Organophotoredox catalytic four-component radical-polar crossover cascade reactions for the stereoselective synthesis of β-amido sulfones
Guo, Sheng-Qiang; Yang, Hui-Qing; Jiang, Yu-Zhen; Wang, Ai-Lian; Xu, Guo-Qiang; Luo, Yong-Chun; Chen, Zhao-Xu; Zheng, Haixue; Xu, Peng-Fei; Green Chemistry 24 (2022) 3120–3124; doi:10.1039/D2GC00224H

data_7244715
_publ_section_title
;
 Organophotoredox catalytic four-component radical-polar crossover cascade
 reactions for the stereoselective synthesis of \b-amido sulfones
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              3120
_journal_page_last               3124
_journal_paper_doi               10.1039/D2GC00224H
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C17 H18 Br N O3 S'
_chemical_formula_sum            'C17 H18 Br N O3 S'
_chemical_formula_weight         396.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-12-08 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.079(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1683(5)
_cell_length_b                   9.4026(4)
_cell_length_c                   16.7625(9)
_cell_measurement_reflns_used    4131
_cell_measurement_temperature    303.84(10)
_cell_measurement_theta_max      26.9630
_cell_measurement_theta_min      2.2610
_cell_volume                     1753.34(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.84(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 0.807
_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    -24.00  15.00   1.00    1.56    --   -6.59  63.00 112.00   39
  2  \w     21.00  65.00   1.00    1.56    --   -6.59  63.00 112.00   44
  3  \w    -75.00 -16.00   1.00    1.56    --   -6.59 -63.00 -24.00   59
  4  \w    -17.00  27.00   1.00    1.56    --   -6.59 -99.00   0.00   44
  5  \w     -7.00  19.00   1.00    1.56    --   -6.59 -99.00-150.00   26
  6  \w    -18.00  27.00   1.00    1.56    --   -6.59 -99.00-180.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0274928000
_diffrn_orient_matrix_UB_12      -0.0602255000
_diffrn_orient_matrix_UB_13      -0.0194389000
_diffrn_orient_matrix_UB_21      0.0223733000
_diffrn_orient_matrix_UB_22      -0.0435777000
_diffrn_orient_matrix_UB_23      0.0324895000
_diffrn_orient_matrix_UB_31      -0.0530155000
_diffrn_orient_matrix_UB_32      0.0128244000
_diffrn_orient_matrix_UB_33      0.0192520000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.807
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15290
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.983
_diffrn_reflns_theta_min         2.108
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.477
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.501
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0475P)^2^+1.1822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3001
_reflns_number_total             4500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00224h2.cif
_cod_data_source_block           guoshengqiang_0517_autored
_cod_depositor_comments          'Adding full bibliography for 7244715.cif.'
_cod_database_code               7244715
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C15(H15), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              29758
_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 1.116
_oxdiff_exptl_absorpt_empirical_full_min 0.864