# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 00:25:14 2020
#   Inital geometry file: a 212 line input string
#   Ligand name: N-(2-{4-[3-(4-{[4-(acetylamino)benzyl]oxy}-2,3-dichlorophenyl)-1-methyl-1H-pyrazol-5-yl]piperidin-1-yl}-2-oxoethyl)-N~2~-carbamimidoyl-D-leucinamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)C[C@@H](NC(N)=N)C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(OCc4ccc(NC(C)=O)cc4)c(Cl)c3Cl
#
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
 FRI  FRI  N-(2-{4-[3-(4-{[4-(acetylamino)benzyl]oxy}-2,3-dichlorophenyl)-1-methyl-1H-pyrazol-5-yl]piperidin-1-yl}-2-oxoethyl)-N~2~-carbamimidoyl-D-leucinamide  ligand  89  47  .  2021-08-09  2021-08-09  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_FRI
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
 FRI  O47   O   O     0  -0.490  -0.4839  -1.6387    5.6289
 FRI  C30   C   C     0   0.541  -1.1181  -0.5970    5.5792
 FRI  C29   C   CH2   0  -0.436  -0.5799   0.6665    6.2582
 FRI  N3    N   NH1   0  -0.636   0.6024   0.3917    7.0180
 FRI  C27   C   C     0   0.590   0.5382  -0.3304    8.1527
 FRI  O46   O   O     0  -0.494  -0.5266  -0.6214    8.6717
 FRI  C26   C   CH1   0  -0.233   1.8669  -0.8374    8.7280
 FRI  C41   C   CH2   0  -0.429   3.1029  -0.0063    8.3651
 FRI  C32   C   CH1   0  -0.222   4.3973  -0.4818    9.0254
 FRI  C37   C   CH3   0  -0.665   4.7252  -1.9319    8.6868
 FRI  C36   C   CH3   0  -0.653   5.5464   0.4353    8.6172
 FRI  N7    N   NH1   0  -0.626   1.7455  -1.0894   10.1405
 FRI  C24   C   C     0   0.558   1.3819  -0.0886   11.0043
 FRI  N5    N   N     0  -0.699   1.3384   1.1300   10.6150
 FRI  N4    N   NH2   0  -0.841   1.0631  -0.5509   12.2647
 FRI  N2    N   NT    0  -0.447  -2.3078  -0.4918    4.9516
 FRI  C31   C   CH2   0  -0.336  -2.9975   0.7573    4.6787
 FRI  C39   C   CH2   0  -0.411  -2.9015   1.1067    3.1981
 FRI  C19   C   CH1   0  -0.389  -3.4385  -0.0412    2.3302
 FRI  C21   C   CH2   0  -0.416  -2.7404  -1.3510    2.7005
 FRI  C43   C   CH2   0  -0.324  -2.8485  -1.6099    4.1970
 FRI  C23   C   CR5   0   0.510  -3.2987   0.2657    0.8755
 FRI  N8    N   NR5   0  -0.330  -4.2119   0.9763    0.1779
 FRI  C38   C   CH3   0  -0.534  -5.4816   1.4775    0.6507
 FRI  N6    N   N     0  -0.299  -3.8701   1.1407   -1.0951
 FRI  C13   C   CR15  0  -0.579  -2.2897  -0.0325   -0.0138
 FRI  C14   C   CR5   0   0.247  -2.6982   0.5391   -1.2325
 FRI  C11   C   CR6   0   0.120  -2.0730   0.4758   -2.5593
 FRI  C15   C   CR16  0  -0.297  -2.8717   0.2400   -3.6746
 FRI  C17   C   CR16  0  -0.374  -2.3560   0.1611   -4.9561
 FRI  C20   C   CR6   0   0.460  -0.9905   0.3150   -5.1685
 FRI  C33   C   CR6   0  -0.107  -0.1693   0.5660   -4.0630
 FRI  C34   C   CR6   0  -0.086  -0.7049   0.6504   -2.7841
 FRI  CL10  CL  CL    0  -0.096   0.3541   1.0168   -1.4750
 FRI  CL9   CL  CL    0  -0.076   1.5158   0.7763   -4.3328
 FRI  O45   O   O2    0  -0.447  -0.3826   0.2450   -6.3553
 FRI  C40   C   CH2   0  -0.276  -1.1580  -0.0887   -7.5069
 FRI  C22   C   CR6   0   0.084  -0.2122  -0.1876   -8.6611
 FRI  C28   C   CR16  0  -0.287  -0.1304   0.8175   -9.6177
 FRI  C25   C   CR16  0  -0.335   0.7711   0.7300  -10.6637
 FRI  C35   C   CR6   0   0.366   1.6278  -0.3670  -10.7790
 FRI  C18   C   CR16  0  -0.304   1.5497  -1.3843   -9.8239
 FRI  C16   C   CR16  0  -0.271   0.6376  -1.2807   -8.7858
 FRI  N1    N   NH1   0  -0.733   2.5069  -0.3674  -11.8632
 FRI  C12   C   C     0   0.510   3.5084  -1.2368  -12.1673
 FRI  O44   O   O     0  -0.469   3.7674  -2.2295  -11.5110
 FRI  C42   C   CH3   0  -0.785   4.3110  -0.8426  -13.3807
 FRI  H291  H   HCH2  0   0.280  -1.3416   1.1106    6.9003
 FRI  H292  H   HCH2  0   0.295  -0.3330   1.4124    5.5007
 FRI  HN3   H   HNH1  0   0.405   1.4859   0.5081    6.5526
 FRI  H26   H   HCH1  0   0.289   1.9970  -1.8236    8.2677
 FRI  H411  H   HCH2  0   0.245   2.9315   1.0385    8.6234
 FRI  H412  H   HCH2  0   0.215   3.2525  -0.0553    7.2806
 FRI  H32   H   HCH1  0   0.223   4.2722  -0.4022   10.1093
 FRI  H371  H   HCH3  0   0.227   5.6705  -2.2328    9.1416
 FRI  H372  H   HCH3  0   0.226   3.9612  -2.6223    9.0457
 FRI  H373  H   HCH3  0   0.213   4.8204  -2.0704    7.6066
 FRI  H361  H   HCH3  0   0.211   5.7130   0.4014    7.5375
 FRI  H362  H   HCH3  0   0.223   5.3459   1.4736    8.8884
 FRI  H363  H   HCH3  0   0.225   6.4781   0.1396    9.1028
 FRI  HN7   H   HNH1  0   0.384   1.4059  -2.0067   10.3776
 FRI  HN5   H   H     0   0.315   1.1196   1.7462   11.3894
 FRI  HN41  H   HNH2  0   0.384   1.0500   0.1515   12.9866
 FRI  HN42  H   HNH2  0   0.382   1.5457  -1.3831   12.5679
 FRI  H311  H   HCH2  0   0.255  -4.0477   0.6388    4.9644
 FRI  H312  H   HCH2  0   0.280  -2.6024   1.5681    5.2849
 FRI  H391  H   HCH2  0   0.241  -1.8586   1.3058    2.9343
 FRI  H392  H   HCH2  0   0.250  -3.4615   2.0260    3.0106
 FRI  H19   H   HCH1  0   0.262  -4.5041  -0.1645    2.5626
 FRI  H211  H   HCH2  0   0.236  -1.6844  -1.3109    2.4184
 FRI  H212  H   HCH2  0   0.253  -3.1889  -2.1832    2.1543
 FRI  H431  H   HCH2  0   0.269  -2.3304  -2.5234    4.4746
 FRI  H432  H   HCH2  0   0.246  -3.8999  -1.7320    4.4766
 FRI  H381  H   HCH3  0   0.260  -6.2228   0.6808    0.7084
 FRI  H382  H   HCH3  0   0.257  -5.3732   1.9299    1.6336
 FRI  H383  H   HCH3  0   0.274  -5.8307   2.2369   -0.0421
 FRI  H13   H   HCR5  0   0.262  -1.3972  -0.5997    0.1879
 FRI  H15   H   HCR6  0   0.267  -3.9349   0.1031   -3.5321
 FRI  H17   H   HCR6  0   0.298  -3.0304  -0.0289   -5.7792
 FRI  H401  H   HCH2  0   0.252  -1.9151   0.6793   -7.6906
 FRI  H402  H   HCH2  0   0.250  -1.6726  -1.0407   -7.3424
 FRI  H28   H   HCR6  0   0.260  -0.7775   1.6838   -9.5528
 FRI  H25   H   HCR6  0   0.272   0.8146   1.5270  -11.3966
 FRI  H18   H   HCR6  0   0.282   2.1856  -2.2515   -9.8811
 FRI  H16   H   HCR6  0   0.257   0.5909  -2.0825   -8.0585
 FRI  HN1   H   HNH1  0   0.416   2.4069   0.4194  -12.4858
 FRI  H421  H   HCH3  0   0.269   4.6702  -1.7334  -13.8907
 FRI  H422  H   HCH3  0   0.258   3.7513  -0.2320  -14.0872
 FRI  H423  H   HCH3  0   0.278   5.1822  -0.2675  -13.0606

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
 FRI  O47  C30   double    1.221  0.020  1.221
 FRI  C30  C29   single    1.532  0.020  1.532
 FRI  C30  N2    single    1.349  0.020  1.349
 FRI  C29  N3    single    1.432  0.020  1.432
 FRI  C29  H291  single    0.970  0.020  1.090
 FRI  C29  H292  single    0.970  0.020  1.090
 FRI  N3   C27   single    1.346  0.020  1.346
 FRI  N3   HN3   single    0.860  0.020  1.020
 FRI  C27  O46   double    1.220  0.020  1.220
 FRI  C27  C26   single    1.534  0.020  1.534
 FRI  C26  C41   single    1.533  0.020  1.533
 FRI  C26  N7    single    1.440  0.020  1.440
 FRI  C26  H26   single    0.970  0.020  1.090
 FRI  C41  C32   single    1.529  0.020  1.529
 FRI  C41  H411  single    0.970  0.020  1.090
 FRI  C41  H412  single    0.970  0.020  1.090
 FRI  C32  C37   single    1.525  0.020  1.525
 FRI  C32  C36   single    1.526  0.020  1.526
 FRI  C32  H32   single    0.970  0.020  1.090
 FRI  C37  H371  single    0.970  0.020  1.090
 FRI  C37  H372  single    0.970  0.020  1.090
 FRI  C37  H373  single    0.970  0.020  1.090
 FRI  C36  H361  single    0.970  0.020  1.090
 FRI  C36  H362  single    0.970  0.020  1.090
 FRI  C36  H363  single    0.970  0.020  1.090
 FRI  N7   C24   single    1.371  0.020  1.371
 FRI  N7   HN7   single    0.890  0.020  1.040
 FRI  C24  N5    double    1.280  0.020  1.280
 FRI  C24  N4    single    1.380  0.020  1.380
 FRI  N5   HN5   single    0.890  0.020  1.040
 FRI  N4   HN41  single    0.890  0.020  1.040
 FRI  N4   HN42  single    0.890  0.020  1.040
 FRI  N2   C31   single    1.453  0.020  1.453
 FRI  N2   C43   single    1.453  0.020  1.453
 FRI  C31  C39   single    1.524  0.020  1.524
 FRI  C31  H311  single    0.970  0.020  1.090
 FRI  C31  H312  single    0.970  0.020  1.090
 FRI  C39  C19   single    1.536  0.020  1.536
 FRI  C39  H391  single    0.970  0.020  1.090
 FRI  C39  H392  single    0.970  0.020  1.090
 FRI  C19  C21   single    1.530  0.020  1.530
 FRI  C19  C23   single    1.493  0.020  1.493
 FRI  C19  H19   single    0.970  0.020  1.090
 FRI  C21  C43   single    1.523  0.020  1.523
 FRI  C21  H211  single    0.970  0.020  1.090
 FRI  C21  H212  single    0.970  0.020  1.090
 FRI  C43  H431  single    0.970  0.020  1.090
 FRI  C43  H432  single    0.970  0.020  1.090
 FRI  C23  N8    aromatic  1.351  0.020  1.351
 FRI  C23  C13   aromatic  1.378  0.020  1.378
 FRI  N8   C38   single    1.445  0.020  1.445
 FRI  N8   N6    aromatic  1.328  0.020  1.328
 FRI  C38  H381  single    0.970  0.020  1.090
 FRI  C38  H382  single    0.970  0.020  1.090
 FRI  C38  H383  single    0.970  0.020  1.090
 FRI  N6   C14   aromatic  1.324  0.020  1.324
 FRI  C13  C14   aromatic  1.407  0.020  1.407
 FRI  C13  H13   single    0.930  0.020  1.080
 FRI  C14  C11   single    1.468  0.020  1.468
 FRI  C11  C15   aromatic  1.392  0.020  1.392
 FRI  C11  C34   aromatic  1.397  0.020  1.397
 FRI  C15  C17   aromatic  1.384  0.020  1.384
 FRI  C15  H15   single    0.930  0.020  1.080
 FRI  C17  C20   aromatic  1.390  0.020  1.390
 FRI  C17  H17   single    0.930  0.020  1.080
 FRI  C20  C33   aromatic  1.400  0.020  1.400
 FRI  C20  O45   single    1.335  0.020  1.335
 FRI  C33  C34   aromatic  1.389  0.020  1.389
 FRI  C33  CL9   single    1.719  0.020  1.719
 FRI  C34  CL10  single    1.723  0.020  1.723
 FRI  O45  C40   single    1.428  0.020  1.428
 FRI  C40  C22   single    1.496  0.020  1.496
 FRI  C40  H401  single    0.970  0.020  1.090
 FRI  C40  H402  single    0.970  0.020  1.090
 FRI  C22  C28   aromatic  1.390  0.020  1.390
 FRI  C22  C16   aromatic  1.390  0.020  1.390
 FRI  C28  C25   aromatic  1.384  0.020  1.384
 FRI  C28  H28   single    0.930  0.020  1.080
 FRI  C25  C35   aromatic  1.397  0.020  1.397
 FRI  C25  H25   single    0.930  0.020  1.080
 FRI  C35  C18   aromatic  1.398  0.020  1.398
 FRI  C35  N1    single    1.396  0.020  1.396
 FRI  C18  C16   aromatic  1.386  0.020  1.386
 FRI  C18  H18   single    0.930  0.020  1.080
 FRI  C16  H16   single    0.930  0.020  1.080
 FRI  N1   C12   single    1.361  0.020  1.361
 FRI  N1   HN1   single    0.860  0.020  1.020
 FRI  C12  O44   double    1.218  0.020  1.218
 FRI  C12  C42   single    1.507  0.020  1.507
 FRI  C42  H421  single    0.970  0.020  1.090
 FRI  C42  H422  single    0.970  0.020  1.090
 FRI  C42  H423  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
 FRI  N2    C30  C29   116.85  3.000
 FRI  N2    C30  O47   122.93  3.000
 FRI  C29   C30  O47   120.22  3.000
 FRI  H292  C29  H291  106.76  3.000
 FRI  H292  C29  N3    108.22  3.000
 FRI  H291  C29  N3    110.02  3.000
 FRI  H292  C29  C30   109.60  3.000
 FRI  H291  C29  C30   110.57  3.000
 FRI  N3    C29  C30   111.52  3.000
 FRI  HN3   N3   C27   119.61  3.000
 FRI  HN3   N3   C29   117.24  3.000
 FRI  C27   N3   C29   120.71  3.000
 FRI  C26   C27  O46   121.18  3.000
 FRI  C26   C27  N3    116.87  3.000
 FRI  O46   C27  N3    121.88  3.000
 FRI  H26   C26  N7    105.34  3.000
 FRI  H26   C26  C41   107.02  3.000
 FRI  N7    C26  C41   113.27  3.000
 FRI  H26   C26  C27   104.04  3.000
 FRI  N7    C26  C27   110.65  3.000
 FRI  C41   C26  C27   115.49  3.000
 FRI  H412  C41  H411  107.38  3.000
 FRI  H412  C41  C32   107.34  3.000
 FRI  H411  C41  C32   109.21  3.000
 FRI  H412  C41  C26   108.67  3.000
 FRI  H411  C41  C26   109.69  3.000
 FRI  C32   C41  C26   114.31  3.000
 FRI  H32   C32  C36   107.91  3.000
 FRI  H32   C32  C37   108.29  3.000
 FRI  C36   C32  C37   110.50  3.000
 FRI  H32   C32  C41   107.97  3.000
 FRI  C36   C32  C41   109.58  3.000
 FRI  C37   C32  C41   112.45  3.000
 FRI  H373  C37  H372  107.82  3.000
 FRI  H373  C37  H371  107.55  3.000
 FRI  H372  C37  H371  107.17  3.000
 FRI  H373  C37  C32   111.02  3.000
 FRI  H372  C37  C32   112.22  3.000
 FRI  H371  C37  C32   110.85  3.000
 FRI  H363  C36  H362  107.70  3.000
 FRI  H363  C36  H361  107.51  3.000
 FRI  H362  C36  H361  107.64  3.000
 FRI  H363  C36  C32   111.16  3.000
 FRI  H362  C36  C32   111.52  3.000
 FRI  H361  C36  C32   111.12  3.000
 FRI  HN7   N7   C24   115.30  3.000
 FRI  HN7   N7   C26   114.78  3.000
 FRI  C24   N7   C26   120.84  3.000
 FRI  N4    C24  N5    126.08  3.000
 FRI  N4    C24  N7    113.09  3.000
 FRI  N5    C24  N7    120.82  3.000
 FRI  HN5   N5   C24   110.72  3.000
 FRI  HN42  N4   HN41  111.48  3.000
 FRI  HN42  N4   C24   116.14  3.000
 FRI  HN41  N4   C24   115.09  3.000
 FRI  C43   N2   C31   112.79  3.000
 FRI  C43   N2   C30   120.64  3.000
 FRI  C31   N2   C30   124.96  3.000
 FRI  H312  C31  H311  106.50  3.000
 FRI  H312  C31  C39   110.36  3.000
 FRI  H311  C31  C39   109.80  3.000
 FRI  H312  C31  N2    111.35  3.000
 FRI  H311  C31  N2    108.25  3.000
 FRI  C39   C31  N2    110.47  3.000
 FRI  H392  C39  H391  107.11  3.000
 FRI  H392  C39  C19   110.65  3.000
 FRI  H391  C39  C19   109.46  3.000
 FRI  H392  C39  C31   109.10  3.000
 FRI  H391  C39  C31   109.63  3.000
 FRI  C19   C39  C31   110.82  3.000
 FRI  H19   C19  C23   108.68  3.000
 FRI  H19   C19  C21   107.19  3.000
 FRI  C23   C19  C21   111.66  3.000
 FRI  H19   C19  C39   107.68  3.000
 FRI  C23   C19  C39   111.35  3.000
 FRI  C21   C19  C39   110.10  3.000
 FRI  H212  C21  H211  107.19  3.000
 FRI  H212  C21  C43   109.45  3.000
 FRI  H211  C21  C43   109.16  3.000
 FRI  H212  C21  C19   110.12  3.000
 FRI  H211  C21  C19   110.29  3.000
 FRI  C43   C21  C19   110.56  3.000
 FRI  H432  C43  H431  107.39  3.000
 FRI  H432  C43  C21   109.76  3.000
 FRI  H431  C43  C21   111.12  3.000
 FRI  H432  C43  N2    108.09  3.000
 FRI  H431  C43  N2    109.69  3.000
 FRI  C21   C43  N2    110.68  3.000
 FRI  C13   C23  N8    106.00  3.000
 FRI  C13   C23  C19   130.76  3.000
 FRI  N8    C23  C19   123.22  3.000
 FRI  N6    N8   C38   119.79  3.000
 FRI  N6    N8   C23   112.71  3.000
 FRI  C38   N8   C23   127.41  3.000
 FRI  H383  C38  H382  108.53  3.000
 FRI  H383  C38  H381  109.06  3.000
 FRI  H382  C38  H381  108.91  3.000
 FRI  H383  C38  N8    108.45  3.000
 FRI  H382  C38  N8    110.64  3.000
 FRI  H381  C38  N8    111.19  3.000
 FRI  C14   N6   N8    105.72  3.000
 FRI  H13   C13  C14   128.11  3.000
 FRI  H13   C13  C23   126.89  3.000
 FRI  C14   C13  C23   104.99  3.000
 FRI  C11   C14  C13   129.93  3.000
 FRI  C11   C14  N6    119.35  3.000
 FRI  C13   C14  N6    110.59  3.000
 FRI  C34   C11  C15   117.01  3.000
 FRI  C34   C11  C14   123.84  3.000
 FRI  C15   C11  C14   119.15  3.000
 FRI  H15   C15  C17   118.77  3.000
 FRI  H15   C15  C11   118.68  3.000
 FRI  C17   C15  C11   122.54  3.000
 FRI  H17   C17  C20   121.05  3.000
 FRI  H17   C17  C15   118.87  3.000
 FRI  C20   C17  C15   120.08  3.000
 FRI  O45   C20  C33   116.37  3.000
 FRI  O45   C20  C17   125.24  3.000
 FRI  C33   C20  C17   118.38  3.000
 FRI  CL9   C33  C34   120.99  3.000
 FRI  CL9   C33  C20   118.23  3.000
 FRI  C34   C33  C20   120.78  3.000
 FRI  CL10  C34  C33   118.39  3.000
 FRI  CL10  C34  C11   120.40  3.000
 FRI  C33   C34  C11   121.20  3.000
 FRI  C40   O45  C20   118.81  3.000
 FRI  H402  C40  H401  108.08  3.000
 FRI  H402  C40  C22   110.84  3.000
 FRI  H401  C40  C22   110.76  3.000
 FRI  H402  C40  O45   109.72  3.000
 FRI  H401  C40  O45   110.32  3.000
 FRI  C22   C40  O45   107.13  3.000
 FRI  C16   C22  C28   118.10  3.000
 FRI  C16   C22  C40   120.51  3.000
 FRI  C28   C22  C40   121.37  3.000
 FRI  H28   C28  C25   119.01  3.000
 FRI  H28   C28  C22   120.13  3.000
 FRI  C25   C28  C22   120.86  3.000
 FRI  H25   C25  C35   119.81  3.000
 FRI  H25   C25  C28   119.41  3.000
 FRI  C35   C25  C28   120.78  3.000
 FRI  N1    C35  C18   124.46  3.000
 FRI  N1    C35  C25   116.79  3.000
 FRI  C18   C35  C25   118.75  3.000
 FRI  H18   C18  C16   119.25  3.000
 FRI  H18   C18  C35   121.12  3.000
 FRI  C16   C18  C35   119.62  3.000
 FRI  H16   C16  C18   118.42  3.000
 FRI  H16   C16  C22   119.69  3.000
 FRI  C18   C16  C22   121.89  3.000
 FRI  HN1   N1   C12   115.69  3.000
 FRI  HN1   N1   C35   114.65  3.000
 FRI  C12   N1   C35   129.59  3.000
 FRI  C42   C12  O44   122.26  3.000
 FRI  C42   C12  N1    113.87  3.000
 FRI  O44   C12  N1    123.84  3.000
 FRI  H423  C42  H422  107.76  3.000
 FRI  H423  C42  H421  107.78  3.000
 FRI  H422  C42  H421  108.96  3.000
 FRI  H423  C42  C12   109.06  3.000
 FRI  H422  C42  C12   113.29  3.000
 FRI  H421  C42  C12   109.82  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
 FRI  CONST_01  C14   N6   N8   C23     0.00   0.0  0
 FRI  CONST_02  N6    C14  C13  C23     0.00   0.0  0
 FRI  CONST_03  C11   C14  C13  C23   180.00   0.0  0
 FRI  CONST_04  C14   C13  C23  N8      0.00   0.0  0
 FRI  CONST_05  C13   C14  N6   N8      0.00   0.0  0
 FRI  CONST_06  C11   C14  N6   N8    180.00   0.0  0
 FRI  CONST_07  C13   C23  N8   N6      0.00   0.0  0
 FRI  CONST_12  C17   C15  C11  C14   180.00   0.0  0
 FRI  CONST_13  C33   C34  C11  C14   180.00   0.0  0
 FRI  CONST_14  C20   C17  C15  C11     0.00   0.0  0
 FRI  CONST_15  C20   C33  C34  C11     0.00   0.0  0
 FRI  CONST_16  C33   C34  C11  C15     0.00   0.0  0
 FRI  CONST_17  C33   C20  C17  C15     0.00   0.0  0
 FRI  CONST_18  C34   C11  C15  C17     0.00   0.0  0
 FRI  CONST_19  C34   C33  C20  C17     0.00   0.0  0
 FRI  CONST_20  C35   C25  C28  C22     0.00   0.0  0
 FRI  CONST_21  C35   C18  C16  C22     0.00   0.0  0
 FRI  CONST_22  C18   C16  C22  C28     0.00   0.0  0
 FRI  CONST_23  C18   C35  C25  C28     0.00   0.0  0
 FRI  CONST_24  C16   C22  C28  C25     0.00   0.0  0
 FRI  CONST_25  C16   C18  C35  C25     0.00   0.0  0
 FRI  CONST_26  N6    N8   C23  C19   180.00   0.0  0
 FRI  CONST_27  C14   C13  C23  C19   180.00   0.0  0
 FRI  CONST_28  C38   N8   C23  C19     0.00   0.0  0
 FRI  CONST_29  C13   C23  N8   C38   180.00   0.0  0
 FRI  CONST_30  C14   N6   N8   C38   180.00   0.0  0
 FRI  CONST_31  CL10  C34  C11  C14     0.00   0.0  0
 FRI  CONST_32  CL9   C33  C34  C11   180.00   0.0  0
 FRI  CONST_33  CL10  C34  C11  C15   180.00   0.0  0
 FRI  CONST_34  O45   C20  C17  C15   180.00   0.0  0
 FRI  CONST_35  CL9   C33  C20  C17   180.00   0.0  0
 FRI  CONST_36  CL10  C34  C33  C20   180.00   0.0  0
 FRI  CONST_37  O45   C20  C33  C34   180.00   0.0  0
 FRI  CONST_38  C25   C28  C22  C40   180.00   0.0  0
 FRI  CONST_39  C18   C16  C22  C40   180.00   0.0  0
 FRI  CONST_40  N1    C35  C25  C28   180.00   0.0  0
 FRI  CONST_41  N1    C35  C18  C16   180.00   0.0  0
 FRI  CONST_42  H13   C13  C23  C19     0.00   0.0  0
 FRI  CONST_43  H15   C15  C11  C14     0.00   0.0  0
 FRI  CONST_44  H17   C17  C15  C11   180.00   0.0  0
 FRI  CONST_45  H25   C25  C28  C22   180.00   0.0  0
 FRI  CONST_46  H18   C18  C16  C22   180.00   0.0  0
 FRI  CONST_47  H16   C16  C22  C28   180.00   0.0  0
 FRI  CONST_48  H28   C28  C25  C35   180.00   0.0  0
 FRI  CONST_49  C31   N2   C30  O47   180.00   0.0  0
 FRI  CONST_50  C43   N2   C30  O47     0.00   0.0  0
 FRI  CONST_51  C31   N2   C30  C29     0.00   0.0  0
 FRI  CONST_52  C43   N2   C30  C29   180.00   0.0  0
 FRI  CONST_53  C12   N1   C35  C25   180.00   0.0  0
 FRI  CONST_54  C12   N1   C35  C18     0.00   0.0  0
 FRI  CONST_55  HN1   N1   C35  C25     0.00   0.0  0
 FRI  CONST_56  O44   C12  N1   C35     0.00   0.0  0
 FRI  CONST_57  C42   C12  N1   C35   180.00   0.0  0
 FRI  CONST_58  O46   C27  N3   C29     0.00   0.0  0
 FRI  CONST_59  C26   C27  N3   C29   180.00   0.0  0
 FRI  CONST_60  N5    C24  N7   C26     0.00   0.0  0
 FRI  CONST_61  N4    C24  N7   C26   180.00   0.0  0
 FRI  CONST_62  HN3   N3   C27  O46   180.00   0.0  0
 FRI  CONST_63  HN5   N5   C24  N7    180.00   0.0  0
 FRI  Var_01    C19   C39  C31  N2     55.60  30.0  1
 FRI  Var_02    C19   C21  C43  N2    -56.20  30.0  1
 FRI  Var_03    C21   C43  N2   C31    59.79  30.0  1
 FRI  Var_04    C43   N2   C31  C39   -59.37  30.0  1
 FRI  Var_05    C22   C40  O45  C20  -176.12  30.0  3
 FRI  Var_06    C28   C22  C40  O45  -104.25  30.0  2
 FRI  Var_07    H381  C38  N8   C23   -76.59  30.0  2
 FRI  Var_08    N2    C30  C29  N3    173.16  30.0  2
 FRI  Var_09    C27   N3   C29  C30   -70.05  30.0  3
 FRI  Var_10    C37   C32  C41  C26    57.96  30.0  3
 FRI  Var_11    H371  C37  C32  C41   177.98  30.0  3
 FRI  Var_12    H361  C36  C32  C41   -62.29  30.0  3
 FRI  Var_13    H421  C42  C12  N1   -148.57  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
 FRI  chir_01  C26  C27  C41  N7   negativ
 FRI  chir_02  C19  C39  C21  C23  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
 FRI  plan-1  C19   0.020
 FRI  plan-1  C23   0.020
 FRI  plan-1  N8    0.020
 FRI  plan-1  C38   0.020
 FRI  plan-1  N6    0.020
 FRI  plan-1  C13   0.020
 FRI  plan-1  C14   0.020
 FRI  plan-1  C11   0.020
 FRI  plan-1  H13   0.020
 FRI  plan-2  C26   0.020
 FRI  plan-2  N7    0.020
 FRI  plan-2  C24   0.020
 FRI  plan-2  N5    0.020
 FRI  plan-2  N4    0.020
 FRI  plan-2  HN7   0.020
 FRI  plan-2  HN5   0.020
 FRI  plan-2  HN41  0.020
 FRI  plan-2  HN42  0.020
 FRI  plan-3  C14   0.020
 FRI  plan-3  C11   0.020
 FRI  plan-3  C15   0.020
 FRI  plan-3  C17   0.020
 FRI  plan-3  C20   0.020
 FRI  plan-3  C33   0.020
 FRI  plan-3  C34   0.020
 FRI  plan-3  CL10  0.020
 FRI  plan-3  CL9   0.020
 FRI  plan-3  O45   0.020
 FRI  plan-3  H15   0.020
 FRI  plan-3  H17   0.020
 FRI  plan-4  C40   0.020
 FRI  plan-4  C22   0.020
 FRI  plan-4  C28   0.020
 FRI  plan-4  C25   0.020
 FRI  plan-4  C35   0.020
 FRI  plan-4  C18   0.020
 FRI  plan-4  C16   0.020
 FRI  plan-4  N1    0.020
 FRI  plan-4  H28   0.020
 FRI  plan-4  H25   0.020
 FRI  plan-4  H18   0.020
 FRI  plan-4  H16   0.020
 FRI  plan-5  C29   0.020
 FRI  plan-5  N3    0.020
 FRI  plan-5  C27   0.020
 FRI  plan-5  O46   0.020
 FRI  plan-5  C26   0.020
 FRI  plan-5  HN3   0.020
 FRI  plan-6  C35   0.020
 FRI  plan-6  N1    0.020
 FRI  plan-6  C12   0.020
 FRI  plan-6  O44   0.020
 FRI  plan-6  C42   0.020
 FRI  plan-6  HN1   0.020
 FRI  plan-7  O47   0.020
 FRI  plan-7  C30   0.020
 FRI  plan-7  C29   0.020
 FRI  plan-7  N2    0.020
 FRI  plan-7  C31   0.020
 FRI  plan-7  C43   0.020

