Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes
Scott E. Denmark; David J. P. Kornfilt; Thomas Vogler; Journal of the American Chemical Society 133 (2011) 15308–15311; doi:10.1021/ja2064395

data_4106882
_publ_section_title
;
 Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15308
_journal_page_last               15311
_journal_paper_doi               10.1021/ja2064395
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 O S'
_chemical_formula_sum            'C17 H18 O S'
_chemical_formula_weight         270.37
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1559(8)
_cell_length_b                   8.6293(11)
_cell_length_c                   27.248(3)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.48
_cell_volume                     1447.4(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, 
(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      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  bm34oas
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18385
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_id                bm34oas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-1 0 0) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.246
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack (1983),  1120 Friedels'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.2219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                2676
_reflns_number_total             2748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2064395_si_002.cif
_cod_data_source_block           bm34oas
_cod_database_code               4106882