Synthesis of 4-sulfonyl-1,7-diesters <i>via</i> K<sub>2</sub>CO<sub>3</sub>-mediated alkylative debenzoylation of α-sulfonyl <i>o</i>-hydroxyacetophenones with acrylates.
Chang, Meng-Yang; Chen, Pin-Hsien; Organic & biomolecular chemistry 22 (2024) 1194–1204; doi:10.1039/d3ob01703f

data_7159754
_publ_section_title
;
 Synthesis of 4-sulfonyl-1,7-diesters <i>via</i>
 K<sub>2</sub>CO<sub>3</sub>-mediated alkylative debenzoylation of
 &#x3b1;-sulfonyl <i>o</i>-hydroxyacetophenones with acrylates.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1194
_journal_page_last               1204
_journal_paper_doi               10.1039/d3ob01703f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H18 O4 S'
_chemical_formula_sum            'C19 H18 O4 S'
_chemical_formula_weight         342.39
_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             2020-12-28
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-07-04 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.600(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5325(5)
_cell_length_b                   5.5611(2)
_cell_length_c                   19.0631(6)
_cell_measurement_reflns_used    8699
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.6650
_cell_measurement_theta_min      2.2260
_cell_volume                     1640.58(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_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     51.00  77.00   0.50   12.54    --   10.60  32.00 -13.00   52
  2  \w    -38.00 -13.00   0.50   12.54    --   10.60 -32.00-172.00   50
  3  \w    -60.00 -34.00   0.50   12.54    --  -10.90 -32.00-172.00   52
  4  \w     11.00  49.00   0.50   12.54    --  -10.90  32.00 -13.00   76
  5  \w     -3.00  49.00   0.50   12.54    --   10.60  82.00  30.00  104
  6  \w     55.00  85.00   0.50   12.54    --   10.60  82.00  30.00   60
  7  \w    -20.00 100.00   0.50   12.54    --   10.60  57.00 120.00  240
  8  \w    -79.00  41.00   0.50   12.54    --   10.60 -57.00-150.00  240
  9  \w    -22.00   3.00   0.50   12.54    --   10.60  38.00 -60.00   50
 10  \w     53.00  99.00   0.50   12.54    --   10.60  38.00 -60.00   92
 11  \w     -4.00  21.00   0.50   12.54    --   10.60  77.00  60.00   50
 12  \w     27.00  52.00   0.50   12.54    --   10.60  77.00  60.00   50
 13  \w     51.00  77.00   0.50   12.54    --   10.60  57.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0414665000
_diffrn_orient_matrix_UB_12      0.0028532000
_diffrn_orient_matrix_UB_13      0.0285011000
_diffrn_orient_matrix_UB_21      0.0174121000
_diffrn_orient_matrix_UB_22      0.0520662000
_diffrn_orient_matrix_UB_23      -0.0255503000
_diffrn_orient_matrix_UB_31      -0.0088146000
_diffrn_orient_matrix_UB_32      0.1164415000
_diffrn_orient_matrix_UB_33      0.0107338000
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15178
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.025
_diffrn_reflns_theta_min         2.197
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
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    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0471P)^2^+0.5776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2736
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01703f2.cif
_cod_data_source_block           k10912-myc-f
_cod_depositor_comments          'Adding full bibliography for 7159754.cif.'
_cod_database_code               7159754
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H19 O5 S1'
_diffrn_oxdiff_digest_frames
;
0188a6239219f339783e29e3285916f24c0002585b3
;
_diffrn_oxdiff_digest_hkl
;
013df897620ed6745bce4edcfac08eb71fcfd0
;
_reflns_odcompleteness_completeness 99.41
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              79866
_shelx_hkl_checksum              86561
_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 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.677