# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 24 06:25:35 2020
#   Inital geometry file: a 93 line input string
#   Ligand name: (1R,3S)-7,8-dihydroxy-1-methoxy-3-methyl-10-oxo-4,10-dihydro-1H,3H-pyrano[4,3-b]chromene-9-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CO[C@@H]1O[C@@H](C)CC2=C1C(=O)c3c(O2)cc(O)c(O)c3C(O)=O
#
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
 113  113  '(1R,3S)-7,8-dihydroxy-1-methoxy-3-methyl-10-oxo-4,10-dihydro-1H,3H-pyrano[4,3-b]chromene-9-carboxylic acid'  ligand  37  23  .  2021-08-03  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_113
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
 113  C1    C  CR6   0   0.339   1.7576  -0.0474  -3.1387
 113  C2    C  CR16  0  -0.450   2.2959  -0.0298  -1.8662
 113  C3    C  CR66  0   0.363   1.4368  -0.0894  -0.7786
 113  C4    C  CR66  0  -0.131   0.0557  -0.1793  -0.9205
 113  C5    C  CR6   0  -0.124  -0.4702  -0.2086  -2.2207
 113  C6    C  CR6   0   0.244   0.3590  -0.1313  -3.3129
 113  O8    O  O     0  -0.458   2.0118  -0.0583   0.4439
 113  C9    C  CR6   0   0.376   1.2609  -0.1249   1.5479
 113  C10   C  CR6   0  -0.261  -0.0821  -0.2164   1.5200
 113  C11   C  CR6   0   0.473  -0.7984  -0.2424   0.2618
 113  C12   C  CH2   0  -0.548   2.0497  -0.1120   2.8085
 113  C13   C  CH1   0   0.018   1.1357   0.1597   3.9963
 113  O14   O  O2    0  -0.497  -0.0276  -0.6519   3.8842
 113  C15   C  CH1   0   0.281  -0.8517  -0.3302   2.8064
 113  O16   O  OH1   0  -0.648  -0.1195  -0.1888  -4.5881
 113  O17   O  OH1   0  -0.607   2.5736   0.0127  -4.1890
 113  C18   C  C     0   0.467  -1.9378  -0.3737  -2.4849
 113  O19   O  OH1   0  -0.577  -2.5409   0.7955  -2.6027
 113  O20   O  O2    0  -0.489  -1.5281   0.8733   2.9882
 113  C22   C  CH3   0  -0.411  -2.5319   0.8286   3.9812
 113  C26   C  CH3   0  -0.689   1.8008  -0.1530   5.3174
 113  O30   O  O     0  -0.419  -2.4600  -1.4417  -2.6565
 113  O31   O  OC    0  -0.432  -2.0169  -0.3307   0.1796
 113  H2    H  HCR6  0   0.300   3.3666   0.0365  -1.7217
 113  H121  H  HCH2  0   0.286   2.8279   0.6527   2.7525
 113  H122  H  HCH2  0   0.283   2.5586  -1.0765   2.9183
 113  H13   H  HCH1  0   0.234   0.8506   1.2183   3.9816
 113  H15   H  HCH1  0   0.234  -1.5666  -1.1618   2.7367
 113  H16   H  HOH1  0   0.489  -0.4644   0.6706  -4.8635
 113  H17   H  HOH1  0   0.481   2.0634  -0.0344  -5.0098
 113  H19   H  HOH1  0   0.490  -3.4826   0.6699  -2.7996
 113  H221  H  HCH3  0   0.239  -3.0770   1.7698   3.9356
 113  H222  H  HCH3  0   0.212  -3.2376   0.0098   3.8039
 113  H223  H  HCH3  0   0.216  -2.1199   0.7163   4.9874
 113  H261  H  HCH3  0   0.246   1.1278   0.0550   6.1493
 113  H262  H  HCH3  0   0.232   2.1075  -1.1987   5.3702
 113  H263  H  HCH3  0   0.237   2.6883   0.4668   5.4440

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
 113  C1   C2    aromatic  1.382  0.020  1.382
 113  C1   C6    aromatic  1.412  0.020  1.412
 113  C1   O17   single    1.331  0.020  1.331
 113  C2   C3    aromatic  1.387  0.020  1.387
 113  C2   H2    single    0.930  0.020  1.080
 113  C3   C4    aromatic  1.391  0.020  1.391
 113  C3   O8    aromatic  1.351  0.020  1.351
 113  C4   C5    aromatic  1.403  0.020  1.403
 113  C4   C11   aromatic  1.460  0.020  1.460
 113  C5   C6    aromatic  1.373  0.020  1.373
 113  C5   C18   single    1.500  0.020  1.500
 113  C6   O16   single    1.363  0.020  1.363
 113  O8   C9    aromatic  1.337  0.020  1.337
 113  C9   C10   aromatic  1.346  0.020  1.346
 113  C9   C12   single    1.487  0.020  1.487
 113  C10  C11   aromatic  1.448  0.020  1.448
 113  C10  C15   single    1.503  0.020  1.503
 113  C11  O31   double    1.224  0.020  1.224
 113  C12  C13   single    1.523  0.020  1.523
 113  C12  H121  single    0.970  0.020  1.090
 113  C12  H122  single    0.970  0.020  1.090
 113  C13  O14   single    1.423  0.020  1.423
 113  C13  C26   single    1.512  0.020  1.512
 113  C13  H13   single    0.970  0.020  1.090
 113  O14  C15   single    1.394  0.020  1.394
 113  C15  O20   single    1.393  0.020  1.393
 113  C15  H15   single    0.970  0.020  1.090
 113  O16  H16   single    0.850  0.020  0.980
 113  O17  H17   single    0.850  0.020  0.980
 113  C18  O19   single    1.321  0.020  1.321
 113  C18  O30   double    1.201  0.020  1.201
 113  O19  H19   single    0.850  0.020  0.980
 113  O20  C22   single    1.413  0.020  1.413
 113  C22  H221  single    0.970  0.020  1.090
 113  C22  H222  single    0.970  0.020  1.090
 113  C22  H223  single    0.970  0.020  1.090
 113  C26  H261  single    0.970  0.020  1.090
 113  C26  H262  single    0.970  0.020  1.090
 113  C26  H263  single    0.970  0.020  1.090

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
 113  O17   C1   C6    120.83  3.000
 113  O17   C1   C2    119.16  3.000
 113  C6    C1   C2    120.02  3.000
 113  H2    C2   C3    120.70  3.000
 113  H2    C2   C1    120.60  3.000
 113  C3    C2   C1    118.70  3.000
 113  O8    C3   C4    121.07  3.000
 113  O8    C3   C2    116.41  3.000
 113  C4    C3   C2    122.52  3.000
 113  C11   C4   C5    122.03  3.000
 113  C11   C4   C3    120.07  3.000
 113  C5    C4   C3    117.90  3.000
 113  C18   C5   C6    117.18  3.000
 113  C18   C5   C4    122.16  3.000
 113  C6    C5   C4    120.63  3.000
 113  O16   C6   C5    121.98  3.000
 113  O16   C6   C1    117.75  3.000
 113  C5    C6   C1    120.22  3.000
 113  C9    O8   C3    120.47  3.000
 113  C12   C9   C10   123.18  3.000
 113  C12   C9   O8    113.69  3.000
 113  C10   C9   O8    123.13  3.000
 113  C15   C10  C11   119.27  3.000
 113  C15   C10  C9    119.87  3.000
 113  C11   C10  C9    120.84  3.000
 113  O31   C11  C10   123.50  3.000
 113  O31   C11  C4    122.07  3.000
 113  C10   C11  C4    114.42  3.000
 113  H122  C12  H121  106.87  3.000
 113  H122  C12  C13   110.94  3.000
 113  H121  C12  C13   110.03  3.000
 113  H122  C12  C9    108.88  3.000
 113  H121  C12  C9    109.91  3.000
 113  C13   C12  C9    110.14  3.000
 113  H13   C13  C26   109.01  3.000
 113  H13   C13  O14   109.70  3.000
 113  C26   C13  O14   108.09  3.000
 113  H13   C13  C12   108.53  3.000
 113  C26   C13  C12   112.37  3.000
 113  O14   C13  C12   109.11  3.000
 113  C15   O14  C13   114.36  3.000
 113  H15   C15  O20   110.26  3.000
 113  H15   C15  O14   105.01  3.000
 113  O20   C15  O14   112.68  3.000
 113  H15   C15  C10   109.63  3.000
 113  O20   C15  C10   107.15  3.000
 113  O14   C15  C10   112.11  3.000
 113  H16   O16  C6    110.76  3.000
 113  H17   O17  C1    110.12  3.000
 113  O30   C18  O19   125.16  3.000
 113  O30   C18  C5    123.25  3.000
 113  O19   C18  C5    111.40  3.000
 113  H19   O19  C18   110.28  3.000
 113  C22   O20  C15   114.18  3.000
 113  H223  C22  H222  108.37  3.000
 113  H223  C22  H221  108.43  3.000
 113  H222  C22  H221  108.48  3.000
 113  H223  C22  O20   112.49  3.000
 113  H222  C22  O20   111.57  3.000
 113  H221  C22  O20   107.39  3.000
 113  H263  C26  H262  108.09  3.000
 113  H263  C26  H261  107.79  3.000
 113  H262  C26  H261  108.64  3.000
 113  H263  C26  C13   110.01  3.000
 113  H262  C26  C13   111.36  3.000
 113  H261  C26  C13   110.84  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
 113  CONST_01  C4    C3   C2   C1      0.00   0.0  0
 113  CONST_02  O8    C3   C2   C1    180.00   0.0  0
 113  CONST_03  C4    C5   C6   C1      0.00   0.0  0
 113  CONST_04  C5    C6   C1   C2      0.00   0.0  0
 113  CONST_05  C5    C4   C3   C2      0.00   0.0  0
 113  CONST_06  C11   C4   C3   C2    180.00   0.0  0
 113  CONST_07  C9    O8   C3   C2    180.00   0.0  0
 113  CONST_08  C6    C1   C2   C3      0.00   0.0  0
 113  CONST_09  C6    C5   C4   C3      0.00   0.0  0
 113  CONST_10  C10   C11  C4   C3      0.00   0.0  0
 113  CONST_11  C10   C9   O8   C3      0.00   0.0  0
 113  CONST_12  C9    O8   C3   C4      0.00   0.0  0
 113  CONST_13  C9    C10  C11  C4      0.00   0.0  0
 113  CONST_14  O8    C3   C4   C5    180.00   0.0  0
 113  CONST_15  C10   C11  C4   C5    180.00   0.0  0
 113  CONST_16  C11   C4   C5   C6    180.00   0.0  0
 113  CONST_17  C11   C4   C3   O8      0.00   0.0  0
 113  CONST_18  C11   C10  C9   O8      0.00   0.0  0
 113  CONST_19  C18   C5   C6   C1    180.00   0.0  0
 113  CONST_20  O16   C6   C1   C2    180.00   0.0  0
 113  CONST_21  O17   C1   C2   C3    180.00   0.0  0
 113  CONST_22  C18   C5   C4   C3    180.00   0.0  0
 113  CONST_23  O31   C11  C4   C3    180.00   0.0  0
 113  CONST_24  O16   C6   C5   C4    180.00   0.0  0
 113  CONST_25  O31   C11  C4   C5      0.00   0.0  0
 113  CONST_26  O17   C1   C6   C5    180.00   0.0  0
 113  CONST_27  O31   C11  C10  C9    180.00   0.0  0
 113  CONST_28  C18   C5   C4   C11     0.00   0.0  0
 113  CONST_29  O31   C11  C10  C15     0.00   0.0  0
 113  CONST_30  H2    C2   C3   C4    180.00   0.0  0
 113  CONST_31  H19   O19  C18  C5    180.00   0.0  0
 113  Var_01    C13   C12  C9   O8    165.90  30.0  1
 113  Var_02    O19   C18  C5   C4     92.99  30.0  2
 113  Var_03    H221  C22  O20  C15  -172.24  30.0  3

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
 113  chir_01  C13  C12  O14  C26  negativ
 113  chir_02  C15  O20  O14  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
 113  plan-1  C4   0.020
 113  plan-1  C10  0.020
 113  plan-1  C11  0.020
 113  plan-1  O31  0.020
 113  plan-2  C1   0.020
 113  plan-2  C2   0.020
 113  plan-2  C3   0.020
 113  plan-2  C4   0.020
 113  plan-2  C5   0.020
 113  plan-2  C6   0.020
 113  plan-2  O8   0.020
 113  plan-2  C11  0.020
 113  plan-2  O16  0.020
 113  plan-2  O17  0.020
 113  plan-2  C18  0.020
 113  plan-2  H2   0.020
 113  plan-3  C5   0.020
 113  plan-3  C18  0.020
 113  plan-3  O19  0.020
 113  plan-3  O30  0.020
 113  plan-3  H19  0.020

