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_7055950
_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         'C F3 O3 S, C10 H15 N4 O'
_chemical_formula_sum            'C11 H15 F3 N4 O4 S'
_chemical_formula_weight         356.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.745(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7859(5)
_cell_length_b                   8.3599(2)
_cell_length_c                   21.9907(5)
_cell_measurement_reflns_used    8632
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5690
_cell_measurement_theta_min      4.0250
_cell_volume                     3085.66(14)
_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 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -93.00  -41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  150.0000 52

  2 omega  -50.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 82

  3 omega  -40.00   25.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 65

  4 omega  -86.00   41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -150.0000 127

  5 omega   23.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000   60.0000 55

  6 omega   71.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  -60.0000 56

  7 omega   20.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  -30.0000 39

  8 omega   40.00   66.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -64.0000   61.8738 26

  9 omega  110.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -10.0000    3.4901 67

 10 omega   45.00  119.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -122.0000   69.4356 74

 11 omega   90.00  117.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -79.0000  -38.8604 27

 12 omega   31.00   56.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 25

 13 omega   45.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 53

 14 omega   35.00   78.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 43

 15 omega   50.00   76.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -79.0000  -38.8604 26

 16 omega  114.00  141.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -10.0000  147.9364 27

 17 omega   28.00   86.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -10.0000    3.4901 58

 18 omega   59.00   94.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 35

 19 omega   36.00   62.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 26

 20 omega   48.00   74.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 26

 21 omega  107.00  146.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 39

 22 omega   73.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 34

 23 omega   79.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 36

 24 omega  108.00  144.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 36

 25 omega   48.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 41

 26 omega   63.00  105.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 42

 27 omega   99.00  125.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

 28 omega   89.00  128.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 39

 29 omega   39.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 50

 30 omega   93.00  126.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 33

 31 omega   74.00  110.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -113.0000  143.0000 36

 32 omega   65.00  100.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -10.0000  147.9364 35

 33 omega   45.00   93.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 48

 34 omega  122.00  147.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 25

 35 omega  109.00  175.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 66

 36 omega   36.00   90.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 54

 37 omega   90.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25

 38 omega  125.00  150.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 25

 39 omega   92.00  124.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 32

 40 omega  139.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 38

 41 omega   55.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 26

 42 omega   35.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 72

 43 omega   76.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 39

 44 omega   80.00  121.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  150.0000 41

 45 omega  135.00  167.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  150.0000 32

 46 omega  104.00  131.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 27

 47 omega  152.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 26

 48 omega   89.00  114.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

 49 omega   97.00  123.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 26

 50 omega  150.00  175.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 25

 51 omega   49.00   99.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 50

 52 omega   60.00  104.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 44

 53 omega   39.00   64.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 25

 54 omega   57.00   83.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

 55 omega   43.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 55

 56 omega   37.00   63.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 26

 57 omega   82.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 25

 58 omega   49.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 32

 59 omega   69.00   94.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 25

 60 omega  123.00  173.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 50

 61 omega  108.00  135.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 27

 62 omega  153.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 25

 63 omega   74.00   99.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -64.0000   61.8738 25

 64 omega   35.00   86.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -26.0000  106.6766 51
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0221222000
_diffrn_orient_matrix_UB_12      0.1784040000
_diffrn_orient_matrix_UB_13      0.0050859000
_diffrn_orient_matrix_UB_21      0.0771199000
_diffrn_orient_matrix_UB_22      0.0308962000
_diffrn_orient_matrix_UB_23      0.0368645000
_diffrn_orient_matrix_UB_31      0.0445170000
_diffrn_orient_matrix_UB_32      0.0344643000
_diffrn_orient_matrix_UB_33      -0.0593819000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1226
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21892
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.503
_diffrn_reflns_theta_min         4.021
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60288
_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    1.534
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+4.6861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2818
_reflns_number_total             3225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03508f2.cif
_cod_data_source_block           5a_OTf
_cod_depositor_comments
'Adding full bibliography for 7055945--7055952.cif.'
_cod_original_cell_volume        3085.67(15)
_cod_database_code               7055950
_chemical_oxdiff_formula         'Zn C22 H28 N8 O8 F6 S2'
_reflns_odcompleteness_completeness 94.95
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C6(H6), C7(H7), C10(H10)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3C,H3D,H3E)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'