# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 30 13:44:57 2022
#   Inital geometry file: a 112 line input string
#   Ligand name: (9~{b}~{R})-2,6-diethanoyl-8,9~{b}-dimethyl-3,7,9-tris(oxidanyl)dibenzofuran-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(=O)C1=C(O)C=C2Oc3c(C(C)=O)c(O)c(C)c(O)c3[C@@]2(C)C1=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
 AIY  AIY  "(9bR)-2,6-diethanoyl-8,9b-dimethyl-3,7,9-tris(oxidanyl)dibenzofuran-1-one"
  ligand  41  25  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_AIY
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
 AIY  C10  C  CR6   0   0.327  15.2878  -2.9048  26.4430
 AIY  C13  C  CR6   0  -0.272  12.9221  -1.5371  27.2704
 AIY  C15  C  C     0   0.460  16.4734  -1.5014  20.8564
 AIY  C20  C  CH3   0  -0.776  15.1728  -4.3942  28.4877
 AIY  C22  C  C     0   0.370  11.7096  -0.7741  27.6604
 AIY  C1   C  CT    0  -0.491  15.2570  -1.1077  24.4958
 AIY  C2   C  C     0   0.544  14.0384  -0.3232  24.1571
 AIY  C3   C  C1    0  -0.482  13.8214   0.2331  22.9599
 AIY  C4   C  C     0   0.472  14.7264  -0.1342  21.9093
 AIY  C5   C  C     0  -0.378  15.7043  -1.1558  22.0354
 AIY  C6   C  C     0   0.491  15.8572  -1.8186  23.3036
 AIY  C7   C  CR6   0  -0.083  14.7332  -1.8935  25.6640
 AIY  C8   C  CR6   0   0.426  13.5749  -1.2735  26.0769
 AIY  C11  C  CR6   0  -0.159  14.6524  -3.2671  27.6392
 AIY  C12  C  CR6   0   0.339  13.5044  -2.5723  28.0338
 AIY  C16  C  CH3   0  -0.754  17.5176  -2.5729  20.8686
 AIY  C23  C  CH3   0  -0.766  11.4748  -0.4389  29.1101
 AIY  C25  C  CH3   0  -0.595  16.3587  -0.1144  24.9789
 AIY  O9   O  O2    0  -0.448  13.1884  -0.2958  25.1876
 AIY  O14  O  OH1   0  -0.569  14.5453   0.4693  20.7809
 AIY  O17  O  O     0  -0.502  16.2821  -0.8816  19.7951
 AIY  O18  O  O     0  -0.456  16.5140  -2.8364  23.4994
 AIY  O19  O  OH1   0  -0.632  16.4004  -3.5389  26.0826
 AIY  O21  O  OH1   0  -0.607  12.8592  -2.9054  29.1592
 AIY  O24  O  O     0  -0.389  10.9439  -0.3780  26.8060
 AIY  H1   H  HCH3  0   0.258  15.5183  -4.0477  29.4654
 AIY  H2   H  HCH3  0   0.254  14.4127  -5.1611  28.6580
 AIY  H3   H  HCH3  0   0.278  16.0158  -4.8927  28.0177
 AIY  H5   H  H     0   0.300  12.9619   0.8494  22.7333
 AIY  H9   H  HCH3  0   0.259  18.0296  -2.5838  19.9090
 AIY  H10  H  HCH3  0   0.267  18.2453  -2.4109  21.6627
 AIY  H11  H  HCH3  0   0.271  17.0697  -3.5507  21.0427
 AIY  H12  H  HCH3  0   0.258  10.9073   0.4886  29.1685
 AIY  H13  H  HCH3  0   0.270  10.8840  -1.2209  29.5886
 AIY  H14  H  HCH3  0   0.253  12.3996  -0.3335  29.6730
 AIY  H15  H  HCH3  0   0.267  15.9818   0.4814  25.8084
 AIY  H16  H  HCH3  0   0.266  17.2254  -0.6768  25.3238
 AIY  H17  H  HCH3  0   0.264  16.6650   0.5523  24.1741
 AIY  H18  H  HOH1  0   0.490  15.2216   0.0543  20.1244
 AIY  H19  H  HOH1  0   0.483  16.5989  -3.3371  25.1378
 AIY  H20  H  HOH1  0   0.492  13.3369  -3.5778  29.6589

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
 AIY  O17  C15  double    1.244  0.020  1.244
 AIY  O14  C4   single    1.292  0.020  1.292
 AIY  C15  C16  single    1.496  0.020  1.496
 AIY  C15  C5   single    1.449  0.020  1.449
 AIY  C4   C5   double    1.420  0.020  1.420
 AIY  C4   C3   single    1.435  0.020  1.435
 AIY  C5   C6   single    1.439  0.020  1.439
 AIY  C3   C2   double    1.338  0.020  1.338
 AIY  C6   O18  double    1.227  0.020  1.227
 AIY  C6   C1   single    1.512  0.020  1.512
 AIY  C2   C1   single    1.488  0.020  1.488
 AIY  C2   O9   single    1.336  0.020  1.336
 AIY  C1   C25  single    1.560  0.020  1.560
 AIY  C1   C7   single    1.502  0.020  1.502
 AIY  O9   C8   single    1.377  0.020  1.377
 AIY  C7   C8   aromatic  1.377  0.020  1.377
 AIY  C7   C10  aromatic  1.392  0.020  1.392
 AIY  O19  C10  single    1.330  0.020  1.330
 AIY  C8   C13  aromatic  1.386  0.020  1.386
 AIY  C10  C11  aromatic  1.402  0.020  1.402
 AIY  O24  C22  double    1.214  0.020  1.214
 AIY  C13  C22  single    1.485  0.020  1.485
 AIY  C13  C12  aromatic  1.412  0.020  1.412
 AIY  C11  C12  aromatic  1.399  0.020  1.399
 AIY  C11  C20  single    1.504  0.020  1.504
 AIY  C22  C23  single    1.506  0.020  1.506
 AIY  C12  O21  single    1.339  0.020  1.339
 AIY  C20  H1   single    0.970  0.020  1.090
 AIY  C20  H2   single    0.970  0.020  1.090
 AIY  C20  H3   single    0.970  0.020  1.090
 AIY  C3   H5   single    0.930  0.020  1.080
 AIY  C16  H9   single    0.970  0.020  1.090
 AIY  C16  H10  single    0.970  0.020  1.090
 AIY  C16  H11  single    0.970  0.020  1.090
 AIY  C23  H12  single    0.970  0.020  1.090
 AIY  C23  H13  single    0.970  0.020  1.090
 AIY  C23  H14  single    0.970  0.020  1.090
 AIY  C25  H15  single    0.970  0.020  1.090
 AIY  C25  H16  single    0.970  0.020  1.090
 AIY  C25  H17  single    0.970  0.020  1.090
 AIY  O14  H18  single    0.850  0.020  0.980
 AIY  O19  H19  single    0.850  0.020  0.980
 AIY  O21  H20  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
 AIY  O19  C10  C11  119.14  3.000
 AIY  C11  C10  C7   118.99  3.000
 AIY  O19  C10  C7   121.87  3.000
 AIY  C12  C13  C8   114.26  3.000
 AIY  C12  C13  C22  124.86  3.000
 AIY  C8   C13  C22  120.88  3.000
 AIY  O17  C15  C16  118.11  3.000
 AIY  C16  C15  C5   122.31  3.000
 AIY  O17  C15  C5   119.58  3.000
 AIY  H3   C20  H2   106.56  3.000
 AIY  H3   C20  H1   106.69  3.000
 AIY  H2   C20  H1   107.62  3.000
 AIY  H3   C20  C11  111.62  3.000
 AIY  H2   C20  C11  111.91  3.000
 AIY  H1   C20  C11  112.11  3.000
 AIY  O24  C22  C23  120.43  3.000
 AIY  C23  C22  C13  119.63  3.000
 AIY  O24  C22  C13  119.87  3.000
 AIY  C25  C1   C7   109.79  3.000
 AIY  C7   C1   C6   120.37  3.000
 AIY  C25  C1   C6   105.25  3.000
 AIY  C7   C1   C2    99.63  3.000
 AIY  C25  C1   C2   108.25  3.000
 AIY  C6   C1   C2   113.16  3.000
 AIY  O9   C2   C3   125.34  3.000
 AIY  O9   C2   C1   110.86  3.000
 AIY  C3   C2   C1   123.76  3.000
 AIY  H5   C3   C4   119.59  3.000
 AIY  H5   C3   C2   123.60  3.000
 AIY  C4   C3   C2   116.53  3.000
 AIY  O14  C4   C5   120.67  3.000
 AIY  C5   C4   C3   123.62  3.000
 AIY  O14  C4   C3   115.56  3.000
 AIY  C6   C5   C4   118.87  3.000
 AIY  C6   C5   C15  123.41  3.000
 AIY  C4   C5   C15  117.70  3.000
 AIY  O18  C6   C5   125.41  3.000
 AIY  O18  C6   C1   118.46  3.000
 AIY  C5   C6   C1   115.85  3.000
 AIY  C8   C7   C1   106.91  3.000
 AIY  C8   C7   C10  119.63  3.000
 AIY  C1   C7   C10  132.57  3.000
 AIY  O9   C8   C7   111.23  3.000
 AIY  C7   C8   C13  124.67  3.000
 AIY  O9   C8   C13  123.99  3.000
 AIY  C12  C11  C20  119.81  3.000
 AIY  C20  C11  C10  121.22  3.000
 AIY  C12  C11  C10  118.96  3.000
 AIY  O21  C12  C11  120.59  3.000
 AIY  O21  C12  C13  115.98  3.000
 AIY  C11  C12  C13  123.38  3.000
 AIY  H11  C16  H10  106.96  3.000
 AIY  H11  C16  H9   109.00  3.000
 AIY  H10  C16  H9   109.28  3.000
 AIY  H11  C16  C15  110.92  3.000
 AIY  H10  C16  C15  111.46  3.000
 AIY  H9   C16  C15  109.18  3.000
 AIY  H14  C23  H13  107.64  3.000
 AIY  H14  C23  H12  109.44  3.000
 AIY  H13  C23  H12  107.75  3.000
 AIY  H14  C23  C22  112.77  3.000
 AIY  H13  C23  C22  110.31  3.000
 AIY  H12  C23  C22  108.81  3.000
 AIY  H17  C25  H16  109.05  3.000
 AIY  H17  C25  H15  108.99  3.000
 AIY  H16  C25  H15  108.47  3.000
 AIY  H17  C25  C1   111.07  3.000
 AIY  H16  C25  C1   109.35  3.000
 AIY  H15  C25  C1   109.87  3.000
 AIY  C8   O9   C2   107.76  3.000
 AIY  H18  O14  C4   106.04  3.000
 AIY  H19  O19  C10  109.29  3.000
 AIY  H20  O21  C12  111.72  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
 AIY  CONST_01  C13  C8   C7   C10     0.00   0.0  0
 AIY  CONST_02  C13  C12  C11  C10     0.00   0.0  0
 AIY  CONST_03  C12  C13  C8   C7      0.00   0.0  0
 AIY  CONST_04  C12  C11  C10  C7      0.00   0.0  0
 AIY  CONST_05  C11  C10  C7   C8      0.00   0.0  0
 AIY  CONST_06  C11  C12  C13  C8      0.00   0.0  0
 AIY  CONST_07  O21  C12  C11  C10   180.00   0.0  0
 AIY  CONST_08  C20  C11  C12  C13   180.00   0.0  0
 AIY  CONST_09  C7   C10  C11  C20   180.00   0.0  0
 AIY  CONST_10  O9   C8   C13  C22     0.00   0.0  0
 AIY  CONST_11  C7   C8   C13  C22   180.00   0.0  0
 AIY  CONST_12  C11  C12  C13  C22   180.00   0.0  0
 AIY  CONST_13  O19  C10  C7   C1      0.00   0.0  0
 AIY  CONST_14  O19  C10  C7   C8    180.00   0.0  0
 AIY  CONST_15  O21  C12  C13  C8    180.00   0.0  0
 AIY  CONST_16  O19  C10  C11  C12   180.00   0.0  0
 AIY  Var_01    C4   C3   C2   C1      9.83   0.0  0
 AIY  Var_02    O9   C2   C3   C4   -167.73   0.0  0
 AIY  Var_03    C2   O9   C8   C13   179.96  30.0  1
 AIY  Var_04    C4   C5   C6   C1    -17.37  30.0  1
 AIY  Var_05    C8   O9   C2   C1    -14.98  30.0  1
 AIY  Var_06    C5   C4   C3   C2      8.07  30.0  1
 AIY  Var_07    C7   C8   O9   C2      3.59  30.0  1
 AIY  Var_08    C6   C5   C4   C3     -3.53  30.0  1
 AIY  Var_09    C8   O9   C2   C3    162.84  30.0  1
 AIY  Var_10    C3   C4   C5   C15   174.72  30.0  1
 AIY  Var_11    C1   C6   C5   C15   164.48  30.0  1
 AIY  Var_12    O14  C4   C3   C2   -176.34  30.0  1
 AIY  Var_13    O18  C6   C5   C4    168.71  30.0  1
 AIY  Var_14    O14  C4   C5   C6   -178.91  30.0  1
 AIY  Var_15    H5   C3   C2   C1   -176.41   0.0  0
 AIY  Var_16    H5   C3   C2   O9      6.04   0.0  0
 AIY  Var_17    H5   C3   C4   C5   -165.96  30.0  1
 AIY  Var_18    O14  C4   C5   C15    -0.65  30.0  1
 AIY  Var_19    O18  C6   C5   C15    -9.44  30.0  1
 AIY  Var_20    O17  C15  C5   C4      1.77  30.0  3
 AIY  Var_21    C16  C15  C5   C4   -179.24  30.0  3
 AIY  Var_22    O17  C15  C5   C6    179.94  30.0  3
 AIY  Var_23    C16  C15  C5   C6     -1.07  30.0  3
 AIY  Var_24    O24  C22  C13  C8     32.63  30.0  2
 AIY  Var_25    C23  C22  C13  C8   -144.36  30.0  2
 AIY  Var_26    O24  C22  C13  C12  -146.80  30.0  2
 AIY  Var_27    C23  C22  C13  C12    36.21  30.0  2
 AIY  Var_28    H1   C20  C11  C10   115.63  30.0  2
 AIY  Var_29    H2   C20  C11  C10  -123.33  30.0  2
 AIY  Var_30    H3   C20  C11  C10    -4.00  30.0  2
 AIY  Var_31    H1   C20  C11  C12   -65.17  30.0  2
 AIY  Var_32    H2   C20  C11  C12    55.87  30.0  2
 AIY  Var_33    H3   C20  C11  C12   175.20  30.0  2
 AIY  Var_34    H5   C3   C4   O14     9.63  30.0  1
 AIY  Var_35    H12  C23  C22  C13   150.77  30.0  3
 AIY  Var_36    H13  C23  C22  C13   -91.23  30.0  3
 AIY  Var_37    H14  C23  C22  C13    29.15  30.0  3
 AIY  Var_38    H9   C16  C15  C5   -174.18  30.0  3
 AIY  Var_39    H10  C16  C15  C5    -53.36  30.0  3
 AIY  Var_40    H11  C16  C15  C5     65.70  30.0  3
 AIY  Var_41    H9   C16  C15  O17     4.82  30.0  3
 AIY  Var_42    H10  C16  C15  O17   125.64  30.0  3
 AIY  Var_43    H11  C16  C15  O17  -115.30  30.0  3
 AIY  Var_44    H12  C23  C22  O24   -26.21  30.0  3
 AIY  Var_45    H13  C23  C22  O24    91.79  30.0  3
 AIY  Var_46    H14  C23  C22  O24  -147.83  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
 AIY  chir_01  C1  C2  C6  C7  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
 AIY  plan-1  C15  0.020
 AIY  plan-1  C5   0.020
 AIY  plan-1  C16  0.020
 AIY  plan-1  O17  0.020
 AIY  plan-2  C10  0.020
 AIY  plan-2  C13  0.020
 AIY  plan-2  C20  0.020
 AIY  plan-2  C22  0.020
 AIY  plan-2  C1   0.020
 AIY  plan-2  C7   0.020
 AIY  plan-2  C8   0.020
 AIY  plan-2  C11  0.020
 AIY  plan-2  C12  0.020
 AIY  plan-2  O9   0.020
 AIY  plan-2  O19  0.020
 AIY  plan-2  O21  0.020
 AIY  plan-3  C13  0.020
 AIY  plan-3  C22  0.020
 AIY  plan-3  C23  0.020
 AIY  plan-3  O24  0.020
 AIY  plan-4  C1   0.020
 AIY  plan-4  C5   0.020
 AIY  plan-4  C6   0.020
 AIY  plan-4  O18  0.020
 AIY  plan-5  C1   0.020
 AIY  plan-5  C2   0.020
 AIY  plan-5  C3   0.020
 AIY  plan-5  C4   0.020
 AIY  plan-5  O9   0.020
 AIY  plan-5  H5   0.020

