One-pot synthesis of sulfonylmethyl phthalides <i>via</i> K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>/DMSO-mediated methylenylation/sulfonylation of eudesmic acid with sulfinates.
Chang, Meng-Yang; Ou, Chen-Yo; Organic & biomolecular chemistry 23 (2025) 6603–6609; doi:10.1039/d5ob00632e

data_7160600
_publ_section_title
;
 One-pot synthesis of sulfonylmethyl phthalides <i>via</i>
 K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>/DMSO-mediated
 methylenylation/sulfonylation of eudesmic acid with sulfinates.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6603
_journal_page_last               6609
_journal_paper_doi               10.1039/d5ob00632e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C12 H12 O6'
_chemical_formula_sum            'C12 H12 O6'
_chemical_formula_weight         252.22
_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     dual
_audit_creation_date             2024-11-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-10 deposited with the CCDC.	2025-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.758(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8823(2)
_cell_length_b                   30.4422(18)
_cell_length_c                   9.0099(6)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.0000
_cell_measurement_theta_min      5.1440
_cell_volume                     1061.17(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.944
_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   -111.00 -86.00   0.50    0.09    --  -57.02 -30.00  60.00   50
  2  \w   -120.00 -94.00   0.50    0.09    --  -77.69 -30.00  30.00   52
  3  \w   -123.00 -90.00   0.50    0.09    --  -77.69 -30.00   0.00   66
  4  \w   -130.00 -87.00   0.50    0.09    --  -77.69 -30.00 150.00   86
  5  \w   -126.00 -99.00   0.50    0.09    --  -77.69 -30.00 -90.00   54
  6  \w   -121.00 -94.00   0.50    0.09    --  -77.69 -30.00-150.00   54
  7  \w    -78.00 -33.00   0.50    0.09    --  -77.69 111.00-180.00   90
  8  \w    -84.00 -59.00   0.50    0.09    --  -77.69  95.00 -93.00   50
  9  \w    -72.00 -46.00   0.50    0.09    --  -68.11  95.00 -93.00   52
 10  \w    -53.00 -12.00   0.50    0.09    --  -57.02  95.00 -93.00   82
 11  \w     53.00  78.00   0.50    0.09    --   83.08 -95.00-180.00   50
 12  \w     58.00  86.00   0.50    0.09    --   83.08 -95.00-120.00   56
 13  \w     39.00  72.00   0.50    0.09    --   83.08-111.00 150.00   66
 14  \w     31.00  56.00   0.50    0.09    --   67.72 -95.00 156.00   50
 15  \w     38.00  63.00   0.50    0.09    --   83.08 -95.00 156.00   50
 16  \w     11.00  36.00   0.50    0.09    --   55.91 -95.00 156.00   50
 17  \w     40.00  90.00   0.50    0.09    --   83.08 -95.00 -30.00  100
 18  \w     76.00 110.00   0.50    0.09    --   55.91  30.00 -90.00   68
 19  \w     76.00 121.00   0.50    0.09    --   67.72  30.00-150.00   90
 20  \w     91.00 126.00   0.50    0.09    --   83.08  30.00-120.00   70
 21  \w     96.00 121.00   0.50    0.09    --   83.08  30.00   0.00   50
 22  \w     90.00 120.00   0.50    0.09    --   83.08  30.00  30.00   60
 23  \w     90.00 137.00   0.50    0.09    --   83.08  30.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0987500000
_diffrn_orient_matrix_UB_12      -0.0399811000
_diffrn_orient_matrix_UB_13      -0.0921552000
_diffrn_orient_matrix_UB_21      0.1164985000
_diffrn_orient_matrix_UB_22      -0.0247766000
_diffrn_orient_matrix_UB_23      0.1446718000
_diffrn_orient_matrix_UB_31      -0.3677945000
_diffrn_orient_matrix_UB_32      -0.0186137000
_diffrn_orient_matrix_UB_33      0.0056795000
_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  0.0392
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5492
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.238
_diffrn_reflns_theta_min         5.136
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0040(13)
_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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0622
_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^)+(0.1193P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1499
_reflns_number_total             2010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00632e2.cif
_cod_data_source_block           241080lt_auto
_cod_depositor_comments
'Adding full bibliography for 7160599--7160600.cif.'
_cod_original_cell_volume        1061.18(11)
_cod_database_code               7160600
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.786
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C11(H11A,H11B)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              19299
_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 1.609
_oxdiff_exptl_absorpt_empirical_full_min 0.566