O7   H7    single    0.850  0.020  0.980
 HFL  O8   H8    single    0.850  0.020  0.980
 HFL  O9   C15   single    1.414  0.020  1.414
 HFL  C10  C11   double    1.332  0.020  1.332
 HFL  C10  H10   single    0.930  0.020  1.080
 HFL  C11  C12   single    1.499  0.020  1.499
 HFL  C11  H11   single    0.930  0.020  1.080
 HFL  C12  O13   single    1.398  0.020  1.398
 HFL  C12  O14   single    1.401  0.020  1.401
 HFL  C12  H12   single    0.970  0.020  1.090
 HFL  O13  H13   single    0.850  0.020  0.980
 HFL  O14  H14   single    0.850  0.020  0.980
 HFL  C15  H151  single    0.970  0.020  1.090
 HFL  C15  H152  single    0.970  0.020  1.090
 HFL  C15  H153  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
 HFL  O7    C1   C6    118.33  3.000
 HFL  O7    C1   C2    122.49  3.000
 HFL  C6    C1   C2    119.18  3.000
 HFL  O9    C2   C3    125.27  3.000
 HFL  O9    C2   C1    114.28  3.000
 HFL  C3    C2   C1    120.45  3.000
 HFL  H3    C3   C4    119.09  3.000
 HFL  H3    C3   C2    120.65  3.000
 HFL  C4    C3   C2    120.25  3.000
 HFL  C10   C4   C5    122.22  3.000
 HFL  C10   C4   C3    118.56  3.000
 HFL  C5    C4   C3    119.22  3.000
 HFL  H5    C5   C6    118.98  3.000
 HFL  H5    C5   C4    120.39  3.000
 HFL  C6    C5   C4    120.62  3.000
 HFL  O8    C6   C5    123.05  3.000
 HFL  O8    C6   C1    116.67  3.000
 HFL  C5    C6   C1    120.28  3.000
 HFL  H7    O7   C1    109.78  3.000
 HFL  H8    O8   C6    109.81  3.000
 HFL  C15   O9   C2    118.74  3.000
 HFL  H10   C10  C11   118.22  3.000
 HFL  H10   C10  C4    115.19  3.000
 HFL  C11   C10  C4    126.57  3.000
 HFL  H11   C11  C12   116.35  3.000
 HFL  H11   C11  C10   120.93  3.000
 HFL  C12   C11  C10   122.72  3.000
 HFL  H12   C12  O14   104.74  3.000
 HFL  H12   C12  O13   111.29  3.000
 HFL  O14   C12  O13   112.18  3.000
 HFL  H12   C12  C11   109.83  3.000
 HFL  O14   C12  C11   111.54  3.000
 HFL  O13   C12  C11   107.30  3.000
 HFL  H13   O13  C12   108.77  3.000
 HFL  H14   O14  C12   108.78  3.000
 HFL  H153  C15  H152  109.00  3.000
 HFL  H153  C15  H151  108.88  3.000
 HFL  H152  C15  H151  108.83  3.000
 HFL  H153  C15  O9    111.77  3.000
 HFL  H152  C15  O9    111.75  3.000
 HFL  H151  C15  O9    106.50  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
 HFL  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 HFL  CONST_02  C4    C5   C6   C1      0.00   0.0  0
 HFL  CONST_03  C5    C6   C1   C2      0.00   0.0  0
 HFL  CONST_04  C5    C4   C3   C2      0.00   0.0  0
 HFL  CONST_05  C6    C1   C2   C3      0.00   0.0  0
 HFL  CONST_06  C6    C5   C4   C3      0.00   0.0  0
 HFL  CONST_07  O8    C6   C1   C2    180.00   0.0  0
 HFL  CONST_08  C10   C4   C3   C2    180.00   0.0  0
 HFL  CONST_09  O7    C1   C2   C3    180.00   0.0  0
 HFL  CONST_10  O9    C2   C3   C4    180.00   0.0  0
 HFL  CONST_11  O8    C6   C5   C4    180.00   0.0  0
 HFL  CONST_12  O7    C1   C6   C5    180.00   0.0  0
 HFL  CONST_13  O9    C2   C1   C6    180.00   0.0  0
 HFL  CONST_14  C10   C4   C5   C6    180.00   0.0  0
 HFL  CONST_15  H3    C3   C2   C1    180.00   0.0  0
 HFL  CONST_16  H5    C5   C6   C1    180.00   0.0  0
 HFL  Var_01    C11   C10  C4   C3    160.82  30.0  2
 HFL  Var_02    C12   C11  C10  C4    178.62   0.0  2
 HFL  Var_03    H151  C15  O9   C2   -178.72  30.0  3
 HFL  Var_04    O13   C12  C11  C10   111.64  30.0  3

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
 HFL  plan-1  C1   0.020
 HFL  plan-1  C2   0.020
 HFL  plan-1  C3   0.020
 HFL  plan-1  C4   0.020
 HFL  plan-1  C5   0.020
 HFL  plan-1  C6   0.020
 HFL  plan-1  O7   0.020
 HFL  plan-1  O8   0.020
 HFL  plan-1  O9   0.020
 HFL  plan-1  C10  0.020
 HFL  plan-1  H3   0.020
 HFL  plan-1  H5   0.020
 HFL  plan-2  C4   0.020
 HFL  plan-2  C10  0.020
 HFL  plan-2  C11  0.020
 HFL  plan-2  C12  0.020
 HFL  plan-2  H10  0.020
 HFL  plan-2  H11  0.020

