Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines.
McCaw, Patrick G.; Khandavilli, U. B. Rao; Lawrence, Simon E.; Maguire, Anita R.; Collins, Stuart G.; Organic & biomolecular chemistry 17 (2019) 622–638; doi:10.1039/c8ob02691b

data_7156616
_publ_section_title
;
 Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of
 nitrile oxides to \a-oxo sulfines.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              622
_journal_page_last               638
_journal_paper_doi               10.1039/c8ob02691b
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C16 H11 N O3 S'
_chemical_formula_sum            'C16 H11 N O3 S'
_chemical_formula_weight         297.32
_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
_audit_update_record
;
2018-10-26 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                70.226(9)
_cell_angle_beta                 83.607(9)
_cell_angle_gamma                72.230(9)
_cell_formula_units_Z            2
_cell_length_a                   7.342(2)
_cell_length_b                   8.954(3)
_cell_length_c                   11.714(3)
_cell_measurement_reflns_used    3237
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.91
_cell_volume                     690.1(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.(2)
_diffrn_detector_area_resol_mean 8.33333
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
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_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6640
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Bruker X2S'
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'SADABS V2014/4 (Bruker AXS Inc.)'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0576P)^2^+0.1657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                1976
_reflns_number_total             2407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02691b2.cif
_cod_data_source_block           I_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7156612--7156616.cif.'
_cod_original_cell_volume        690.1(3)
_cod_database_code               7156616
_shelx_res_checksum              31720
_shelx_hkl_checksum              11833