# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 11:22:14 2022
#   Inital geometry file: a 130 line input string
#   Ligand name: 7-(5-hydroxy-2-methylphenyl)-8-(2-methoxyphenyl)-1-methyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccccc1n2c(cn3c2nc4N(C)C(=O)NC(=O)c34)c5cc(O)ccc5C
#
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
 L66  L66  7-(5-hydroxy-2-methylphenyl)-8-(2-methoxyphenyl)-1-methyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione  ligand  50  31  .  2022-03-22  2022-03-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_L66
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
 L66  O2   O  O     0  -0.487  -6.3774  -0.5276   0.4254
 L66  C17  C  CR6   0   0.688  -5.2271  -0.1358   0.3754
 L66  N4   N  NR16  0  -0.740  -4.9198   1.1943   0.5742
 L66  C16  C  CR6   0   0.525  -3.6802   1.8316   0.5452
 L66  O3   O  O     0  -0.473  -3.5726   3.0318   0.7385
 L66  N5   N  NR6   0  -0.591  -4.1628  -0.9704   0.1248
 L66  C18  C  CH3   0  -0.533  -4.3608  -2.3924  -0.0990
 L66  C2   C  CR56  0   0.447  -2.9002  -0.4520   0.0636
 L66  C3   C  CR56  0   0.113  -2.6594   0.8979   0.2697
 L66  N1   N  N     0  -0.514  -1.7912  -1.1639  -0.1899
 L66  C1   C  CR55  0   0.769  -0.8477  -0.2328  -0.1335
 L66  N2   N  N     0  -0.562  -1.2900   1.0120   0.1315
 L66  C4   C  CR15  0  -0.157  -0.2309   1.8930   0.1377
 L66  N3   N  NR5   0  -0.640   0.4872  -0.1731  -0.2974
 L66  C5   C  CR5   0   0.226   0.8785   1.1573  -0.1252
 L66  C10  C  CR6   0   0.021   2.2882   1.5561  -0.1914
 L66  C11  C  CR6   0   0.059   2.7380   2.4552  -1.1626
 L66  C40  C  CH3   0  -0.743   1.8185   3.0670  -2.1803
 L66  C12  C  CR16  0  -0.285   4.0965   2.7662  -1.1642
 L66  C13  C  CR16  0  -0.325   4.9819   2.2162  -0.2540
 L66  C15  C  CR16  0  -0.398   3.1704   0.9940   0.7301
 L66  C14  C  CR6   0   0.359   4.5194   1.3204   0.7056
 L66  O41  O  OH1   0  -0.633   5.4108   0.8089   1.5785
 L66  C32  C  CR6   0   0.179   1.3198  -1.2695  -0.6203
 L66  C33  C  CR16  0  -0.245   1.9254  -1.3407  -1.8615
 L66  C34  C  CR16  0  -0.284   2.7509  -2.4116  -2.1713
 L66  C35  C  CR16  0  -0.235   2.9472  -3.4084  -1.2278
 L66  C36  C  CR16  0  -0.384   2.3434  -3.3449   0.0217
 L66  C37  C  CR6   0   0.387   1.5279  -2.2631   0.3434
 L66  O38  O  O2    0  -0.460   0.9191  -2.0799   1.5206
 L66  C39  C  CH3   0  -0.439   1.0361  -3.0862   2.5106
 L66  H1   H  HNR6  0   0.425  -5.7201   1.7850   0.7607
 L66  H2   H  HCH3  0   0.270  -5.3874  -2.6516   0.1300
 L66  H3   H  HCH3  0   0.258  -4.1495  -2.6497  -1.1357
 L66  H4   H  HCH3  0   0.259  -3.6987  -2.9624   0.5485
 L66  H5   H  HCR5  0   0.315  -0.3346   2.9434   0.3422
 L66  H6   H  HCH3  0   0.247   1.1307   3.7852  -1.7319
 L66  H7   H  HCH3  0   0.251   2.3894   3.5949  -2.9428
 L66  H8   H  HCH3  0   0.243   1.2087   2.3155  -2.6841
 L66  H9   H  HCR6  0   0.255   4.4780   3.4551  -1.9083
 L66  H10  H  HCR6  0   0.266   6.0319   2.4790  -0.2859
 L66  H11  H  HCR6  0   0.267   2.7912   0.3087   1.4812
 L66  H12  H  HOH1  0   0.474   4.9722   0.2199   2.2022
 L66  H13  H  HCR6  0   0.271   1.7471  -0.5541  -2.5840
 L66  H14  H  HCR6  0   0.263   3.2267  -2.4679  -3.1404
 L66  H15  H  HCR6  0   0.268   3.5813  -4.2543  -1.4590
 L66  H16  H  HCR6  0   0.289   2.5218  -4.1372   0.7354
 L66  H17  H  HCH3  0   0.264   0.4431  -2.7519   3.3575
 L66  H18  H  HCH3  0   0.235   0.6459  -4.0443   2.1602
 L66  H19  H  HCH3  0   0.234   2.0706  -3.2188   2.8356

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
 L66  C35  C36  aromatic  1.389  0.020  1.389
 L66  C35  C34  aromatic  1.387  0.020  1.387
 L66  C36  C37  aromatic  1.392  0.020  1.392
 L66  C34  C33  aromatic  1.387  0.020  1.387
 L66  C37  O38  single    1.338  0.020  1.338
 L66  C37  C32  aromatic  1.400  0.020  1.400
 L66  C33  C32  aromatic  1.383  0.020  1.383
 L66  C39  O38  single    1.416  0.020  1.416
 L66  C32  N3   single    1.414  0.020  1.414
 L66  O41  C14  single    1.348  0.020  1.348
 L66  C14  C15  aromatic  1.388  0.020  1.388
 L66  C14  C13  aromatic  1.392  0.020  1.392
 L66  N3   C1   aromatic  1.346  0.020  1.346
 L66  N3   C5   aromatic  1.397  0.020  1.397
 L66  C15  C10  aromatic  1.394  0.020  1.394
 L66  N1   C1   aromatic  1.327  0.020  1.327
 L66  N1   C2   aromatic  1.342  0.020  1.342
 L66  C18  N5   single    1.453  0.020  1.453
 L66  C13  C12  aromatic  1.384  0.020  1.384
 L66  C1   N2   aromatic  1.347  0.020  1.347
 L66  C10  C5   single    1.466  0.020  1.466
 L66  C10  C11  aromatic  1.398  0.020  1.398
 L66  C5   C4   aromatic  1.357  0.020  1.357
 L66  C12  C11  aromatic  1.394  0.020  1.394
 L66  C2   N5   single    1.366  0.020  1.366
 L66  C2   C3   aromatic  1.387  0.020  1.387
 L66  C11  C40  single    1.502  0.020  1.502
 L66  N5   C17  single    1.376  0.020  1.376
 L66  N2   C4   aromatic  1.378  0.020  1.378
 L66  N2   C3   aromatic  1.381  0.020  1.381
 L66  C3   C16  single    1.411  0.020  1.411
 L66  C17  O2   double    1.216  0.020  1.216
 L66  C17  N4   single    1.380  0.020  1.380
 L66  C16  N4   single    1.394  0.020  1.394
 L66  C16  O3   double    1.220  0.020  1.220
 L66  N4   H1   single    0.860  0.020  1.020
 L66  C18  H2   single    0.970  0.020  1.090
 L66  C18  H3   single    0.970  0.020  1.090
 L66  C18  H4   single    0.970  0.020  1.090
 L66  C4   H5   single    0.930  0.020  1.080
 L66  C40  H6   single    0.970  0.020  1.090
 L66  C40  H7   single    0.970  0.020  1.090
 L66  C40  H8   single    0.970  0.020  1.090
 L66  C12  H9   single    0.930  0.020  1.080
 L66  C13  H10  single    0.930  0.020  1.080
 L66  C15  H11  single    0.930  0.020  1.080
 L66  O41  H12  single    0.850  0.020  0.980
 L66  C33  H13  single    0.930  0.020  1.080
 L66  C34  H14  single    0.930  0.020  1.080
 L66  C35  H15  single    0.930  0.020  1.080
 L66  C36  H16  single    0.930  0.020  1.080
 L66  C39  H17  single    0.970  0.020  1.090
 L66  C39  H18  single    0.970  0.020  1.090
 L66  C39  H19  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
 L66  N5   C17  N4   116.04  3.000
 L66  N4   C17  O2   121.02  3.000
 L66  N5   C17  O2   122.94  3.000
 L66  H1   N4   C16  116.12  3.000
 L66  H1   N4   C17  114.41  3.000
 L66  C16  N4   C17  129.48  3.000
 L66  C3   C16  O3   128.18  3.000
 L66  O3   C16  N4   121.64  3.000
 L66  C3   C16  N4   110.18  3.000
 L66  C2   N5   C18  119.37  3.000
 L66  C2   N5   C17  119.53  3.000
 L66  C18  N5   C17  121.09  3.000
 L66  H4   C18  H3   108.96  3.000
 L66  H4   C18  H2   109.01  3.000
 L66  H3   C18  H2   109.19  3.000
 L66  H4   C18  N5   109.77  3.000
 L66  H3   C18  N5   110.57  3.000
 L66  H2   C18  N5   109.31  3.000
 L66  N1   C2   C3   113.64  3.000
 L66  C3   C2   N5   121.55  3.000
 L66  N1   C2   N5   124.81  3.000
 L66  N2   C3   C2   103.76  3.000
 L66  N2   C3   C16  133.03  3.000
 L66  C2   C3   C16  123.21  3.000
 L66  C1   N1   C2   101.97  3.000
 L66  N3   C1   N2   107.97  3.000
 L66  N2   C1   N1   115.04  3.000
 L66  N3   C1   N1   136.98  3.000
 L66  C4   N2   C1   109.83  3.000
 L66  C4   N2   C3   144.56  3.000
 L66  C1   N2   C3   105.60  3.000
 L66  H5   C4   C5   130.20  3.000
 L66  H5   C4   N2   123.46  3.000
 L66  C5   C4   N2   106.32  3.000
 L66  C32  N3   C5   126.97  3.000
 L66  C5   N3   C1   107.75  3.000
 L66  C32  N3   C1   125.26  3.000
 L66  C10  C5   N3   121.50  3.000
 L66  C10  C5   C4   130.34  3.000
 L66  N3   C5   C4   108.12  3.000
 L66  C15  C10  C11  121.00  3.000
 L66  C11  C10  C5   121.04  3.000
 L66  C15  C10  C5   117.96  3.000
 L66  C12  C11  C40  120.34  3.000
 L66  C40  C11  C10  122.40  3.000
 L66  C12  C11  C10  117.26  3.000
 L66  H8   C40  H7   107.68  3.000
 L66  H8   C40  H6   106.91  3.000
 L66  H7   C40  H6   107.41  3.000
 L66  H8   C40  C11  111.99  3.000
 L66  H7   C40  C11  110.55  3.000
 L66  H6   C40  C11  112.07  3.000
 L66  H9   C12  C13  118.63  3.000
 L66  H9   C12  C11  119.07  3.000
 L66  C13  C12  C11  122.29  3.000
 L66  H10  C13  C14  119.92  3.000
 L66  H10  C13  C12  120.30  3.000
 L66  C14  C13  C12  119.78  3.000
 L66  H11  C15  C14  120.02  3.000
 L66  H11  C15  C10  119.40  3.000
 L66  C14  C15  C10  120.56  3.000
 L66  O41  C14  C15  122.81  3.000
 L66  C15  C14  C13  119.11  3.000
 L66  O41  C14  C13  118.08  3.000
 L66  H12  O41  C14  110.48  3.000
 L66  C37  C32  C33  121.09  3.000
 L66  C33  C32  N3   120.18  3.000
 L66  C37  C32  N3   118.73  3.000
 L66  H13  C33  C34  120.65  3.000
 L66  H13  C33  C32  119.31  3.000
 L66  C34  C33  C32  120.05  3.000
 L66  H14  C34  C35  120.68  3.000
 L66  H14  C34  C33  120.15  3.000
 L66  C35  C34  C33  119.17  3.000
 L66  H15  C35  C36  118.86  3.000
 L66  H15  C35  C34  119.97  3.000
 L66  C36  C35  C34  121.18  3.000
 L66  H16  C36  C37  120.89  3.000
 L66  H16  C36  C35  119.24  3.000
 L66  C37  C36  C35  119.86  3.000
 L66  O38  C37  C36  125.18  3.000
 L66  O38  C37  C32  116.17  3.000
 L66  C36  C37  C32  118.65  3.000
 L66  C39  O38  C37  118.69  3.000
 L66  H19  C39  H18  109.10  3.000
 L66  H19  C39  H17  108.80  3.000
 L66  H18  C39  H17  108.96  3.000
 L66  H19  C39  O38  111.86  3.000
 L66  H18  C39  O38  111.69  3.000
 L66  H17  C39  O38  106.33  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
 L66  CONST_01  N3   C1   N1   C2    180.00   0.0  0
 L66  CONST_02  N2   C1   N1   C2      0.00   0.0  0
 L66  CONST_03  C1   N2   C3   C2      0.00   0.0  0
 L66  CONST_04  C4   N2   C3   C2    180.00   0.0  0
 L66  CONST_05  C1   N1   C2   C3      0.00   0.0  0
 L66  CONST_06  N3   C1   N2   C3    180.00   0.0  0
 L66  CONST_07  N1   C1   N2   C3      0.00   0.0  0
 L66  CONST_08  C5   C4   N2   C3    180.00   0.0  0
 L66  CONST_09  C32  N3   C1   N1      0.00   0.0  0
 L66  CONST_10  C5   N3   C1   N1    180.00   0.0  0
 L66  CONST_11  C4   N2   C1   N1    180.00   0.0  0
 L66  CONST_12  N2   C3   C2   N1      0.00   0.0  0
 L66  CONST_15  C10  C5   N3   C1    180.00   0.0  0
 L66  CONST_16  C4   C5   N3   C1      0.00   0.0  0
 L66  CONST_17  C5   C4   N2   C1      0.00   0.0  0
 L66  CONST_18  C32  N3   C1   N2    180.00   0.0  0
 L66  CONST_19  C5   N3   C1   N2      0.00   0.0  0
 L66  CONST_20  N3   C5   C4   N2      0.00   0.0  0
 L66  CONST_21  C10  C5   C4   N2    180.00   0.0  0
 L66  CONST_22  C32  N3   C5   C4    180.00   0.0  0
 L66  CONST_25  N3   C1   N2   C4      0.00   0.0  0
 L66  CONST_26  C36  C37  C32  N3    180.00   0.0  0
 L66  CONST_27  C34  C33  C32  N3    180.00   0.0  0
 L66  CONST_32  C14  C15  C10  C5    180.00   0.0  0
 L66  CONST_33  C12  C11  C10  C5    180.00   0.0  0
 L66  CONST_34  C13  C14  C15  C10     0.00   0.0  0
 L66  CONST_35  C32  N3   C5   C10     0.00   0.0  0
 L66  CONST_36  C13  C12  C11  C10     0.00   0.0  0
 L66  CONST_37  C14  C15  C10  C11     0.00   0.0  0
 L66  CONST_38  C14  C13  C12  C11     0.00   0.0  0
 L66  CONST_39  C15  C14  C13  C12     0.00   0.0  0
 L66  CONST_40  C15  C10  C11  C12     0.00   0.0  0
 L66  CONST_41  C35  C36  C37  C32     0.00   0.0  0
 L66  CONST_42  C35  C34  C33  C32     0.00   0.0  0
 L66  CONST_43  C36  C35  C34  C33     0.00   0.0  0
 L66  CONST_44  C36  C37  C32  C33     0.00   0.0  0
 L66  CONST_45  C37  C36  C35  C34     0.00   0.0  0
 L66  CONST_46  C37  C32  C33  C34     0.00   0.0  0
 L66  CONST_47  C2   N5   C17  N4      0.00   0.0  0
 L66  CONST_48  N5   C17  N4   C16     0.00   0.0  0
 L66  CONST_49  O38  C37  C32  N3      0.00   0.0  0
 L66  CONST_50  C40  C11  C10  C5      0.00   0.0  0
 L66  CONST_51  O41  C14  C15  C10   180.00   0.0  0
 L66  CONST_52  C15  C10  C11  C40   180.00   0.0  0
 L66  CONST_53  C13  C12  C11  C40   180.00   0.0  0
 L66  CONST_54  O41  C14  C13  C12   180.00   0.0  0
 L66  CONST_55  O38  C37  C32  C33   180.00   0.0  0
 L66  CONST_56  O38  C37  C36  C35   180.00   0.0  0
 L66  CONST_57  C2   N5   C17  O2    180.00   0.0  0
 L66  CONST_58  C16  N4   C17  O2    180.00   0.0  0
 L66  CONST_59  C18  N5   C17  N4    180.00   0.0  0
 L66  CONST_60  H5   C4   N2   C3      0.00   0.0  0
 L66  CONST_61  H13  C33  C32  N3      0.00   0.0  0
 L66  CONST_62  H11  C15  C10  C5      0.00   0.0  0
 L66  CONST_63  H9   C12  C11  C10   180.00   0.0  0
 L66  CONST_64  H10  C13  C12  C11   180.00   0.0  0
 L66  CONST_65  H16  C36  C37  C32   180.00   0.0  0
 L66  CONST_66  H14  C34  C33  C32   180.00   0.0  0
 L66  CONST_67  H15  C35  C34  C33   180.00   0.0  0
 L66  CONST_68  H1   N4   C17  N5    180.00   0.0  0
 L66  CONST_69  C18  N5   C17  O2      0.00   0.0  0
 L66  Var_01    H2   C18  N5   C17    -9.37  30.0  3
 L66  Var_02    H6   C40  C11  C10    70.11  30.0  2
 L66  Var_03    H17  C39  O38  C37  -177.95  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
 L66  plan-1  C5   0.020
 L66  plan-1  C10  0.020
 L66  plan-1  C11  0.020
 L66  plan-1  C40  0.020
 L66  plan-1  C12  0.020
 L66  plan-1  C13  0.020
 L66  plan-1  C15  0.020
 L66  plan-1  C14  0.020
 L66  plan-1  O41  0.020
 L66  plan-1  H9   0.020
 L66  plan-1  H10  0.020
 L66  plan-1  H11  0.020
 L66  plan-2  N3   0.020
 L66  plan-2  C32  0.020
 L66  plan-2  C33  0.020
 L66  plan-2  C34  0.020
 L66  plan-2  C35  0.020
 L66  plan-2  C36  0.020
 L66  plan-2  C37  0.020
 L66  plan-2  O38  0.020
 L66  plan-2  H13  0.020
 L66  plan-2  H14  0.020
 L66  plan-2  H15  0.020
 L66  plan-2  H16  0.020
 L66  plan-3  O2   0.020
 L66  plan-3  C17  0.020
 L66  plan-3  N4   0.020
 L66  plan-3  C16  0.020
 L66  plan-3  O3   0.020
 L66  plan-3  N5   0.020
 L66  plan-3  C18  0.020
 L66  plan-3  C2   0.020
 L66  plan-3  C3   0.020
 L66  plan-3  N1   0.020
 L66  plan-3  C1   0.020
 L66  plan-3  N2   0.020
 L66  plan-3  C4   0.020
 L66  plan-3  N3   0.020
 L66  plan-3  C5   0.020
 L66  plan-3  C10  0.020
 L66  plan-3  C32  0.020
 L66  plan-3  H1   0.020
 L66  plan-3  H5   0.020

