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_7156615
_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         'C17 H12 F N O3 S'
_chemical_formula_sum            'C17 H12 F N O3 S'
_chemical_formula_weight         329.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.237(3)
_cell_length_b                   11.212(2)
_cell_length_c                   17.948(3)
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      67.1151
_cell_measurement_theta_min      2.9001
_cell_volume                     3066.2(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker ACS Kappa APEX II DUO diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Incoatec Montel Multilayer Mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16848
_diffrn_reflns_theta_full        67.14
_diffrn_reflns_theta_max         67.14
_diffrn_reflns_theta_min         5.72
_diffrn_source                   'Incoatec Microfocus X-ray Source I\mS'
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    2.111
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.191
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0709P)^2^+1.4891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                2617
_reflns_number_total             2637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02691b2.cif
_cod_data_source_block           I_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7156612--7156616.cif.'
_cod_database_code               7156615
_shelx_res_checksum              79755
_shelx_hkl_checksum              82595