Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.
Roos, Casey B.; Demaerel, Joachim; Graff, David E.; Knowles, Robert R.; Journal of the American Chemical Society 142 (2020) 5974–5979; doi:10.1021/jacs.0c01332

data_4134513
_publ_section_title
;
 Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by
 Proton-Coupled Electron Transfer.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5974
_journal_page_last               5979
_journal_paper_doi               10.1021/jacs.0c01332
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H20 N2 O2 S2'
_chemical_formula_weight         288.42
_chemical_name_common            CR-172
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4499(2)
_cell_length_b                   10.1587(3)
_cell_length_c                   19.0266(5)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.0856
_cell_measurement_theta_min      4.6481
_cell_volume                     1439.96(7)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.165
_diffrn_reflns_theta_min         4.648
_diffrn_source                   'I\mS microfocus source'
_exptl_absorpt_coefficient_mu    3.330
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.072(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0231
_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^)+(0.0337P)^2^+0.2490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0601
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2639
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01332_si_002.cif
_cod_data_source_block           cu_PDJCBR2_0m
_cod_depositor_comments
'Adding full bibliography for 4134513--4134514.cif.'
_cod_database_code               4134513
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.586
_shelx_estimated_absorpt_t_max   0.685
_shelx_res_checksum              74668
_shelx_hkl_checksum              94383