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_7160498
_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         'C27 H20 N2 O8 S'
_chemical_formula_sum            'C27 H20 N2 O8 S'
_chemical_formula_weight         532.51
_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     iterative
_audit_creation_date             2022-07-19
_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                74.0530(10)
_cell_angle_beta                 77.7610(10)
_cell_angle_gamma                86.0010(10)
_cell_formula_units_Z            2
_cell_length_a                   8.08950(10)
_cell_length_b                   10.48040(10)
_cell_length_c                   14.8834(2)
_cell_measurement_reflns_used    23188
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9630
_cell_measurement_theta_min      2.0130
_cell_volume                     1185.61(3)
_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 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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_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    -17.00 100.00   0.50   14.00    --   10.60  82.00  60.00  234
  2  \w    -15.00 100.00   0.50   14.00    --   10.60  77.00 -60.00  230
  3  \w    -15.00 100.00   0.50   14.00    --   10.60  77.00 -30.00  230
  4  \w    -17.00 100.00   0.50   14.00    --   10.60  82.00-150.00  234
  5  \w    -79.00  38.00   0.50   14.00    --   10.60 -82.00  30.00  234
  6  \w    -17.00 100.00   0.50   14.00    --   10.60  82.00 -90.00  234
  7  \w    -17.00 100.00   0.50   14.00    --   10.60  82.00 120.00  234
  8  \w    -79.00  41.00   0.50   14.00    --   10.60 -57.00  30.00  240
  9  \w    -79.00  38.00   0.50   14.00    --   10.60 -82.00 120.00  234
 10  \w    -79.00  36.00   0.50   14.00    --   10.60 -77.00-180.00  230
 11  \w   -100.00  17.00   0.50   14.00    --  -10.90 -82.00 -90.00  234
 12  \w    -79.00  11.00   0.50   14.00    --   10.60 -82.00  60.00  180
 13  \w    -79.00  38.00   0.50   14.00    --   10.60 -82.00-120.00  234
 14  \w    -79.00  38.00   0.50   14.00    --   10.60 -82.00 -30.00  234
 15  \w    -79.00  41.00   0.50   14.00    --   10.60 -57.00-120.00  240
 16  \w    -79.00  38.00   0.50   14.00    --   10.60 -82.00   0.00  234
 17  \w    -38.00  79.00   0.50   14.00    --  -10.90  82.00 -90.00  234
 18  \w    -38.00  79.00   0.50   14.00    --  -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      0.0306766000
_diffrn_orient_matrix_UB_12      0.0111699000
_diffrn_orient_matrix_UB_13      -0.0498034000
_diffrn_orient_matrix_UB_21      -0.0814550000
_diffrn_orient_matrix_UB_22      0.0227317000
_diffrn_orient_matrix_UB_23      -0.0083783000
_diffrn_orient_matrix_UB_31      0.0217976000
_diffrn_orient_matrix_UB_32      0.0656780000
_diffrn_orient_matrix_UB_33      -0.0030908000
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0208
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39857
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.021
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48157
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0412P)^2^+0.4895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3675
_reflns_number_total             4183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00380f2.cif
_cod_data_source_block           k11108-myc-d(qyk609)
_cod_depositor_comments
'Adding full bibliography for 7160498--7160503.cif.'
_cod_database_code               7160498
_shelx_shelxl_version_number     2018/3
_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. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim O7
\\sim O8 \\sim S1: within 3.8A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 3.8A
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              31146
_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 2.256
_oxdiff_exptl_absorpt_empirical_full_min 0.725