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_4134514
_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            'C15 H21 N O3 S'
_chemical_formula_weight         295.39
_chemical_name_common            CR-173
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5385(3)
_cell_length_b                   11.3360(4)
_cell_length_c                   17.2319(6)
_cell_measurement_reflns_used    118
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      39.8450
_cell_measurement_theta_min      5.9858
_cell_volume                     1472.58(9)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19399
_diffrn_reflns_theta_full        68.45
_diffrn_reflns_theta_max         68.45
_diffrn_reflns_theta_min         4.67
_diffrn_source                   'I\mS microfocus source'
_exptl_absorpt_coefficient_mu    2.015
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.173
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.263
_refine_ls_abs_structure_details
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.085(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0224
_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^)+(0.0287P)^2^+0.3211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0583
_reflns_number_gt                2639
_reflns_number_total             2664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01332_si_001.cif
_cod_data_source_block           PDJCBR1
_cod_depositor_comments
'Adding full bibliography for 4134513--4134514.cif.'
_cod_database_code               4134514
_shelx_res_checksum              92984
_shelx_hkl_checksum              32999