Cleavage of oxygen–sulfur double bonds and carbon–sulfur bonds: unusual highly selective electrophilic addition of allenylic sulfoxides
Wang, Minyan; Fu, Chunling; Ma, Shengming; Chemical Science 4 (2013) 1016–; doi:10.1039/c2sc21920d

data_1514597
_publ_section_title
;
 Cleavage of oxygen--sulfur double bonds and carbon--sulfur bonds: unusual
 highly selective electrophilic addition of allenylic sulfoxides
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              1016
_journal_paper_doi               10.1039/c2sc21920d
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C15 H19 I N4 O4'
_chemical_formula_sum            'C15 H19 I N4 O4'
_chemical_formula_weight         446.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.258(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5720(7)
_cell_length_b                   9.3235(5)
_cell_length_c                   15.1484(6)
_cell_measurement_reflns_used    2620
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2177
_cell_measurement_theta_min      3.0250
_cell_volume                     1775.60(15)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9033
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    1.830
_exptl_absorpt_correction_T_max  0.6783
_exptl_absorpt_correction_T_min  0.5355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0401P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                2579
_reflns_number_total             3241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc21920d.txt
_cod_data_source_block           111031_wmy_4_61
_cod_original_cell_volume        1775.61(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1514597