Generation of sulfones utilizing β-sulfinyl esters as masked aryl sulfinates under redox-neutral conditions.
Zhang, Yixin; Yang, Zhu; Yang, Hongjun; Li, Xuefeng; Yang, Lu; Organic & biomolecular chemistry 22 (2024) 3381–3385; doi:10.1039/d4ob00238e

data_7159885
_publ_section_title
;
 Generation of sulfones utilizing &#x3b2;-sulfinyl esters as masked aryl
 sulfinates under redox-neutral conditions.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3381
_journal_page_last               3385
_journal_paper_doi               10.1039/d4ob00238e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C13 H12 O2 S'
_chemical_formula_sum            'C13 H12 O2 S'
_chemical_formula_weight         232.29
_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             2023-12-03
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-01-18 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.948(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0408(8)
_cell_length_b                   7.8341(5)
_cell_length_c                   11.5786(8)
_cell_measurement_reflns_used    5078
_cell_measurement_temperature    295.64(10)
_cell_measurement_theta_max      76.9840
_cell_measurement_theta_min      3.2850
_cell_volume                     1176.54(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (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      295.64(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -46.00 -21.00   0.50    0.36    --  -91.75  45.00 120.00   50
  2  \w    -56.00 -21.00   0.50    0.36    --  -91.75  61.00 120.00   70
  3  \w    -64.00 -20.00   0.50    0.36    --  -91.75  61.00  90.00   88
  4  \w    -49.00 -21.00   0.50    0.36    --  -91.75  45.00  30.00   56
  5  \w    -50.00 -25.00   0.50    0.36    --  -91.75  45.00   0.00   50
  6  \w    -88.00 -25.00   0.50    0.36    --  -91.75 125.00 -90.00  126
  7  \w    -72.00 -41.00   0.50    0.36    --  -91.75 125.00 120.00   62
  8  \w   -131.00 -74.00   0.50    0.36    --  -91.75 -14.00-122.00  114
  9  \w   -154.00-101.00   0.50    0.36    --  -91.75 -94.00-150.00  106
 10  \w   -122.00 -30.00   0.50    0.09    --  -47.39 -14.00-122.00  184
 11  \w    -26.00  14.00   0.50    0.09    --  -47.39  19.00 -90.00   80
 12  \w    -20.00  23.00   0.50    0.09    --  -47.39  19.00-180.00   86
 13  \w    -24.00  29.00   0.50    0.09    --  -47.39  14.00  48.00  106
 14  \w     38.00  95.00   0.50    0.09    --   47.39  14.00  48.00  114
 15  \w     92.00 176.00   0.50    0.36    --  108.42  14.00  48.00  168
 16  \w     38.00  64.00   0.50    0.36    --  108.42 -61.00 150.00   52
 17  \w     37.00  71.00   0.50    0.36    --  108.42 -61.00  60.00   68
 18  \w    -28.00  24.00   0.50    0.09    --   47.39 -14.00-122.00  104
 19  \w     33.00  59.00   0.50    0.09    --   47.39-125.00-180.00   52
 20  \w     41.00  98.00   0.50    0.36    --  108.42-125.00-120.00  114
 21  \w     60.00 112.00   0.50    0.36    --  108.42-125.00 150.00  104
 22  \w     40.00 106.00   0.50    0.36    --  108.42 -94.00 150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0369658000
_diffrn_orient_matrix_UB_12      -0.0291531000
_diffrn_orient_matrix_UB_13      -0.1205866000
_diffrn_orient_matrix_UB_21      -0.1113211000
_diffrn_orient_matrix_UB_22      0.0226402000
_diffrn_orient_matrix_UB_23      -0.0568323000
_diffrn_orient_matrix_UB_31      0.0185595000
_diffrn_orient_matrix_UB_32      0.1931562000
_diffrn_orient_matrix_UB_33      -0.0113627000
_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  0.0752
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7411
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         6.601
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0.0052(19)
_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   1.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.945
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0981
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2493
_refine_ls_wR_factor_ref         0.2639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1757
_reflns_number_total             2068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00238e2.cif
_cod_data_source_block           fl230331
_cod_depositor_comments          'Adding full bibliography for 7159885.cif.'
_cod_database_code               7159885
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.786
_shelx_estimated_absorpt_t_min   0.710
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              26259
_shelx_hkl_checksum              6041
_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 3.043
_oxdiff_exptl_absorpt_empirical_full_min 0.496