# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 30 12:34:19 2022
#   Inital geometry file: a 143 line input string
#   Ligand name: N-[(2-methoxypyridin-4-yl)methyl]-2-[(1R)-1-(naphthalen-1-yl)ethyl]-2-azaspiro[3.3]heptane-6-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1cc(CNC(=O)C2CC3(C2)CN(C3)[C@H](C)c4cccc5ccccc45)ccn1
#
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
 9OZ  9OZ  "N-[(2-methoxypyridin-4-yl)methyl]-2-[(1R)-1-(naphthalen-1-yl)ethyl]-2-azaspiro[3.3]heptane-6-carboxamide"
  ligand  60  31  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_9OZ
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
 9OZ  C1   C  CH3   0  -0.414  -39.2050  -47.1953  -21.9242
 9OZ  C2   C  CR6   0   0.543  -39.3820  -47.4803  -19.5833
 9OZ  C3   C  CR16  0  -0.445  -39.3226  -48.3310  -18.4740
 9OZ  C4   C  CR6   0   0.188  -39.5281  -47.7950  -17.2183
 9OZ  C5   C  CH2   0  -0.332  -39.3991  -48.6790  -16.0023
 9OZ  C6   C  C     0   0.556  -41.3890  -48.2201  -14.6592
 9OZ  C7   C  C     0  -0.410  -41.8669  -47.7290  -13.3180
 9OZ  C8   C  C     0  -0.411  -43.3763  -47.6706  -13.0477
 9OZ  C9   C  C     0  -0.060  -43.1022  -48.2324  -11.6446
 9OZ  C10  C  C     0  -0.430  -41.7392  -48.7214  -12.1339
 9OZ  C11  C  C     0  -0.262  -43.2067  -47.2527  -10.4696
 9OZ  C12  C  CH1   0  -0.140  -44.7831  -48.0487   -8.7094
 9OZ  C13  C  CH3   0  -0.658  -46.0112  -48.9419   -8.5463
 9OZ  C14  C  CR6   0   0.092  -45.0231  -46.7097   -8.0438
 9OZ  C15  C  CR16  0  -0.328  -45.4822  -45.6491   -8.7837
 9OZ  C16  C  CR16  0  -0.237  -45.7616  -44.4004   -8.1949
 9OZ  C17  C  CR16  0  -0.333  -45.5840  -44.2158   -6.8540
 9OZ  C18  C  CR66  0   0.110  -45.1199  -45.2797   -6.0464
 9OZ  C19  C  CR16  0  -0.309  -44.9417  -45.1047   -4.6537
 9OZ  C20  C  CR16  0  -0.261  -44.5039  -46.1321   -3.8652
 9OZ  C21  C  CR16  0  -0.247  -44.2211  -47.3847   -4.4443
 9OZ  C22  C  CR16  0  -0.345  -44.3805  -47.5826   -5.7895
 9OZ  C23  C  CR66  0   0.093  -44.8340  -46.5416   -6.6390
 9OZ  C24  C  C     0  -0.271  -44.1379  -49.0663  -10.8942
 9OZ  C25  C  CR16  0  -0.386  -39.7975  -46.4276  -17.1201
 9OZ  C26  C  CR16  0  -0.051  -39.8407  -45.6850  -18.2806
 9OZ  N1   N  NH1   0  -0.637  -40.0509  -48.1824  -14.8212
 9OZ  N2   N  N     0  -0.419  -44.4848  -47.8751  -10.1109
 9OZ  N3   N  N     0  -0.469  -39.6364  -46.1916  -19.4971
 9OZ  O1   O  O2    0  -0.473  -39.1688  -48.0341  -20.7796
 9OZ  O2   O  O     0  -0.475  -42.1361  -48.6614  -15.5186
 9OZ  H1   H  HCH3  0   0.244  -38.9880  -47.8399  -22.7722
 9OZ  H2   H  HCH3  0   0.227  -40.1855  -46.7373  -22.0627
 9OZ  H3   H  HCH3  0   0.227  -38.4561  -46.4037  -21.8732
 9OZ  H4   H  HCR6  0   0.264  -39.1175  -49.3864  -18.6079
 9OZ  H5   H  HCH2  0   0.263  -39.7634  -49.6800  -16.2423
 9OZ  H6   H  HCH2  0   0.285  -38.3390  -48.7873  -15.7673
 9OZ  H7   H  H     0   0.281  -41.3813  -46.7820  -13.0676
 9OZ  H8   H  H     0   0.240  -43.8631  -46.6973  -13.1172
 9OZ  H9   H  H     0   0.237  -43.9214  -48.3846  -13.6669
 9OZ  H10  H  H     0   0.244  -41.7824  -49.7595  -12.4717
 9OZ  H11  H  H     0   0.244  -40.8865  -48.6030  -11.4646
 9OZ  H12  H  H     0   0.209  -42.4193  -47.4305   -9.7222
 9OZ  H13  H  H     0   0.227  -43.2477  -46.1829  -10.6913
 9OZ  H14  H  HCH1  0   0.206  -43.9299  -48.5468   -8.2167
 9OZ  H15  H  HCH3  0   0.239  -46.2609  -49.0751   -7.4940
 9OZ  H16  H  HCH3  0   0.228  -46.8726  -48.4979   -9.0465
 9OZ  H17  H  HCH3  0   0.238  -45.8405  -49.9327   -8.9708
 9OZ  H18  H  HCR6  0   0.253  -45.6352  -45.7762   -9.8474
 9OZ  H19  H  HCR6  0   0.251  -46.1196  -43.5890   -8.8156
 9OZ  H20  H  HCR6  0   0.251  -45.7957  -43.2587   -6.3926
 9OZ  H21  H  HCR6  0   0.253  -45.1619  -44.1363   -4.2200
 9OZ  H22  H  HCR6  0   0.255  -44.3736  -45.9877   -2.8007
 9OZ  H23  H  HCR6  0   0.255  -43.8730  -48.1973   -3.8198
 9OZ  H24  H  HCR6  0   0.249  -44.1526  -48.5570   -6.1996
 9OZ  H25  H  H     0   0.226  -44.9532  -49.5091  -11.4722
 9OZ  H26  H  H     0   0.207  -43.6611  -49.8554  -10.2933
 9OZ  H27  H  HCR6  0   0.254  -39.9713  -45.9518  -16.1648
 9OZ  H28  H  HCR6  0   0.259  -40.0491  -44.6218  -18.2378
 9OZ  H29  H  HNH1  0   0.406  -39.4820  -47.7755  -14.0970

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
 9OZ  C1   O1   single    1.419  0.020  1.419
 9OZ  O1   C2   single    1.335  0.020  1.335
 9OZ  C2   N3   aromatic  1.316  0.020  1.316
 9OZ  C2   C3   aromatic  1.399  0.020  1.399
 9OZ  N3   C26  aromatic  1.333  0.020  1.333
 9OZ  C3   C4   aromatic  1.381  0.020  1.381
 9OZ  C26  C25  aromatic  1.378  0.020  1.378
 9OZ  C4   C25  aromatic  1.397  0.020  1.397
 9OZ  C4   C5   single    1.509  0.020  1.509
 9OZ  C5   N1   single    1.437  0.020  1.437
 9OZ  O2   C6   double    1.221  0.020  1.221
 9OZ  C6   N1   single    1.348  0.020  1.348
 9OZ  C6   C7   single    1.506  0.020  1.506
 9OZ  C7   C8   single    1.535  0.020  1.535
 9OZ  C7   C10  single    1.550  0.020  1.550
 9OZ  C8   C9   single    1.536  0.020  1.536
 9OZ  C10  C9   single    1.528  0.020  1.528
 9OZ  C9   C11  single    1.533  0.020  1.533
 9OZ  C9   C24  single    1.527  0.020  1.527
 9OZ  C11  N2   single    1.466  0.020  1.466
 9OZ  C24  N2   single    1.467  0.020  1.467
 9OZ  N2   C12  single    1.443  0.020  1.443
 9OZ  C12  C14  single    1.514  0.020  1.514
 9OZ  C12  C13  single    1.527  0.020  1.527
 9OZ  C15  C14  aromatic  1.372  0.020  1.372
 9OZ  C15  C16  aromatic  1.409  0.020  1.409
 9OZ  C14  C23  aromatic  1.427  0.020  1.427
 9OZ  C16  C17  aromatic  1.365  0.020  1.365
 9OZ  C23  C22  aromatic  1.418  0.020  1.418
 9OZ  C23  C18  aromatic  1.423  0.020  1.423
 9OZ  C17  C18  aromatic  1.414  0.020  1.414
 9OZ  C22  C21  aromatic  1.369  0.020  1.369
 9OZ  C18  C19  aromatic  1.415  0.020  1.415
 9OZ  C21  C20  aromatic  1.409  0.020  1.409
 9OZ  C19  C20  aromatic  1.367  0.020  1.367
 9OZ  C1   H1   single    0.970  0.020  1.090
 9OZ  C1   H2   single    0.970  0.020  1.090
 9OZ  C1   H3   single    0.970  0.020  1.090
 9OZ  C3   H4   single    0.930  0.020  1.080
 9OZ  C5   H5   single    0.970  0.020  1.090
 9OZ  C5   H6   single    0.970  0.020  1.090
 9OZ  C7   H7   single    0.970  0.020  1.090
 9OZ  C8   H8   single    0.970  0.020  1.090
 9OZ  C8   H9   single    0.970  0.020  1.090
 9OZ  C10  H10  single    0.970  0.020  1.090
 9OZ  C10  H11  single    0.970  0.020  1.090
 9OZ  C11  H12  single    0.970  0.020  1.090
 9OZ  C11  H13  single    0.970  0.020  1.090
 9OZ  C12  H14  single    0.970  0.020  1.090
 9OZ  C13  H15  single    0.970  0.020  1.090
 9OZ  C13  H16  single    0.970  0.020  1.090
 9OZ  C13  H17  single    0.970  0.020  1.090
 9OZ  C15  H18  single    0.930  0.020  1.080
 9OZ  C16  H19  single    0.930  0.020  1.080
 9OZ  C17  H20  single    0.930  0.020  1.080
 9OZ  C19  H21  single    0.930  0.020  1.080
 9OZ  C20  H22  single    0.930  0.020  1.080
 9OZ  C21  H23  single    0.930  0.020  1.080
 9OZ  C22  H24  single    0.930  0.020  1.080
 9OZ  C24  H25  single    0.970  0.020  1.090
 9OZ  C24  H26  single    0.970  0.020  1.090
 9OZ  C25  H27  single    0.930  0.020  1.080
 9OZ  C26  H28  single    0.930  0.020  1.080
 9OZ  N1   H29  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
 9OZ  H3   C1   H2   108.56  3.000
 9OZ  H3   C1   H1   109.25  3.000
 9OZ  H2   C1   H1   109.22  3.000
 9OZ  H3   C1   O1   111.94  3.000
 9OZ  H2   C1   O1   111.92  3.000
 9OZ  H1   C1   O1   105.88  3.000
 9OZ  O1   C2   N3   119.70  3.000
 9OZ  N3   C2   C3   123.47  3.000
 9OZ  O1   C2   C3   116.82  3.000
 9OZ  H4   C3   C4   121.25  3.000
 9OZ  H4   C3   C2   120.16  3.000
 9OZ  C4   C3   C2   118.60  3.000
 9OZ  C25  C4   C5   122.22  3.000
 9OZ  C5   C4   C3   119.52  3.000
 9OZ  C25  C4   C3   118.20  3.000
 9OZ  H6   C5   H5   106.29  3.000
 9OZ  H6   C5   N1   107.33  3.000
 9OZ  H5   C5   N1   110.25  3.000
 9OZ  H6   C5   C4   108.34  3.000
 9OZ  H5   C5   C4   109.35  3.000
 9OZ  N1   C5   C4   114.89  3.000
 9OZ  O2   C6   N1   122.19  3.000
 9OZ  N1   C6   C7   114.37  3.000
 9OZ  O2   C6   C7   123.39  3.000
 9OZ  H7   C7   C10  110.06  3.000
 9OZ  H7   C7   C8   111.32  3.000
 9OZ  C10  C7   C8    88.33  3.000
 9OZ  H7   C7   C6   110.21  3.000
 9OZ  C10  C7   C6   116.44  3.000
 9OZ  C8   C7   C6   118.77  3.000
 9OZ  H9   C8   H8   108.96  3.000
 9OZ  H9   C8   C9   111.60  3.000
 9OZ  H8   C8   C9   117.67  3.000
 9OZ  H9   C8   C7   111.50  3.000
 9OZ  H8   C8   C7   117.51  3.000
 9OZ  C9   C8   C7    88.36  3.000
 9OZ  C24  C9   C11   85.76  3.000
 9OZ  C24  C9   C10  125.98  3.000
 9OZ  C11  C9   C10  120.69  3.000
 9OZ  C24  C9   C8   121.85  3.000
 9OZ  C11  C9   C8   117.00  3.000
 9OZ  C10  C9   C8    89.07  3.000
 9OZ  H11  C10  H10  108.90  3.000
 9OZ  H11  C10  C9   117.78  3.000
 9OZ  H10  C10  C9   111.57  3.000
 9OZ  H11  C10  C7   117.63  3.000
 9OZ  H10  C10  C7   111.64  3.000
 9OZ  C9   C10  C7    88.07  3.000
 9OZ  H13  C11  H12  108.83  3.000
 9OZ  H13  C11  N2   115.62  3.000
 9OZ  H12  C11  N2   112.90  3.000
 9OZ  H13  C11  C9   118.19  3.000
 9OZ  H12  C11  C9   111.63  3.000
 9OZ  N2   C11  C9    88.60  3.000
 9OZ  H14  C12  N2   109.13  3.000
 9OZ  H14  C12  C14  108.98  3.000
 9OZ  N2   C12  C14  110.68  3.000
 9OZ  H14  C12  C13  108.05  3.000
 9OZ  C14  C12  C13  110.05  3.000
 9OZ  N2   C12  C13  109.89  3.000
 9OZ  H17  C13  H16  108.35  3.000
 9OZ  H17  C13  H15  107.48  3.000
 9OZ  H16  C13  H15  108.16  3.000
 9OZ  H17  C13  C12  111.33  3.000
 9OZ  H16  C13  C12  110.37  3.000
 9OZ  H15  C13  C12  111.03  3.000
 9OZ  C23  C14  C15  118.94  3.000
 9OZ  C23  C14  C12  121.04  3.000
 9OZ  C15  C14  C12  119.96  3.000
 9OZ  H18  C15  C16  119.14  3.000
 9OZ  H18  C15  C14  119.11  3.000
 9OZ  C16  C15  C14  121.75  3.000
 9OZ  H19  C16  C17  120.33  3.000
 9OZ  H19  C16  C15  119.37  3.000
 9OZ  C17  C16  C15  120.30  3.000
 9OZ  H20  C17  C18  119.05  3.000
 9OZ  H20  C17  C16  120.81  3.000
 9OZ  C18  C17  C16  120.13  3.000
 9OZ  C23  C18  C19  119.62  3.000
 9OZ  C19  C18  C17  120.69  3.000
 9OZ  C23  C18  C17  119.69  3.000
 9OZ  H21  C19  C20  120.39  3.000
 9OZ  H21  C19  C18  118.61  3.000
 9OZ  C20  C19  C18  121.00  3.000
 9OZ  H22  C20  C21  119.92  3.000
 9OZ  H22  C20  C19  120.37  3.000
 9OZ  C21  C20  C19  119.70  3.000
 9OZ  H23  C21  C22  119.72  3.000
 9OZ  H23  C21  C20  119.68  3.000
 9OZ  C22  C21  C20  120.60  3.000
 9OZ  H24  C22  C23  120.11  3.000
 9OZ  H24  C22  C21  118.58  3.000
 9OZ  C23  C22  C21  121.31  3.000
 9OZ  C22  C23  C18  117.76  3.000
 9OZ  C18  C23  C14  119.18  3.000
 9OZ  C22  C23  C14  123.06  3.000
 9OZ  H26  C24  H25  108.75  3.000
 9OZ  H26  C24  N2   113.15  3.000
 9OZ  H25  C24  N2   115.77  3.000
 9OZ  H26  C24  C9   111.48  3.000
 9OZ  H25  C24  C9   117.86  3.000
 9OZ  N2   C24  C9    88.81  3.000
 9OZ  H27  C25  C26  120.12  3.000
 9OZ  H27  C25  C4   121.58  3.000
 9OZ  C26  C25  C4   118.30  3.000
 9OZ  H28  C26  N3   115.97  3.000
 9OZ  H28  C26  C25  120.07  3.000
 9OZ  N3   C26  C25  123.96  3.000
 9OZ  H29  N1   C6   119.06  3.000
 9OZ  H29  N1   C5   118.32  3.000
 9OZ  C6   N1   C5   122.61  3.000
 9OZ  C24  N2   C12  118.01  3.000
 9OZ  C12  N2   C11  117.96  3.000
 9OZ  C24  N2   C11   90.46  3.000
 9OZ  C26  N3   C2   117.46  3.000
 9OZ  C2   O1   C1   118.24  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
 9OZ  CONST_01  C25  C26  N3   C2      0.00   0.0  0
 9OZ  CONST_02  C25  C4   C3   C2      0.00   0.0  0
 9OZ  CONST_03  C26  N3   C2   C3      0.00   0.0  0
 9OZ  CONST_04  C26  C25  C4   C3      0.00   0.0  0
 9OZ  CONST_05  N3   C2   C3   C4      0.00   0.0  0
 9OZ  CONST_06  N3   C26  C25  C4      0.00   0.0  0
 9OZ  CONST_07  C17  C16  C15  C14     0.00   0.0  0
 9OZ  CONST_08  C21  C22  C23  C14   180.00   0.0  0
 9OZ  CONST_09  C17  C18  C23  C14     0.00   0.0  0
 9OZ  CONST_10  C19  C18  C23  C14   180.00   0.0  0
 9OZ  CONST_11  C22  C23  C14  C15   180.00   0.0  0
 9OZ  CONST_12  C18  C23  C14  C15     0.00   0.0  0
 9OZ  CONST_13  C18  C17  C16  C15     0.00   0.0  0
 9OZ  CONST_14  C23  C14  C15  C16     0.00   0.0  0
 9OZ  CONST_15  C23  C18  C17  C16     0.00   0.0  0
 9OZ  CONST_16  C19  C18  C17  C16   180.00   0.0  0
 9OZ  CONST_17  C22  C23  C18  C17   180.00   0.0  0
 9OZ  CONST_18  C20  C19  C18  C17   180.00   0.0  0
 9OZ  CONST_19  C21  C22  C23  C18     0.00   0.0  0
 9OZ  CONST_20  C21  C20  C19  C18     0.00   0.0  0
 9OZ  CONST_21  C22  C23  C18  C19     0.00   0.0  0
 9OZ  CONST_22  C22  C21  C20  C19     0.00   0.0  0
 9OZ  CONST_23  C23  C22  C21  C20     0.00   0.0  0
 9OZ  CONST_24  C23  C18  C19  C20     0.00   0.0  0
 9OZ  CONST_25  C5   C4   C3   C2    180.00   0.0  0
 9OZ  CONST_26  O1   C2   C3   C4    180.00   0.0  0
 9OZ  CONST_27  C26  C25  C4   C5    180.00   0.0  0
 9OZ  CONST_28  C16  C15  C14  C12   180.00   0.0  0
 9OZ  CONST_29  C22  C23  C14  C12     0.00   0.0  0
 9OZ  CONST_30  C18  C23  C14  C12   180.00   0.0  0
 9OZ  CONST_31  O1   C2   N3   C26   180.00   0.0  0
 9OZ  CONST_32  H28  C26  N3   C2    180.00   0.0  0
 9OZ  CONST_33  H27  C25  C4   C3    180.00   0.0  0
 9OZ  CONST_34  H28  C26  C25  C4    180.00   0.0  0
 9OZ  CONST_35  H19  C16  C15  C14   180.00   0.0  0
 9OZ  CONST_36  H24  C22  C23  C14     0.00   0.0  0
 9OZ  CONST_37  H20  C17  C16  C15   180.00   0.0  0
 9OZ  CONST_38  H18  C15  C16  C17   180.00   0.0  0
 9OZ  CONST_39  H21  C19  C18  C17     0.00   0.0  0
 9OZ  CONST_40  H24  C22  C23  C18   180.00   0.0  0
 9OZ  CONST_41  H19  C16  C17  C18   180.00   0.0  0
 9OZ  CONST_42  H22  C20  C19  C18   180.00   0.0  0
 9OZ  CONST_43  H20  C17  C18  C19     0.00   0.0  0
 9OZ  CONST_44  H23  C21  C20  C19   180.00   0.0  0
 9OZ  CONST_45  H24  C22  C21  C20   180.00   0.0  0
 9OZ  CONST_46  H21  C19  C20  C21   180.00   0.0  0
 9OZ  CONST_47  H22  C20  C21  C22   180.00   0.0  0
 9OZ  CONST_48  H18  C15  C14  C23   180.00   0.0  0
 9OZ  CONST_49  H23  C21  C22  C23   180.00   0.0  0
 9OZ  CONST_50  H20  C17  C18  C23   180.00   0.0  0
 9OZ  CONST_51  H21  C19  C18  C23   180.00   0.0  0
 9OZ  CONST_52  H4   C3   C4   C25   180.00   0.0  0
 9OZ  CONST_53  H4   C3   C2   N3    180.00   0.0  0
 9OZ  CONST_54  H27  C25  C26  N3    180.00   0.0  0
 9OZ  CONST_55  C7   C6   N1   C5    180.00   0.0  0
 9OZ  CONST_56  H29  N1   C6   C7      0.00   0.0  0
 9OZ  CONST_57  O2   C6   N1   C5      0.00   0.0  0
 9OZ  CONST_58  H29  N1   C6   O2    180.00   0.0  0
 9OZ  Var_01    C10  C9   C8   C7    -18.80  30.0  3
 9OZ  Var_02    C11  C9   C8   C7    105.59  30.0  3
 9OZ  Var_03    C24  C9   C8   C7   -151.77  30.0  3
 9OZ  Var_04    C11  C9   C10  C7   -102.63  30.0  3
 9OZ  Var_05    C24  C9   C10  C7    148.42  30.0  3
 9OZ  Var_06    N2   C11  C9   C8    105.25  30.0  1
 9OZ  Var_07    N2   C24  C9   C8   -100.82  30.0  1
 9OZ  Var_08    C24  N2   C11  C9     19.27  30.0  1
 9OZ  Var_09    N2   C11  C9   C10  -148.42  30.0  1
 9OZ  Var_10    N2   C24  C9   C10   143.89  30.0  1
 9OZ  Var_11    C12  N2   C11  C9    141.67  30.0  1
 9OZ  Var_12    C12  N2   C24  C9   -141.71  30.0  1
 9OZ  Var_13    H10  C10  C9   C8    -93.95  30.0  3
 9OZ  Var_14    H11  C10  C9   C8    139.04  30.0  3
 9OZ  Var_15    H12  C11  C9   C8   -140.61  30.0  1
 9OZ  Var_16    H13  C11  C9   C8    -13.28  30.0  1
 9OZ  Var_17    H25  C24  C9   C8     17.93  30.0  1
 9OZ  Var_18    H26  C24  C9   C8    144.71  30.0  1
 9OZ  Var_19    H8   C8   C9   C10  -139.24  30.0  3
 9OZ  Var_20    H9   C8   C9   C10    93.73  30.0  3
 9OZ  Var_21    H12  C11  C9   C10   -34.27  30.0  1
 9OZ  Var_22    H13  C11  C9   C10    93.05  30.0  1
 9OZ  Var_23    H25  C24  C9   C10   -97.36  30.0  1
 9OZ  Var_24    H26  C24  C9   C10    29.41  30.0  1
 9OZ  Var_25    H8   C8   C9   C11   -14.86  30.0  3
 9OZ  Var_26    H9   C8   C9   C11  -141.89  30.0  3
 9OZ  Var_27    H10  C10  C9   C11   144.83  30.0  3
 9OZ  Var_28    H11  C10  C9   C11    17.82  30.0  3
 9OZ  Var_29    H25  C24  C9   C11   137.27  30.0  1
 9OZ  Var_30    H26  C24  C9   C11   -95.96  30.0  1
 9OZ  Var_31    H25  C24  N2   C11  -139.95  30.0  1
 9OZ  Var_32    H26  C24  N2   C11    93.57  30.0  1
 9OZ  Var_33    H8   C8   C9   C24    87.79  30.0  3
 9OZ  Var_34    H9   C8   C9   C24   -39.24  30.0  3
 9OZ  Var_35    H10  C10  C9   C24    35.87  30.0  3
 9OZ  Var_36    H11  C10  C9   C24   -91.14  30.0  3
 9OZ  Var_37    H12  C11  C9   C24    95.61  30.0  1
 9OZ  Var_38    H13  C11  C9   C24  -137.07  30.0  1
 9OZ  Var_39    H12  C11  N2   C24   -93.68  30.0  1
 9OZ  Var_40    H13  C11  N2   C24   140.08  30.0  1
 9OZ  Var_41    N3   C2   O1   C1      0.98  30.0  2
 9OZ  Var_42    C3   C2   O1   C1   -179.21  30.0  2
 9OZ  Var_43    N1   C5   C4   C3   -159.94  30.0  2
 9OZ  Var_44    N1   C5   C4   C25    22.73  30.0  2
 9OZ  Var_45    H5   C5   C4   C3    -35.37  30.0  2
 9OZ  Var_46    H6   C5   C4   C3     80.07  30.0  2
 9OZ  Var_47    H12  C11  N2   C12    28.72  30.0  1
 9OZ  Var_48    H13  C11  N2   C12   -97.51  30.0  1
 9OZ  Var_49    H25  C24  N2   C12    97.69  30.0  1
 9OZ  Var_50    H26  C24  N2   C12   -28.79  30.0  1
 9OZ  Var_51    H5   C5   C4   C25   147.30  30.0  2
 9OZ  Var_52    H6   C5   C4   C25   -97.26  30.0  2
 9OZ  Var_53    C6   N1   C5   C4     74.94  30.0  3
 9OZ  Var_54    H1   C1   O1   C2    178.84  30.0  3
 9OZ  Var_55    H2   C1   O1   C2    -62.25  30.0  3
 9OZ  Var_56    H3   C1   O1   C2     59.88  30.0  3
 9OZ  Var_57    H29  N1   C5   C4   -103.88  30.0  3
 9OZ  Var_58    H5   C5   N1   C6    -49.15  30.0  2
 9OZ  Var_59    H6   C5   N1   C6   -164.51  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
 9OZ  chir_01  C7   C6  C8   C10  negativ
 9OZ  chir_02  C12  N2  C14  C13  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
 9OZ  plan-1  C2   0.020
 9OZ  plan-1  C3   0.020
 9OZ  plan-1  C4   0.020
 9OZ  plan-1  C5   0.020
 9OZ  plan-1  C25  0.020
 9OZ  plan-1  C26  0.020
 9OZ  plan-1  N3   0.020
 9OZ  plan-1  O1   0.020
 9OZ  plan-1  H4   0.020
 9OZ  plan-1  H27  0.020
 9OZ  plan-1  H28  0.020
 9OZ  plan-2  C12  0.020
 9OZ  plan-2  C14  0.020
 9OZ  plan-2  C15  0.020
 9OZ  plan-2  C16  0.020
 9OZ  plan-2  C17  0.020
 9OZ  plan-2  C18  0.020
 9OZ  plan-2  C19  0.020
 9OZ  plan-2  C20  0.020
 9OZ  plan-2  C21  0.020
 9OZ  plan-2  C22  0.020
 9OZ  plan-2  C23  0.020
 9OZ  plan-2  H18  0.020
 9OZ  plan-2  H19  0.020
 9OZ  plan-2  H20  0.020
 9OZ  plan-2  H21  0.020
 9OZ  plan-2  H22  0.020
 9OZ  plan-2  H23  0.020
 9OZ  plan-2  H24  0.020
 9OZ  plan-3  C5   0.020
 9OZ  plan-3  C6   0.020
 9OZ  plan-3  C7   0.020
 9OZ  plan-3  N1   0.020
 9OZ  plan-3  O2   0.020
 9OZ  plan-3  H29  0.020

