# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Apr  9 15:49:42 2020
#   Inital geometry file: a 94 line input string
#   Ligand name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(O)c2C(=O)C=C(Oc2c1)c3ccc(O)c(O)c3
#
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
 6B5  6B5  2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one  ligand  34  22  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_6B5
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
 6B5  C10   C  CR16  0  -0.354   4.4491   0.9597  -0.2772
 6B5  C02   C  CR6   0   0.536  -1.1984   2.1663   0.0975
 6B5  C03   C  CR66  0  -0.357  -2.0207   0.9803   0.0087
 6B5  C04   C  CR66  0   0.422  -1.4251  -0.2807  -0.0779
 6B5  O05   O  O     0  -0.472  -0.0788  -0.3956  -0.0951
 6B5  C06   C  CR6   0   0.418   0.7196   0.6764  -0.0031
 6B5  C07   C  CR16  0  -0.525   0.2188   1.9302   0.1017
 6B5  C08   C  CR6   0   0.013   2.1395   0.3240  -0.0203
 6B5  C09   C  CR16  0  -0.322   3.1061   1.2952  -0.2719
 6B5  C11   C  CR6   0   0.266   4.8509  -0.3455  -0.0353
 6B5  O12   O  OH1   0  -0.630   6.1321  -0.7522  -0.0242
 6B5  C13   C  CR6   0   0.321   3.8860  -1.3331   0.2155
 6B5  O14   O  OH1   0  -0.630   4.2325  -2.6121   0.4582
 6B5  C15   C  CR16  0  -0.373   2.5467  -0.9937   0.2175
 6B5  C16   C  CR16  0  -0.476  -2.1540  -1.4472  -0.1552
 6B5  C17   C  CR6   0   0.421  -3.5480  -1.3516  -0.1465
 6B5  O18   O  O2    0  -0.462  -4.2033  -2.5117  -0.2258
 6B5  C19   C  CH3   0  -0.443  -5.6213  -2.5100  -0.2253
 6B5  C20   C  CR16  0  -0.497  -4.1878  -0.1129  -0.0619
 6B5  C21   C  CR6   0   0.414  -3.4298   1.0463   0.0153
 6B5  O22   O  OH1   0  -0.627  -4.0476   2.2196   0.0965
 6B5  H101  H  HCR6  0   0.286   5.1926   1.7216  -0.4788
 6B5  H071  H  HCR6  0   0.282   0.8857   2.7738   0.2021
 6B5  H091  H  HCR6  0   0.266   2.8280   2.3170  -0.4881
 6B5  H121  H  HOH1  0   0.488   6.7329  -0.0229  -0.2158
 6B5  H141  H  HOH1  0   0.476   5.1906  -2.7191   0.4275
 6B5  H151  H  HCR6  0   0.273   1.8264  -1.7755   0.4191
 6B5  H161  H  HCR6  0   0.285  -1.6644  -2.4096  -0.2241
 6B5  H193  H  HCH3  0   0.237  -6.0254  -1.9623  -1.0794
 6B5  H192  H  HCH3  0   0.268  -5.9259  -3.5504  -0.2976
 6B5  H191  H  HCH3  0   0.237  -6.0258  -2.0857   0.6961
 6B5  H201  H  HCR6  0   0.293  -5.2655  -0.0269  -0.0558
 6B5  H221  H  HOH1  0   0.476  -3.3489   2.9179   0.1435
 6B5  O01   O  O     0  -0.511  -1.6946   3.3027   0.1749

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
 6B5  O14  C13   single    1.347  0.020  1.347
 6B5  C13  C15   aromatic  1.382  0.020  1.382
 6B5  C13  C11   aromatic  1.403  0.020  1.403
 6B5  O01  C02   double    1.242  0.020  1.242
 6B5  C15  C08   aromatic  1.400  0.020  1.400
 6B5  C07  C02   single    1.437  0.020  1.437
 6B5  C07  C06   double    1.354  0.020  1.354
 6B5  C02  C03   single    1.446  0.020  1.446
 6B5  O22  C21   single    1.328  0.020  1.328
 6B5  O12  C11   single    1.344  0.020  1.344
 6B5  C11  C10   aromatic  1.387  0.020  1.387
 6B5  C08  C06   single    1.463  0.020  1.463
 6B5  C08  C09   aromatic  1.393  0.020  1.393
 6B5  C06  O05   single    1.340  0.020  1.340
 6B5  C03  C21   aromatic  1.411  0.020  1.411
 6B5  C03  C04   aromatic  1.397  0.020  1.397
 6B5  C21  C20   aromatic  1.387  0.020  1.387
 6B5  O05  C04   single    1.351  0.020  1.351
 6B5  C04  C16   aromatic  1.378  0.020  1.378
 6B5  C20  C17   aromatic  1.397  0.020  1.397
 6B5  C10  C09   aromatic  1.384  0.020  1.384
 6B5  C16  C17   aromatic  1.397  0.020  1.397
 6B5  C17  O18   single    1.335  0.020  1.335
 6B5  C19  O18   single    1.418  0.020  1.418
 6B5  C10  H101  single    0.930  0.020  1.080
 6B5  C07  H071  single    0.930  0.020  1.080
 6B5  C09  H091  single    0.930  0.020  1.080
 6B5  O12  H121  single    0.850  0.020  0.980
 6B5  O14  H141  single    0.850  0.020  0.980
 6B5  C15  H151  single    0.930  0.020  1.080
 6B5  C16  H161  single    0.930  0.020  1.080
 6B5  C19  H193  single    0.970  0.020  1.090
 6B5  C19  H192  single    0.970  0.020  1.090
 6B5  C19  H191  single    0.970  0.020  1.090
 6B5  C20  H201  single    0.930  0.020  1.080
 6B5  O22  H221  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
 6B5  H101  C10  C11   119.70  3.000
 6B5  H101  C10  C09   119.74  3.000
 6B5  C11   C10  C09   120.57  3.000
 6B5  C07   C02  C03   115.24  3.000
 6B5  C03   C02  O01   121.80  3.000
 6B5  C07   C02  O01   122.96  3.000
 6B5  C21   C03  C04   117.92  3.000
 6B5  C04   C03  C02   120.11  3.000
 6B5  C21   C03  C02   121.97  3.000
 6B5  C16   C04  O05   117.03  3.000
 6B5  C16   C04  C03   122.83  3.000
 6B5  O05   C04  C03   120.15  3.000
 6B5  C06   O05  C04   121.66  3.000
 6B5  C08   C06  C07   125.65  3.000
 6B5  C08   C06  O05   112.63  3.000
 6B5  C07   C06  O05   121.72  3.000
 6B5  H071  C07  C06   120.14  3.000
 6B5  H071  C07  C02   118.75  3.000
 6B5  C06   C07  C02   121.11  3.000
 6B5  C15   C08  C09   119.02  3.000
 6B5  C09   C08  C06   120.50  3.000
 6B5  C15   C08  C06   120.48  3.000
 6B5  H091  C09  C08   121.11  3.000
 6B5  H091  C09  C10   118.56  3.000
 6B5  C08   C09  C10   120.32  3.000
 6B5  C13   C11  O12   116.16  3.000
 6B5  O12   C11  C10   124.21  3.000
 6B5  C13   C11  C10   119.62  3.000
 6B5  H121  O12  C11   111.31  3.000
 6B5  C15   C13  O14   118.84  3.000
 6B5  C15   C13  C11   119.59  3.000
 6B5  O14   C13  C11   121.57  3.000
 6B5  H141  O14  C13   110.80  3.000
 6B5  H151  C15  C13   117.91  3.000
 6B5  H151  C15  C08   121.22  3.000
 6B5  C13   C15  C08   120.87  3.000
 6B5  H161  C16  C17   120.84  3.000
 6B5  H161  C16  C04   121.15  3.000
 6B5  C17   C16  C04   118.01  3.000
 6B5  C20   C17  O18   123.33  3.000
 6B5  O18   C17  C16   115.47  3.000
 6B5  C20   C17  C16   121.21  3.000
 6B5  C19   O18  C17   119.34  3.000
 6B5  H191  C19  H192  108.92  3.000
 6B5  H191  C19  H193  109.15  3.000
 6B5  H192  C19  H193  108.93  3.000
 6B5  H191  C19  O18   111.78  3.000
 6B5  H192  C19  O18   106.21  3.000
 6B5  H193  C19  O18   111.74  3.000
 6B5  H201  C20  C21   118.55  3.000
 6B5  H201  C20  C17   121.84  3.000
 6B5  C21   C20  C17   119.61  3.000
 6B5  O22   C21  C20   119.17  3.000
 6B5  C20   C21  C03   120.43  3.000
 6B5  O22   C21  C03   120.41  3.000
 6B5  H221  O22  C21   107.34  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
 6B5  CONST_01  C15   C13  C11  C10     0.00   0.0  0
 6B5  CONST_02  C15   C08  C09  C10     0.00   0.0  0
 6B5  CONST_03  C17   C20  C21  C03     0.00   0.0  0
 6B5  CONST_04  C17   C16  C04  C03     0.00   0.0  0
 6B5  CONST_05  C20   C21  C03  C04     0.00   0.0  0
 6B5  CONST_06  C20   C17  C16  C04     0.00   0.0  0
 6B5  CONST_07  C11   C13  C15  C08     0.00   0.0  0
 6B5  CONST_08  C11   C10  C09  C08     0.00   0.0  0
 6B5  CONST_09  C13   C15  C08  C09     0.00   0.0  0
 6B5  CONST_10  C13   C11  C10  C09     0.00   0.0  0
 6B5  CONST_11  C21   C03  C04  C16     0.00   0.0  0
 6B5  CONST_12  C21   C20  C17  C16     0.00   0.0  0
 6B5  CONST_13  C06   C08  C09  C10   180.00   0.0  0
 6B5  CONST_14  C13   C15  C08  C06   180.00   0.0  0
 6B5  CONST_15  O14   C13  C11  C10   180.00   0.0  0
 6B5  CONST_16  O22   C21  C03  C02     0.00   0.0  0
 6B5  CONST_17  O22   C21  C03  C04   180.00   0.0  0
 6B5  CONST_18  O18   C17  C16  C04   180.00   0.0  0
 6B5  CONST_19  O14   C13  C15  C08   180.00   0.0  0
 6B5  CONST_20  O12   C11  C10  C09   180.00   0.0  0
 6B5  CONST_21  C15   C13  C11  O12   180.00   0.0  0
 6B5  CONST_22  O22   C21  C20  C17   180.00   0.0  0
 6B5  CONST_23  C21   C20  C17  O18   180.00   0.0  0
 6B5  CONST_24  H201  C20  C21  C03   180.00   0.0  0
 6B5  CONST_25  H161  C16  C04  C03   180.00   0.0  0
 6B5  CONST_26  H151  C15  C08  C06     0.00   0.0  0
 6B5  CONST_27  H091  C09  C08  C06     0.00   0.0  0
 6B5  CONST_28  H101  C10  C09  C08   180.00   0.0  0
 6B5  Var_01    C08   C06  C07  C02   179.48  30.0  1
 6B5  Var_02    C06   C07  C02  C03     1.47  30.0  1
 6B5  Var_03    C07   C02  C03  C04    -0.59  30.0  1
 6B5  Var_04    C07   C06  O05  C04    -0.51  30.0  1
 6B5  Var_05    C15   C08  C06  O05   -16.33  30.0  2
 6B5  Var_06    C16   C04  O05  C06  -178.90  30.0  1
 6B5  Var_07    C20   C17  O18  C19    -0.02  30.0  3
 6B5  Var_08    H193  C19  O18  C17    61.28  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
 6B5  plan-1  C10   0.020
 6B5  plan-1  C06   0.020
 6B5  plan-1  C08   0.020
 6B5  plan-1  C09   0.020
 6B5  plan-1  C11   0.020
 6B5  plan-1  O12   0.020
 6B5  plan-1  C13   0.020
 6B5  plan-1  O14   0.020
 6B5  plan-1  C15   0.020
 6B5  plan-1  H101  0.020
 6B5  plan-1  H091  0.020
 6B5  plan-1  H151  0.020
 6B5  plan-2  C02   0.020
 6B5  plan-2  C03   0.020
 6B5  plan-2  C04   0.020
 6B5  plan-2  O05   0.020
 6B5  plan-2  C16   0.020
 6B5  plan-2  C17   0.020
 6B5  plan-2  O18   0.020
 6B5  plan-2  C20   0.020
 6B5  plan-2  C21   0.020
 6B5  plan-2  O22   0.020
 6B5  plan-2  H161  0.020
 6B5  plan-2  H201  0.020
 6B5  plan-3  C02   0.020
 6B5  plan-3  C03   0.020
 6B5  plan-3  C07   0.020
 6B5  plan-3  O01   0.020

