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_7160503
_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         '0.5(C21 H16 N2 O8 S)'
_chemical_formula_sum            'C10.5 H8 N O4 S0.5'
_chemical_formula_weight         228.21
_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             2022-08-04
_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                73.673(3)
_cell_angle_beta                 77.253(3)
_cell_angle_gamma                66.575(4)
_cell_formula_units_Z            4
_cell_length_a                   8.6503(4)
_cell_length_b                   9.5028(4)
_cell_length_c                   13.7219(5)
_cell_measurement_reflns_used    14175
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.7100
_cell_measurement_theta_min      2.3740
_cell_volume                     985.64(8)
_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      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -17.00 100.00   0.50    8.05    --   10.60  82.00-180.00  234
  2  \w    -79.00 100.00   0.50    8.05    --   10.60 -19.00 120.00  358
  3  \w    -79.00 100.00   0.50    8.05    --   10.60 -19.00 120.00  358
  4  \w    -17.00 100.00   0.50    8.05    --   10.60  82.00  30.00  234
  5  \w    -79.00  36.00   0.50    8.05    --   10.60 -77.00-150.00  230
  6  \w    -17.00 100.00   0.50    8.05    --   10.60  82.00 -90.00  234
  7  \w    -17.00 100.00   0.50    8.05    --   10.60  82.00 120.00  234
  8  \w    -79.00  36.00   0.50    8.05    --   10.60 -77.00 -60.00  230
  9  \w   -100.00  17.00   0.50    8.05    --  -10.90 -82.00  30.00  234
 10  \w    -79.00  38.00   0.50    8.05    --   10.60 -82.00 120.00  234
 11  \w    -79.00 -54.00   0.50    8.05    --   10.60 -82.00-180.00   50
 12  \w    -38.00  79.00   0.50    8.05    --  -10.90  82.00 -30.00  234
 13  \w    -38.00  79.00   0.50    8.05    --  -10.90  82.00  30.00  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      0.0622732000
_diffrn_orient_matrix_UB_12      -0.0760782000
_diffrn_orient_matrix_UB_13      0.0122576000
_diffrn_orient_matrix_UB_21      -0.0275542000
_diffrn_orient_matrix_UB_22      -0.0018119000
_diffrn_orient_matrix_UB_23      0.0528562000
_diffrn_orient_matrix_UB_31      -0.0589263000
_diffrn_orient_matrix_UB_32      -0.0339131000
_diffrn_orient_matrix_UB_33      -0.0015047000
_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  0.0700
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22256
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.558
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57262
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0507P)^2^+0.5744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2984
_reflns_number_total             3455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00380f2.cif
_cod_data_source_block           k11108-myc-a(lyf728)_auto
_cod_depositor_comments
'Adding full bibliography for 7160498--7160503.cif.'
_cod_original_formula_sum        'C10.50 H8 N O4 S0.50'
_cod_database_code               7160503
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.898
_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 Ternary CH refined with riding coordinates:
 C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C21(H21), C6(H6), C3(H3), C20(H20), C9(H9), C18(H18), C5(H5),
 C19(H19), C4(H4), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 3.372
_oxdiff_exptl_absorpt_empirical_full_min 0.538