# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 01:17:52 2020
#   Inital geometry file: a 79 line input string
#   Ligand name: 2,3,7,8-tetrahydroxychromeno[5,4,3-cde]chromene-5,10-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc2C(=O)Oc3c(O)c(O)cc4C(=O)Oc(c1O)c2c34
#
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
 REF  REF  2,3,7,8-tetrahydroxychromeno[5,4,3-cde]chromene-5,10-dione  ligand  28  22  .  2021-08-23  2021-08-23  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_REF
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
 REF  C1    C  CR66  0  -0.250  -1.1480   1.3317   0.0079
 REF  C2    C  C     0   0.164  -0.6723   0.0253   0.0050
 REF  C3    C  C     0   0.163   0.7224  -0.2404  -0.0079
 REF  C4    C  CR66  0   0.272   1.5958   0.8307  -0.0161
 REF  O5    O  O     0  -0.491   1.1322   2.1092  -0.0137
 REF  C6    C  CR6   0   0.556  -0.1909   2.4353  -0.0033
 REF  C7    C  CR66  0  -0.247   1.2019  -1.5450  -0.0109
 REF  C8    C  CR16  0  -0.416   2.5739  -1.7719  -0.0230
 REF  C9    C  CR6   0   0.307   3.4503  -0.6985  -0.0312
 REF  C10   C  CR6   0   0.220   2.9664   0.6256  -0.0267
 REF  C11   C  CR66  0   0.287  -1.5444  -1.0484   0.0158
 REF  O12   O  O     0  -0.474  -1.0792  -2.3252   0.0119
 REF  C13   C  CR6   0   0.548   0.2413  -2.6479  -0.0011
 REF  C14   C  CR16  0  -0.437  -2.5217   1.5599   0.0226
 REF  C15   C  CR6   0   0.280  -3.3920   0.4849   0.0361
 REF  C16   C  CR6   0   0.238  -2.9151  -0.8429   0.0319
 REF  O19   O  OH1   0  -0.615   3.8772   1.6039  -0.0330
 REF  O20   O  OH1   0  -0.621   4.7682  -0.9453  -0.0433
 REF  O21   O  O     0  -0.402   0.5224  -3.8161  -0.0035
 REF  O22   O  OH1   0  -0.596  -3.7283  -1.8979   0.0435
 REF  O23   O  OH1   0  -0.633  -4.7311   0.5963   0.0534
 REF  O24   O  O     0  -0.400  -0.4685   3.6036  -0.0037
 REF  H8    H  HCR6  0   0.289   2.9707  -2.7787  -0.0268
 REF  H14   H  HCR6  0   0.297  -2.9113   2.5706   0.0252
 REF  HO19  H  HOH1  0   0.495   3.4746   2.4816  -0.0312
 REF  HO20  H  HOH1  0   0.482   5.2832  -0.1288  -0.0474
 REF  HO22  H  HOH1  0   0.489  -4.6537  -1.6207   0.0530
 REF  HO23  H  HOH1  0   0.492  -5.0095   1.5196   0.0530

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
 REF  C1   C2    aromatic  1.390  0.020  1.390
 REF  C1   C6    single    1.461  0.020  1.461
 REF  C1   C14   aromatic  1.393  0.020  1.393
 REF  C2   C3    aromatic  1.420  0.020  1.420
 REF  C2   C11   aromatic  1.383  0.020  1.383
 REF  C3   C4    aromatic  1.382  0.020  1.382
 REF  C3   C7    aromatic  1.390  0.020  1.390
 REF  C4   O5    single    1.360  0.020  1.360
 REF  C4   C10   aromatic  1.386  0.020  1.386
 REF  O5   C6    single    1.363  0.020  1.363
 REF  C6   O24   double    1.201  0.020  1.201
 REF  C7   C8    aromatic  1.391  0.020  1.391
 REF  C7   C13   single    1.463  0.020  1.463
 REF  C8   C9    aromatic  1.386  0.020  1.386
 REF  C9   C10   aromatic  1.410  0.020  1.410
 REF  C9   O20   single    1.341  0.020  1.341
 REF  C10  O19   single    1.337  0.020  1.337
 REF  C11  O12   single    1.359  0.020  1.359
 REF  C11  C16   aromatic  1.386  0.020  1.386
 REF  O12  C13   single    1.359  0.020  1.359
 REF  C13  O21   double    1.202  0.020  1.202
 REF  C14  C15   aromatic  1.383  0.020  1.383
 REF  C15  C16   aromatic  1.411  0.020  1.411
 REF  C15  O23   single    1.344  0.020  1.344
 REF  C16  O22   single    1.332  0.020  1.332
 REF  C8   H8    single    0.930  0.020  1.080
 REF  C14  H14   single    0.930  0.020  1.080
 REF  O19  HO19  single    0.850  0.020  0.980
 REF  O20  HO20  single    0.850  0.020  0.980
 REF  O22  HO22  single    0.850  0.020  0.980
 REF  O23  HO23  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
 REF  C14   C1   C6   121.51  3.000
 REF  C14   C1   C2   119.44  3.000
 REF  C6    C1   C2   119.05  3.000
 REF  C11   C2   C3   118.30  3.000
 REF  C11   C2   C1   120.90  3.000
 REF  C3    C2   C1   120.80  3.000
 REF  C7    C3   C4   120.62  3.000
 REF  C7    C3   C2   120.97  3.000
 REF  C4    C3   C2   118.41  3.000
 REF  C10   C4   O5   118.44  3.000
 REF  C10   C4   C3   120.68  3.000
 REF  O5    C4   C3   120.87  3.000
 REF  C6    O5   C4   123.78  3.000
 REF  O24   C6   O5   117.21  3.000
 REF  O24   C6   C1   125.70  3.000
 REF  O5    C6   C1   117.09  3.000
 REF  C13   C7   C8   121.67  3.000
 REF  C13   C7   C3   118.76  3.000
 REF  C8    C7   C3   119.57  3.000
 REF  H8    C8   C9   119.26  3.000
 REF  H8    C8   C7   120.90  3.000
 REF  C9    C8   C7   119.84  3.000
 REF  O20   C9   C10  120.69  3.000
 REF  O20   C9   C8   118.62  3.000
 REF  C10   C9   C8   120.69  3.000
 REF  O19   C10  C9   116.97  3.000
 REF  O19   C10  C4   124.44  3.000
 REF  C9    C10  C4   118.59  3.000
 REF  C16   C11  O12  118.55  3.000
 REF  C16   C11  C2   120.56  3.000
 REF  O12   C11  C2   120.89  3.000
 REF  C13   O12  C11  123.75  3.000
 REF  O21   C13  O12  117.26  3.000
 REF  O21   C13  C7   125.41  3.000
 REF  O12   C13  C7   117.32  3.000
 REF  H14   C14  C15  119.92  3.000
 REF  H14   C14  C1   120.51  3.000
 REF  C15   C14  C1   119.57  3.000
 REF  O23   C15  C16  114.51  3.000
 REF  O23   C15  C14  124.24  3.000
 REF  C16   C15  C14  121.25  3.000
 REF  O22   C16  C15  122.62  3.000
 REF  O22   C16  C11  119.10  3.000
 REF  C15   C16  C11  118.28  3.000
 REF  HO19  O19  C10  112.40  3.000
 REF  HO20  O20  C9   111.63  3.000
 REF  HO22  O22  C16  110.95  3.000
 REF  HO23  O23  C15  111.53  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
 REF  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 REF  CONST_02  C7   C3   C2   C1    180.00   0.0  0
 REF  CONST_03  C16  C11  C2   C1      0.00   0.0  0
 REF  CONST_04  C16  C15  C14  C1      0.00   0.0  0
 REF  CONST_05  C15  C14  C1   C2      0.00   0.0  0
 REF  CONST_06  C10  C4   C3   C2    180.00   0.0  0
 REF  CONST_07  C8   C7   C3   C2    180.00   0.0  0
 REF  CONST_08  C15  C16  C11  C2      0.00   0.0  0
 REF  CONST_09  C14  C1   C2   C3    180.00   0.0  0
 REF  CONST_10  C16  C11  C2   C3    180.00   0.0  0
 REF  CONST_11  C9   C10  C4   C3      0.00   0.0  0
 REF  CONST_12  C9   C8   C7   C3      0.00   0.0  0
 REF  CONST_13  C11  C2   C3   C4    180.00   0.0  0
 REF  CONST_14  C8   C7   C3   C4      0.00   0.0  0
 REF  CONST_15  C8   C9   C10  C4      0.00   0.0  0
 REF  CONST_16  C11  C2   C3   C7      0.00   0.0  0
 REF  CONST_17  C10  C4   C3   C7      0.00   0.0  0
 REF  CONST_18  C10  C9   C8   C7      0.00   0.0  0
 REF  CONST_19  C14  C1   C2   C11     0.00   0.0  0
 REF  CONST_20  C14  C15  C16  C11     0.00   0.0  0
 REF  CONST_21  O23  C15  C14  C1    180.00   0.0  0
 REF  CONST_22  O22  C16  C11  C2    180.00   0.0  0
 REF  CONST_23  O19  C10  C4   C3    180.00   0.0  0
 REF  CONST_24  O20  C9   C10  C4    180.00   0.0  0
 REF  CONST_25  O19  C10  C4   O5      0.00   0.0  0
 REF  CONST_26  O20  C9   C8   C7    180.00   0.0  0
 REF  CONST_27  O19  C10  C9   C8    180.00   0.0  0
 REF  CONST_28  O23  C15  C16  C11   180.00   0.0  0
 REF  CONST_29  O22  C16  C11  O12     0.00   0.0  0
 REF  CONST_30  O22  C16  C15  C14   180.00   0.0  0
 REF  CONST_31  H14  C14  C1   C2    180.00   0.0  0
 REF  CONST_32  H8   C8   C7   C3    180.00   0.0  0
 REF  Var_01    O5   C6   C1   C2     -0.12  30.0  1
 REF  Var_02    O12  C13  C7   C3     -0.07  30.0  1
 REF  Var_03    C10  C4   O5   C6   -179.99  30.0  1
 REF  Var_04    C16  C11  O12  C13  -179.88  30.0  1

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
 REF  plan-1  C7   0.020
 REF  plan-1  O12  0.020
 REF  plan-1  C13  0.020
 REF  plan-1  O21  0.020
 REF  plan-2  C1   0.020
 REF  plan-2  C2   0.020
 REF  plan-2  C3   0.020
 REF  plan-2  C6   0.020
 REF  plan-2  C11  0.020
 REF  plan-2  O12  0.020
 REF  plan-2  C14  0.020
 REF  plan-2  C15  0.020
 REF  plan-2  C16  0.020
 REF  plan-2  O22  0.020
 REF  plan-2  O23  0.020
 REF  plan-2  H14  0.020
 REF  plan-3  C2   0.020
 REF  plan-3  C3   0.020
 REF  plan-3  C4   0.020
 REF  plan-3  O5   0.020
 REF  plan-3  C7   0.020
 REF  plan-3  C8   0.020
 REF  plan-3  C9   0.020
 REF  plan-3  C10  0.020
 REF  plan-3  C13  0.020
 REF  plan-3  O19  0.020
 REF  plan-3  O20  0.020
 REF  plan-3  H8   0.020
 REF  plan-4  C1   0.020
 REF  plan-4  O5   0.020
 REF  plan-4  C6   0.020
 REF  plan-4  O24  0.020

