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_1553559
_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         'C27 H31 N O7 S3'
_chemical_formula_sum            'C27 H31 N O7 S3'
_chemical_formula_weight         577.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_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                 109.610(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.226(3)
_cell_length_b                   8.2493(7)
_cell_length_c                   16.985(2)
_cell_measurement_reflns_used    2159
_cell_measurement_temperature    294.74(10)
_cell_measurement_theta_max      25.3360
_cell_measurement_theta_min      3.1170
_cell_volume                     2801.6(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      294.74(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0181216000
_diffrn_orient_matrix_UB_12      -0.0737410000
_diffrn_orient_matrix_UB_13      -0.0053069000
_diffrn_orient_matrix_UB_21      -0.0292130000
_diffrn_orient_matrix_UB_22      0.0404101000
_diffrn_orient_matrix_UB_23      -0.0255899000
_diffrn_orient_matrix_UB_31      0.0087218000
_diffrn_orient_matrix_UB_32      -0.0179684000
_diffrn_orient_matrix_UB_33      -0.0359091000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6637
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.945
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0909
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1484P)^2^+0.7259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2444
_refine_ls_wR_factor_ref         0.2645
_reflns_number_gt                4056
_reflns_number_total             6637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00535g2.cif
_cod_data_source_block           zhounn0416_twin1_hklf4
_cod_original_cell_volume        2801.5(6)
_cod_database_code               1553559
_chemical_oxdiff_formula         'C11 H10 N O'
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19),
 C22(H22), C24(H24), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;