Lewis base catalyzed, enantioselective, intramolecular sulfenoamination of olefins.
Denmark, Scott E.; Chi, Hyung Min; Journal of the American Chemical Society 136 (2014) 8915–8918; doi:10.1021/ja5046296

data_4122018
_publ_contact_author
; 
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Lewis base catalyzed, enantioselective, intramolecular sulfenoamination
 of olefins.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8915
_journal_page_last               8918
_journal_paper_doi               10.1021/ja5046296
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H27 N O2 S2'
_chemical_formula_sum            'C25 H27 N O2 S2'
_chemical_formula_weight         437.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0841(5)
_cell_length_b                   15.6924(12)
_cell_length_c                   22.5997(18)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.12
_cell_measurement_theta_min      2.60
_cell_volume                     2157.7(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2013.10-0 (Bruker, 2013)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2013/3, SADABS V2012/1, TWINABS V2012/1 
(Bruker, 2012 & 2013) 
;
_computing_molecular_graphics
; 
SHELXTL v2013-4 (Bruker, 2013), CrystalMaker v2.7.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V2013-1 (Bruker, 2013)'
_computing_structure_refinement  'SHELX-2013-4 (Sheldrick, 2013)'
_computing_structure_solution    'SHELX-2013-4 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  cd24gsa
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            40407
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.186
_diffrn_reflns_theta_min         2.596
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.97430
_exptl_absorpt_correction_T_min  0.91819
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SAINT/SADABS v2012/1 (Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             928
_exptl_crystal_id                cd24gsa
_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 -2 3) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack (1983),  2495 Friedels'
_refine_ls_abs_structure_Flack   -0.034(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.6577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0634
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5583
_reflns_number_total             5825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5046296_si_002.cif
_cod_data_source_block           cd24gsa
_cod_depositor_comments          'Adding full bibliography for 4122018.cif.'
_cod_database_code               4122018
_shelx_estimated_absorpt_t_min   0.863
_shelx_estimated_absorpt_t_max   0.967
_refine_ls_abs_structure_hooft   -0.027(14)
_shelxl_version_number           2013-4
_shelx_res_checksum              8466
_shelx_hkl_checksum              7740