K<sub>2</sub>CO<sub>3</sub>/TFAA-activated diarylation of α-sulfonyl <i>o</i>-hydroxyacetophenones with <i>o</i>-nitroaryl disulfides to construct sulfonyl bis-<i>o</i>-nitroaryl acetophenones.
Chang, Meng-Yang; Hsueh, Nai-Chen; Organic & biomolecular chemistry 23 (2025) 4751–4757; doi:10.1039/d5ob00380f

data_7160502
_publ_section_title
;
 K<sub>2</sub>CO<sub>3</sub>/TFAA-activated diarylation of
 &#x3b1;-sulfonyl <i>o</i>-hydroxyacetophenones with <i>o</i>-nitroaryl
 disulfides to construct sulfonyl bis-<i>o</i>-nitroaryl acetophenones.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4751
_journal_page_last               4757
_journal_paper_doi               10.1039/d5ob00380f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '0.4(C27 H17 F3 N2 O8 S)'
_chemical_formula_sum            'C10.8 H6.8 F1.2 N0.8 O3.2 S0.4'
_chemical_formula_weight         234.59
_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             2022-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-25 deposited with the CCDC.	2025-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                104.0290(10)
_cell_angle_beta                 91.0020(10)
_cell_angle_gamma                107.6750(10)
_cell_formula_units_Z            5
_cell_length_a                   8.30070(10)
_cell_length_b                   9.92720(10)
_cell_length_c                   16.4260(2)
_cell_measurement_reflns_used    33248
_cell_measurement_temperature    135(2)
_cell_measurement_theta_max      27.0080
_cell_measurement_theta_min      2.2180
_cell_volume                     1245.10(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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_temperature      135(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_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    -79.00 100.00   0.50    5.31    --   10.60 -24.00 -49.00  358
  2  \w   -100.00  78.00   0.50    5.31    --  -10.90 -24.00 -49.00  356
  3  \w   -100.00  78.00   0.50    5.31    --  -10.90  24.00 114.00  356
  4  \w    -79.00 100.00   0.50    5.31    --   10.60  24.00 114.00  358
  5  \w    -15.00 100.00   0.50    5.31    --   10.60  77.00 -60.00  230
  6  \w    -15.00 100.00   0.50    5.31    --   10.60  77.00-150.00  230
  7  \w    -15.00 100.00   0.50    5.31    --   10.60  77.00 120.00  230
  8  \w    -17.00 100.00   0.50    5.31    --   10.60  82.00  30.00  234
  9  \w    -15.00 100.00   0.50    5.31    --   10.60  77.00-180.00  230
 10  \w    -17.00 100.00   0.50    5.31    --   10.60  82.00 150.00  234
 11  \w    -17.00 100.00   0.50    5.31    --   10.60  82.00 -90.00  234
 12  \w    -17.00 100.00   0.50    5.31    --   10.60  82.00-120.00  234
 13  \w    -15.00 100.00   0.50    5.31    --   10.60  77.00   0.00  230
 14  \w   -100.00  20.00   0.50    5.31    --  -10.90 -57.00 -30.00  240
 15  \w   -100.00  17.00   0.50    5.31    --  -10.90 -82.00 -30.00  234
 16  \w   -100.00  17.00   0.50    5.31    --  -10.90 -82.00-150.00  234
 17  \w   -100.00  17.00   0.50    5.31    --  -10.90 -82.00 -60.00  234
 18  \w    -79.00  41.00   0.50    5.31    --   10.60 -57.00-150.00  240
 19  \w    -79.00  36.00   0.50    5.31    --   10.60 -77.00 -60.00  230
 20  \w    -79.00 -54.00   0.50    5.31    --   10.60 -82.00  90.00   50
 21  \w    -38.00  79.00   0.50    5.31    --  -10.90  82.00 150.00  234
;
_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      -0.0301083000
_diffrn_orient_matrix_UB_12      -0.0662502000
_diffrn_orient_matrix_UB_13      0.0123752000
_diffrn_orient_matrix_UB_21      -0.0786423000
_diffrn_orient_matrix_UB_22      0.0128153000
_diffrn_orient_matrix_UB_23      0.0074919000
_diffrn_orient_matrix_UB_31      -0.0321092000
_diffrn_orient_matrix_UB_32      -0.0384442000
_diffrn_orient_matrix_UB_33      -0.0423227000
_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  0.0621
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            54640
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.127
_diffrn_reflns_theta_min         2.230
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.954
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0579P)^2^+1.2775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4534
_reflns_number_total             5289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00380f2.cif
_cod_data_source_block           k11110-myc-f(lyf1006)_auto
_cod_depositor_comments
'Adding full bibliography for 7160498--7160503.cif.'
_cod_original_formula_sum        'C10.80 H6.80 F1.20 N0.80 O3.20 S0.40'
_cod_database_code               7160502
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C22(H22), C5(H5), C7(H7), C8(H8), C14(H14), C16(H16), C17(H17),
 C19(H19), C26(H26), C11(H11), C24(H24), C13(H13), C12(H12), C18(H18), C25(H25)
;
_shelx_res_checksum              21663
_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 3.626
_oxdiff_exptl_absorpt_empirical_full_min 0.551