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_7160499
_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         'C12 H8 N2 O5'
_chemical_formula_sum            'C12 H8 N2 O5'
_chemical_formula_weight         260.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-12
_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                90
_cell_angle_beta                 92.643(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.16580(10)
_cell_length_b                   20.4831(4)
_cell_length_c                   7.7993(2)
_cell_measurement_reflns_used    8947
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.7970
_cell_measurement_theta_min      1.9860
_cell_volume                     1143.55(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -14.00 100.00   0.50    4.69    --   10.60  68.00-179.00  228
  2  \w    -79.00  35.00   0.50    4.69    --   10.60 -68.00  47.00  228
  3  \w    -35.00  78.00   0.50    4.69    --  -10.90  68.00-179.00  226
  4  \w   -100.00  13.00   0.50    4.69    --  -10.90 -68.00  47.00  226
  5  \w    -79.00  36.00   0.50    4.69    --   10.60 -77.00 -30.00  230
  6  \w    -17.00 100.00   0.50    4.69    --   10.60  82.00-150.00  234
  7  \w    -17.00 100.00   0.50    4.69    --   10.60  82.00  30.00  234
  8  \w    -17.00 100.00   0.50    4.69    --   10.60  82.00 -90.00  234
  9  \w    -27.00 100.00   0.50    4.69    --   10.60  37.00-120.00  254
 10  \w    -17.00 100.00   0.50    4.69    --   10.60  82.00   0.00  234
 11  \w   -100.00   2.00   0.50    4.69    --  -10.90 -82.00-180.00  204
 12  \w    -96.00  17.00   0.50    4.69    --  -10.90 -82.00   0.00  226
 13  \w    -35.00  76.00   0.50    4.69    --  -10.90  77.00-120.00  222
 14  \w    -19.00   7.00   0.50    4.69    --  -10.90 -77.00 -60.00   52
 15  \w    -99.00 -44.00   0.50    4.69    --  -10.90 -77.00 -60.00  110
;
_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      -0.0719258000
_diffrn_orient_matrix_UB_12      0.0110104000
_diffrn_orient_matrix_UB_13      0.0524028000
_diffrn_orient_matrix_UB_21      0.0242212000
_diffrn_orient_matrix_UB_22      -0.0245633000
_diffrn_orient_matrix_UB_23      0.0610776000
_diffrn_orient_matrix_UB_31      0.0637699000
_diffrn_orient_matrix_UB_32      0.0217660000
_diffrn_orient_matrix_UB_33      0.0425592000
_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  0.0996
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13291
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         1.988
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73330
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 801 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.6(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1944
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0388
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                1829
_reflns_number_total             1944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00380f2.cif
_cod_data_source_block           k11109-myc-c(lyf1536)-2_auto
_cod_depositor_comments
'Adding full bibliography for 7160498--7160503.cif.'
_cod_database_code               7160499
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C3(H3), C11(H11), C12(H12), C6(H6), C4(H4), C5(H5)
;
_shelx_res_checksum              52058
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.672