CO2-Promoted photoredox-catalyzed hydrosulfonylation of alkenes with sulfinates
Huang, Wanhui; Liu, Ge; Yang, Fangyuanhang; Ren, Yuxi; Gao, Yuzhen; Su, Weiping; Green Chemistry 27 (2025) 3627–3633; doi:10.1039/D5GC00057B

data_7250062
_publ_section_title
;
 CO2-Promoted photoredox-catalyzed hydrosulfonylation of alkenes with
 sulfinates
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              3627
_journal_page_last               3633
_journal_paper_doi               10.1039/D5GC00057B
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C17 H25 O2 S'
_chemical_formula_sum            'C17 H25 O2 S'
_chemical_formula_weight         293.43
_chemical_name_systematic
1-(((4-isopropylcyclohex-1-en-1-yl)methyl)sulfonyl)-4-methylbenzene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-06-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-07-02 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                86.315(2)
_cell_angle_beta                 76.450(3)
_cell_angle_gamma                73.545(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1654(2)
_cell_length_b                   10.1994(3)
_cell_length_c                   11.9077(4)
_cell_measurement_reflns_used    5888
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.4790
_cell_measurement_theta_min      3.7700
_cell_volume                     811.37(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_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 0.941
_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     26.00 115.00   0.50    0.07    --   47.60  77.00  90.00  178
  2  \w    114.00 152.00   0.50    0.28    --  113.25 106.00 100.00   76
  3  \w    126.00 164.00   0.50    0.28    --  113.25  45.00  30.00   76
  4  \w     98.00 164.00   0.50    0.28    --  113.25  15.00 -60.00  132
  5  \w     47.00 103.00   0.50    0.28    --  113.25 -77.00   0.00  112
  6  \w     44.00  71.00   0.50    0.28    --  113.25 -61.00 -90.00   54
  7  \w     41.00  66.00   0.50    0.28    --  113.25 -61.00-120.00   50
  8  \w     41.00  67.00   0.50    0.28    --  113.25 -61.00-180.00   52
  9  \w    -21.00   4.00   0.50    0.07    --   47.60 -19.00 -60.00   50
 10  \w     41.00  66.00   0.50    0.28    --  113.25 -61.00  30.00   50
 11  \w     41.00  68.00   0.50    0.28    --  113.25 -95.00   0.00   54
 12  \w     75.00 108.00   0.50    0.28    --  113.25-106.00   0.00   66
 13  \w     55.00 103.00   0.50    0.28    --  113.25 -95.00 -60.00   96
 14  \w     69.00  94.00   0.50    0.28    --  113.25 -95.00 -90.00   50
 15  \w     64.00  89.00   0.50    0.28    --  113.25-125.00 -90.00   50
 16  \w     43.00 104.00   0.50    0.28    --  113.25-125.00-150.00  122
 17  \w     15.00  44.00   0.50    0.07    --   47.60-125.00 -30.00   58
 18  \w     48.00  92.00   0.50    0.07    --   47.60-125.00 -30.00   88
 19  \w     24.00  64.00   0.50    0.07    --   47.60-106.00   0.00   80
 20  \w    -23.00  11.00   0.50    0.07    --  -47.60  19.00-180.00   68
 21  \w    -25.00  26.00   0.50    0.07    --  -47.60  19.00 -90.00  102
 22  \w    -40.00  26.00   0.50    0.07    --  -47.60  38.00  60.00  132
 23  \w    -67.00 -33.00   0.50    0.28    -- -105.00  61.00   0.00   68
 24  \w    -95.00 -55.00   0.50    0.28    -- -105.00 125.00 120.00   80
 25  \w    -70.00 -39.00   0.50    0.28    -- -105.00  61.00  90.00   62
 26  \w   -112.00 -35.00   0.50    0.28    -- -105.00 125.00  90.00  154
 27  \w    -61.00 -32.00   0.50    0.28    -- -105.00  77.00-150.00   58
 28  \w    -73.00 -46.00   0.50    0.28    -- -105.00 125.00-120.00   54
 29  \w   -112.00 -35.00   0.50    0.28    -- -105.00 125.00-150.00  154
 30  \w   -111.00 -81.00   0.50    0.28    -- -105.00 125.00-120.00   60
 31  \w   -108.00 -82.00   0.50    0.28    -- -105.00 110.00  35.07   52
 32  \w   -106.00 -39.00   0.50    0.28    -- -105.00 106.00 100.00  134
 33  \w    -63.00   2.00   0.50    0.07    --  -47.60 106.00 100.00  130
 34  \w   -142.00 -87.00   0.50    0.28    -- -105.00 -15.00  60.00  110
 35  \w   -169.00-136.00   0.50    0.28    -- -105.00 -61.00  90.00   66
 36  \w   -129.00 -89.00   0.50    0.28    -- -105.00 -61.00  90.00   80
 37  \w   -173.00 -88.00   0.50    0.28    -- -105.00 -61.00  30.00  170
 38  \w   -148.00 -91.00   0.50    0.28    -- -105.00 -95.00  60.00  114
 39  \w   -132.00-102.00   0.50    0.28    -- -105.00-106.00   0.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1753186000
_diffrn_orient_matrix_UB_12      0.0427776000
_diffrn_orient_matrix_UB_13      -0.0800689000
_diffrn_orient_matrix_UB_21      -0.1077617000
_diffrn_orient_matrix_UB_22      0.0188301000
_diffrn_orient_matrix_UB_23      -0.1001494000
_diffrn_orient_matrix_UB_31      -0.1029916000
_diffrn_orient_matrix_UB_32      0.1504002000
_diffrn_orient_matrix_UB_33      0.0356246000
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9076
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.801
_diffrn_reflns_theta_min         3.818
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0569P)^2^+0.6152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1712
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3032
_reflns_number_total             3293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc00057b2.cif
_cod_data_source_block           s20-1_auto
_cod_depositor_comments
'Adding full bibliography for 7250062--7250063.cif.'
_cod_database_code               7250062
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         CHON
_shelx_estimated_absorpt_t_max   0.621
_shelx_estimated_absorpt_t_min   0.301
_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:
 C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B), C13(H13A,H13B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
;
_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 1.110
_oxdiff_exptl_absorpt_empirical_full_min 0.886