Mechanistic investigation of the NH-sulfoximination of sulfide. Evidence for λ(6)-sulfanenitrile intermediates.
Lohier, Jean-François; Glachet, Thomas; Marzag, Hamid; Gaumont, Annie-Claude; Reboul, Vincent; Chemical communications (Cambridge, England) 53 (2017) 2064–2067; doi:10.1039/c6cc09940h

data_7119569
_publ_section_title
;
 Mechanistic investigation of the NH-sulfoximination of sulfide. Evidence
 for \l(6)-sulfanenitrile intermediates.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2064
_journal_page_last               2067
_journal_paper_doi               10.1039/c6cc09940h
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H18 N2 O4 S'
_chemical_formula_sum            'C10 H18 N2 O4 S'
_chemical_formula_weight         262.32
_chemical_melting_point          326
_chemical_name_systematic
tert-butyl(1-methyl-1-oxido-3-oxo-3,4,5,6-tetrahydro-2-thiazin-4-yl)carbamate
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-13 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7140(3)
_cell_length_b                   6.7632(3)
_cell_length_c                   27.8703(12)
_cell_measurement_reflns_used    6200
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      2.92
_cell_volume                     1265.54(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13623
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         2.924
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2015/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.6987
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1019 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0340P)^2^+0.2850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0731
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2661
_reflns_number_total             3007
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09940h2.cif
_cod_data_source_block           lohier25_0m
_cod_depositor_comments
'Adding full bibliography for 7119568--7119569.cif.'
_cod_database_code               7119569
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              55554