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_7243896
_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 H22 N4 O2 S'
_chemical_formula_sum            'C23 H22 N4 O2 S'
_chemical_formula_weight         418.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-03-28 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.65981(14)
_cell_length_b                   17.7339(2)
_cell_length_c                   27.7046(4)
_cell_measurement_reflns_used    3580
_cell_measurement_temperature    293.41(10)
_cell_measurement_theta_max      69.6750
_cell_measurement_theta_min      8.0040
_cell_volume                     4254.66(10)
_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      293.41(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -20.00  18.00   1.00    1.00    --    0.00 -57.00   0.00   38
  2  \w     23.00 111.00   1.00    1.00    --   54.00-125.00   0.00   88
  3  \w     39.00 105.00   1.00    2.00    --  108.00-111.00 -60.00   66
  4  \w     41.00  71.00   1.00    2.00    --  108.00-111.00 120.00   30
  5  \w     55.00 113.00   1.00    2.00    --  108.00-111.00 150.00   58
  6  \w     76.00 150.00   1.00    2.00    --  108.00  25.00  60.00   74
  7  \w     66.00 125.00   1.00    1.00    --   54.00  38.00 -60.00   59
  8  \w     39.00 107.00   1.00    1.00    --   54.00  57.00-120.00   68
  9  \w     66.00 133.00   1.00    2.00    --  108.00 178.00  60.00   67
 10  \w    -66.00 -23.00   1.00    1.00    --    0.00 -57.00   0.00   43
 11  \w    -68.00 -42.00   1.00    1.00    --    0.00 169.00  81.00   26
;
_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      0.0511451000
_diffrn_orient_matrix_UB_12      0.0398865000
_diffrn_orient_matrix_UB_13      -0.0467508000
_diffrn_orient_matrix_UB_21      0.1678643000
_diffrn_orient_matrix_UB_22      0.0013109000
_diffrn_orient_matrix_UB_23      0.0183982000
_diffrn_orient_matrix_UB_31      0.0293374000
_diffrn_orient_matrix_UB_32      -0.0771461000
_diffrn_orient_matrix_UB_33      -0.0238379000
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.988
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31459
_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    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00149(11)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0554P)^2^+1.0068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3091
_reflns_number_total             3766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03048e2.cif
_cod_data_source_block           guoshq_0603
_cod_depositor_comments
'Adding full bibliography for 7243893--7243896.cif.'
_cod_original_cell_volume        4254.66(11)
_cod_database_code               7243896
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.84
_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:
 C11(H11), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C13(H13), C17(H17), C19(H19), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              76452
_olex2_date_sample_data_collection 2020-06-03
_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 2.723
_oxdiff_exptl_absorpt_empirical_full_min 0.558