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_4341086
_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         'C5 H12 Cl2 N4 O Zn'
_chemical_formula_sum            'C5 H12 Cl2 N4 O Zn'
_chemical_formula_weight         280.46
_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                101.170(13)
_cell_angle_beta                 93.970(12)
_cell_angle_gamma                91.685(12)
_cell_formula_units_Z            2
_cell_length_a                   7.8776(11)
_cell_length_b                   7.8954(12)
_cell_length_c                   9.1597(15)
_cell_measurement_reflns_used    1503
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8831
_cell_measurement_theta_min      3.1161
_cell_volume                     557.04(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9701
_diffrn_measured_fraction_theta_max 0.9701
_diffrn_measurement_details
;
  1 omega  -81.00   -5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  123.0000  -85.0000 76

  2 omega  -87.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223 -178.0000  150.0000 52

  3 omega  -97.00  -51.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  149.0000   77.0000 46

  4 omega   59.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   57.0000   90.0000 26

  5 omega  -41.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -57.0000   30.0000 85

  6 omega  -46.00   43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -19.0000   90.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0431835000
_diffrn_orient_matrix_UB_12      -0.0653644000
_diffrn_orient_matrix_UB_13      -0.0456173000
_diffrn_orient_matrix_UB_21      0.0450222000
_diffrn_orient_matrix_UB_22      -0.0185520000
_diffrn_orient_matrix_UB_23      0.0644305000
_diffrn_orient_matrix_UB_31      -0.0653460000
_diffrn_orient_matrix_UB_32      -0.0615214000
_diffrn_orient_matrix_UB_33      0.0058831000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4142
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.12
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2051
_reflns_number_total             2477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501333s_si_001.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 4341086--4341092.cif.'
_cod_database_code               4341086
_chemical_oxdiff_formula         'c5 h12 n4 cl2 o1 zn1'
_reflns_odcompleteness_completeness 97.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51