α-Amino Radical-Mediated Diverse Difunctionalization of Alkenes: Construction of C–C, C–N, and C–S Bonds
Su, Yong-Liang; Tram, Linh; Wherritt, Daniel; Arman, Hadi; Griffith, Wendell P.; Doyle, Michael P.; ACS Catalysis 10 (2020) 13682–13687; doi:10.1021/acscatal.0c04243

data_4518215
_publ_section_title
;
 \a-Amino Radical-Mediated Diverse Difunctionalization of Alkenes:
 Construction of C--C, C--N, and C--S Bonds
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              13682
_journal_page_last               13687
_journal_paper_doi               10.1021/acscatal.0c04243
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H11 Cl2 N S'
_chemical_formula_sum            'C14 H11 Cl2 N S'
_chemical_formula_weight         296.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.677(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.92080(10)
_cell_length_b                   5.96410(10)
_cell_length_c                   13.9611(2)
_cell_measurement_reflns_used    4342
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2520
_cell_measurement_theta_min      3.1680
_cell_volume                     656.294(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     32.00 121.00   0.50    0.70    --   46.87  37.00  90.00  178
  2  \w     83.00 120.00   0.50    0.70    --   46.87  57.00 120.00   74
  3  \w     83.00 120.00   0.50    0.70    --   46.87  57.00 150.00   74
  4  \w    103.00 178.00   0.50    2.80    --  106.69 110.00 156.00  150
  5  \w     95.00 178.00   0.50    2.80    --  106.69 125.00 -90.00  166
  6  \w     83.00 120.00   0.50    0.70    --   46.87  57.00-120.00   74
  7  \w     34.00  71.00   0.50    2.80    --  106.69 -61.00-150.00   74
  8  \w     34.00 101.00   0.50    2.80    --  106.69 -77.00-150.00  134
  9  \w     34.00  71.00   0.50    2.80    --  106.69 -61.00 -90.00   74
 10  \w     34.00 111.00   0.50    2.80    --  106.69-125.00   0.00  154
 11  \w     34.00 107.00   0.50    2.80    --  106.69-110.00  62.00  146
 12  \w     34.00 105.00   0.50    2.80    --  106.69 -94.00  90.00  142
 13  \w     23.00  88.00   0.50    0.70    --   46.87-110.00  62.00  130
 14  \w     32.00 121.00   0.50    0.70    --   46.87  37.00 -90.00  178
 15  \w     32.00  57.00   0.50    0.70    --   46.87  37.00-180.00   50
 16  \w     32.00 121.00   0.50    0.70    --   46.87  37.00   0.00  178
 17  \w    -51.00 -16.00   0.50    2.80    --  -88.50  45.00  90.00   70
 18  \w    -51.00 -16.00   0.50    2.80    --  -88.50  45.00   0.00   70
 19  \w    -51.00 -16.00   0.50    2.80    --  -88.50  45.00 -30.00   70
 20  \w    -51.00 -16.00   0.50    2.80    --  -88.50  45.00 -60.00   70
 21  \w    -82.00  -1.00   0.50    0.70    --  -46.87 110.00 156.00  162
 22  \w    -82.00 -15.00   0.50    2.80    --  -88.50 110.00 156.00  134
 23  \w   -160.00 -82.00   0.50    2.80    --  -88.50-110.00  62.00  156
 24  \w   -120.00 -87.00   0.50    0.70    --  -46.87-125.00 -60.00   66
 25  \w   -120.00 -83.00   0.50    0.70    --  -46.87 -57.00-180.00   74
 26  \w   -160.00-101.00   0.50    2.80    --  -88.50 -77.00-150.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1341171000
_diffrn_orient_matrix_UB_12      -0.0848001000
_diffrn_orient_matrix_UB_13      -0.0791239000
_diffrn_orient_matrix_UB_21      -0.0164522000
_diffrn_orient_matrix_UB_22      0.2384878000
_diffrn_orient_matrix_UB_23      -0.0424531000
_diffrn_orient_matrix_UB_31      0.1411478000
_diffrn_orient_matrix_UB_32      -0.0523867000
_diffrn_orient_matrix_UB_33      -0.0649893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6720
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.485
_diffrn_reflns_theta_min         3.181
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.756
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 823 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0327P)^2^+0.0875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0642
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.817
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                2213
_reflns_number_total             2304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04243_si_003.cif
_cod_data_source_block           hpd113
_cod_depositor_comments
'Adding full bibliography for 4518214--4518215.cif.'
_cod_database_code               4518215
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H10S1N1Cl2
_chemical_oxdiff_usercomment     5-86-5-1
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.611
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C10(H10), C9(H9), C5(H5)
;
_olex2_exptl_crystal_mounting_method 'nlon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.755