Catalytic, Enantioselective, Intramolecular Carbosulfenylation of Olefins
Scott E. Denmark; Alex Jaunet; Journal of the American Chemical Society 135 (2013) 6419–6422; doi:10.1021/ja401867b

data_4119697
_publ_section_title
;
 Catalytic, Enantioselective, Intramolecular Carbosulfenylation of Olefins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6419
_journal_page_last               6422
_journal_paper_doi               10.1021/ja401867b
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 O4 S'
_chemical_formula_sum            'C24 H22 O4 S'
_chemical_formula_weight         406.48
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.598(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7172(12)
_cell_length_b                   10.941(2)
_cell_length_c                   15.717(3)
_cell_measurement_reflns_used    3320
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      22.81
_cell_measurement_theta_min      2.27
_cell_volume                     982.1(3)
_computing_cell_refinement       'SAINT V7.68A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2010.11-3 (Bruker, 2010)'
_computing_data_reduction
; 
SAINT V7.68A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens Platform/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  bm53uas
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11732
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       Prism
_exptl_crystal_F_000             428
_exptl_crystal_id                bm53uas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (0 -1 -2) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
Flack (1983),  1900 Friedels 
Hooft,R.; Straver, L.; Spek, A. (2008) 
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0427P)^2^+0.0034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                3571
_reflns_number_total             4038
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja401867b_si_002.cif
_cod_data_source_block           bm53uas
_cod_original_cell_volume        982.1(4)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4119697
_refine_ls_abs_structure_hooft   0.07(4)