Divergent Ritter-type amination via photoredox catalytic four-component radical-polar crossover reactions
Guo, Sheng-Qiang; Yang, Hui-Qing; Wang, Ai-Lian; Jiang, Yu-Zhen; Xu, Guo-Qiang; Luo, Yong-Chun; Chen, Zhao-Xu; Xu, Peng-Fei; Green Chemistry 23 (2021) 9571–9576; doi:10.1039/D1GC03048E

data_7243894
_publ_section_title
;
 Divergent Ritter-type amination via photoredox catalytic four-component
 radical-polar crossover reactions
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              9571
_journal_page_last               9576
_journal_paper_doi               10.1039/D1GC03048E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C23 H20 Cl N O4 S'
_chemical_formula_sum            'C23 H20 Cl N O4 S'
_chemical_formula_weight         441.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-03-28 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.273(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7213(3)
_cell_length_b                   10.0584(3)
_cell_length_c                   17.2909(5)
_cell_measurement_reflns_used    3180
_cell_measurement_temperature    292.4(4)
_cell_measurement_theta_max      69.8100
_cell_measurement_theta_min      9.6830
_cell_volume                     2123.84(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.4(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     87.00 176.00   1.00    1.00    --  108.00  63.00 -30.00   89
  2  \w    135.00 161.00   1.00    1.00    --  108.00  63.00 -60.00   26
  3  \w    101.00 127.00   1.00    1.00    --  108.00  63.00 -60.00   26
  4  \w     92.00 118.00   1.00    1.00    --   54.00  57.00-150.00   26
  5  \w     33.00 112.00   1.00    1.00    --   54.00  57.00-180.00   79
  6  \w     38.00 130.00   1.00    1.00    --  108.00 -50.00-180.00   92
  7  \w     59.00 138.00   1.00    1.00    --  108.00 -91.00-180.00   79
  8  \w     36.00 115.00   1.00    1.00    --  108.00-111.00   0.00   79
  9  \w     99.00 173.00   1.00    1.00    --  108.00 -12.00  90.00   74
 10  \w     37.00 100.00   1.00    1.00    --   54.00-125.00  90.00   63
 11  \w    -12.00  16.00   1.00    1.00    --    0.00 -57.00  60.00   28
 12  \w    -62.00 -37.00   1.00    1.00    --    0.00 -57.00  60.00   25
 13  \w    -17.00  80.00   1.00    1.00    --   54.00 -38.00-120.00   97
 14  \w     29.00  60.00   1.00    1.00    --   54.00 -77.00-180.00   31
 15  \w     36.00 104.00   1.00    1.00    --  108.00-111.00-180.00   68
 16  \w    -20.00   5.00   1.00    1.00    --    0.00  57.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1166793000
_diffrn_orient_matrix_UB_12      0.0496070000
_diffrn_orient_matrix_UB_13      -0.0416672000
_diffrn_orient_matrix_UB_21      0.0424123000
_diffrn_orient_matrix_UB_22      0.1441930000
_diffrn_orient_matrix_UB_23      0.0058870000
_diffrn_orient_matrix_UB_31      0.0221615000
_diffrn_orient_matrix_UB_32      -0.0147092000
_diffrn_orient_matrix_UB_33      -0.0827350000
_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  0.0205
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7861
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.619
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.765
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0528P)^2^+0.6113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3133
_reflns_number_total             3741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03048e2.cif
_cod_data_source_block           guoshq_0910
_cod_depositor_comments
'Adding full bibliography for 7243893--7243896.cif.'
_cod_original_cell_volume        2123.83(10)
_cod_database_code               7243894
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.751
_reflns_odcompleteness_completeness 99.60
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C20(H20), C22(H22), C26(H26), C30(H30)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              13125
_olex2_date_sample_data_collection 2020-09-10
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.779