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_4518214
_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         'C16 H13 Cl2 N S'
_chemical_formula_sum            'C16 H13 Cl2 N S'
_chemical_formula_weight         322.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-27
_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                 95.870(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7514(4)
_cell_length_b                   13.3298(5)
_cell_length_c                   9.6736(3)
_cell_measurement_reflns_used    4279
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.1430
_cell_measurement_theta_min      5.0120
_cell_volume                     1507.36(9)
_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 n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.960
_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    -80.00  14.00   0.50    0.39    --  -46.62 102.00 179.00  188
  2  \w      8.00  83.00   0.50    0.39    --   46.62-102.00  75.00  150
  3  \w    -80.00 -15.00   0.50    1.57    --  -88.50 102.00 179.00  130
  4  \w    106.00 178.00   0.50    1.57    --  106.69 102.00 179.00  144
  5  \w     34.00 107.00   0.50    1.57    --  106.69-102.00  75.00  146
  6  \w   -119.00 -87.00   0.50    0.39    --  -46.62-125.00 -30.00   64
  7  \w   -119.00 -87.00   0.50    0.39    --  -46.62-125.00-150.00   64
  8  \w   -119.00 -83.00   0.50    0.39    --  -46.62 -57.00  60.00   72
  9  \w   -119.00 -83.00   0.50    0.39    --  -46.62 -57.00-180.00   72
 10  \w     83.00 120.00   0.50    0.39    --   46.62  57.00 120.00   74
 11  \w    -51.00 -16.00   0.50    1.57    --  -88.50  45.00  30.00   70
 12  \w   -160.00 -85.00   0.50    1.57    --  -88.50-102.00  75.00  150
 13  \w    -51.00 -16.00   0.50    1.57    --  -88.50  45.00 120.00   70
 14  \w    -51.00 -16.00   0.50    1.57    --  -88.50  45.00   0.00   70
 15  \w     34.00 105.00   0.50    1.57    --  106.69 -94.00-120.00  142
 16  \w     34.00 101.00   0.50    1.57    --  106.69 -77.00 120.00  134
 17  \w     34.00  71.00   0.50    1.57    --  106.69 -61.00 -60.00   74
 18  \w     34.00  71.00   0.50    1.57    --  106.69 -61.00  90.00   74
 19  \w    101.00 178.00   0.50    1.57    --  106.69  77.00  60.00  154
 20  \w     34.00 111.00   0.50    1.57    --  106.69-125.00 150.00  154
 21  \w     92.00 178.00   0.50    1.57    --  106.69  45.00  60.00  172
 22  \w     34.00 101.00   0.50    1.57    --  106.69 -77.00-120.00  134
 23  \w   -120.00 -32.00   0.50    0.39    --  -46.62 -37.00-180.00  176
 24  \w   -120.00 -32.00   0.50    0.39    --  -46.62 -37.00  60.00  176
 25  \w   -120.00 -32.00   0.50    0.39    --  -46.62 -37.00 -30.00  176
 26  \w   -120.00 -32.00   0.50    0.39    --  -46.62 -37.00 120.00  176
 27  \w   -120.00 -32.00   0.50    0.39    --  -46.62 -37.00-150.00  176
 28  \w   -120.00 -94.00   0.50    0.39    --  -46.62 -37.00   0.00   52
 29  \w   -120.00 -32.00   0.50    0.39    --  -46.62 -37.00 -90.00  176
;
_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      -0.1071170000
_diffrn_orient_matrix_UB_12      -0.0673049000
_diffrn_orient_matrix_UB_13      -0.0108995000
_diffrn_orient_matrix_UB_21      -0.0727430000
_diffrn_orient_matrix_UB_22      0.0879494000
_diffrn_orient_matrix_UB_23      -0.0634159000
_diffrn_orient_matrix_UB_31      0.0247176000
_diffrn_orient_matrix_UB_32      -0.0329984000
_diffrn_orient_matrix_UB_33      -0.1465676000
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8324
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.756
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.173
_diffrn_reflns_theta_min         5.032
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.060
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.693
_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    1.420
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0550P)^2^+3.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_full    0.623
_reflns_Friedel_fraction_max     0.551
_reflns_number_gt                2329
_reflns_number_total             2381
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04243_si_002.cif
_cod_data_source_block           hpd212
_cod_depositor_comments
'Adding full bibliography for 4518214--4518215.cif.'
_cod_database_code               4518214
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N S Cl'
_chemical_oxdiff_usercomment     G-54-C
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.470
_reflns_odcompleteness_completeness 99.72
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C14(H14), C13(H13), C12(H12), C5(H5), C6(H6), C7(H7),
 C8(H8), C9(H9)
;
_shelx_res_checksum              88081
_shelx_hkl_checksum              44723
_olex2_exptl_crystal_mounting_method 'nylon 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 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.691