# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Mon Jun  1 20:27:52 2020
#   Inital geometry file: a 231 line input string
#   Ligand name: 3-[[6-chloranyl-3-[3-[(1~{S})-1-(2,4-dichlorophenyl)ethyl]-5-phenyl-imidazol-4-yl]-1~{H}-indol-2-yl]carbonylamino]-4-[4-(2-oxidanylidene-1,3-oxazinan-3-yl)piperidin-1-yl]benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](n1cnc(c2ccccc2)c1c3c([nH]c4cc(Cl)ccc34)C(=O)Nc5cc(ccc5N6CCC(CC6)N7CCCOC7=O)C(O)=O)c8ccc(Cl)cc8Cl
#
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
 HRN  HRN  '3-[[6-chloranyl-3-[3-[(1~{S})-1-(2,4-dichlorophenyl)ethyl]-5-phenyl-imidazol-4-yl]-1~{H}-indol-2-yl]carbonylamino]-4-[4-(2-oxidanylidene-1,3-oxazinan-3-yl)piperidin-1-yl]benzoic acid'  ligand  92  56  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_HRN
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
 HRN  C2   C   CR6    0  -0.141  -2.0552  -0.0432   2.1179
 HRN  C3   C   CR6    0   0.204  -2.9900   0.2718   1.1377
 HRN  C42  C   CR16   0  -0.356   3.7841   5.7202   0.9809
 HRN  C44  C   CR6    0  -0.121   2.4347   5.8185   0.6634
 HRN  C45  C   CR16   0  -0.392   1.7004   4.6568   0.4341
 HRN  C47  C   C      0   0.391   1.7499   7.1779   0.5792
 HRN  C52  C   CH2    0  -0.359   5.1600   1.7411   1.9738
 HRN  C55  C   CH2    0  -0.491   5.1312   0.2461   2.2489
 HRN  C58  C   CH1    0  -0.101   5.4197  -0.5557   0.9780
 HRN  C60  C   CH2    0  -0.484   4.6598  -0.0703  -0.2582
 HRN  C12  C   CH1    0  -0.164  -3.0878   1.6369   0.4925
 HRN  C15  C   CR15   0   0.059  -3.9643   1.9645  -1.8523
 HRN  C18  C   CR5    0   0.042  -2.4864   0.9343  -2.9968
 HRN  C19  C   CR5    0   0.327  -2.0989   0.8282  -1.6808
 HRN  C20  C   CR5    0  -0.041  -1.0344   0.0649  -1.0450
 HRN  C21  C   CR5    0   0.173   0.0650   0.5095  -0.3446
 HRN  C24  C   CR56   0   0.323   0.0760  -1.7197  -0.1693
 HRN  C25  C   CR56   0   0.098  -1.0263  -1.3587  -0.9620
 HRN  C26  C   CR16   0  -0.393  -1.8709  -2.3500  -1.4684
 HRN  C28  C   CR16   0  -0.261  -1.6153  -3.6656  -1.1591
 HRN  C30  C   CR6    0  -0.051  -0.5206  -3.9889  -0.3409
 HRN  CL1  CL  CL     0  -0.117  -0.9795   1.1684   2.7405
 HRN  C4   C   CR16   0  -0.335  -3.8459  -0.7442   0.7245
 HRN  C6   C   CR16   0  -0.215  -3.7406  -2.0346   1.2088
 HRN  C8   C   CR6    0  -0.057  -2.7511  -2.3215   2.1340
 HRN  C9   C   CR16   0  -0.178  -1.9127  -1.3309   2.6121
 HRN  CL2  CL  CL     0  -0.130  -2.5510  -3.9430   2.6980
 HRN  N14  N   NR5    0  -0.462  -3.0667   1.4902  -0.9612
 HRN  N17  N   N      0  -0.469  -3.6493   1.6505  -3.0787
 HRN  N22  N   NR15   0  -0.788   0.7280  -0.5751   0.1820
 HRN  C31  C   CR16   0  -0.289   0.3447  -3.0478   0.1667
 HRN  CL3  CL  CL     0  -0.150  -0.2551  -5.6595   0.0489
 HRN  C34  C   C      0   0.539   0.4773   1.9264  -0.2529
 HRN  O35  O   O      0  -0.462  -0.2338   2.7910  -0.7409
 HRN  N36  N   NH1    0  -0.755   1.6552   2.1815   0.3565
 HRN  C38  C   CR6    0   0.334   2.3086   3.4096   0.5102
 HRN  C39  C   CR6    0   0.235   3.6798   3.3174   0.8182
 HRN  C40  C   CR16   0  -0.356   4.3992   4.4786   1.0571
 HRN  O48  O   OC    -1  -0.599   2.4635   8.1754   0.7992
 HRN  O49  O   O      0  -0.597   0.5359   7.1776   0.2976
 HRN  N51  N   NT     0  -0.535   4.2274   2.0217   0.8978
 HRN  C63  C   CH2    0  -0.403   4.6880   1.4461  -0.3611
 HRN  N66  N   NT     0  -0.503   5.2725  -1.9987   1.1829
 HRN  C67  C   CH2    0  -0.356   6.5035  -2.7809   1.1054
 HRN  C70  C   CH2    0  -0.574   6.2971  -4.1828   1.6320
 HRN  C73  C   CH2    0  -0.178   4.9946  -4.7030   1.0854
 HRN  O76  O   O2     0  -0.469   3.9253  -3.8477   1.4923
 HRN  C77  C   C      0   0.735   4.0580  -2.5198   1.4370
 HRN  O78  O   O      0  -0.534   3.0496  -1.8570   1.6323
 HRN  C79  C   CR6    0   0.030  -1.8454   0.3954  -4.1970
 HRN  C80  C   CR16   0  -0.291  -2.5851   0.2670  -5.3761
 HRN  C82  C   CR16   0  -0.227  -2.0063  -0.2430  -6.5282
 HRN  C84  C   CR16   0  -0.263  -0.6735  -0.6346  -6.5304
 HRN  C86  C   CR16   0  -0.230   0.0737  -0.5039  -5.3672
 HRN  C88  C   CR16   0  -0.329  -0.5028   0.0086  -4.2145
 HRN  C90  C   CH3    0  -0.670  -4.3217   2.3862   0.9741
 HRN  H1   H   HCR6   0   0.290   4.3593   6.6178   1.1626
 HRN  H2   H   HCR6   0   0.294   0.6488   4.7456   0.2169
 HRN  H3   H   HCH2   0   0.268   4.8539   2.2827   2.8692
 HRN  H4   H   HCH2   0   0.283   6.1808   2.0693   1.7246
 HRN  H5   H   HCH2   0   0.274   5.8760  -0.0057   3.0079
 HRN  H6   H   HCH2   0   0.255   4.1504  -0.0049   2.6484
 HRN  H7   H   HCH1   0   0.334   6.4802  -0.4098   0.7539
 HRN  H8   H   HCH2   0   0.296   5.1084  -0.5114  -1.1509
 HRN  H9   H   HCH2   0   0.196   3.6212  -0.3990  -0.2346
 HRN  H10  H   HCH1   0   0.305  -2.2171   2.2327   0.7598
 HRN  H11  H   HCR5   0   0.319  -4.8332   2.5333  -1.5613
 HRN  H12  H   HCR6   0   0.300  -2.7228  -2.0893  -2.0830
 HRN  H13  H   HCR6   0   0.320  -2.2579  -4.4509  -1.5319
 HRN  H14  H   HCR6   0   0.326  -4.5916  -0.5358  -0.0337
 HRN  H15  H   HCR6   0   0.335  -4.4009  -2.8094   0.8458
 HRN  H16  H   HCR6   0   0.348  -1.1528  -1.5530   3.3481
 HRN  H17  H   HNR5   0   0.421   1.5396  -0.5863   0.7848
 HRN  H18  H   HCR6   0   0.309   1.1818  -3.3196   0.7926
 HRN  H19  H   HNH1   0   0.393   2.2423   1.4245   0.6896
 HRN  H20  H   HCR6   0   0.341   5.4530   4.4104   1.2987
 HRN  H22  H   HCH2   0   0.339   5.7012   1.8029  -0.5994
 HRN  H23  H   HCH2   0   0.272   4.0383   1.7730  -1.1745
 HRN  H24  H   HCH2   0   0.302   6.8465  -2.8122   0.0672
 HRN  H25  H   HCH2   0   0.326   7.2710  -2.2667   1.6862
 HRN  H26  H   HCH2   0   0.301   7.1218  -4.8202   1.3137
 HRN  H27  H   HCH2   0   0.287   6.2761  -4.1919   2.7240
 HRN  H28  H   HCH2   0   0.213   5.0206  -4.7566  -0.0068
 HRN  H29  H   HCH2   0   0.230   4.7471  -5.6907   1.4688
 HRN  H30  H   HCR6   0   0.223  -3.6249   0.5665  -5.3860
 HRN  H31  H   HCR6   0   0.233  -2.6012  -0.3359  -7.4280
 HRN  H32  H   HCR6   0   0.234  -0.2217  -1.0326  -7.4296
 HRN  H33  H   HCR6   0   0.238   1.1165  -0.7941  -5.3563
 HRN  H34  H   HCR6   0   0.251   0.1072   0.1167  -3.3278
 HRN  H35  H   HCH3   0   0.235  -5.2457   1.8669   0.7196
 HRN  H36  H   HCH3   0   0.250  -4.2730   2.4695   2.0585
 HRN  H37  H   HCH3   0   0.247  -4.3604   3.3972   0.5685

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
 HRN  O49  C47  deloc     1.246  0.020  1.246
 HRN  O48  C47  deloc     1.246  0.020  1.246
 HRN  C47  C44  single    1.525  0.020  1.525
 HRN  C44  C42  aromatic  1.390  0.020  1.390
 HRN  C44  C45  aromatic  1.393  0.020  1.393
 HRN  C42  C40  aromatic  1.388  0.020  1.388
 HRN  C45  C38  aromatic  1.390  0.020  1.390
 HRN  CL1  C2   single    1.736  0.020  1.736
 HRN  C40  C39  aromatic  1.387  0.020  1.387
 HRN  O35  C34  double    1.221  0.020  1.221
 HRN  C38  C39  aromatic  1.408  0.020  1.408
 HRN  C38  N36  single    1.400  0.020  1.400
 HRN  C39  N51  single    1.409  0.020  1.409
 HRN  C90  C12  single    1.522  0.020  1.522
 HRN  C2   C9   aromatic  1.387  0.020  1.387
 HRN  C2   C3   aromatic  1.391  0.020  1.391
 HRN  C34  N36  single    1.350  0.020  1.350
 HRN  C34  C21  single    1.479  0.020  1.479
 HRN  C9   C8   aromatic  1.383  0.020  1.383
 HRN  C12  C3   single    1.513  0.020  1.513
 HRN  C12  N14  single    1.461  0.020  1.461
 HRN  C3   C4   aromatic  1.391  0.020  1.391
 HRN  N51  C52  single    1.451  0.020  1.451
 HRN  N51  C63  single    1.459  0.020  1.459
 HRN  C21  N22  aromatic  1.376  0.020  1.376
 HRN  C21  C20  aromatic  1.377  0.020  1.377
 HRN  C52  C55  single    1.520  0.020  1.520
 HRN  N22  C24  aromatic  1.363  0.020  1.363
 HRN  C8   CL2  single    1.728  0.020  1.728
 HRN  C8   C6   aromatic  1.385  0.020  1.385
 HRN  C63  C60  single    1.520  0.020  1.520
 HRN  N14  C15  aromatic  1.351  0.020  1.351
 HRN  N14  C19  aromatic  1.376  0.020  1.376
 HRN  C4   C6   aromatic  1.382  0.020  1.382
 HRN  C20  C19  single    1.456  0.020  1.456
 HRN  C20  C25  aromatic  1.426  0.020  1.426
 HRN  C24  C31  aromatic  1.396  0.020  1.396
 HRN  C24  C25  aromatic  1.405  0.020  1.405
 HRN  C15  N17  aromatic  1.305  0.020  1.305
 HRN  C19  C18  aromatic  1.376  0.020  1.376
 HRN  C31  C30  aromatic  1.376  0.020  1.376
 HRN  C55  C58  single    1.530  0.020  1.530
 HRN  C25  C26  aromatic  1.397  0.020  1.397
 HRN  C60  C58  single    1.530  0.020  1.530
 HRN  C58  N66  single    1.465  0.020  1.465
 HRN  N17  C18  aromatic  1.368  0.020  1.368
 HRN  C18  C79  single    1.463  0.020  1.463
 HRN  C30  CL3  single    1.736  0.020  1.736
 HRN  C30  C28  aromatic  1.404  0.020  1.404
 HRN  O78  C77  double    1.222  0.020  1.222
 HRN  C26  C28  aromatic  1.375  0.020  1.375
 HRN  N66  C77  single    1.346  0.020  1.346
 HRN  N66  C67  single    1.460  0.020  1.460
 HRN  C88  C79  aromatic  1.397  0.020  1.397
 HRN  C88  C86  aromatic  1.387  0.020  1.387
 HRN  C79  C80  aromatic  1.398  0.020  1.398
 HRN  C77  O76  single    1.336  0.020  1.336
 HRN  C67  C70  single    1.512  0.020  1.512
 HRN  C86  C84  aromatic  1.389  0.020  1.389
 HRN  C80  C82  aromatic  1.387  0.020  1.387
 HRN  O76  C73  single    1.428  0.020  1.428
 HRN  C70  C73  single    1.505  0.020  1.505
 HRN  C84  C82  aromatic  1.389  0.020  1.389
 HRN  C42  H1   single    0.930  0.020  1.080
 HRN  C45  H2   single    0.930  0.020  1.080
 HRN  C52  H3   single    0.970  0.020  1.090
 HRN  C52  H4   single    0.970  0.020  1.090
 HRN  C55  H5   single    0.970  0.020  1.090
 HRN  C55  H6   single    0.970  0.020  1.090
 HRN  C58  H7   single    0.970  0.020  1.090
 HRN  C60  H8   single    0.970  0.020  1.090
 HRN  C60  H9   single    0.970  0.020  1.090
 HRN  C12  H10  single    0.970  0.020  1.090
 HRN  C15  H11  single    0.930  0.020  1.080
 HRN  C26  H12  single    0.930  0.020  1.080
 HRN  C28  H13  single    0.930  0.020  1.080
 HRN  C4   H14  single    0.930  0.020  1.080
 HRN  C6   H15  single    0.930  0.020  1.080
 HRN  C9   H16  single    0.930  0.020  1.080
 HRN  N22  H17  single    0.860  0.020  1.020
 HRN  C31  H18  single    0.930  0.020  1.080
 HRN  N36  H19  single    0.860  0.020  1.020
 HRN  C40  H20  single    0.930  0.020  1.080
 HRN  C63  H22  single    0.970  0.020  1.090
 HRN  C63  H23  single    0.970  0.020  1.090
 HRN  C67  H24  single    0.970  0.020  1.090
 HRN  C67  H25  single    0.970  0.020  1.090
 HRN  C70  H26  single    0.970  0.020  1.090
 HRN  C70  H27  single    0.970  0.020  1.090
 HRN  C73  H28  single    0.970  0.020  1.090
 HRN  C73  H29  single    0.970  0.020  1.090
 HRN  C80  H30  single    0.930  0.020  1.080
 HRN  C82  H31  single    0.930  0.020  1.080
 HRN  C84  H32  single    0.930  0.020  1.080
 HRN  C86  H33  single    0.930  0.020  1.080
 HRN  C88  H34  single    0.930  0.020  1.080
 HRN  C90  H35  single    0.970  0.020  1.090
 HRN  C90  H36  single    0.970  0.020  1.090
 HRN  C90  H37  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
 HRN  C9   C2   CL1  117.17  3.000
 HRN  C9   C2   C3   122.05  3.000
 HRN  CL1  C2   C3   120.76  3.000
 HRN  C4   C3   C12  119.50  3.000
 HRN  C4   C3   C2   117.23  3.000
 HRN  C12  C3   C2   123.25  3.000
 HRN  H1   C42  C40  119.84  3.000
 HRN  H1   C42  C44  119.74  3.000
 HRN  C40  C42  C44  120.41  3.000
 HRN  C47  C44  C45  119.85  3.000
 HRN  C45  C44  C42  119.36  3.000
 HRN  C47  C44  C42  120.79  3.000
 HRN  H2   C45  C38  120.80  3.000
 HRN  H2   C45  C44  118.61  3.000
 HRN  C38  C45  C44  120.57  3.000
 HRN  O49  C47  O48  126.73  3.000
 HRN  O48  C47  C44  116.54  3.000
 HRN  O49  C47  C44  116.73  3.000
 HRN  H4   C52  H3   107.35  3.000
 HRN  H4   C52  N51  111.74  3.000
 HRN  H3   C52  N51  109.42  3.000
 HRN  H4   C52  C55  110.59  3.000
 HRN  H3   C52  C55  109.54  3.000
 HRN  N51  C52  C55  108.18  3.000
 HRN  H6   C55  H5   107.82  3.000
 HRN  H6   C55  C58  110.73  3.000
 HRN  H5   C55  C58  109.12  3.000
 HRN  H6   C55  C52  108.08  3.000
 HRN  H5   C55  C52  109.83  3.000
 HRN  C58  C55  C52  111.19  3.000
 HRN  H7   C58  N66  104.92  3.000
 HRN  H7   C58  C60  105.88  3.000
 HRN  N66  C58  C60  112.06  3.000
 HRN  H7   C58  C55  106.44  3.000
 HRN  N66  C58  C55  112.40  3.000
 HRN  C60  C58  C55  114.28  3.000
 HRN  H9   C60  H8   106.70  3.000
 HRN  H9   C60  C63  108.67  3.000
 HRN  H8   C60  C63  109.87  3.000
 HRN  H9   C60  C58  111.11  3.000
 HRN  H8   C60  C58  109.16  3.000
 HRN  C63  C60  C58  111.22  3.000
 HRN  H10  C12  C90  107.54  3.000
 HRN  H10  C12  N14  106.72  3.000
 HRN  C90  C12  N14  112.08  3.000
 HRN  H10  C12  C3   109.72  3.000
 HRN  N14  C12  C3   109.43  3.000
 HRN  C90  C12  C3   111.21  3.000
 HRN  H11  C15  N17  125.10  3.000
 HRN  H11  C15  N14  122.86  3.000
 HRN  N17  C15  N14  112.04  3.000
 HRN  C79  C18  N17  121.06  3.000
 HRN  C79  C18  C19  129.25  3.000
 HRN  N17  C18  C19  109.69  3.000
 HRN  N14  C19  C20  122.56  3.000
 HRN  C20  C19  C18  131.60  3.000
 HRN  N14  C19  C18  105.37  3.000
 HRN  C25  C20  C21  106.75  3.000
 HRN  C25  C20  C19  123.57  3.000
 HRN  C21  C20  C19  129.52  3.000
 HRN  C34  C21  N22  126.68  3.000
 HRN  N22  C21  C20  108.95  3.000
 HRN  C34  C21  C20  124.30  3.000
 HRN  C31  C24  N22  130.14  3.000
 HRN  C31  C24  C25  122.09  3.000
 HRN  N22  C24  C25  107.75  3.000
 HRN  C26  C25  C24  119.76  3.000
 HRN  C26  C25  C20  133.14  3.000
 HRN  C24  C25  C20  107.08  3.000
 HRN  H12  C26  C28  120.28  3.000
 HRN  H12  C26  C25  120.71  3.000
 HRN  C28  C26  C25  119.00  3.000
 HRN  H13  C28  C30  119.80  3.000
 HRN  H13  C28  C26  120.45  3.000
 HRN  C30  C28  C26  119.74  3.000
 HRN  CL3  C30  C31  118.64  3.000
 HRN  CL3  C30  C28  118.14  3.000
 HRN  C31  C30  C28  123.22  3.000
 HRN  H14  C4   C6   118.49  3.000
 HRN  H14  C4   C3   119.39  3.000
 HRN  C6   C4   C3   122.06  3.000
 HRN  H15  C6   C8   120.83  3.000
 HRN  H15  C6   C4   120.33  3.000
 HRN  C8   C6   C4   118.81  3.000
 HRN  CL2  C8   C9   119.27  3.000
 HRN  CL2  C8   C6   119.68  3.000
 HRN  C9   C8   C6   121.05  3.000
 HRN  H16  C9   C8   120.96  3.000
 HRN  H16  C9   C2   120.38  3.000
 HRN  C8   C9   C2   118.66  3.000
 HRN  C19  N14  C15  106.94  3.000
 HRN  C19  N14  C12  125.37  3.000
 HRN  C15  N14  C12  127.69  3.000
 HRN  C18  N17  C15  105.96  3.000
 HRN  H17  N22  C24  121.89  3.000
 HRN  H17  N22  C21  128.59  3.000
 HRN  C24  N22  C21  109.43  3.000
 HRN  H18  C31  C30  121.95  3.000
 HRN  H18  C31  C24  121.88  3.000
 HRN  C30  C31  C24  116.17  3.000
 HRN  N36  C34  O35  123.68  3.000
 HRN  N36  C34  C21  116.88  3.000
 HRN  O35  C34  C21  119.42  3.000
 HRN  H19  N36  C38  110.40  3.000
 HRN  H19  N36  C34  120.81  3.000
 HRN  C38  N36  C34  128.49  3.000
 HRN  C39  C38  N36  114.90  3.000
 HRN  N36  C38  C45  125.26  3.000
 HRN  C39  C38  C45  119.79  3.000
 HRN  N51  C39  C40  123.97  3.000
 HRN  N51  C39  C38  116.81  3.000
 HRN  C40  C39  C38  119.21  3.000
 HRN  H20  C40  C39  119.37  3.000
 HRN  H20  C40  C42  119.98  3.000
 HRN  C39  C40  C42  120.65  3.000
 HRN  C63  N51  C39  115.90  3.000
 HRN  C63  N51  C52  111.14  3.000
 HRN  C39  N51  C52  118.00  3.000
 HRN  H23  C63  H22  106.84  3.000
 HRN  H23  C63  N51  109.70  3.000
 HRN  H22  C63  N51  110.46  3.000
 HRN  H23  C63  C60  109.77  3.000
 HRN  H22  C63  C60  110.81  3.000
 HRN  N51  C63  C60  109.23  3.000
 HRN  C77  N66  C67  124.29  3.000
 HRN  C67  N66  C58  115.82  3.000
 HRN  C77  N66  C58  119.90  3.000
 HRN  H25  C67  H24  107.35  3.000
 HRN  H25  C67  C70  110.34  3.000
 HRN  H24  C67  C70  110.30  3.000
 HRN  H25  C67  N66  108.19  3.000
 HRN  H24  C67  N66  109.27  3.000
 HRN  C70  C67  N66  111.29  3.000
 HRN  H27  C70  H26  107.56  3.000
 HRN  H27  C70  C73  110.09  3.000
 HRN  H26  C70  C73  110.28  3.000
 HRN  H27  C70  C67  111.02  3.000
 HRN  H26  C70  C67  109.72  3.000
 HRN  C73  C70  C67  108.19  3.000
 HRN  H29  C73  H28  108.22  3.000
 HRN  H29  C73  O76  105.84  3.000
 HRN  H28  C73  O76  109.36  3.000
 HRN  H29  C73  C70  112.50  3.000
 HRN  H28  C73  C70  111.04  3.000
 HRN  O76  C73  C70  109.72  3.000
 HRN  C77  O76  C73  120.60  3.000
 HRN  O78  C77  O76  116.77  3.000
 HRN  O76  C77  N66  118.84  3.000
 HRN  O78  C77  N66  124.38  3.000
 HRN  C88  C79  C80  118.19  3.000
 HRN  C80  C79  C18  119.59  3.000
 HRN  C88  C79  C18  122.21  3.000
 HRN  H30  C80  C82  119.69  3.000
 HRN  H30  C80  C79  119.39  3.000
 HRN  C82  C80  C79  120.92  3.000
 HRN  H31  C82  C84  120.11  3.000
 HRN  H31  C82  C80  119.52  3.000
 HRN  C84  C82  C80  120.37  3.000
 HRN  H32  C84  C86  120.39  3.000
 HRN  H32  C84  C82  120.37  3.000
 HRN  C86  C84  C82  119.24  3.000
 HRN  H33  C86  C88  119.41  3.000
 HRN  H33  C86  C84  120.11  3.000
 HRN  C88  C86  C84  120.48  3.000
 HRN  H34  C88  C86  118.94  3.000
 HRN  H34  C88  C79  120.26  3.000
 HRN  C86  C88  C79  120.80  3.000
 HRN  H37  C90  H36  107.53  3.000
 HRN  H37  C90  H35  108.96  3.000
 HRN  H36  C90  H35  107.88  3.000
 HRN  H37  C90  C12  111.58  3.000
 HRN  H36  C90  C12  108.46  3.000
 HRN  H35  C90  C12  112.26  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
 HRN  CONST_01   C6   C8   C9   C2      0.00   0.0  0
 HRN  CONST_02   C6   C4   C3   C2      0.00   0.0  0
 HRN  CONST_03   C8   C9   C2   C3      0.00   0.0  0
 HRN  CONST_04   C8   C6   C4   C3      0.00   0.0  0
 HRN  CONST_05   C38  C45  C44  C42     0.00   0.0  0
 HRN  CONST_06   C38  C39  C40  C42     0.00   0.0  0
 HRN  CONST_07   C39  C40  C42  C44     0.00   0.0  0
 HRN  CONST_08   C39  C38  C45  C44     0.00   0.0  0
 HRN  CONST_09   C40  C42  C44  C45     0.00   0.0  0
 HRN  CONST_10   C40  C39  C38  C45     0.00   0.0  0
 HRN  CONST_11   C20  C19  N14  C15   180.00   0.0  0
 HRN  CONST_12   C18  C19  N14  C15     0.00   0.0  0
 HRN  CONST_13   C19  C18  N17  C15     0.00   0.0  0
 HRN  CONST_14   C79  C18  N17  C15   180.00   0.0  0
 HRN  CONST_17   N14  C15  N17  C18     0.00   0.0  0
 HRN  CONST_18   C86  C88  C79  C18   180.00   0.0  0
 HRN  CONST_19   C82  C80  C79  C18   180.00   0.0  0
 HRN  CONST_20   N17  C15  N14  C19     0.00   0.0  0
 HRN  CONST_21   N22  C21  C20  C19   180.00   0.0  0
 HRN  CONST_22   C24  C25  C20  C19   180.00   0.0  0
 HRN  CONST_23   C26  C25  C20  C19     0.00   0.0  0
 HRN  CONST_26   C24  N22  C21  C20     0.00   0.0  0
 HRN  CONST_27   N17  C18  C19  C20   180.00   0.0  0
 HRN  CONST_28   C79  C18  C19  C20     0.00   0.0  0
 HRN  CONST_29   N22  C24  C25  C20     0.00   0.0  0
 HRN  CONST_30   C31  C24  C25  C20   180.00   0.0  0
 HRN  CONST_31   C28  C26  C25  C20   180.00   0.0  0
 HRN  CONST_32   C31  C24  N22  C21   180.00   0.0  0
 HRN  CONST_33   C25  C24  N22  C21     0.00   0.0  0
 HRN  CONST_35   C24  C25  C20  C21     0.00   0.0  0
 HRN  CONST_36   C26  C25  C20  C21   180.00   0.0  0
 HRN  CONST_37   C28  C30  C31  C24     0.00   0.0  0
 HRN  CONST_38   C28  C26  C25  C24     0.00   0.0  0
 HRN  CONST_39   N22  C21  C20  C25     0.00   0.0  0
 HRN  CONST_41   C30  C31  C24  C25     0.00   0.0  0
 HRN  CONST_42   C30  C28  C26  C25     0.00   0.0  0
 HRN  CONST_43   N22  C24  C25  C26   180.00   0.0  0
 HRN  CONST_44   C31  C24  C25  C26     0.00   0.0  0
 HRN  CONST_45   C31  C30  C28  C26     0.00   0.0  0
 HRN  CONST_46   N22  C24  C31  C30   180.00   0.0  0
 HRN  CONST_47   C9   C2   C3   C4      0.00   0.0  0
 HRN  CONST_48   C9   C8   C6   C4      0.00   0.0  0
 HRN  CONST_49   N17  C18  C19  N14     0.00   0.0  0
 HRN  CONST_50   C79  C18  C19  N14   180.00   0.0  0
 HRN  CONST_53   C84  C86  C88  C79     0.00   0.0  0
 HRN  CONST_54   C84  C82  C80  C79     0.00   0.0  0
 HRN  CONST_55   C86  C88  C79  C80     0.00   0.0  0
 HRN  CONST_56   C86  C84  C82  C80     0.00   0.0  0
 HRN  CONST_57   C88  C79  C80  C82     0.00   0.0  0
 HRN  CONST_58   C88  C86  C84  C82     0.00   0.0  0
 HRN  CONST_59   N51  C39  C40  C42   180.00   0.0  0
 HRN  CONST_60   N51  C39  C38  C45   180.00   0.0  0
 HRN  CONST_61   CL2  C8   C9   C2    180.00   0.0  0
 HRN  CONST_62   N36  C38  C45  C44   180.00   0.0  0
 HRN  CONST_63   C40  C42  C44  C47   180.00   0.0  0
 HRN  CONST_64   C38  C45  C44  C47   180.00   0.0  0
 HRN  CONST_65   C9   C2   C3   C12   180.00   0.0  0
 HRN  CONST_66   C6   C4   C3   C12   180.00   0.0  0
 HRN  CONST_67   N17  C15  N14  C12   180.00   0.0  0
 HRN  CONST_68   C20  C19  N14  C12     0.00   0.0  0
 HRN  CONST_69   C18  C19  N14  C12   180.00   0.0  0
 HRN  CONST_70   C34  C21  C20  C19     0.00   0.0  0
 HRN  CONST_71   C34  C21  N22  C24   180.00   0.0  0
 HRN  CONST_72   CL3  C30  C31  C24   180.00   0.0  0
 HRN  CONST_73   C34  C21  C20  C25   180.00   0.0  0
 HRN  CONST_74   CL3  C30  C28  C26   180.00   0.0  0
 HRN  CONST_75   C8   C9   C2   CL1   180.00   0.0  0
 HRN  CONST_76   C4   C3   C2   CL1   180.00   0.0  0
 HRN  CONST_77   CL2  C8   C6   C4    180.00   0.0  0
 HRN  CONST_78   C40  C39  C38  N36   180.00   0.0  0
 HRN  CONST_79   N51  C39  C38  N36     0.00   0.0  0
 HRN  CONST_80   H14  C4   C3   C2    180.00   0.0  0
 HRN  CONST_81   H16  C9   C2   C3    180.00   0.0  0
 HRN  CONST_82   H15  C6   C4   C3    180.00   0.0  0
 HRN  CONST_83   H2   C45  C44  C42   180.00   0.0  0
 HRN  CONST_84   H20  C40  C42  C44   180.00   0.0  0
 HRN  CONST_85   H1   C42  C44  C45   180.00   0.0  0
 HRN  CONST_86   H11  C15  N17  C18   180.00   0.0  0
 HRN  CONST_87   H34  C88  C79  C18     0.00   0.0  0
 HRN  CONST_88   H30  C80  C79  C18     0.00   0.0  0
 HRN  CONST_89   H17  N22  C21  C20   180.00   0.0  0
 HRN  CONST_90   H12  C26  C25  C20     0.00   0.0  0
 HRN  CONST_91   H18  C31  C24  C25   180.00   0.0  0
 HRN  CONST_92   H13  C28  C26  C25   180.00   0.0  0
 HRN  CONST_93   H33  C86  C88  C79   180.00   0.0  0
 HRN  CONST_94   H31  C82  C80  C79   180.00   0.0  0
 HRN  CONST_95   H32  C84  C82  C80   180.00   0.0  0
 HRN  CONST_96   C38  N36  C34  C21   180.00   0.0  0
 HRN  CONST_99   H19  N36  C38  C45   180.00   0.0  0
 HRN  CONST_100  C38  N36  C34  O35     0.00   0.0  0
 HRN  Var_01     C40  C39  N51  C52    39.93  30.0  1
 HRN  Var_02     C60  C63  N51  C52    66.59  30.0  1
 HRN  Var_03     C39  N51  C52  C55   155.06  30.0  1
 HRN  Var_04     N51  C52  C55  C58    55.15  30.0  1
 HRN  Var_05     N51  C63  C60  C58   -52.62  30.0  1
 HRN  Var_06     O76  C77  N66  C58   173.61  30.0  1
 HRN  Var_07     C70  C67  N66  C58   167.17  30.0  1
 HRN  Var_08     C73  C70  C67  N66    43.86  30.0  1
 HRN  Var_09     O76  C73  C70  C67   -59.11  30.0  1
 HRN  Var_10     O49  C47  C44  C42  -179.54  30.0  3
 HRN  Var_11     O35  C34  C21  C20     5.40  30.0  2

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
 HRN  chir_01  C58  C55  C60  N66  positiv
 HRN  chir_02  C12  C90  C3   N14  negativ

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
 HRN  plan-1  C12  0.020
 HRN  plan-1  C15  0.020
 HRN  plan-1  C18  0.020
 HRN  plan-1  C19  0.020
 HRN  plan-1  C20  0.020
 HRN  plan-1  N14  0.020
 HRN  plan-1  N17  0.020
 HRN  plan-1  C79  0.020
 HRN  plan-1  H11  0.020
 HRN  plan-2  C44  0.020
 HRN  plan-2  C47  0.020
 HRN  plan-2  O48  0.020
 HRN  plan-2  O49  0.020
 HRN  plan-3  N66  0.020
 HRN  plan-3  O76  0.020
 HRN  plan-3  C77  0.020
 HRN  plan-3  O78  0.020
 HRN  plan-4  C2   0.020
 HRN  plan-4  C3   0.020
 HRN  plan-4  C12  0.020
 HRN  plan-4  CL1  0.020
 HRN  plan-4  C4   0.020
 HRN  plan-4  C6   0.020
 HRN  plan-4  C8   0.020
 HRN  plan-4  C9   0.020
 HRN  plan-4  CL2  0.020
 HRN  plan-4  H14  0.020
 HRN  plan-4  H15  0.020
 HRN  plan-4  H16  0.020
 HRN  plan-5  C42  0.020
 HRN  plan-5  C44  0.020
 HRN  plan-5  C45  0.020
 HRN  plan-5  C47  0.020
 HRN  plan-5  N36  0.020
 HRN  plan-5  C38  0.020
 HRN  plan-5  C39  0.020
 HRN  plan-5  C40  0.020
 HRN  plan-5  N51  0.020
 HRN  plan-5  H1   0.020
 HRN  plan-5  H2   0.020
 HRN  plan-5  H20  0.020
 HRN  plan-6  C18  0.020
 HRN  plan-6  C79  0.020
 HRN  plan-6  C80  0.020
 HRN  plan-6  C82  0.020
 HRN  plan-6  C84  0.020
 HRN  plan-6  C86  0.020
 HRN  plan-6  C88  0.020
 HRN  plan-6  H30  0.020
 HRN  plan-6  H31  0.020
 HRN  plan-6  H32  0.020
 HRN  plan-6  H33  0.020
 HRN  plan-6  H34  0.020
 HRN  plan-7  C19  0.020
 HRN  plan-7  C20  0.020
 HRN  plan-7  C21  0.020
 HRN  plan-7  C24  0.020
 HRN  plan-7  C25  0.020
 HRN  plan-7  C26  0.020
 HRN  plan-7  C28  0.020
 HRN  plan-7  C30  0.020
 HRN  plan-7  N22  0.020
 HRN  plan-7  C31  0.020
 HRN  plan-7  CL3  0.020
 HRN  plan-7  C34  0.020
 HRN  plan-7  H12  0.020
 HRN  plan-7  H13  0.020
 HRN  plan-7  H17  0.020
 HRN  plan-7  H18  0.020
 HRN  plan-8  C21  0.020
 HRN  plan-8  C34  0.020
 HRN  plan-8  O35  0.020
 HRN  plan-8  N36  0.020
 HRN  plan-8  C38  0.020
 HRN  plan-8  H19  0.020
 HRN  plan-9  C58  0.020
 HRN  plan-9  N66  0.020
 HRN  plan-9  C67  0.020
 HRN  plan-9  C77  0.020

