# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 30 05:44:26 2022
#   Inital geometry file: a 166 line input string
#   Ligand name: 3-[4-(5-chloropyridin-3-yl)-2-[(R)-cyclopropyl(ethoxy)methyl]-3-{(1R)-1-[(1r,4R)-4-methylcyclohexyl]ethyl}-3H-imidazo[4,5-c]pyridin-6-yl]-1,2,4-oxadiazol-5(4H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCO[C@H](C1CC1)c2nc3cc(nc(c4cncc(Cl)c4)c3n2[C@H](C)[C@H]5CC[C@H](C)CC5)C6=NOC(=O)N6
#
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
 1I9  1I9  "3-[4-(5-chloropyridin-3-yl)-2-[(R)-cyclopropyl(ethoxy)methyl]-3-{(1R)-1-[(1r,4R)-4-methylcyclohexyl]ethyl}-3H-imidazo[4,5-c]pyridin-6-yl]-1,2,4-oxadiazol-5(4H)-one"  ligand  71  38  .  2022-09-22  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_1I9
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
 1I9  C1    C   CH3   0  -0.652   -3.8593  16.8759  -0.7840
 1I9  C2    C   CH1   0  -0.226   -4.4638  15.4805  -0.8393
 1I9  C3    C   CH2   0  -0.409   -4.2483  14.7228   0.4658
 1I9  C4    C   CH2   0  -0.427   -4.8483  13.3231   0.4193
 1I9  C5    C   CH1   0  -0.241   -6.3397  13.3380   0.0700
 1I9  C6    C   CH2   0  -0.439   -6.5691  14.1286  -1.2180
 1I9  C7    C   CH2   0  -0.408   -5.9551  15.5219  -1.1552
 1I9  C8    C   CH1   0  -0.124   -6.8436  11.8863  -0.0324
 1I9  C12   C   CR56  0   0.254   -8.2518  11.3030  -2.0534
 1I9  C15   C   CR6   0   0.181   -9.1576  10.6361  -4.5098
 1I9  C16   C   CR16  0  -0.369  -10.0857  11.1540  -3.6282
 1I9  C17   C   CR56  0   0.257   -9.6061  11.4987  -2.3698
 1I9  C19   C   CR5   0   0.497   -9.3477  12.2168  -0.3945
 1I9  C24   C   CH3   0  -0.682  -10.4180  10.5968   3.8066
 1I9  C27   C   CH2   0  -0.493  -10.1919  15.2586   0.4549
 1I9  C30   C   CR5   0   0.657  -10.7216   9.9266  -7.6997
 1I9  C34   C   CR6   0  -0.119   -5.9602  10.4450  -2.7934
 1I9  C35   C   CR16  0  -0.104   -4.9776  11.2878  -3.2948
 1I9  C36   C   CR6   0  -0.103   -3.6563  10.9668  -3.0432
 1I9  C38   C   CR16  0  -0.028   -3.3524   9.8120  -2.3351
 1I9  C40   C   CR16  0  -0.051   -5.5622   9.3053  -2.1018
 1I9  C10   C   CH3   0  -0.667   -6.8899  11.1392   1.2957
 1I9  N11   N   NR5   0  -0.567   -8.1117  11.7750  -0.7703
 1I9  C13   C   CR6   0   0.199   -7.3985  10.7399  -3.0136
 1I9  N14   N   N     0  -0.433   -7.8685  10.4360  -4.2043
 1I9  N18   N   N     0  -0.457  -10.2583  12.0597  -1.3193
 1I9  C20   C   CH1   0  -0.066   -9.6780  12.7838   0.9582
 1I9  O22   O   O2    0  -0.493  -10.1308  11.6838   1.7106
 1I9  C25   C   CH1   0  -0.255  -10.6854  13.8974   0.8391
 1I9  C26   C   CH2   0  -0.488  -10.6821  15.0069   1.8456
 1I9  C28   C   CR5   0   0.467   -9.5254  10.2656  -5.8779
 1I9  N29   N   NR15  0  -0.733  -10.7784  10.3468  -6.4042
 1I9  O32   O   O     0  -0.365   -9.4264   9.6060  -7.8985
 1I9  N33   N   N     0  -0.165   -8.6863   9.8243  -6.7492
 1I9  CL37  CL  CL    0  -0.101   -2.3883  11.9989  -3.5883
 1I9  N39   N   N     0  -0.383   -4.2921   8.9963  -1.8835
 1I9  H1    H   HCH3  0   0.223   -2.7881  16.8358  -0.5781
 1I9  H2    H   HCH3  0   0.223   -3.9970  17.4093  -1.7263
 1I9  H3    H   HCH3  0   0.212   -4.3252  17.4710   0.0051
 1I9  H4    H   HCH1  0   0.205   -3.9661  14.9163  -1.6397
 1I9  H5    H   HCH2  0   0.226   -3.1804  14.6535   0.6905
 1I9  H6    H   HCH2  0   0.207   -4.7016  15.2897   1.2878
 1I9  H7    H   HCH2  0   0.240   -4.6814  12.8279   1.3782
 1I9  H8    H   HCH2  0   0.217   -4.3159  12.7311  -0.3354
 1I9  H9    H   HCH1  0   0.233   -6.8699  13.8497   0.8834
 1I9  H10   H   HCH2  0   0.240   -7.6372  14.2213  -1.4287
 1I9  H11   H   HCH2  0   0.222   -6.1315  13.5842  -2.0621
 1I9  H12   H   HCH2  0   0.227   -6.1277  16.0372  -2.1039
 1I9  H13   H   HCH2  0   0.209   -6.4664  16.1118  -0.3842
 1I9  H14   H   HCH1  0   0.278   -6.1267  11.3596  -0.6560
 1I9  H15   H   HCR6  0   0.281  -11.1270  11.3086  -3.8771
 1I9  H16   H   HCH2  0   0.201   -9.3261  12.4208   3.4683
 1I9  H17   H   HCH2  0   0.218  -11.0744  12.5887   3.3226
 1I9  H18   H   HCH3  0   0.231  -10.5180  10.7609   4.8793
 1I9  H19   H   HCH3  0   0.230  -11.3176  10.0855   3.4626
 1I9  H20   H   HCH3  0   0.228   -9.5636   9.9387   3.6455
 1I9  H21   H   HCH2  0   0.256   -9.1250  15.3911   0.3128
 1I9  H22   H   HCH2  0   0.257  -10.8040  15.8488  -0.2138
 1I9  H23   H   HCR6  0   0.299   -5.2405  12.1796  -3.8491
 1I9  H24   H   HCR6  0   0.291   -2.3209   9.5462  -2.1333
 1I9  H25   H   HCR6  0   0.277   -6.3069   8.6231  -1.7062
 1I9  H26   H   HCH3  0   0.254   -5.8746  10.9475   1.6376
 1I9  H27   H   HCH3  0   0.240   -7.3955  11.6966   2.0824
 1I9  H28   H   HCH3  0   0.251   -7.3810  10.1736   1.1808
 1I9  H29   H   HCH1  0   0.235   -8.7709  13.2066   1.4117
 1I9  H30   H   HCH1  0   0.264  -11.6483  13.6000   0.4399
 1I9  H31   H   HCH2  0   0.249   -9.9486  14.9761   2.6425
 1I9  H32   H   HCH2  0   0.257  -11.6377  15.4214   2.1395
 1I9  H33   H   HNR5  0   0.452  -11.6254  10.6518  -5.9482
 1I9  O31   O   O     0  -0.444  -11.5801   9.8373  -8.5326
 1I9  C23   C   CH2   0  -0.153  -10.2339  11.9216   3.1031

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
 1I9  O31   C30  double    1.199  0.020  1.199
 1I9  O32   C30  single    1.349  0.020  1.349
 1I9  O32   N33  single    1.384  0.020  1.384
 1I9  C30   N29  single    1.363  0.020  1.363
 1I9  N33   C28  double    1.288  0.020  1.288
 1I9  N29   C28  single    1.361  0.020  1.361
 1I9  C28   C15  single    1.464  0.020  1.464
 1I9  C15   N14  aromatic  1.340  0.020  1.340
 1I9  C15   C16  aromatic  1.381  0.020  1.381
 1I9  CL37  C36  single    1.723  0.020  1.723
 1I9  N14   C13  aromatic  1.316  0.020  1.316
 1I9  C35   C36  aromatic  1.383  0.020  1.383
 1I9  C35   C34  aromatic  1.388  0.020  1.388
 1I9  C16   C17  aromatic  1.390  0.020  1.390
 1I9  C36   C38  aromatic  1.388  0.020  1.388
 1I9  C13   C34  single    1.485  0.020  1.485
 1I9  C13   C12  aromatic  1.403  0.020  1.403
 1I9  C34   C40  aromatic  1.391  0.020  1.391
 1I9  C38   N39  aromatic  1.324  0.020  1.324
 1I9  C17   C12  aromatic  1.405  0.020  1.405
 1I9  C17   N18  aromatic  1.358  0.020  1.358
 1I9  C40   N39  aromatic  1.325  0.020  1.325
 1I9  C12   N11  aromatic  1.374  0.020  1.374
 1I9  N18   C19  aromatic  1.307  0.020  1.307
 1I9  C6    C7   single    1.524  0.020  1.524
 1I9  C6    C5   single    1.529  0.020  1.529
 1I9  C7    C2   single    1.525  0.020  1.525
 1I9  N11   C19  aromatic  1.365  0.020  1.365
 1I9  N11   C8   single    1.471  0.020  1.471
 1I9  C2    C1   single    1.522  0.020  1.522
 1I9  C2    C3   single    1.524  0.020  1.524
 1I9  C19   C20  single    1.503  0.020  1.503
 1I9  C8    C5   single    1.540  0.020  1.540
 1I9  C8    C10  single    1.525  0.020  1.525
 1I9  C5    C4   single    1.532  0.020  1.532
 1I9  C27   C25  single    1.498  0.020  1.498
 1I9  C27   C26  single    1.496  0.020  1.496
 1I9  C4    C3   single    1.524  0.020  1.524
 1I9  C25   C20  single    1.506  0.020  1.506
 1I9  C25   C26  single    1.498  0.020  1.498
 1I9  C20   O22  single    1.408  0.020  1.408
 1I9  O22   C23  single    1.416  0.020  1.416
 1I9  C23   C24  single    1.511  0.020  1.511
 1I9  C1    H1   single    0.970  0.020  1.090
 1I9  C1    H2   single    0.970  0.020  1.090
 1I9  C1    H3   single    0.970  0.020  1.090
 1I9  C2    H4   single    0.970  0.020  1.090
 1I9  C3    H5   single    0.970  0.020  1.090
 1I9  C3    H6   single    0.970  0.020  1.090
 1I9  C4    H7   single    0.970  0.020  1.090
 1I9  C4    H8   single    0.970  0.020  1.090
 1I9  C5    H9   single    0.970  0.020  1.090
 1I9  C6    H10  single    0.970  0.020  1.090
 1I9  C6    H11  single    0.970  0.020  1.090
 1I9  C7    H12  single    0.970  0.020  1.090
 1I9  C7    H13  single    0.970  0.020  1.090
 1I9  C8    H14  single    0.970  0.020  1.090
 1I9  C16   H15  single    0.930  0.020  1.080
 1I9  C23   H16  single    0.970  0.020  1.090
 1I9  C23   H17  single    0.970  0.020  1.090
 1I9  C24   H18  single    0.970  0.020  1.090
 1I9  C24   H19  single    0.970  0.020  1.090
 1I9  C24   H20  single    0.970  0.020  1.090
 1I9  C27   H21  single    0.970  0.020  1.090
 1I9  C27   H22  single    0.970  0.020  1.090
 1I9  C35   H23  single    0.930  0.020  1.080
 1I9  C38   H24  single    0.930  0.020  1.080
 1I9  C40   H25  single    0.930  0.020  1.080
 1I9  C10   H26  single    0.970  0.020  1.090
 1I9  C10   H27  single    0.970  0.020  1.090
 1I9  C10   H28  single    0.970  0.020  1.090
 1I9  C20   H29  single    0.970  0.020  1.090
 1I9  C25   H30  single    0.970  0.020  1.090
 1I9  C26   H31  single    0.970  0.020  1.090
 1I9  C26   H32  single    0.970  0.020  1.090
 1I9  N29   H33  single    0.860  0.020  1.020

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
 1I9  H3    C1   H2   107.66  3.000
 1I9  H3    C1   H1   107.59  3.000
 1I9  H2    C1   H1   107.73  3.000
 1I9  H3    C1   C2   110.87  3.000
 1I9  H2    C1   C2   111.51  3.000
 1I9  H1    C1   C2   111.29  3.000
 1I9  H4    C2   C7   107.82  3.000
 1I9  H4    C2   C3   107.72  3.000
 1I9  C7    C2   C3   109.22  3.000
 1I9  H4    C2   C1   108.51  3.000
 1I9  C3    C2   C1   111.62  3.000
 1I9  C7    C2   C1   111.78  3.000
 1I9  H6    C3   H5   106.41  3.000
 1I9  H6    C3   C4   109.57  3.000
 1I9  H5    C3   C4   109.43  3.000
 1I9  H6    C3   C2   109.05  3.000
 1I9  H5    C3   C2   110.21  3.000
 1I9  C4    C3   C2   112.01  3.000
 1I9  H8    C4   H7   106.58  3.000
 1I9  H8    C4   C5   108.72  3.000
 1I9  H7    C4   C5   110.70  3.000
 1I9  H8    C4   C3   109.00  3.000
 1I9  H7    C4   C3   109.24  3.000
 1I9  C5    C4   C3   112.42  3.000
 1I9  H9    C5   C8   109.31  3.000
 1I9  H9    C5   C6   108.11  3.000
 1I9  C8    C5   C6   112.48  3.000
 1I9  H9    C5   C4   107.82  3.000
 1I9  C8    C5   C4   108.94  3.000
 1I9  C6    C5   C4   110.08  3.000
 1I9  H11   C6   H10  106.50  3.000
 1I9  H11   C6   C7   108.97  3.000
 1I9  H10   C6   C7   108.92  3.000
 1I9  H11   C6   C5   109.41  3.000
 1I9  H10   C6   C5   110.68  3.000
 1I9  C7    C6   C5   112.19  3.000
 1I9  H13   C7   H12  106.43  3.000
 1I9  H13   C7   C6   109.43  3.000
 1I9  H12   C7   C6   109.36  3.000
 1I9  H13   C7   C2   108.95  3.000
 1I9  H12   C7   C2   110.30  3.000
 1I9  C6    C7   C2   112.19  3.000
 1I9  H14   C8   N11  104.14  3.000
 1I9  H14   C8   C10  106.41  3.000
 1I9  N11   C8   C10  111.94  3.000
 1I9  H14   C8   C5   106.22  3.000
 1I9  C10   C8   C5   114.45  3.000
 1I9  N11   C8   C5   112.75  3.000
 1I9  C13   C12  N11  135.64  3.000
 1I9  N11   C12  C17  105.12  3.000
 1I9  C13   C12  C17  119.23  3.000
 1I9  C28   C15  N14  114.64  3.000
 1I9  N14   C15  C16  123.86  3.000
 1I9  C28   C15  C16  121.50  3.000
 1I9  H15   C16  C17  120.33  3.000
 1I9  H15   C16  C15  123.63  3.000
 1I9  C17   C16  C15  116.04  3.000
 1I9  N18   C17  C16  129.58  3.000
 1I9  N18   C17  C12  110.26  3.000
 1I9  C16   C17  C12  120.14  3.000
 1I9  C20   C19  N18  121.92  3.000
 1I9  C20   C19  N11  124.65  3.000
 1I9  N18   C19  N11  113.39  3.000
 1I9  H20   C24  H19  108.47  3.000
 1I9  H20   C24  H18  107.94  3.000
 1I9  H19   C24  H18  107.78  3.000
 1I9  H20   C24  C23  111.40  3.000
 1I9  H19   C24  C23  111.39  3.000
 1I9  H18   C24  C23  109.72  3.000
 1I9  H22   C27  H21  114.14  3.000
 1I9  H22   C27  C26  118.76  3.000
 1I9  H21   C27  C26  117.69  3.000
 1I9  H22   C27  C25  117.90  3.000
 1I9  H21   C27  C25  117.95  3.000
 1I9  C26   C27  C25   60.05  3.000
 1I9  O32   C30  O31  124.56  3.000
 1I9  O32   C30  N29  104.67  3.000
 1I9  O31   C30  N29  130.77  3.000
 1I9  C13   C34  C40  120.90  3.000
 1I9  C40   C34  C35  118.32  3.000
 1I9  C13   C34  C35  120.77  3.000
 1I9  H23   C35  C36  121.10  3.000
 1I9  H23   C35  C34  120.87  3.000
 1I9  C36   C35  C34  118.01  3.000
 1I9  CL37  C36  C38  119.89  3.000
 1I9  C38   C36  C35  119.67  3.000
 1I9  CL37  C36  C35  120.43  3.000
 1I9  H24   C38  N39  117.44  3.000
 1I9  H24   C38  C36  120.47  3.000
 1I9  N39   C38  C36  122.08  3.000
 1I9  H25   C40  N39  116.82  3.000
 1I9  H25   C40  C34  120.02  3.000
 1I9  N39   C40  C34  123.16  3.000
 1I9  H28   C10  H27  108.70  3.000
 1I9  H28   C10  H26  107.32  3.000
 1I9  H27   C10  H26  107.24  3.000
 1I9  H28   C10  C8   110.87  3.000
 1I9  H27   C10  C8   113.12  3.000
 1I9  H26   C10  C8   109.37  3.000
 1I9  C19   N11  C12  106.01  3.000
 1I9  C19   N11  C8   128.15  3.000
 1I9  C12   N11  C8   125.60  3.000
 1I9  N14   C13  C34  115.75  3.000
 1I9  C34   C13  C12  124.58  3.000
 1I9  N14   C13  C12  119.67  3.000
 1I9  C13   N14  C15  121.03  3.000
 1I9  C19   N18  C17  105.21  3.000
 1I9  H29   C20  C25  107.47  3.000
 1I9  H29   C20  O22  110.23  3.000
 1I9  C25   C20  O22  113.88  3.000
 1I9  H29   C20  C19  109.58  3.000
 1I9  O22   C20  C19  104.89  3.000
 1I9  C25   C20  C19  110.77  3.000
 1I9  C20   O22  C23  114.69  3.000
 1I9  H30   C25  C26  116.91  3.000
 1I9  H30   C25  C20  114.86  3.000
 1I9  C26   C25  C20  119.53  3.000
 1I9  H30   C25  C27  116.58  3.000
 1I9  C26   C25  C27   59.91  3.000
 1I9  C20   C25  C27  118.14  3.000
 1I9  H32   C26  H31  114.13  3.000
 1I9  H32   C26  C25  117.65  3.000
 1I9  H31   C26  C25  118.34  3.000
 1I9  H32   C26  C27  118.51  3.000
 1I9  H31   C26  C27  117.82  3.000
 1I9  C25   C26  C27   60.05  3.000
 1I9  N33   C28  N29  111.02  3.000
 1I9  N29   C28  C15  125.25  3.000
 1I9  N33   C28  C15  123.72  3.000
 1I9  H33   N29  C28  128.01  3.000
 1I9  H33   N29  C30  123.89  3.000
 1I9  C28   N29  C30  108.10  3.000
 1I9  N33   O32  C30  110.71  3.000
 1I9  O32   N33  C28  105.51  3.000
 1I9  C40   N39  C38  118.72  3.000
 1I9  H17   C23  H16  106.90  3.000
 1I9  H17   C23  O22  110.80  3.000
 1I9  H16   C23  O22  110.06  3.000
 1I9  H17   C23  C24  110.31  3.000
 1I9  H16   C23  C24  110.14  3.000
 1I9  O22   C23  C24  108.62  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
 1I9  CONST_01  C15   N14  C13  C12      0.00   0.0  0
 1I9  CONST_04  C15   C16  C17  C12      0.00   0.0  0
 1I9  CONST_05  C19   N18  C17  C12      0.00   0.0  0
 1I9  CONST_06  N18   C19  N11  C12      0.00   0.0  0
 1I9  CONST_07  C34   C13  N14  C15    180.00   0.0  0
 1I9  CONST_08  N18   C17  C16  C15    180.00   0.0  0
 1I9  CONST_09  C13   N14  C15  C16      0.00   0.0  0
 1I9  CONST_10  C13   C12  C17  C16      0.00   0.0  0
 1I9  CONST_11  N11   C12  C17  C16    180.00   0.0  0
 1I9  CONST_12  C19   N18  C17  C16    180.00   0.0  0
 1I9  CONST_13  N14   C15  C16  C17      0.00   0.0  0
 1I9  CONST_14  N14   C13  C12  C17      0.00   0.0  0
 1I9  CONST_15  C34   C13  C12  C17    180.00   0.0  0
 1I9  CONST_16  C19   N11  C12  C17      0.00   0.0  0
 1I9  CONST_17  N11   C19  N18  C17      0.00   0.0  0
 1I9  CONST_18  C13   C12  N11  C19    180.00   0.0  0
 1I9  CONST_19  C38   C36  C35  C34      0.00   0.0  0
 1I9  CONST_20  N11   C12  C13  C34      0.00   0.0  0
 1I9  CONST_21  C38   N39  C40  C34      0.00   0.0  0
 1I9  CONST_22  N39   C38  C36  C35      0.00   0.0  0
 1I9  CONST_24  N39   C40  C34  C35      0.00   0.0  0
 1I9  CONST_25  C13   C34  C35  C36    180.00   0.0  0
 1I9  CONST_26  C40   C34  C35  C36      0.00   0.0  0
 1I9  CONST_27  C40   N39  C38  C36      0.00   0.0  0
 1I9  CONST_29  N14   C13  C12  N11    180.00   0.0  0
 1I9  CONST_30  N18   C17  C12  N11      0.00   0.0  0
 1I9  CONST_31  N39   C40  C34  C13    180.00   0.0  0
 1I9  CONST_32  N18   C17  C12  C13    180.00   0.0  0
 1I9  CONST_33  C28   C15  C16  C17    180.00   0.0  0
 1I9  CONST_34  C28   C15  N14  C13    180.00   0.0  0
 1I9  CONST_35  O32   N33  C28  C15    180.00   0.0  0
 1I9  CONST_36  C30   N29  C28  C15    180.00   0.0  0
 1I9  CONST_37  C28   N33  O32  C30      0.00   0.0  0
 1I9  CONST_38  N33   C28  N29  C30      0.00   0.0  0
 1I9  CONST_39  O32   C30  N29  C28      0.00   0.0  0
 1I9  CONST_40  N33   O32  C30  N29      0.00   0.0  0
 1I9  CONST_41  O32   N33  C28  N29      0.00   0.0  0
 1I9  CONST_42  C13   C12  N11  C8       0.00   0.0  0
 1I9  CONST_43  C17   C12  N11  C8     180.00   0.0  0
 1I9  CONST_44  N18   C19  N11  C8     180.00   0.0  0
 1I9  CONST_45  C20   C19  N11  C12    180.00   0.0  0
 1I9  CONST_46  C20   C19  N18  C17    180.00   0.0  0
 1I9  CONST_47  CL37  C36  C35  C34    180.00   0.0  0
 1I9  CONST_48  N39   C38  C36  CL37   180.00   0.0  0
 1I9  CONST_49  H15   C16  C17  C12    180.00   0.0  0
 1I9  CONST_50  H24   C38  C36  C35    180.00   0.0  0
 1I9  CONST_51  H25   C40  C34  C35    180.00   0.0  0
 1I9  CONST_52  H23   C35  C36  C38    180.00   0.0  0
 1I9  CONST_53  H25   C40  N39  C38    180.00   0.0  0
 1I9  CONST_54  H23   C35  C34  C40    180.00   0.0  0
 1I9  CONST_55  H24   C38  N39  C40    180.00   0.0  0
 1I9  CONST_56  H23   C35  C34  C13      0.00   0.0  0
 1I9  CONST_57  H25   C40  C34  C13      0.00   0.0  0
 1I9  CONST_58  H15   C16  C15  N14    180.00   0.0  0
 1I9  CONST_59  H15   C16  C17  N18      0.00   0.0  0
 1I9  CONST_60  H15   C16  C15  C28      0.00   0.0  0
 1I9  CONST_61  H33   N29  C28  C15      0.00   0.0  0
 1I9  CONST_62  H33   N29  C30  O32    180.00   0.0  0
 1I9  CONST_63  H33   N29  C28  N33    180.00   0.0  0
 1I9  Var_01    C5    C6   C7   C2      56.11  30.0  1
 1I9  Var_02    C5    C4   C3   C2     -55.88  30.0  1
 1I9  Var_03    N33   C28  C15  C16    177.44  30.0  3
 1I9  Var_04    N29   C28  C15  C16     -2.03  30.0  3
 1I9  Var_05    N33   C28  C15  N14     -2.29  30.0  3
 1I9  Var_06    N29   C28  C15  N14    178.25  30.0  3
 1I9  Var_07    C20   C25  C26  C27    107.36  30.0  1
 1I9  Var_08    H10   C6   C7   C2     179.00  30.0  1
 1I9  Var_09    H11   C6   C7   C2     -65.20  30.0  1
 1I9  Var_10    H7    C4   C3   C2    -179.18  30.0  1
 1I9  Var_11    H8    C4   C3   C2      64.73  30.0  1
 1I9  Var_12    H12   C7   C6   C5     178.83  30.0  1
 1I9  Var_13    H13   C7   C6   C5     -64.95  30.0  1
 1I9  Var_14    H5    C3   C4   C5    -178.42  30.0  1
 1I9  Var_15    H6    C3   C4   C5      65.27  30.0  1
 1I9  Var_16    H31   C26  C25  C27   -107.53  30.0  1
 1I9  Var_17    H32   C26  C25  C27    108.66  30.0  1
 1I9  Var_18    H30   C25  C26  C27   -106.61  30.0  1
 1I9  Var_19    H21   C27  C26  C25   -107.97  30.0  1
 1I9  Var_20    H22   C27  C26  C25    107.44  30.0  1
 1I9  Var_21    H21   C27  C25  C20     -2.09  30.0  1
 1I9  Var_22    H22   C27  C25  C20    141.50  30.0  1
 1I9  Var_23    H31   C26  C25  C20     -0.18  30.0  1
 1I9  Var_24    H32   C26  C25  C20   -143.98  30.0  1
 1I9  Var_25    C20   O22  C23  C24   -167.24  30.0  2
 1I9  Var_26    H16   C23  O22  C20    -46.59  30.0  3
 1I9  Var_27    H17   C23  O22  C20     71.44  30.0  3
 1I9  Var_28    H18   C24  C23  O22   -178.96  30.0  3
 1I9  Var_29    H19   C24  C23  O22    -59.69  30.0  3
 1I9  Var_30    H20   C24  C23  O22     61.57  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
 1I9  chir_01  C2   C7   C1   C3   negativ
 1I9  chir_02  C5   C4   C8   C6   positiv
 1I9  chir_03  C8   N11  C5   C10  negativ
 1I9  chir_04  C20  O22  C25  C19  positiv
 1I9  chir_05  C25  C27  C20  C26  both

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
 1I9  plan-1  C15   0.020
 1I9  plan-1  C30   0.020
 1I9  plan-1  C28   0.020
 1I9  plan-1  N29   0.020
 1I9  plan-1  O32   0.020
 1I9  plan-1  N33   0.020
 1I9  plan-1  H33   0.020
 1I9  plan-1  O31   0.020
 1I9  plan-2  C34   0.020
 1I9  plan-2  C35   0.020
 1I9  plan-2  C36   0.020
 1I9  plan-2  C38   0.020
 1I9  plan-2  C40   0.020
 1I9  plan-2  C13   0.020
 1I9  plan-2  CL37  0.020
 1I9  plan-2  N39   0.020
 1I9  plan-2  H23   0.020
 1I9  plan-2  H24   0.020
 1I9  plan-2  H25   0.020
 1I9  plan-3  C8    0.020
 1I9  plan-3  C12   0.020
 1I9  plan-3  C15   0.020
 1I9  plan-3  C16   0.020
 1I9  plan-3  C17   0.020
 1I9  plan-3  C19   0.020
 1I9  plan-3  C34   0.020
 1I9  plan-3  N11   0.020
 1I9  plan-3  C13   0.020
 1I9  plan-3  N14   0.020
 1I9  plan-3  N18   0.020
 1I9  plan-3  C20   0.020
 1I9  plan-3  C28   0.020
 1I9  plan-3  H15   0.020

