One-pot synthesis of symmetrical bis-sulfonyl 2,6-diarylpyridines <i>via</i> BiCl<sub>3</sub>-catalyzed and K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-mediated domino annulation of β-ketosulfones and <i>N</i>,<i>N</i>-dimethylacetamide.
Chang, Meng-Yang; Lin, Chun-Yi; Organic & biomolecular chemistry 23 (2025) 844–853; doi:10.1039/d4ob01681e

data_7160261
_publ_section_title
;
 One-pot synthesis of symmetrical bis-sulfonyl 2,6-diarylpyridines
 <i>via</i> BiCl<sub>3</sub>-catalyzed and
 K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-mediated domino annulation of
 &#x3b2;-ketosulfones and <i>N</i>,<i>N</i>-dimethylacetamide.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              844
_journal_page_last               853
_journal_paper_doi               10.1039/d4ob01681e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C31 H23 F2 N O4 S2'
_chemical_formula_sum            'C31 H23 F2 N O4 S2'
_chemical_formula_weight         575.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-12-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-09-09 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.144(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1425(3)
_cell_length_b                   13.6754(3)
_cell_length_c                   18.9825(4)
_cell_measurement_reflns_used    14800
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      26.9960
_cell_measurement_theta_min      1.8940
_cell_volume                     3042.65(12)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      133(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    -79.00  38.00   0.50   13.20    --   10.60 -82.00  60.00  234
  2  \w    -15.00 100.00   0.50   13.20    --   10.60  77.00 -60.00  230
  3  \w    -79.00  36.00   0.50   13.20    --   10.60 -77.00   0.00  230
  4  \w    -79.00  41.00   0.50   13.20    --   10.60 -57.00 120.00  240
  5  \w    -79.00  41.00   0.50   13.20    --   10.60 -57.00  60.00  240
  6  \w    -79.00  38.00   0.50   13.20    --   10.60 -82.00 -90.00  234
  7  \w   -100.00  10.00   0.50   13.20    --  -10.90 -82.00  30.00  220
;
_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      0.0159513000
_diffrn_orient_matrix_UB_12      -0.0168890000
_diffrn_orient_matrix_UB_13      0.0365875000
_diffrn_orient_matrix_UB_21      0.0319454000
_diffrn_orient_matrix_UB_22      -0.0383291000
_diffrn_orient_matrix_UB_23      -0.0103008000
_diffrn_orient_matrix_UB_31      0.0488599000
_diffrn_orient_matrix_UB_32      0.0305967000
_diffrn_orient_matrix_UB_33      0.0072891000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19630
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.858
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42062
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0440P)^2^+4.3156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2467
_reflns_number_total             2685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01681e2.cif
_cod_data_source_block           k11110-myc-e(ycm927)_auto-mask
_cod_depositor_comments
'Adding full bibliography for 7160261--7160263.cif.'
_cod_database_code               7160261
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.967
_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
S1 \\sim O1 \\sim O2 \\sim F1: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 3.8A
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              51221
_shelx_fab_checksum              94911
_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 1.775
_oxdiff_exptl_absorpt_empirical_full_min 0.563