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_4341089
_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         '2(C12 H16 Cl2 N4 O2 Zn)'
_chemical_formula_sum            'C24 H32 Cl4 N8 O4 Zn2'
_chemical_formula_weight         769.12
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
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_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
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_audit_creation_date             2014-05-21
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  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                75.307(4)
_cell_angle_beta                 82.409(3)
_cell_angle_gamma                82.776(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2094(4)
_cell_length_b                   10.2736(6)
_cell_length_c                   15.7530(6)
_cell_measurement_reflns_used    4239
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7170
_cell_measurement_theta_min      2.6827
_cell_volume                     1576.90(13)
_computing_cell_refinement
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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)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
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_computing_data_reduction
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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_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    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_details
;
  1 omega  -83.00   -4.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661  -77.0000   30.0000 79

  2 omega  -88.00    2.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661  -77.0000  120.0000 90

  3 omega  -53.00   44.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661   77.0000 -120.0000 97

  4 omega   59.00   94.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2036   57.0000    0.0000 35

  5 omega  -18.00   65.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2036  -99.0000  -30.0000 83

  6 omega   56.00   94.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2036   57.0000 -150.0000 38

  7 omega   36.00   62.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.2036  178.0000  -90.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0507420000
_diffrn_orient_matrix_UB_12      -0.0526548000
_diffrn_orient_matrix_UB_13      0.0127178000
_diffrn_orient_matrix_UB_21      0.0475465000
_diffrn_orient_matrix_UB_22      0.0392679000
_diffrn_orient_matrix_UB_23      -0.0288747000
_diffrn_orient_matrix_UB_31      0.0110902000
_diffrn_orient_matrix_UB_32      0.0287667000
_diffrn_orient_matrix_UB_33      0.0345713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14286
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.69
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99487
_exptl_absorpt_correction_type   multi-scan
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.621
_refine_diff_density_min         -1.395
_refine_diff_density_rms         0.108
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         7259
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0224P)^2^+3.9404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                5373
_reflns_number_total             7259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501333s_si_001.cif
_cod_data_source_block           3d
_cod_depositor_comments
'Adding full bibliography for 4341086--4341092.cif.'
_cod_original_cell_volume        1576.90(12)
_cod_database_code               4341089
_chemical_oxdiff_formula         'zn1 C12 H16 O2 n4 cl2'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51