tert-Butyl nitrite-mediated vicinal sulfoximation of alkenes with sulfinic acids: a highly efficient approach toward α-sulfonyl ketoximes
Chen, Fei; Zhou, Neng-Neng; Zhan, Jun-Long; Han, Bing; Yu, Wei; Organic Chemistry Frontiers 4 (2017) 135–; doi:10.1039/C6QO00535G

data_1553560
_publ_section_title
;
 &#x000D; tert-Butyl nitrite-mediated vicinal sulfoximation of alkenes
 with sulfinic acids: a highly efficient approach toward \a-sulfonyl
 ketoximes
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              135
_journal_paper_doi               10.1039/C6QO00535G
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C15 H21 N O3 S'
_chemical_formula_sum            'C15 H21 N O3 S'
_chemical_formula_weight         295.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2016-05-23 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.088(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.9610(17)
_cell_length_b                   5.7930(3)
_cell_length_c                   22.2512(17)
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    293.64(10)
_cell_measurement_theta_max      23.8010
_cell_measurement_theta_min      3.6590
_cell_volume                     3055.0(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.64(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   48.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  165.0000  108.0000 35

  2 omega  -49.00   46.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -77.0000  150.0000 95

  3 omega    2.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   57.0000  -90.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0033761000
_diffrn_orient_matrix_UB_12      0.1172264000
_diffrn_orient_matrix_UB_13      -0.0068878000
_diffrn_orient_matrix_UB_21      -0.0293423000
_diffrn_orient_matrix_UB_22      0.0078704000
_diffrn_orient_matrix_UB_23      -0.0197984000
_diffrn_orient_matrix_UB_31      -0.0047378000
_diffrn_orient_matrix_UB_32      0.0345409000
_diffrn_orient_matrix_UB_33      0.0279208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5734
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0667P)^2^+1.3096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1744
_reflns_number_gt                1731
_reflns_number_total             2998
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00535g2.cif
_cod_data_source_block           zhounn0528
_cod_original_cell_volume        3055.0(3)
_cod_database_code               1553560
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_date_sample_data_collection 2015-05-29
_olex2_submission_special_instructions 'No special instructions were received'