# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar  9 20:27:29 2022
#   Inital geometry file: a 84 line input string
#   Ligand name: (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc(cc1)[C@@H]2CC(=O)c3ccc(O)cc3O2
#
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
 DFV  DFV  (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one  ligand  31  19  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_DFV
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
 DFV  C1   C  CR6   0   0.392   1.3324   0.2801  -3.9170
 DFV  C2   C  CR16  0  -0.347   0.0676   0.0459  -4.4788
 DFV  C3   C  CR16  0  -0.260  -1.0050  -0.1542  -3.6464
 DFV  C4   C  CR6   0  -0.170  -0.8722  -0.1292  -2.2515
 DFV  C5   C  CR6   0   0.425   0.3961   0.1245  -1.7100
 DFV  C6   C  CR16  0  -0.498   1.4943   0.3254  -2.5388
 DFV  C7   C  C     0   0.393  -2.0002  -0.4433  -1.3757
 DFV  C8   C  CH2   0  -0.604  -1.6505  -0.5369   0.0875
 DFV  C9   C  CH1   0  -0.051  -0.5187   0.4115   0.4496
 DFV  O1   O  O2    0  -0.476   0.6188   0.1811  -0.3888
 DFV  C10  C  CR6   0   0.091  -0.0753   0.2592   1.8737
 DFV  C11  C  CR16  0  -0.281   0.5404  -0.9131   2.3106
 DFV  C12  C  CR16  0  -0.323   0.9148  -1.0725   3.6317
 DFV  C13  C  CR6   0   0.348   0.6704  -0.0537   4.5536
 DFV  C14  C  CR16  0  -0.369   0.0563   1.1206   4.1301
 DFV  C15  C  CR16  0  -0.306  -0.3049   1.2688   2.7979
 DFV  O2   O  O     0  -0.409  -3.1222  -0.6626  -1.7900
 DFV  O3   O  OH1   0  -0.615   2.3520   0.4668  -4.7611
 DFV  O4   O  OH1   0  -0.629   1.0475  -0.2630   5.8288
 DFV  H2   H  HCR6  0   0.271  -0.0476   0.0182  -5.5541
 DFV  H3   H  HCR6  0   0.270  -1.9799  -0.3513  -4.0734
 DFV  H6   H  HCR6  0   0.287   2.4648   0.5263  -2.0993
 DFV  H81  H  HCH2  0   0.290  -1.3587  -1.5727   0.2977
 DFV  H82  H  HCH2  0   0.289  -2.5259  -0.3183   0.7001
 DFV  H9   H  HCH1  0   0.267  -0.8560   1.4425   0.2834
 DFV  H11  H  HCR6  0   0.258   0.7320  -1.7205   1.6140
 DFV  H12  H  HCR6  0   0.266   1.3937  -1.9871   3.9580
 DFV  H14  H  HCR6  0   0.273  -0.1375   1.9228   4.8331
 DFV  H15  H  HCR6  0   0.260  -0.7768   2.1912   2.4807
 DFV  HO3  H  HOH1  0   0.483   3.1747   0.6168  -4.2804
 DFV  HO4  H  HOH1  0   0.475   0.8113   0.4917   6.3794

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
 DFV  C1   C2   aromatic  1.404  0.020  1.404
 DFV  C1   C6   aromatic  1.388  0.020  1.388
 DFV  C1   O3   single    1.337  0.020  1.337
 DFV  C2   C3   aromatic  1.372  0.020  1.372
 DFV  C2   H2   single    0.930  0.020  1.080
 DFV  C3   C4   aromatic  1.402  0.020  1.402
 DFV  C3   H3   single    0.930  0.020  1.080
 DFV  C4   C5   aromatic  1.402  0.020  1.402
 DFV  C4   C7   single    1.462  0.020  1.462
 DFV  C5   C6   aromatic  1.390  0.020  1.390
 DFV  C5   O1   single    1.341  0.020  1.341
 DFV  C6   H6   single    0.930  0.020  1.080
 DFV  C7   C8   single    1.507  0.020  1.507
 DFV  C7   O2   double    1.216  0.020  1.216
 DFV  C8   C9   single    1.520  0.020  1.520
 DFV  C8   H81  single    0.970  0.020  1.090
 DFV  C8   H82  single    0.970  0.020  1.090
 DFV  C9   O1   single    1.432  0.020  1.432
 DFV  C9   C10  single    1.499  0.020  1.499
 DFV  C9   H9   single    0.970  0.020  1.090
 DFV  C10  C11  aromatic  1.394  0.020  1.394
 DFV  C10  C15  aromatic  1.388  0.020  1.388
 DFV  C11  C12  aromatic  1.382  0.020  1.382
 DFV  C11  H11  single    0.930  0.020  1.080
 DFV  C12  C13  aromatic  1.395  0.020  1.395
 DFV  C12  H12  single    0.930  0.020  1.080
 DFV  C13  C14  aromatic  1.391  0.020  1.391
 DFV  C13  O4   single    1.346  0.020  1.346
 DFV  C14  C15  aromatic  1.388  0.020  1.388
 DFV  C14  H14  single    0.930  0.020  1.080
 DFV  C15  H15  single    0.930  0.020  1.080
 DFV  O3   HO3  single    0.850  0.020  0.980
 DFV  O4   HO4  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
 DFV  O3   C1   C6   122.23  3.000
 DFV  O3   C1   C2   117.25  3.000
 DFV  C6   C1   C2   120.52  3.000
 DFV  H2   C2   C3   121.05  3.000
 DFV  H2   C2   C1   119.87  3.000
 DFV  C3   C2   C1   119.07  3.000
 DFV  H3   C3   C4   118.77  3.000
 DFV  H3   C3   C2   119.42  3.000
 DFV  C4   C3   C2   121.80  3.000
 DFV  C7   C4   C5   120.36  3.000
 DFV  C7   C4   C3   121.28  3.000
 DFV  C5   C4   C3   118.25  3.000
 DFV  O1   C5   C6   116.74  3.000
 DFV  O1   C5   C4   122.57  3.000
 DFV  C6   C5   C4   120.69  3.000
 DFV  H6   C6   C5   119.48  3.000
 DFV  H6   C6   C1   120.85  3.000
 DFV  C5   C6   C1   119.66  3.000
 DFV  O2   C7   C8   122.25  3.000
 DFV  O2   C7   C4   123.13  3.000
 DFV  C8   C7   C4   114.57  3.000
 DFV  H82  C8   H81  107.17  3.000
 DFV  H82  C8   C9   109.80  3.000
 DFV  H81  C8   C9   110.22  3.000
 DFV  H82  C8   C7   110.28  3.000
 DFV  H81  C8   C7   107.84  3.000
 DFV  C9   C8   C7   111.42  3.000
 DFV  H9   C9   C10  109.28  3.000
 DFV  H9   C9   O1   107.86  3.000
 DFV  C10  C9   O1   107.75  3.000
 DFV  H9   C9   C8   108.73  3.000
 DFV  C10  C9   C8   112.52  3.000
 DFV  O1   C9   C8   110.59  3.000
 DFV  C9   O1   C5   116.85  3.000
 DFV  C15  C10  C11  118.42  3.000
 DFV  C15  C10  C9   120.65  3.000
 DFV  C11  C10  C9   120.90  3.000
 DFV  H11  C11  C12  118.73  3.000
 DFV  H11  C11  C10  120.21  3.000
 DFV  C12  C11  C10  121.06  3.000
 DFV  H12  C12  C13  119.67  3.000
 DFV  H12  C12  C11  120.35  3.000
 DFV  C13  C12  C11  119.98  3.000
 DFV  O4   C13  C14  122.90  3.000
 DFV  O4   C13  C12  117.60  3.000
 DFV  C14  C13  C12  119.50  3.000
 DFV  H14  C14  C15  119.79  3.000
 DFV  H14  C14  C13  120.41  3.000
 DFV  C15  C14  C13  119.81  3.000
 DFV  H15  C15  C14  119.02  3.000
 DFV  H15  C15  C10  119.75  3.000
 DFV  C14  C15  C10  121.22  3.000
 DFV  HO3  O3   C1   110.95  3.000
 DFV  HO4  O4   C13  110.54  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
 DFV  CONST_01  C4   C3   C2   C1     0.00   0.0  0
 DFV  CONST_02  C4   C5   C6   C1     0.00   0.0  0
 DFV  CONST_03  C5   C6   C1   C2     0.00   0.0  0
 DFV  CONST_04  C5   C4   C3   C2     0.00   0.0  0
 DFV  CONST_05  C6   C1   C2   C3     0.00   0.0  0
 DFV  CONST_06  C6   C5   C4   C3     0.00   0.0  0
 DFV  CONST_07  C13  C12  C11  C10    0.00   0.0  0
 DFV  CONST_08  C13  C14  C15  C10    0.00   0.0  0
 DFV  CONST_09  C14  C15  C10  C11    0.00   0.0  0
 DFV  CONST_10  C14  C13  C12  C11    0.00   0.0  0
 DFV  CONST_11  C15  C10  C11  C12    0.00   0.0  0
 DFV  CONST_12  C15  C14  C13  C12    0.00   0.0  0
 DFV  CONST_13  C12  C11  C10  C9   180.00   0.0  0
 DFV  CONST_14  C14  C15  C10  C9   180.00   0.0  0
 DFV  CONST_15  O3   C1   C2   C3   180.00   0.0  0
 DFV  CONST_16  O3   C1   C6   C5   180.00   0.0  0
 DFV  CONST_17  O4   C13  C12  C11  180.00   0.0  0
 DFV  CONST_18  O4   C13  C14  C15  180.00   0.0  0
 DFV  CONST_19  H3   C3   C2   C1   180.00   0.0  0
 DFV  CONST_20  H6   C6   C1   C2   180.00   0.0  0
 DFV  CONST_21  H2   C2   C3   C4   180.00   0.0  0
 DFV  CONST_22  H11  C11  C10  C9     0.00   0.0  0
 DFV  CONST_23  H15  C15  C10  C9     0.00   0.0  0
 DFV  CONST_24  H12  C12  C11  C10  180.00   0.0  0
 DFV  CONST_25  H14  C14  C15  C10  180.00   0.0  0
 DFV  Var_01    C8   C7   C4   C3   172.84  30.0  1
 DFV  Var_02    C9   C8   C7   C4    32.07  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
 DFV  chir_01  C9  C8  O1  C10  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
 DFV  plan-1  C9   0.020
 DFV  plan-1  C10  0.020
 DFV  plan-1  C11  0.020
 DFV  plan-1  C12  0.020
 DFV  plan-1  C13  0.020
 DFV  plan-1  C14  0.020
 DFV  plan-1  C15  0.020
 DFV  plan-1  O4   0.020
 DFV  plan-1  H11  0.020
 DFV  plan-1  H12  0.020
 DFV  plan-1  H14  0.020
 DFV  plan-1  H15  0.020
 DFV  plan-2  C1   0.020
 DFV  plan-2  C2   0.020
 DFV  plan-2  C3   0.020
 DFV  plan-2  C4   0.020
 DFV  plan-2  C5   0.020
 DFV  plan-2  C6   0.020
 DFV  plan-2  C7   0.020
 DFV  plan-2  O1   0.020
 DFV  plan-2  O3   0.020
 DFV  plan-2  H2   0.020
 DFV  plan-2  H3   0.020
 DFV  plan-2  H6   0.020
 DFV  plan-3  C4   0.020
 DFV  plan-3  C7   0.020
 DFV  plan-3  C8   0.020
 DFV  plan-3  O2   0.020

