A novel approach to bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes <i>via</i> the [3 + 2]-dipolar cycloaddition of imidazole <i>N</i>-oxides and 2-heteroaryl-3,3-dimethylacrylonitriles.
Kutasevich, Anton V.; Niktarov, Anton S.; Uvarova, Ekaterina S.; Karnoukhova, Valentina A.; Mityanov, Vitaly S.; Organic & biomolecular chemistry 19 (2021) 8988–8998; doi:10.1039/d1ob01441b

data_7158334
_publ_section_title
;
 A novel approach to bis(1,3-azol-2-yl)acetonitriles and
 bis(1,3-azol-2-yl)methanes <i>via</i> the [3 + 2]-dipolar cycloaddition
 of imidazole <i>N</i>-oxides and 2-heteroaryl-3,3-dimethylacrylonitriles.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8988
_journal_page_last               8998
_journal_paper_doi               10.1039/d1ob01441b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C21 H18 N4 O S'
_chemical_formula_sum            'C21 H18 N4 O S'
_chemical_formula_weight         374.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-06-30 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.923(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   17.7917(6)
_cell_measurement_reflns_used    451
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1821.72(11)
_computing_cell_refinement       'Bruker SAINT'
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_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
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_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_type            'Bruker PHOTON II CPAD detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_max         30.523
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_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
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_exptl_crystal_description       prism
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_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0535P)^2^+0.3530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4240
_reflns_number_total             5572
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d1ob01441b2.cif
_cod_data_source_block           mvs693
_cod_depositor_comments
'Adding full bibliography for 7158333--7158334.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158334
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              80211