# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr 23 03:08:30 2020
#   Inital geometry file: a 82 line input string
#   Ligand name: (2S)-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)c3ccccc3O2
#
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
 DFL  DFL  (2S)-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one  ligand  30  18  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_DFL
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
 DFL  C1   C  CR16  0  -0.233   1.9311   0.4586  -3.9658
 DFL  C2   C  CR16  0  -0.265   0.7715   0.1368  -4.6732
 DFL  C3   C  CR16  0  -0.271  -0.3810  -0.1608  -3.9781
 DFL  C4   C  CR6   0  -0.142  -0.4017  -0.1396  -2.5792
 DFL  C5   C  CR6   0   0.402   0.7647   0.2037  -1.8840
 DFL  C6   C  CR16  0  -0.354   1.9345   0.4965  -2.5849
 DFL  C7   C  C     0   0.396  -1.6081  -0.5391  -1.8368
 DFL  C8   C  CH2   0  -0.603  -1.4319  -0.6144  -0.3428
 DFL  C9   C  CH1   0  -0.053  -0.4267   0.4175   0.1437
 DFL  O1   O  O2    0  -0.474   0.8191   0.2631  -0.5433
 DFL  C10  C  CR6   0   0.094  -0.1565   0.3148   1.6144
 DFL  C11  C  CR16  0  -0.280   0.4616  -0.8097   2.1550
 DFL  C12  C  CR16  0  -0.370   0.6825  -0.9158   3.5178
 DFL  C13  C  CR6   0   0.349   0.2773   0.1084   4.3733
 DFL  C14  C  CR16  0  -0.323  -0.3419   1.2373   3.8440
 DFL  C15  C  CR16  0  -0.307  -0.5477   1.3323   2.4768
 DFL  O2   O  O     0  -0.396  -2.6504  -0.8286  -2.3866
 DFL  O4   O  OH1   0  -0.629   0.4618   0.0567   5.7057
 DFL  H1   H  HCR6  0   0.271   2.8414   0.6937  -4.5020
 DFL  H2   H  HCR6  0   0.263   0.7800   0.1169  -5.7541
 DFL  H3   H  HCR6  0   0.268  -1.2846  -0.4280  -4.5106
 DFL  H6   H  HCR6  0   0.274   2.8320   0.7606  -2.0406
 DFL  H81  H  HCH2  0   0.292  -1.0878  -1.6256  -0.0947
 DFL  H82  H  HCH2  0   0.292  -2.3893  -0.4666   0.1576
 DFL  H9   H  HCH1  0   0.267  -0.8148   1.4189  -0.0833
 DFL  H11  H  HCR6  0   0.260   0.7833  -1.6221   1.5142
 DFL  H12  H  HCR6  0   0.274   1.1672  -1.7999   3.9161
 DFL  H14  H  HCR6  0   0.265  -0.6571   2.0381   4.5011
 DFL  H15  H  HCR6  0   0.259  -1.0233   2.2205   2.0782
 DFL  HO4  H  HOH1  0   0.475   0.8863  -0.7714   5.9561

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
 DFL  C1   C2   aromatic  1.396  0.020  1.396
 DFL  C1   C6   aromatic  1.381  0.020  1.381
 DFL  C1   H1   single    0.930  0.020  1.080
 DFL  C2   C3   aromatic  1.378  0.020  1.378
 DFL  C2   H2   single    0.930  0.020  1.080
 DFL  C3   C4   aromatic  1.399  0.020  1.399
 DFL  C3   H3   single    0.930  0.020  1.080
 DFL  C4   C5   aromatic  1.401  0.020  1.401
 DFL  C4   C7   single    1.472  0.020  1.472
 DFL  C5   C6   aromatic  1.395  0.020  1.395
 DFL  C5   O1   single    1.343  0.020  1.343
 DFL  C6   H6   single    0.930  0.020  1.080
 DFL  C7   C8   single    1.506  0.020  1.506
 DFL  C7   O2   double    1.213  0.020  1.213
 DFL  C8   C9   single    1.520  0.020  1.520
 DFL  C8   H81  single    0.970  0.020  1.090
 DFL  C8   H82  single    0.970  0.020  1.090
 DFL  C9   O1   single    1.431  0.020  1.431
 DFL  C9   C10  single    1.499  0.020  1.499
 DFL  C9   H9   single    0.970  0.020  1.090
 DFL  C10  C11  aromatic  1.392  0.020  1.392
 DFL  C10  C15  aromatic  1.390  0.020  1.390
 DFL  C11  C12  aromatic  1.385  0.020  1.385
 DFL  C11  H11  single    0.930  0.020  1.080
 DFL  C12  C13  aromatic  1.395  0.020  1.395
 DFL  C12  H12  single    0.930  0.020  1.080
 DFL  C13  C14  aromatic  1.392  0.020  1.392
 DFL  C13  O4   single    1.346  0.020  1.346
 DFL  C14  C15  aromatic  1.386  0.020  1.386
 DFL  C14  H14  single    0.930  0.020  1.080
 DFL  C15  H15  single    0.930  0.020  1.080
 DFL  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
 DFL  H1   C1   C6   119.16  3.000
 DFL  H1   C1   C2   119.85  3.000
 DFL  C6   C1   C2   120.99  3.000
 DFL  H2   C2   C3   120.45  3.000
 DFL  H2   C2   C1   120.28  3.000
 DFL  C3   C2   C1   119.26  3.000
 DFL  H3   C3   C4   118.89  3.000
 DFL  H3   C3   C2   120.22  3.000
 DFL  C4   C3   C2   120.88  3.000
 DFL  C7   C4   C5   119.92  3.000
 DFL  C7   C4   C3   120.82  3.000
 DFL  C5   C4   C3   119.18  3.000
 DFL  O1   C5   C6   117.28  3.000
 DFL  O1   C5   C4   122.69  3.000
 DFL  C6   C5   C4   120.03  3.000
 DFL  H6   C6   C5   119.60  3.000
 DFL  H6   C6   C1   120.76  3.000
 DFL  C5   C6   C1   119.64  3.000
 DFL  O2   C7   C8   122.55  3.000
 DFL  O2   C7   C4   122.70  3.000
 DFL  C8   C7   C4   114.71  3.000
 DFL  H82  C8   H81  107.26  3.000
 DFL  H82  C8   C9   109.98  3.000
 DFL  H81  C8   C9   110.24  3.000
 DFL  H82  C8   C7   110.22  3.000
 DFL  H81  C8   C7   107.89  3.000
 DFL  C9   C8   C7   111.15  3.000
 DFL  H9   C9   C10  109.22  3.000
 DFL  H9   C9   O1   107.87  3.000
 DFL  C10  C9   O1   107.87  3.000
 DFL  H9   C9   C8   108.61  3.000
 DFL  C10  C9   C8   112.74  3.000
 DFL  O1   C9   C8   110.41  3.000
 DFL  C9   O1   C5   116.66  3.000
 DFL  C15  C10  C11  118.37  3.000
 DFL  C15  C10  C9   120.52  3.000
 DFL  C11  C10  C9   121.09  3.000
 DFL  H11  C11  C12  118.50  3.000
 DFL  H11  C11  C10  120.51  3.000
 DFL  C12  C11  C10  120.99  3.000
 DFL  H12  C12  C13  120.23  3.000
 DFL  H12  C12  C11  119.70  3.000
 DFL  C13  C12  C11  120.07  3.000
 DFL  O4   C13  C14  117.93  3.000
 DFL  O4   C13  C12  122.63  3.000
 DFL  C14  C13  C12  119.44  3.000
 DFL  H14  C14  C15  120.31  3.000
 DFL  H14  C14  C13  119.91  3.000
 DFL  C15  C14  C13  119.78  3.000
 DFL  H15  C15  C14  118.96  3.000
 DFL  H15  C15  C10  119.70  3.000
 DFL  C14  C15  C10  121.34  3.000
 DFL  HO4  O4   C13  110.52  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
 DFL  CONST_01  C4   C3   C2   C1     0.00   0.0  0
 DFL  CONST_02  C4   C5   C6   C1     0.00   0.0  0
 DFL  CONST_03  C5   C6   C1   C2     0.00   0.0  0
 DFL  CONST_04  C5   C4   C3   C2     0.00   0.0  0
 DFL  CONST_05  C6   C1   C2   C3     0.00   0.0  0
 DFL  CONST_06  C6   C5   C4   C3     0.00   0.0  0
 DFL  CONST_07  C13  C12  C11  C10    0.00   0.0  0
 DFL  CONST_08  C13  C14  C15  C10    0.00   0.0  0
 DFL  CONST_09  C14  C15  C10  C11    0.00   0.0  0
 DFL  CONST_10  C14  C13  C12  C11    0.00   0.0  0
 DFL  CONST_11  C15  C10  C11  C12    0.00   0.0  0
 DFL  CONST_12  C15  C14  C13  C12    0.00   0.0  0
 DFL  CONST_13  C12  C11  C10  C9   180.00   0.0  0
 DFL  CONST_14  C14  C15  C10  C9   180.00   0.0  0
 DFL  CONST_15  O4   C13  C12  C11  180.00   0.0  0
 DFL  CONST_16  O4   C13  C14  C15  180.00   0.0  0
 DFL  CONST_17  H3   C3   C2   C1   180.00   0.0  0
 DFL  CONST_18  H6   C6   C1   C2   180.00   0.0  0
 DFL  CONST_19  H1   C1   C2   C3   180.00   0.0  0
 DFL  CONST_20  H2   C2   C3   C4   180.00   0.0  0
 DFL  CONST_21  H11  C11  C10  C9     0.00   0.0  0
 DFL  CONST_22  H15  C15  C10  C9     0.00   0.0  0
 DFL  CONST_23  H12  C12  C11  C10  180.00   0.0  0
 DFL  CONST_24  H14  C14  C15  C10  180.00   0.0  0
 DFL  Var_01    C8   C7   C4   C3   173.41  30.0  1
 DFL  Var_02    C9   C8   C7   C4    32.38  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
 DFL  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
 DFL  plan-1  C9   0.020
 DFL  plan-1  C10  0.020
 DFL  plan-1  C11  0.020
 DFL  plan-1  C12  0.020
 DFL  plan-1  C13  0.020
 DFL  plan-1  C14  0.020
 DFL  plan-1  C15  0.020
 DFL  plan-1  O4   0.020
 DFL  plan-1  H11  0.020
 DFL  plan-1  H12  0.020
 DFL  plan-1  H14  0.020
 DFL  plan-1  H15  0.020
 DFL  plan-2  C1   0.020
 DFL  plan-2  C2   0.020
 DFL  plan-2  C3   0.020
 DFL  plan-2  C4   0.020
 DFL  plan-2  C5   0.020
 DFL  plan-2  C6   0.020
 DFL  plan-2  C7   0.020
 DFL  plan-2  O1   0.020
 DFL  plan-2  H1   0.020
 DFL  plan-2  H2   0.020
 DFL  plan-2  H3   0.020
 DFL  plan-2  H6   0.020
 DFL  plan-3  C4   0.020
 DFL  plan-3  C7   0.020
 DFL  plan-3  C8   0.020
 DFL  plan-3  O2   0.020

