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_7243895
_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         'C25 H25 N O4 S'
_chemical_formula_sum            'C25 H25 N O4 S'
_chemical_formula_weight         435.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-03-28 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.6714(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.8661(3)
_cell_length_b                   9.09317(15)
_cell_length_c                   25.7813(4)
_cell_measurement_reflns_used    8979
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.5340
_cell_measurement_theta_min      3.6380
_cell_volume                     4385.48(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_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 0.947
_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    -14.00  21.00   1.00    0.10    --   43.05 -19.00 -60.00   35
  2  \w    -26.00   7.00   1.00    0.10    --   43.05 -37.00 -60.00   33
  3  \w     -2.00  76.00   1.00    0.10    --   43.05-103.00  58.00   78
  4  \w     63.00 107.00   1.00    0.10    --  109.26-103.00  58.00   44
  5  \w     77.00 102.00   1.00    0.10    --  109.26 -77.00  90.00   25
  6  \w     37.00  67.00   1.00    0.10    --  109.26 -61.00 120.00   30
  7  \w     40.00  68.00   1.00    0.10    --  109.26 -77.00  90.00   28
  8  \w     35.00  60.00   1.00    0.10    --  109.26 -61.00  60.00   25
  9  \w     36.00  64.00   1.00    0.10    --  109.26 -61.00 -60.00   28
 10  \w     35.00  68.00   1.00    0.10    --  109.26 -61.00-120.00   33
 11  \w     37.00  63.00   1.00    0.10    --  109.26 -61.00 -90.00   26
 12  \w     42.00  68.00   1.00    0.10    --  109.26 -61.00-150.00   26
 13  \w     35.00  66.00   1.00    0.10    --  109.26 -61.00-180.00   31
 14  \w     26.00 112.00   1.00    0.10    --   43.05  57.00-120.00   86
 15  \w     87.00 166.00   1.00    0.10    --  109.26 103.00 160.00   79
 16  \w    -49.00 -24.00   1.00    0.10    -- -100.00  45.00 150.00   25
 17  \w    -52.00 -25.00   1.00    0.10    -- -100.00  45.00  90.00   27
 18  \w    -50.00 -25.00   1.00    0.10    -- -100.00  45.00  30.00   25
 19  \w    -50.00 -24.00   1.00    0.10    -- -100.00  45.00 -30.00   26
 20  \w    -54.00 -29.00   1.00    0.10    -- -100.00  45.00   0.00   25
 21  \w    -67.00 -39.00   1.00    0.10    -- -100.00  61.00 -60.00   28
 22  \w    -54.00 -27.00   1.00    0.10    -- -100.00  45.00 -90.00   27
 23  \w    -73.00 -44.00   1.00    0.10    -- -100.00  61.00   0.00   29
 24  \w    -73.00 -33.00   1.00    0.10    -- -100.00  61.00 120.00   40
 25  \w    -74.00 -49.00   1.00    0.10    -- -100.00  61.00 150.00   25
 26  \w    -70.00  -3.00   1.00    0.10    --  -43.05 103.00 160.00   67
 27  \w   -106.00 -51.00   1.00    0.10    -- -100.00 103.00 160.00   55
 28  \w   -149.00 -90.00   1.00    0.10    -- -100.00 -94.00  90.00   59
 29  \w   -152.00-108.00   1.00    0.10    -- -100.00-103.00  58.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0289302000
_diffrn_orient_matrix_UB_12      -0.0556424000
_diffrn_orient_matrix_UB_13      0.0599084000
_diffrn_orient_matrix_UB_21      -0.0121411000
_diffrn_orient_matrix_UB_22      0.1533416000
_diffrn_orient_matrix_UB_23      0.0206439000
_diffrn_orient_matrix_UB_31      -0.0761133000
_diffrn_orient_matrix_UB_32      -0.0457305000
_diffrn_orient_matrix_UB_33      -0.0035850000
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            13779
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.911
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0776P)^2^+1.9746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3926
_reflns_number_total             4342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03048e2.cif
_cod_data_source_block           guoshq_1229
_cod_depositor_comments
'Adding full bibliography for 7243893--7243896.cif.'
_cod_database_code               7243895
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.810
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              78772
_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 9.271
_oxdiff_exptl_absorpt_empirical_full_min 0.440