Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes.
Roth, Aaron; Denmark, Scott E.; Journal of the American Chemical Society 141 (2019) 13767–13771; doi:10.1021/jacs.9b07019

data_4128886
_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
;
 Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination
 of Alkenes.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13767
_journal_page_last               13771
_journal_paper_doi               10.1021/jacs.9b07019
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H32 F N S'
_chemical_formula_sum            'C27 H32 F N S'
_chemical_formula_weight         421.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9111(2)
_cell_length_b                   19.1719(4)
_cell_length_c                   24.7720(5)
_cell_measurement_reflns_used    46569
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.57
_cell_volume                     4707.04(17)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2014)'
_computing_data_collection       'APEX3 V2018.7-2 (Bruker, 2018)'
_computing_data_reduction
; 
SAINT V8.38A, XPREP v2014/2, (Bruker, 2014), 
SADABS V2016/2 (Krause et al., 2015) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-7 (Bruker, 2014), CrystalMaker v9.2.8 (CrystalMaker, 2016) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2018-3 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT-2014-5 (Sheldrick, 2015b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture/Photon II'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_wavelength_id  dd75usa
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            49018
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         3.568
_exptl_absorpt_coefficient_mu    1.375
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6467
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1808
_exptl_crystal_id                dd75usa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Paratone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 4 2) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.148
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack (1983),  1904 Friedels'
_refine_ls_abs_structure_Flack   0.000(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4304
_refine_ls_number_restraints     223
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+1.9782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0621
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4296
_reflns_number_total             4304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07019_si_002.cif
_cod_data_source_block           dd75usa
_cod_database_code               4128886
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.520
_shelx_estimated_absorpt_t_max   0.822
_shelx_res_checksum              7458
_shelx_hkl_checksum              66451