# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Aug  1 15:08:21 2022
#   Inital geometry file: a 163 line input string
#   Ligand name: 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCCN(CCO)c1nc(N2CCCCC2)c3nc(nc(N4CCCCC4)c3n1)N(CCO)CCO
#
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
 H9F  H9F  "2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol"
  ligand  76  36  .  2022-08-10  2022-08-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_H9F
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
 H9F  N1   N  N     0  -0.515  -1.5530  -34.7644  -24.8783
 H9F  N3   N  N     0  -0.530  -6.3856  -34.4826  -24.1219
 H9F  C4   C  CR66  0   0.130  -4.0761  -33.9299  -24.4412
 H9F  C5   C  CR6   0   0.501  -5.4579  -33.5489  -24.1867
 H9F  C6   C  CR6   0   0.617  -6.0545  -35.7745  -24.2717
 H9F  C7   C  CH2   0  -0.338  -1.1239  -31.1627  -24.6735
 H9F  C8   C  CH2   0  -0.148  -1.2122  -30.5928  -23.2707
 H9F  C10  C  CH2   0  -0.160   1.1533  -33.6246  -23.7001
 H9F  C13  C  CH2   0  -0.342  -6.7815  -38.0891  -24.3978
 H9F  C15  C  CH2   0  -0.329  -0.6886  -37.2835  -25.0805
 H9F  C17  C  CH2   0  -0.437  -0.9085  -38.1965  -27.3975
 H9F  C20  C  CH2   0  -0.339  -5.0938  -31.1122  -23.6982
 H9F  C21  C  CH2   0  -0.437  -5.1473  -30.0627  -24.8051
 H9F  C22  C  CH2   0  -0.435  -6.5423  -30.0344  -25.4467
 H9F  C24  C  CH2   0  -0.264  -7.3216  -32.0107  -24.1179
 H9F  C1   C  CR66  0   0.135  -3.8691  -35.2976  -24.6154
 H9F  C2   C  CR6   0   0.487  -2.4955  -35.6806  -24.8811
 H9F  C3   C  CR6   0   0.616  -1.8738  -33.4731  -24.6967
 H9F  N2   N  N     0  -0.539  -3.0908  -33.0139  -24.5080
 H9F  N4   N  N     0  -0.541  -4.8416  -36.2251  -24.5043
 H9F  N5   N  NT    0  -0.505  -0.8421  -32.5810  -24.7485
 H9F  O1   O  OH1   0  -0.659   0.0735  -30.5567  -22.6926
 H9F  C9   C  CH2   0  -0.317   0.5159  -33.0401  -24.9527
 H9F  O2   O  OH1   0  -0.671   2.4450  -34.0742  -24.0545
 H9F  N6   N  NT    0  -0.499  -7.0651  -36.6870  -24.1884
 H9F  C11  C  CH2   0  -0.340  -8.4251  -36.3098  -23.8694
 H9F  C12  C  CH2   0  -0.163  -8.8793  -36.7495  -22.4900
 H9F  O3   O  OH1   0  -0.664  -8.0349  -36.1796  -21.5184
 H9F  C14  C  CH2   0  -0.150  -6.1409  -38.7796  -23.1999
 H9F  O4   O  OH1   0  -0.669  -5.8767  -40.1134  -23.5800
 H9F  N7   N  NT    0  -0.463  -2.1127  -36.9745  -25.0529
 H9F  N8   N  NT    0  -0.480  -5.8856  -32.2765  -24.0661
 H9F  C16  C  CH2   0  -0.438  -0.1238  -37.2481  -26.4961
 H9F  C18  C  CH2   0  -0.429  -2.4055  -37.9238  -27.2992
 H9F  C19  C  CH2   0  -0.354  -2.8796  -37.9312  -25.8480
 H9F  C23  C  CH2   0  -0.493  -7.5795  -30.5397  -24.4519
 H9F  H1   H  HCH2  0   0.246  -0.3488  -30.6298  -25.2287
 H9F  H2   H  HCH2  0   0.255  -2.0678  -30.9567  -25.1790
 H9F  H3   H  HCH2  0   0.194  -1.6462  -29.5863  -23.3442
 H9F  H4   H  HCH2  0   0.201  -1.9063  -31.1989  -22.6770
 H9F  H5   H  HCH2  0   0.197   0.5308  -34.4456  -23.3263
 H9F  H6   H  HCH2  0   0.199   1.1874  -32.8551  -22.9224
 H9F  H7   H  HCH2  0   0.246  -7.7253  -38.5845  -24.6377
 H9F  H8   H  HCH2  0   0.251  -6.1278  -38.2083  -25.2647
 H9F  H9   H  HCH2  0   0.238  -0.5781  -38.2945  -24.6747
 H9F  H10  H  HCH2  0   0.265  -0.1525  -36.6057  -24.4214
 H9F  H11  H  HCH2  0   0.213  -0.7139  -39.2286  -27.0863
 H9F  H12  H  HCH2  0   0.232  -0.5694  -38.1129  -28.4323
 H9F  H13  H  HCH2  0   0.298  -4.0749  -31.4016  -23.4814
 H9F  H14  H  HCH2  0   0.240  -5.5186  -30.7047  -22.7749
 H9F  H15  H  HCH2  0   0.232  -4.3851  -30.2764  -25.5576
 H9F  H16  H  HCH2  0   0.224  -4.9004  -29.0908  -24.3718
 H9F  H17  H  HCH2  0   0.223  -6.5606  -30.6733  -26.3338
 H9F  H18  H  HCH2  0   0.237  -6.7900  -29.0283  -25.7879
 H9F  H19  H  HCH2  0   0.232  -7.8075  -32.2897  -23.1766
 H9F  H20  H  HCH2  0   0.241  -7.7582  -32.6391  -24.8943
 H9F  H21  H  HOH1  0   0.452  -0.0183  -30.3330  -21.7623
 H9F  H22  H  HCH2  0   0.240   1.1061  -32.1871  -25.2907
 H9F  H23  H  HCH2  0   0.237   0.5438  -33.7859  -25.7505
 H9F  H24  H  HOH1  0   0.451   2.8661  -34.4273  -23.2662
 H9F  H25  H  HCH2  0   0.266  -8.5182  -35.2309  -23.9615
 H9F  H26  H  HCH2  0   0.237  -9.1043  -36.7561  -24.6025
 H9F  H27  H  HCH2  0   0.207  -9.9230  -36.4296  -22.3680
 H9F  H28  H  HCH2  0   0.196  -8.8806  -37.8458  -22.4319
 H9F  H29  H  HOH1  0   0.452  -8.2930  -36.5214  -20.6579
 H9F  H30  H  HCH2  0   0.200  -5.2243  -38.2479  -22.9244
 H9F  H31  H  HCH2  0   0.194  -6.8164  -38.7328  -22.3373
 H9F  H32  H  HOH1  0   0.452  -5.4486  -40.5571  -22.8428
 H9F  H33  H  HCH2  0   0.231   0.9323  -37.5265  -26.4713
 H9F  H34  H  HCH2  0   0.226  -0.1767  -36.2259  -26.8805
 H9F  H35  H  HCH2  0   0.219  -2.6415  -36.9525  -27.7460
 H9F  H36  H  HCH2  0   0.234  -2.9696  -38.6738  -27.8590
 H9F  H37  H  HCH2  0   0.297  -3.9377  -37.7114  -25.7753
 H9F  H38  H  HCH2  0   0.227  -2.7227  -38.9242  -25.4148
 H9F  H39  H  HCH2  0   0.231  -7.5577  -29.9237  -23.5491
 H9F  H40  H  HCH2  0   0.249  -8.5894  -30.4544  -24.8561

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
 H9F  C17  C18  single    1.525  0.020  1.525
 H9F  C17  C16  single    1.526  0.020  1.526
 H9F  C18  C19  single    1.527  0.020  1.527
 H9F  C16  C15  single    1.524  0.020  1.524
 H9F  C22  C23  single    1.523  0.020  1.523
 H9F  C22  C21  single    1.536  0.020  1.536
 H9F  C19  N7   single    1.461  0.020  1.461
 H9F  O2   C10  single    1.413  0.020  1.413
 H9F  C23  C24  single    1.530  0.020  1.530
 H9F  C21  C20  single    1.526  0.020  1.526
 H9F  C9   C10  single    1.522  0.020  1.522
 H9F  C9   N5   single    1.448  0.020  1.448
 H9F  C15  N7   single    1.457  0.020  1.457
 H9F  N7   C2   single    1.360  0.020  1.360
 H9F  C2   N1   aromatic  1.315  0.020  1.315
 H9F  C2   C1   aromatic  1.451  0.020  1.451
 H9F  N1   C3   aromatic  1.343  0.020  1.343
 H9F  C1   N4   aromatic  1.349  0.020  1.349
 H9F  C1   C4   aromatic  1.394  0.020  1.394
 H9F  N4   C6   aromatic  1.315  0.020  1.315
 H9F  C13  N6   single    1.446  0.020  1.446
 H9F  C13  C14  single    1.524  0.020  1.524
 H9F  C6   N6   single    1.364  0.020  1.364
 H9F  C6   N3   aromatic  1.342  0.020  1.342
 H9F  C3   N2   aromatic  1.314  0.020  1.314
 H9F  C3   N5   single    1.365  0.020  1.365
 H9F  C4   N2   aromatic  1.347  0.020  1.347
 H9F  C4   C5   aromatic  1.456  0.020  1.456
 H9F  C24  N8   single    1.461  0.020  1.461
 H9F  N5   C7   single    1.448  0.020  1.448
 H9F  N6   C11  single    1.447  0.020  1.447
 H9F  C5   N3   aromatic  1.318  0.020  1.318
 H9F  C5   N8   single    1.348  0.020  1.348
 H9F  N8   C20  single    1.455  0.020  1.455
 H9F  C11  C12  single    1.517  0.020  1.517
 H9F  C7   C8   single    1.517  0.020  1.517
 H9F  C14  O4   single    1.412  0.020  1.412
 H9F  C12  O3   single    1.408  0.020  1.408
 H9F  C8   O1   single    1.410  0.020  1.410
 H9F  C7   H1   single    0.970  0.020  1.090
 H9F  C7   H2   single    0.970  0.020  1.090
 H9F  C8   H3   single    0.970  0.020  1.090
 H9F  C8   H4   single    0.970  0.020  1.090
 H9F  C10  H5   single    0.970  0.020  1.090
 H9F  C10  H6   single    0.970  0.020  1.090
 H9F  C13  H7   single    0.970  0.020  1.090
 H9F  C13  H8   single    0.970  0.020  1.090
 H9F  C15  H9   single    0.970  0.020  1.090
 H9F  C15  H10  single    0.970  0.020  1.090
 H9F  C17  H11  single    0.970  0.020  1.090
 H9F  C17  H12  single    0.970  0.020  1.090
 H9F  C20  H13  single    0.970  0.020  1.090
 H9F  C20  H14  single    0.970  0.020  1.090
 H9F  C21  H15  single    0.970  0.020  1.090
 H9F  C21  H16  single    0.970  0.020  1.090
 H9F  C22  H17  single    0.970  0.020  1.090
 H9F  C22  H18  single    0.970  0.020  1.090
 H9F  C24  H19  single    0.970  0.020  1.090
 H9F  C24  H20  single    0.970  0.020  1.090
 H9F  O1   H21  single    0.850  0.020  0.980
 H9F  C9   H22  single    0.970  0.020  1.090
 H9F  C9   H23  single    0.970  0.020  1.090
 H9F  O2   H24  single    0.850  0.020  0.980
 H9F  C11  H25  single    0.970  0.020  1.090
 H9F  C11  H26  single    0.970  0.020  1.090
 H9F  C12  H27  single    0.970  0.020  1.090
 H9F  C12  H28  single    0.970  0.020  1.090
 H9F  O3   H29  single    0.850  0.020  0.980
 H9F  C14  H30  single    0.970  0.020  1.090
 H9F  C14  H31  single    0.970  0.020  1.090
 H9F  O4   H32  single    0.850  0.020  0.980
 H9F  C16  H33  single    0.970  0.020  1.090
 H9F  C16  H34  single    0.970  0.020  1.090
 H9F  C18  H35  single    0.970  0.020  1.090
 H9F  C18  H36  single    0.970  0.020  1.090
 H9F  C19  H37  single    0.970  0.020  1.090
 H9F  C19  H38  single    0.970  0.020  1.090
 H9F  C23  H39  single    0.970  0.020  1.090
 H9F  C23  H40  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
 H9F  C3   N1   C2   119.95  3.000
 H9F  C6   N3   C5   120.19  3.000
 H9F  N2   C4   C1   123.52  3.000
 H9F  N2   C4   C5   121.67  3.000
 H9F  C1   C4   C5   114.81  3.000
 H9F  N8   C5   C4   124.33  3.000
 H9F  N8   C5   N3   116.17  3.000
 H9F  C4   C5   N3   119.43  3.000
 H9F  N6   C6   N4   117.71  3.000
 H9F  N6   C6   N3   117.02  3.000
 H9F  N4   C6   N3   125.26  3.000
 H9F  H2   C7   H1   106.65  3.000
 H9F  H2   C7   N5   109.24  3.000
 H9F  H1   C7   N5   108.27  3.000
 H9F  H2   C7   C8   107.90  3.000
 H9F  H1   C7   C8   109.15  3.000
 H9F  N5   C7   C8   115.29  3.000
 H9F  H4   C8   H3   107.02  3.000
 H9F  H4   C8   O1   111.68  3.000
 H9F  H3   C8   O1   111.36  3.000
 H9F  H4   C8   C7   109.27  3.000
 H9F  H3   C8   C7   107.78  3.000
 H9F  O1   C8   C7   109.61  3.000
 H9F  H6   C10  H5   107.57  3.000
 H9F  H6   C10  O2   111.93  3.000
 H9F  H5   C10  O2   111.50  3.000
 H9F  H6   C10  C9   109.13  3.000
 H9F  H5   C10  C9   109.29  3.000
 H9F  O2   C10  C9   107.38  3.000
 H9F  H8   C13  H7   107.05  3.000
 H9F  H8   C13  C14  108.84  3.000
 H9F  H7   C13  C14  109.29  3.000
 H9F  H8   C13  N6   109.76  3.000
 H9F  H7   C13  N6   107.58  3.000
 H9F  C14  C13  N6   114.08  3.000
 H9F  H10  C15  H9   107.53  3.000
 H9F  H10  C15  C16  111.47  3.000
 H9F  H9   C15  C16  109.15  3.000
 H9F  H10  C15  N7   109.77  3.000
 H9F  H9   C15  N7   106.70  3.000
 H9F  C16  C15  N7   112.00  3.000
 H9F  H12  C17  H11  106.63  3.000
 H9F  H12  C17  C18  110.62  3.000
 H9F  H11  C17  C18  108.94  3.000
 H9F  H12  C17  C16  110.64  3.000
 H9F  H11  C17  C16  109.06  3.000
 H9F  C18  C17  C16  110.83  3.000
 H9F  H14  C20  H13  107.23  3.000
 H9F  H14  C20  N8   107.45  3.000
 H9F  H13  C20  N8   110.44  3.000
 H9F  H14  C20  C21  110.00  3.000
 H9F  H13  C20  C21  111.25  3.000
 H9F  N8   C20  C21  110.35  3.000
 H9F  H16  C21  H15  106.83  3.000
 H9F  H16  C21  C22  110.77  3.000
 H9F  H15  C21  C22  110.47  3.000
 H9F  H16  C21  C20  108.44  3.000
 H9F  H15  C21  C20  109.92  3.000
 H9F  C22  C21  C20  110.34  3.000
 H9F  H18  C22  H17  106.34  3.000
 H9F  H18  C22  C23  110.83  3.000
 H9F  H17  C22  C23  108.94  3.000
 H9F  H18  C22  C21  110.73  3.000
 H9F  H17  C22  C21  110.08  3.000
 H9F  C23  C22  C21  109.85  3.000
 H9F  H20  C24  H19  106.71  3.000
 H9F  H20  C24  C23  109.34  3.000
 H9F  H19  C24  C23  110.95  3.000
 H9F  H20  C24  N8   108.30  3.000
 H9F  H19  C24  N8   111.04  3.000
 H9F  C23  C24  N8   110.38  3.000
 H9F  N4   C1   C2   121.09  3.000
 H9F  N4   C1   C4   123.87  3.000
 H9F  C2   C1   C4   115.00  3.000
 H9F  N7   C2   C1   122.74  3.000
 H9F  C1   C2   N1   119.64  3.000
 H9F  N7   C2   N1   117.48  3.000
 H9F  N5   C3   N2   118.49  3.000
 H9F  N5   C3   N1   116.28  3.000
 H9F  N2   C3   N1   125.21  3.000
 H9F  C3   N2   C4   116.54  3.000
 H9F  C1   N4   C6   116.37  3.000
 H9F  C9   N5   C3   120.46  3.000
 H9F  C3   N5   C7   119.42  3.000
 H9F  C9   N5   C7   120.03  3.000
 H9F  H21  O1   C8   108.40  3.000
 H9F  H23  C9   H22  107.08  3.000
 H9F  H23  C9   N5   110.09  3.000
 H9F  H22  C9   N5   107.64  3.000
 H9F  H23  C9   C10  109.15  3.000
 H9F  H22  C9   C10  109.19  3.000
 H9F  N5   C9   C10  113.48  3.000
 H9F  H24  O2   C10  108.17  3.000
 H9F  C11  N6   C13  117.97  3.000
 H9F  C11  N6   C6   122.38  3.000
 H9F  C13  N6   C6   119.64  3.000
 H9F  H26  C11  H25  107.15  3.000
 H9F  H26  C11  C12  107.76  3.000
 H9F  H25  C11  C12  109.82  3.000
 H9F  H26  C11  N6   109.23  3.000
 H9F  H25  C11  N6   108.70  3.000
 H9F  C12  C11  N6   113.97  3.000
 H9F  H28  C12  H27  106.48  3.000
 H9F  H28  C12  O3   111.62  3.000
 H9F  H27  C12  O3   112.04  3.000
 H9F  H28  C12  C11  109.75  3.000
 H9F  H27  C12  C11  107.52  3.000
 H9F  O3   C12  C11  109.31  3.000
 H9F  H29  O3   C12  108.24  3.000
 H9F  H31  C14  H30  107.28  3.000
 H9F  H31  C14  O4   111.55  3.000
 H9F  H30  C14  O4   111.70  3.000
 H9F  H31  C14  C13  109.89  3.000
 H9F  H30  C14  C13  109.25  3.000
 H9F  O4   C14  C13  107.16  3.000
 H9F  H32  O4   C14  108.24  3.000
 H9F  C19  N7   C2   122.94  3.000
 H9F  C2   N7   C15  118.62  3.000
 H9F  C19  N7   C15  111.32  3.000
 H9F  C24  N8   C20  113.46  3.000
 H9F  C20  N8   C5   127.25  3.000
 H9F  C24  N8   C5   118.71  3.000
 H9F  H34  C16  H33  107.03  3.000
 H9F  H34  C16  C17  110.40  3.000
 H9F  H33  C16  C17  110.62  3.000
 H9F  H34  C16  C15  109.28  3.000
 H9F  H33  C16  C15  109.34  3.000
 H9F  C17  C16  C15  110.10  3.000
 H9F  H36  C18  H35  106.78  3.000
 H9F  H36  C18  C19  108.87  3.000
 H9F  H35  C18  C19  108.99  3.000
 H9F  H36  C18  C17  110.55  3.000
 H9F  H35  C18  C17  110.11  3.000
 H9F  C19  C18  C17  111.42  3.000
 H9F  H38  C19  H37  107.31  3.000
 H9F  H38  C19  C18  109.64  3.000
 H9F  H37  C19  C18  111.48  3.000
 H9F  H38  C19  N7   107.66  3.000
 H9F  H37  C19  N7   110.07  3.000
 H9F  C18  C19  N7   110.55  3.000
 H9F  H40  C23  H39  106.28  3.000
 H9F  H40  C23  C24  108.18  3.000
 H9F  H39  C23  C24  110.98  3.000
 H9F  H40  C23  C22  111.25  3.000
 H9F  H39  C23  C22  109.81  3.000
 H9F  C24  C23  C22  110.28  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
 H9F  CONST_01  N4   C1   C2   N1    180.00   0.0  0
 H9F  CONST_02  C4   C1   C2   N1      0.00   0.0  0
 H9F  CONST_03  C4   N2   C3   N1      0.00   0.0  0
 H9F  CONST_04  C1   N4   C6   N3      0.00   0.0  0
 H9F  CONST_05  C1   C4   C5   N3      0.00   0.0  0
 H9F  CONST_06  N2   C4   C5   N3    180.00   0.0  0
 H9F  CONST_07  C6   N4   C1   C4      0.00   0.0  0
 H9F  CONST_08  C6   N3   C5   C4      0.00   0.0  0
 H9F  CONST_09  C2   C1   C4   C5    180.00   0.0  0
 H9F  CONST_10  N4   C1   C4   C5      0.00   0.0  0
 H9F  CONST_11  C3   N2   C4   C5    180.00   0.0  0
 H9F  CONST_12  N4   C6   N3   C5      0.00   0.0  0
 H9F  CONST_13  C2   C1   N4   C6    180.00   0.0  0
 H9F  CONST_14  C3   N1   C2   C1      0.00   0.0  0
 H9F  CONST_15  C3   N2   C4   C1      0.00   0.0  0
 H9F  CONST_16  N2   C3   N1   C2      0.00   0.0  0
 H9F  CONST_17  N2   C4   C1   C2      0.00   0.0  0
 H9F  CONST_18  N4   C1   C4   N2    180.00   0.0  0
 H9F  CONST_19  N7   C2   C1   C4    180.00   0.0  0
 H9F  CONST_20  N8   C5   N3   C6    180.00   0.0  0
 H9F  CONST_21  N8   C5   C4   C1    180.00   0.0  0
 H9F  CONST_22  N7   C2   N1   C3    180.00   0.0  0
 H9F  CONST_23  N8   C5   C4   N2      0.00   0.0  0
 H9F  CONST_24  N7   C2   C1   N4      0.00   0.0  0
 H9F  CONST_25  N5   C3   N2   C4    180.00   0.0  0
 H9F  CONST_26  N6   C6   N3   C5    180.00   0.0  0
 H9F  CONST_27  N6   C6   N4   C1    180.00   0.0  0
 H9F  CONST_28  N5   C3   N1   C2    180.00   0.0  0
 H9F  CONST_29  C9   N5   C3   N1      0.00   0.0  0
 H9F  CONST_30  C7   N5   C3   N1    180.00   0.0  0
 H9F  CONST_31  C13  N6   C6   N3    180.00   0.0  0
 H9F  CONST_32  C11  N6   C6   N3      0.00   0.0  0
 H9F  CONST_33  N2   C3   N5   C7      0.00   0.0  0
 H9F  CONST_34  N4   C6   N6   C13     0.00   0.0  0
 H9F  CONST_35  C9   N5   C3   N2    180.00   0.0  0
 H9F  CONST_36  C11  N6   C6   N4    180.00   0.0  0
 H9F  Var_01    C19  N7   C2   N1   -141.52  30.0  2
 H9F  Var_02    C15  N7   C2   N1      6.40  30.0  2
 H9F  Var_03    C24  N8   C5   N3    -10.85  30.0  2
 H9F  Var_04    C20  N8   C5   N3    159.80  30.0  2
 H9F  Var_05    C24  N8   C5   C4    166.15  30.0  2
 H9F  Var_06    C20  N8   C5   C4    -23.20  30.0  2
 H9F  Var_07    C23  C24  N8   C5   -160.32  30.0  1
 H9F  Var_08    C21  C20  N8   C5    121.04  30.0  1
 H9F  Var_09    C18  C17  C16  C15    51.89  30.0  1
 H9F  Var_10    C18  C19  N7   C15   -59.09  30.0  1
 H9F  Var_11    C1   C2   N7   C15  -169.36  30.0  2
 H9F  Var_12    N7   C19  C18  C17    55.70  30.0  1
 H9F  Var_13    N7   C15  C16  C17   -55.89  30.0  1
 H9F  Var_14    C23  C22  C21  C20    25.54  30.0  1
 H9F  Var_15    C23  C24  N8   C20    27.78  30.0  1
 H9F  Var_16    C24  C23  C22  C21   -64.51  30.0  1
 H9F  Var_17    C24  N8   C20  C21   -67.89  30.0  1
 H9F  Var_18    N8   C24  C23  C22    36.57  30.0  1
 H9F  Var_19    N8   C20  C21  C22    36.59  30.0  1
 H9F  Var_20    C19  N7   C2   C1     42.73  30.0  2
 H9F  Var_21    C18  C19  N7   C2     90.87  30.0  1
 H9F  Var_22    C16  C15  N7   C2    -91.41  30.0  1
 H9F  Var_23    C19  C18  C17  C16   -52.57  30.0  1
 H9F  Var_24    C19  N7   C15  C16    60.00  30.0  1
 H9F  Var_25    H19  C24  N8   C5     76.21  30.0  1
 H9F  Var_26    H20  C24  N8   C5    -40.65  30.0  1
 H9F  Var_27    H13  C20  N8   C5     -2.38  30.0  1
 H9F  Var_28    H14  C20  N8   C5   -119.03  30.0  1
 H9F  Var_29    H11  C17  C16  C15   -68.03  30.0  1
 H9F  Var_30    H12  C17  C16  C15   174.99  30.0  1
 H9F  Var_31    H37  C19  N7   C15   177.31  30.0  1
 H9F  Var_32    H38  C19  N7   C15    60.64  30.0  1
 H9F  Var_33    H37  C19  C18  C17   178.48  30.0  1
 H9F  Var_34    H38  C19  C18  C17   -62.84  30.0  1
 H9F  Var_35    H9   C15  C16  C17    62.04  30.0  1
 H9F  Var_36    H10  C15  C16  C17  -179.32  30.0  1
 H9F  Var_37    H17  C22  C21  C20   -94.42  30.0  1
 H9F  Var_38    H18  C22  C21  C20   148.28  30.0  1
 H9F  Var_39    H19  C24  N8   C20   -95.69  30.0  1
 H9F  Var_40    H20  C24  N8   C20   147.45  30.0  1
 H9F  Var_41    H39  C23  C22  C21    58.09  30.0  1
 H9F  Var_42    H40  C23  C22  C21   175.46  30.0  1
 H9F  Var_43    H19  C24  C23  C22   160.10  30.0  1
 H9F  Var_44    H20  C24  C23  C22   -82.47  30.0  1
 H9F  Var_45    H13  C20  C21  C22   159.54  30.0  1
 H9F  Var_46    H14  C20  C21  C22   -81.79  30.0  1
 H9F  Var_47    H17  C22  C23  C24    56.14  30.0  1
 H9F  Var_48    H18  C22  C23  C24   172.81  30.0  1
 H9F  Var_49    H13  C20  N8   C24   168.68  30.0  1
 H9F  Var_50    H14  C20  N8   C24    52.04  30.0  1
 H9F  Var_51    H37  C19  N7   C2    -32.72  30.0  1
 H9F  Var_52    H38  C19  N7   C2   -149.39  30.0  1
 H9F  Var_53    H9   C15  N7   C2    149.20  30.0  1
 H9F  Var_54    H10  C15  N7   C2     32.97  30.0  1
 H9F  Var_55    H35  C18  C19  N7    -66.02  30.0  1
 H9F  Var_56    H36  C18  C19  N7    177.87  30.0  1
 H9F  Var_57    H33  C16  C15  N7   -177.62  30.0  1
 H9F  Var_58    H34  C16  C15  N7     65.53  30.0  1
 H9F  Var_59    H39  C23  C24  N8    -85.34  30.0  1
 H9F  Var_60    H40  C23  C24  N8    158.43  30.0  1
 H9F  Var_61    H15  C21  C20  N8    -85.48  30.0  1
 H9F  Var_62    H16  C21  C20  N8    158.06  30.0  1
 H9F  Var_63    H35  C18  C17  C16    68.49  30.0  1
 H9F  Var_64    H36  C18  C17  C16  -173.77  30.0  1
 H9F  Var_65    H33  C16  C17  C18   172.86  30.0  1
 H9F  Var_66    H34  C16  C17  C18   -68.86  30.0  1
 H9F  Var_67    H11  C17  C18  C19    67.43  30.0  1
 H9F  Var_68    H12  C17  C18  C19  -175.68  30.0  1
 H9F  Var_69    H9   C15  N7   C19   -59.39  30.0  1
 H9F  Var_70    H10  C15  N7   C19  -175.62  30.0  1
 H9F  Var_71    H15  C21  C22  C23   147.29  30.0  1
 H9F  Var_72    H16  C21  C22  C23   -94.54  30.0  1
 H9F  Var_73    C14  C13  N6   C6     78.21  30.0  2
 H9F  Var_74    C12  C11  N6   C6   -109.18  30.0  3
 H9F  Var_75    C3   N5   C7   C8     86.84  30.0  2
 H9F  Var_76    C3   N5   C9   C10   -77.76  30.0  3
 H9F  Var_77    H7   C13  N6   C6   -160.38  30.0  2
 H9F  Var_78    H8   C13  N6   C6    -44.23  30.0  2
 H9F  Var_79    H25  C11  N6   C6     13.65  30.0  3
 H9F  Var_80    H26  C11  N6   C6    130.25  30.0  3
 H9F  Var_81    H22  C9   N5   C3    161.30  30.0  2
 H9F  Var_82    H23  C9   N5   C3     44.91  30.0  2
 H9F  Var_83    H1   C7   N5   C3   -150.60  30.0  3
 H9F  Var_84    H2   C7   N5   C3    -34.82  30.0  3
 H9F  Var_85    C10  C9   N5   C7    105.76  30.0  2
 H9F  Var_86    C9   N5   C7   C8    -96.63  30.0  2
 H9F  Var_87    C12  C11  N6   C13    69.61  30.0  3
 H9F  Var_88    O2   C10  C9   N5    177.82  30.0  3
 H9F  Var_89    O1   C8   C7   N5     71.19  30.0  3
 H9F  Var_90    O4   C14  C13  N6   -177.53  30.0  3
 H9F  Var_91    O3   C12  C11  N6     59.29  30.0  3
 H9F  Var_92    C14  C13  N6   C11  -100.61  30.0  2
 H9F  Var_93    H22  C9   N5   C7    -15.19  30.0  2
 H9F  Var_94    H23  C9   N5   C7   -131.57  30.0  2
 H9F  Var_95    H25  C11  N6   C13  -167.56  30.0  3
 H9F  Var_96    H26  C11  N6   C13   -50.96  30.0  3
 H9F  Var_97    H5   C10  C9   N5     56.72  30.0  3
 H9F  Var_98    H6   C10  C9   N5    -60.66  30.0  3
 H9F  Var_99    H3   C8   C7   N5   -167.46  30.0  3
 H9F  Var_100   H4   C8   C7   N5    -51.49  30.0  3
 H9F  Var_101   H1   C7   C8   O1    -50.89  30.0  1
 H9F  Var_102   H2   C7   C8   O1   -166.42  30.0  1
 H9F  Var_103   H1   C7   N5   C9     25.93  30.0  3
 H9F  Var_104   H2   C7   N5   C9    141.70  30.0  3
 H9F  Var_105   H22  C9   C10  O2    -62.11  30.0  2
 H9F  Var_106   H23  C9   C10  O2     54.63  30.0  2
 H9F  Var_107   H30  C14  C13  N6    -56.34  30.0  3
 H9F  Var_108   H31  C14  C13  N6     61.10  30.0  3
 H9F  Var_109   H27  C12  C11  N6   -178.86  30.0  3
 H9F  Var_110   H28  C12  C11  N6    -63.43  30.0  3
 H9F  Var_111   H7   C13  N6   C11    20.80  30.0  2
 H9F  Var_112   H8   C13  N6   C11   136.95  30.0  2
 H9F  Var_113   H25  C11  C12  O3    -62.92  30.0  2
 H9F  Var_114   H26  C11  C12  O3   -179.32  30.0  2
 H9F  Var_115   H7   C13  C14  O4     62.01  30.0  1
 H9F  Var_116   H8   C13  C14  O4    -54.59  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
 H9F  plan-1  C7   0.020
 H9F  plan-1  C3   0.020
 H9F  plan-1  N5   0.020
 H9F  plan-1  C9   0.020
 H9F  plan-2  N1   0.020
 H9F  plan-2  N3   0.020
 H9F  plan-2  C4   0.020
 H9F  plan-2  C5   0.020
 H9F  plan-2  C6   0.020
 H9F  plan-2  C1   0.020
 H9F  plan-2  C2   0.020
 H9F  plan-2  C3   0.020
 H9F  plan-2  N2   0.020
 H9F  plan-2  N4   0.020
 H9F  plan-2  N5   0.020
 H9F  plan-2  N6   0.020
 H9F  plan-2  N7   0.020
 H9F  plan-2  N8   0.020
 H9F  plan-3  C6   0.020
 H9F  plan-3  C13  0.020
 H9F  plan-3  N6   0.020
 H9F  plan-3  C11  0.020

