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_7160599
_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         'C18 H18 O7 S'
_chemical_formula_sum            'C18 H18 O7 S'
_chemical_formula_weight         378.38
_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     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                109.751(3)
_cell_angle_beta                 93.260(3)
_cell_angle_gamma                105.188(4)
_cell_formula_units_Z            4
_cell_length_a                   10.5691(4)
_cell_length_b                   12.9071(5)
_cell_length_c                   14.2075(4)
_cell_measurement_reflns_used    10193
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.5260
_cell_measurement_theta_min      4.0170
_cell_volume                     1737.70(12)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(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 0.984
_diffrn_measured_fraction_theta_max 0.984
_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   -104.00 -76.00   0.50    0.12    --  -57.22 -30.00-150.00   56
  2  \w   -103.00 -72.00   0.50    0.12    --  -57.22 -30.00-120.00   62
  3  \w   -108.00 -64.00   0.50    0.12    --  -57.22 -30.00 -90.00   88
  4  \w   -116.00 -89.00   0.50    0.12    --  -77.69 -30.00-120.00   54
  5  \w   -118.00 -40.00   0.50    0.12    --  -77.69 -15.00-180.00  156
  6  \w   -130.00 -88.00   0.50    0.12    --  -77.69 -15.00 -90.00   84
  7  \w    -87.00 -60.00   0.50    0.12    --  -77.69 -15.00 -90.00   54
  8  \w   -123.00 -49.00   0.50    0.12    --  -77.69 -15.00 -30.00  148
  9  \w   -128.00 -90.00   0.50    0.12    --  -77.69 -30.00  60.00   76
 10  \w   -108.00 -73.00   0.50    0.12    --  -57.22 -30.00 120.00   70
 11  \w    -97.00 -41.00   0.50    0.12    --  -81.75 115.00  40.95  112
 12  \w    -91.00 -31.00   0.50    0.12    --  -77.69 111.00  90.00  120
 13  \w    -92.00 -31.00   0.50    0.12    --  -77.69 111.00 -30.00  122
 14  \w    -97.00 -34.00   0.50    0.12    --  -81.75 114.00 -52.76  126
 15  \w    -91.00 -39.00   0.50    0.12    --  -77.69 111.00 -90.00  104
 16  \w    -92.00 -36.00   0.50    0.12    --  -80.00 101.00-169.03  112
 17  \w    -92.00 -37.00   0.50    0.12    --  -81.75  96.00-140.63  110
 18  \w    -91.00 -39.00   0.50    0.12    --  -81.75  98.00 150.72  104
 19  \w     63.00 107.00   0.50    0.12    --   55.91  30.00 120.00   88
 20  \w    102.00 129.00   0.50    0.12    --   83.08  30.00 150.00   54
 21  \w    104.00 134.00   0.50    0.12    --   83.08  30.00 120.00   60
 22  \w     91.00 125.00   0.50    0.12    --   83.08  30.00  60.00   68
 23  \w     90.00 115.00   0.50    0.12    --   83.08  30.00   0.00   50
 24  \w     98.00 136.00   0.50    0.12    --   83.08  30.00-150.00   76
 25  \w     94.00 136.00   0.50    0.12    --   83.08  30.00-180.00   84
 26  \w     23.00  51.00   0.50    0.12    --   67.72 -95.00 -90.00   56
 27  \w     13.00  56.00   0.50    0.12    --   55.91 -95.00-150.00   86
 28  \w     23.00  66.00   0.50    0.12    --   67.72-125.00-180.00   86
 29  \w     38.00  63.00   0.50    0.12    --   83.08 -95.00-150.00   50
 30  \w     51.00  92.00   0.50    0.12    --   86.20 -97.00 -67.47   82
 31  \w     64.00  89.00   0.50    0.12    --   83.08 -95.00-120.00   50
 32  \w     39.00  92.00   0.50    0.12    --   83.08 -95.00 -90.00  106
 33  \w     57.00  92.00   0.50    0.12    --   83.08 -95.00  30.00   70
 34  \w     13.00  59.00   0.50    0.12    --   55.91 -95.00  30.00   92
 35  \w     27.00  70.00   0.50    0.12    --   67.72 -95.00  60.00   86
 36  \w     38.00  67.00   0.50    0.12    --   83.08-111.00  90.00   58
 37  \w     45.00  92.00   0.50    0.12    --   86.20-100.00 153.08   94
 38  \w     65.00  92.00   0.50    0.12    --   83.08 -95.00  90.00   54
;
_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      0.0543880000
_diffrn_orient_matrix_UB_12      0.1159655000
_diffrn_orient_matrix_UB_13      -0.0139806000
_diffrn_orient_matrix_UB_21      0.0892363000
_diffrn_orient_matrix_UB_22      -0.0516969000
_diffrn_orient_matrix_UB_23      -0.0725765000
_diffrn_orient_matrix_UB_31      -0.1117608000
_diffrn_orient_matrix_UB_32      -0.0392972000
_diffrn_orient_matrix_UB_33      -0.0903309000
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18448
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.348
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.009
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90843
_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    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0012(2)
_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   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         6117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0694P)^2^+0.2451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5049
_reflns_number_total             6117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00632e2.cif
_cod_data_source_block           241079lt_auto
_cod_depositor_comments
'Adding full bibliography for 7160599--7160600.cif.'
_cod_original_cell_volume        1737.72(12)
_cod_database_code               7160599
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.780
_shelx_estimated_absorpt_t_min   0.739
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C34(H34A,H34B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C48(H48), C49(H49),
 C50(H50), C51(H51), C52(H52)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C41(H41A,H41B,
 H41C), C43(H43A,H43B,H43C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              9467
_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 1.178
_oxdiff_exptl_absorpt_empirical_full_min 0.884