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_7160500
_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         'C24 H16 N2 O8 S2'
_chemical_formula_sum            'C24 H16 N2 O8 S2'
_chemical_formula_weight         524.51
_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             2022-07-28
_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                82.0990(10)
_cell_angle_beta                 83.390(2)
_cell_angle_gamma                67.477(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3670(2)
_cell_length_b                   9.8898(2)
_cell_length_c                   14.7637(2)
_cell_measurement_reflns_used    16260
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9270
_cell_measurement_theta_min      2.2350
_cell_volume                     1115.16(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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      113(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 0.998
_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    -23.00 100.00   0.50    2.38    --   10.60  50.00 150.00  246
  2  \w    -79.00  44.00   0.50    2.38    --   10.60 -50.00   3.00  246
  3  \w   -100.00  22.00   0.50    2.38    --  -10.90 -50.00   3.00  244
  4  \w    -44.00  78.00   0.50    2.38    --  -10.90  50.00 150.00  244
  5  \w    -17.00 100.00   0.50    2.38    --   10.60  82.00-120.00  234
  6  \w    -20.00 100.00   0.50    2.38    --   10.60  57.00 -30.00  240
  7  \w    -17.00 100.00   0.50    2.38    --   10.60  82.00-180.00  234
  8  \w    -15.00 100.00   0.50    2.38    --   10.60  77.00  60.00  230
  9  \w    -15.00 100.00   0.50    2.38    --   10.60  77.00-150.00  230
 10  \w    -15.00 100.00   0.50    2.38    --   10.60  77.00  90.00  230
 11  \w   -100.00  17.00   0.50    2.38    --  -10.90 -82.00-120.00  234
 12  \w   -100.00  17.00   0.50    2.38    --  -10.90 -82.00 -30.00  234
 13  \w   -100.00 -15.00   0.50    2.38    --  -10.90 -82.00 -60.00  170
 14  \w    -23.00  16.00   0.50    2.38    --  -10.90 -82.00-150.00   78
;
_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      0.0792280000
_diffrn_orient_matrix_UB_12      0.0116879000
_diffrn_orient_matrix_UB_13      -0.0069522000
_diffrn_orient_matrix_UB_21      -0.0403309000
_diffrn_orient_matrix_UB_22      0.0654993000
_diffrn_orient_matrix_UB_23      -0.0287079000
_diffrn_orient_matrix_UB_31      -0.0236251000
_diffrn_orient_matrix_UB_32      0.0407994000
_diffrn_orient_matrix_UB_33      0.0386157000
_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  0.0458
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27573
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.241
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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    1.562
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         3913
_refine_ls_number_restraints     1359
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0424P)^2^+0.4874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3512
_reflns_number_total             3913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00380f2.cif
_cod_data_source_block           K11108-MYC-G(LYF726)
_cod_depositor_comments
'Adding full bibliography for 7160498--7160503.cif.'
_cod_original_cell_volume        1115.17(4)
_cod_database_code               7160500
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S2-C21 \\sim S3-C21
 with sigma of 0.02
 C21-C24 \\sim C21-C27
 with sigma of 0.04
 S2-C24 \\sim S3-C27
 with sigma of 0.02
 C22-C21 \\sim C25-C21
 with sigma of 0.02
 C22-C23 \\sim C25-C26
 with sigma of 0.02
 C23-C24 \\sim C26-C27
 with sigma of 0.02
 C21-C23 \\sim C21-C26
 with sigma of 0.04
 S2-C23 \\sim S3-C26
 with sigma of 0.04
 C22-C24 \\sim C25-C27
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim N1 \\sim N2 \\sim O1 \\sim O2 \\sim O3 \\sim O4 \\sim
O5 \\sim O6 \\sim O7 \\sim O8 \\sim S1 \\sim S2 \\sim S3: within 3.8A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 3.8A
4. Others
 Sof(S3)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=1-FVAR(1)
 Sof(S2)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27)
;
_shelx_res_checksum              33678
_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 3.104
_oxdiff_exptl_absorpt_empirical_full_min 0.548