# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 20:27:13 2020
#   Inital geometry file: a 94 line input string
#   Ligand name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1c(O)cc2OC(=CC(=O)c2c1O)c3ccc(O)cc3
#
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
 HUL  HUL  5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one  ligand  34  22  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_HUL
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
 HUL  C1   C  CR6   0   0.182  -3.6021  -0.3546  -0.1467
 HUL  C2   C  CR6   0   0.323  -2.8407   0.8055  -0.1503
 HUL  C3   C  CR66  0  -0.343  -1.4313   0.7259  -0.0929
 HUL  C4   C  CR66  0   0.403  -0.8381  -0.5336  -0.0322
 HUL  C5   C  CR16  0  -0.522  -1.5762  -1.7013  -0.0220
 HUL  C6   C  CR6   0   0.317  -2.9634  -1.6025  -0.0744
 HUL  C7   C  CH3   0  -0.409  -5.6141  -0.1684   1.0248
 HUL  C8   C  CR6   0   0.532  -0.6046   1.9134  -0.1100
 HUL  C9   C  CR16  0  -0.524   0.8106   1.6740  -0.0734
 HUL  C10  C  CR6   0   0.420   1.3081   0.4160  -0.0013
 HUL  C11  C  CR6   0  -0.005   2.7246   0.0608   0.0411
 HUL  C12  C  CR16  0  -0.291   3.6861   1.0107   0.3932
 HUL  C13  C  CR16  0  -0.365   5.0297   0.6942   0.4164
 HUL  C14  C  CR6   0   0.366   5.4492  -0.5942   0.0843
 HUL  C15  C  CR16  0  -0.323   4.4996  -1.5559  -0.2608
 HUL  O21  O  O2    0  -0.483  -4.9553  -0.2884  -0.2309
 HUL  O19  O  OH1   0  -0.620  -3.4559   1.9811  -0.2161
 HUL  O20  O  OH1   0  -0.604  -3.7580  -2.6747  -0.0678
 HUL  O17  O  O     0  -0.470   0.5056  -0.6563   0.0252
 HUL  O18  O  O     0  -0.511  -1.0969   3.0529  -0.1644
 HUL  O22  O  OH1   0  -0.617   6.7379  -0.9587   0.0843
 HUL  C16  C  CR16  0  -0.259   3.1580  -1.2309  -0.2773
 HUL  H1   H  HCR6  0   0.297  -1.0832  -2.6643   0.0297
 HUL  H2   H  HCH3  0   0.223  -5.4271  -1.0337   1.6651
 HUL  H3   H  HCH3  0   0.224  -5.3088   0.7355   1.5565
 HUL  H4   H  HCH3  0   0.239  -6.6817  -0.1096   0.8213
 HUL  H5   H  HCR6  0   0.282   1.4809   2.5195  -0.1246
 HUL  H6   H  HCR6  0   0.269   3.3919   2.0125   0.6761
 HUL  H7   H  HCR6  0   0.283   5.7530   1.4497   0.7002
 HUL  H8   H  HCR6  0   0.275   4.8186  -2.5571  -0.5204
 HUL  H9   H  HOH1  0   0.476  -2.7529   2.6763  -0.2115
 HUL  H10  H  HOH1  0   0.485  -3.2365  -3.4848  -0.0232
 HUL  H11  H  HOH1  0   0.481   7.3036  -0.2172   0.3297
 HUL  H12  H  HCR6  0   0.267   2.4491  -1.9980  -0.5569

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
 HUL  C7   O21  single    1.423  0.020  1.423
 HUL  O19  C2   single    1.328  0.020  1.328
 HUL  O18  C8   double    1.242  0.020  1.242
 HUL  O21  C1   single    1.357  0.020  1.357
 HUL  C2   C1   aromatic  1.388  0.020  1.388
 HUL  C2   C3   aromatic  1.413  0.020  1.413
 HUL  C8   C3   single    1.447  0.020  1.447
 HUL  C8   C9   single    1.436  0.020  1.436
 HUL  C1   C6   aromatic  1.404  0.020  1.404
 HUL  C3   C4   aromatic  1.394  0.020  1.394
 HUL  C9   C10  double    1.355  0.020  1.355
 HUL  C6   O20  single    1.335  0.020  1.335
 HUL  C6   C5   aromatic  1.392  0.020  1.392
 HUL  C4   C5   aromatic  1.381  0.020  1.381
 HUL  C4   O17  single    1.351  0.020  1.351
 HUL  C10  O17  single    1.340  0.020  1.340
 HUL  C10  C11  single    1.461  0.020  1.461
 HUL  C12  C11  aromatic  1.397  0.020  1.397
 HUL  C12  C13  aromatic  1.381  0.020  1.381
 HUL  C11  C16  aromatic  1.399  0.020  1.399
 HUL  C13  C14  aromatic  1.395  0.020  1.395
 HUL  C16  C15  aromatic  1.381  0.020  1.381
 HUL  C14  C15  aromatic  1.395  0.020  1.395
 HUL  C14  O22  single    1.339  0.020  1.339
 HUL  C5   H1   single    0.930  0.020  1.080
 HUL  C7   H2   single    0.970  0.020  1.090
 HUL  C7   H3   single    0.970  0.020  1.090
 HUL  C7   H4   single    0.970  0.020  1.090
 HUL  C9   H5   single    0.930  0.020  1.080
 HUL  C12  H6   single    0.930  0.020  1.080
 HUL  C13  H7   single    0.930  0.020  1.080
 HUL  C15  H8   single    0.930  0.020  1.080
 HUL  O19  H9   single    0.850  0.020  0.980
 HUL  O20  H10  single    0.850  0.020  0.980
 HUL  O22  H11  single    0.850  0.020  0.980
 HUL  C16  H12  single    0.930  0.020  1.080

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
 HUL  O21  C1   C6   120.01  3.000
 HUL  C6   C1   C2   119.58  3.000
 HUL  O21  C1   C2   120.40  3.000
 HUL  O19  C2   C3   120.92  3.000
 HUL  C3   C2   C1   120.01  3.000
 HUL  O19  C2   C1   119.07  3.000
 HUL  C8   C3   C4   119.94  3.000
 HUL  C4   C3   C2   118.51  3.000
 HUL  C8   C3   C2   121.55  3.000
 HUL  O17  C4   C5   117.03  3.000
 HUL  O17  C4   C3   120.49  3.000
 HUL  C5   C4   C3   122.47  3.000
 HUL  H1   C5   C6   121.25  3.000
 HUL  H1   C5   C4   120.58  3.000
 HUL  C6   C5   C4   118.18  3.000
 HUL  O20  C6   C5   122.43  3.000
 HUL  C5   C6   C1   121.25  3.000
 HUL  O20  C6   C1   116.33  3.000
 HUL  H4   C7   H3   108.69  3.000
 HUL  H4   C7   H2   108.67  3.000
 HUL  H3   C7   H2   108.80  3.000
 HUL  H4   C7   O21  107.08  3.000
 HUL  H3   C7   O21  111.71  3.000
 HUL  H2   C7   O21  111.78  3.000
 HUL  O18  C8   C9   123.00  3.000
 HUL  C9   C8   C3   115.21  3.000
 HUL  O18  C8   C3   121.79  3.000
 HUL  H5   C9   C10  120.10  3.000
 HUL  H5   C9   C8   118.68  3.000
 HUL  C10  C9   C8   121.21  3.000
 HUL  O17  C10  C11  112.69  3.000
 HUL  C11  C10  C9   125.69  3.000
 HUL  O17  C10  C9   121.63  3.000
 HUL  C16  C11  C12  118.16  3.000
 HUL  C16  C11  C10  121.21  3.000
 HUL  C12  C11  C10  120.62  3.000
 HUL  H6   C12  C13  118.20  3.000
 HUL  H6   C12  C11  120.57  3.000
 HUL  C13  C12  C11  121.22  3.000
 HUL  H7   C13  C14  120.36  3.000
 HUL  H7   C13  C12  119.61  3.000
 HUL  C14  C13  C12  120.02  3.000
 HUL  O22  C14  C15  117.87  3.000
 HUL  O22  C14  C13  122.73  3.000
 HUL  C15  C14  C13  119.40  3.000
 HUL  H8   C15  C16  120.08  3.000
 HUL  H8   C15  C14  119.76  3.000
 HUL  C16  C15  C14  120.15  3.000
 HUL  C7   O21  C1   114.26  3.000
 HUL  H9   O19  C2   107.03  3.000
 HUL  H10  O20  C6   110.67  3.000
 HUL  C10  O17  C4   121.50  3.000
 HUL  H11  O22  C14  110.81  3.000
 HUL  H12  C16  C15  118.24  3.000
 HUL  H12  C16  C11  120.71  3.000
 HUL  C15  C16  C11  121.04  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
 HUL  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 HUL  CONST_02  C4   C5   C6   C1      0.00   0.0  0
 HUL  CONST_03  C5   C6   C1   C2      0.00   0.0  0
 HUL  CONST_04  C5   C4   C3   C2      0.00   0.0  0
 HUL  CONST_05  C6   C1   C2   C3      0.00   0.0  0
 HUL  CONST_06  C6   C5   C4   C3      0.00   0.0  0
 HUL  CONST_07  C14  C13  C12  C11     0.00   0.0  0
 HUL  CONST_08  C14  C15  C16  C11     0.00   0.0  0
 HUL  CONST_09  C15  C16  C11  C12     0.00   0.0  0
 HUL  CONST_10  C15  C14  C13  C12     0.00   0.0  0
 HUL  CONST_11  C16  C11  C12  C13     0.00   0.0  0
 HUL  CONST_12  C16  C15  C14  C13     0.00   0.0  0
 HUL  CONST_13  C13  C12  C11  C10   180.00   0.0  0
 HUL  CONST_14  C15  C16  C11  C10   180.00   0.0  0
 HUL  CONST_15  O20  C6   C1   C2    180.00   0.0  0
 HUL  CONST_16  O21  C1   C2   C3    180.00   0.0  0
 HUL  CONST_17  O19  C2   C3   C4    180.00   0.0  0
 HUL  CONST_18  O20  C6   C5   C4    180.00   0.0  0
 HUL  CONST_19  O21  C1   C6   C5    180.00   0.0  0
 HUL  CONST_20  O19  C2   C1   C6    180.00   0.0  0
 HUL  CONST_21  O19  C2   C3   C8      0.00   0.0  0
 HUL  CONST_22  O22  C14  C13  C12   180.00   0.0  0
 HUL  CONST_23  C16  C15  C14  O22   180.00   0.0  0
 HUL  CONST_24  H1   C5   C6   C1    180.00   0.0  0
 HUL  CONST_25  H6   C12  C11  C10     0.00   0.0  0
 HUL  CONST_26  H12  C16  C11  C10     0.00   0.0  0
 HUL  CONST_27  H7   C13  C12  C11   180.00   0.0  0
 HUL  CONST_28  H8   C15  C16  C11   180.00   0.0  0
 HUL  Var_01    C9   C8   C3   C2   -178.78  30.0  1
 HUL  Var_02    C10  C9   C8   C3     -1.25  30.0  1
 HUL  Var_03    C9   C10  O17  C4      0.67  30.0  1
 HUL  Var_04    O17  C10  C9   C8      0.69  30.0  1
 HUL  Var_05    C12  C11  C10  C9     18.58  30.0  2
 HUL  Var_06    H2   C7   O21  C1    -61.95  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
 HUL  plan-1  C10  0.020
 HUL  plan-1  C11  0.020
 HUL  plan-1  C12  0.020
 HUL  plan-1  C13  0.020
 HUL  plan-1  C14  0.020
 HUL  plan-1  C15  0.020
 HUL  plan-1  O22  0.020
 HUL  plan-1  C16  0.020
 HUL  plan-1  H6   0.020
 HUL  plan-1  H7   0.020
 HUL  plan-1  H8   0.020
 HUL  plan-1  H12  0.020
 HUL  plan-2  C1   0.020
 HUL  plan-2  C2   0.020
 HUL  plan-2  C3   0.020
 HUL  plan-2  C4   0.020
 HUL  plan-2  C5   0.020
 HUL  plan-2  C6   0.020
 HUL  plan-2  C8   0.020
 HUL  plan-2  O21  0.020
 HUL  plan-2  O19  0.020
 HUL  plan-2  O20  0.020
 HUL  plan-2  O17  0.020
 HUL  plan-2  H1   0.020
 HUL  plan-3  C3   0.020
 HUL  plan-3  C8   0.020
 HUL  plan-3  C9   0.020
 HUL  plan-3  O18  0.020

