Trinuclear (aminonitrone)ZnII complexes as key intermediates in zinc(ii)-mediated generation of 1,2,4-oxadiazoles from amidoximes and nitriles
Bolotin, Dmitrii S.; Il'in, Mikhail V.; Novikov, Alexander S.; Bokach, Nadezhda A.; Suslonov, Vitalii V.; Kukushkin, Vadim Yu.; New J. Chem. 41 (2017) 1940–; doi:10.1039/C6NJ03508F

data_7055952
_publ_section_title
;
 Trinuclear (aminonitrone)ZnII complexes as key intermediates in
 zinc(ii)-mediated generation of 1,2,4-oxadiazoles from amidoximes and
 nitriles
;
_journal_issue                   5
_journal_name_full               'New J. Chem.'
_journal_page_first              1940
_journal_paper_doi               10.1039/C6NJ03508F
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         '2(C16 H25 N4 O7 Zn1.5), 4(C F3 O3 S)'
_chemical_formula_sum            'C36 H50 F12 N8 O26 S4 Zn3'
_chemical_formula_weight         1563.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-01-09 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                74.733(4)
_cell_angle_beta                 89.846(4)
_cell_angle_gamma                82.485(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9101(6)
_cell_length_b                   17.0394(9)
_cell_length_c                   18.2463(6)
_cell_measurement_reflns_used    5447
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.2150
_cell_measurement_theta_min      5.0300
_cell_volume                     2945.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -51.00   27.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000   60.0000 78

  2 omega  -41.00   22.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -120.0000 63

  3 omega  -34.00   32.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 66

  4 omega  -49.00   36.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 85

  5 omega   82.00  127.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -30.0000 45

  6 omega   11.00   64.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   57.0000 -180.0000 53

  7 omega   96.00  129.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  150.0000 33

  8 omega   53.00   90.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 37

  9 omega   36.00   66.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 30

 10 omega   53.00   92.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -21.0000   79.8107 39

 11 omega   35.00   88.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 53

 12 omega   92.00  119.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 27

 13 omega  102.00  172.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   90.0000 70

 14 omega   83.00  177.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 94

 15 omega  117.00  152.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 35

 16 omega   54.00   79.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25

 17 omega   75.00  104.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 29

 18 omega  152.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 26

 19 omega   67.00  101.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 34

 20 omega   84.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 31

 21 omega  126.00  163.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 37

 22 omega   72.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 43

 23 omega   68.00  129.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 61

 24 omega   43.00   70.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 27

 25 omega   59.00   84.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 25

 26 omega  120.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 58

 27 omega  106.00  132.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 26

 28 omega   51.00   78.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 27

 29 omega   48.00  106.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 58

 30 omega   88.00  148.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 60

 31 omega   41.00  143.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000    0.0000 102

 32 omega  111.00  149.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 38

 33 omega   81.00  108.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 27

 34 omega   58.00  128.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 70

 35 omega   34.00   59.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 25

 36 omega   61.00   88.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 27

 37 omega   87.00  112.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

 38 omega   67.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 48

 39 omega  112.00  175.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 63

 40 omega   78.00  105.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 27

 41 omega   89.00  144.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 55

 42 omega   31.00   65.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 34

 43 omega   41.00   66.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1186772000
_diffrn_orient_matrix_UB_12      0.0601600000
_diffrn_orient_matrix_UB_13      0.0166618000
_diffrn_orient_matrix_UB_21      -0.0586662000
_diffrn_orient_matrix_UB_22      -0.0721933000
_diffrn_orient_matrix_UB_23      0.0542336000
_diffrn_orient_matrix_UB_31      0.0841852000
_diffrn_orient_matrix_UB_32      0.0107269000
_diffrn_orient_matrix_UB_33      0.0667042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32356
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.499
_diffrn_reflns_theta_min         3.171
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.664
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     813
_refine_ls_number_reflns         11567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0793
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1329P)^2^+5.3109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2065
_refine_ls_wR_factor_ref         0.2495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7579
_reflns_number_total             11567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03508f2.cif
_cod_data_source_block           3a_OTf4
_cod_depositor_comments
'Adding full bibliography for 7055945--7055952.cif.'
_cod_database_code               7055952
_chemical_oxdiff_formula         'c12 h9 n3 o3 s1 f3 zn1'
_reflns_odcompleteness_completeness 92.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O5(H5A,H5B), O4B(H4BA,H4BB), O4(H4A,H4B), O5B(H5BA,H5BB), O6(H6A,H6B),
 O6B(H6BA,H6BB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N1A(H1A), N1B(H1B), N1C(H1C), C3(H3), C3A(H3A), C7B(H7B), C7C(H7C),
 C4(H4), C4A(H4AA), C6B(H6BC), C6C(H6C), C5(H5), C5A(H5AA), C5B(H5BC), C5C(H5C),
  C6(H6), C6A(H6AA), C4B(H4BC), C4C(H4C), C7(H7), C7A(H7A), C3B(H3B), C3C(H3C)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N2A(H2AA,H2AB), N2B(H2BA,H2BB), N2C(H2CA,H2CB)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9B(H9BA,H9BB,H9BC)
;
_shelx_res_checksum              79024
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'