Zinc(II)-Mediated Nitrile-Amidoxime Coupling Gives New Insights into H(+)-Assisted Generation of 1,2,4-Oxadiazoles.
Bolotin, Dmitrii S.; Kulish, Kirill I.; Bokach, Nadezhda A.; Starova, Galina L.; Gurzhiy, Vladislav V.; Kukushkin, Vadim Yu; Inorganic chemistry 53 (2014) 10312–10324; doi:10.1021/ic501333s

data_4341090
_publ_section_title
;
 Zinc(II)-Mediated Nitrile-Amidoxime Coupling Gives New Insights into
 H(+)-Assisted Generation of 1,2,4-Oxadiazoles.
;
_journal_issue                   19
_journal_name_full               'Inorganic chemistry'
_journal_page_first              10312
_journal_page_last               10324
_journal_paper_doi               10.1021/ic501333s
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C10 H12 Cl2 N4 O2 Zn'
_chemical_formula_sum            'C10 H12 Cl2 N4 O2 Zn'
_chemical_formula_weight         356.51
_chemical_name_systematic
;
 ? 
;
_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             2014-05-21
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                106.485(8)
_cell_angle_beta                 106.955(9)
_cell_angle_gamma                102.763(9)
_cell_formula_units_Z            2
_cell_length_a                   7.1856(8)
_cell_length_b                   9.5278(10)
_cell_length_c                   11.3728(9)
_cell_measurement_reflns_used    1569
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.5630
_cell_measurement_theta_min      4.3910
_cell_volume                     673.88(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
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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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9750
_diffrn_measured_fraction_theta_max 0.9750
_diffrn_measurement_details
;
  1 omega  -49.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0037   38.0000 -120.0000 84

  2 omega  -95.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0037  126.0000 -120.0000 91

  3 omega -104.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0037  -57.0000   90.0000 93

  4 omega -116.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0037  -38.0000  -30.0000 101

  5 omega   63.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0037 -126.0000   60.0000 25

  6 omega   38.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 54

  7 omega   74.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 32

  8 omega  104.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 73

  9 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 26

 10 omega  138.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 27

 11 omega   58.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 50

 12 omega   70.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 45

 13 omega   45.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 52

 14 omega   35.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 61

 15 omega   77.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 31

 16 omega  138.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 37

 17 omega   74.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 44

 18 omega  104.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 26

 19 omega   63.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 38

 20 omega   80.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 34

 21 omega   41.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 52

 22 omega   68.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 30

 23 omega   37.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 35

 24 omega   80.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 34

 25 omega   59.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 29

 26 omega   43.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 35

 27 omega   57.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 35

 28 omega   40.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1889732000
_diffrn_orient_matrix_UB_12      0.0276706000
_diffrn_orient_matrix_UB_13      0.0277147000
_diffrn_orient_matrix_UB_21      -0.0780567000
_diffrn_orient_matrix_UB_22      -0.1692551000
_diffrn_orient_matrix_UB_23      -0.0112152000
_diffrn_orient_matrix_UB_31      0.1209083000
_diffrn_orient_matrix_UB_32      0.0502106000
_diffrn_orient_matrix_UB_33      0.1496898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4676
_diffrn_reflns_theta_full        76.41
_diffrn_reflns_theta_max         69.95
_diffrn_reflns_theta_min         4.38
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71715
_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            colorless
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.5859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                1825
_reflns_number_total             2433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501333s_si_001.cif
_cod_data_source_block           3e
_cod_depositor_comments
'Adding full bibliography for 4341086--4341092.cif.'
_cod_original_cell_volume        673.88(12)
_cod_database_code               4341090
_chemical_oxdiff_formula         'c10 h12 o2 n4 cl2 zn1'
_reflns_odcompleteness_completeness 88.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95