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_7160263
_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         '2(C29 H21 N O4 S2)'
_chemical_formula_sum            'C58 H42 N2 O8 S4'
_chemical_formula_weight         1023.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-09-27
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1179(3)
_cell_length_b                   12.2499(2)
_cell_length_c                   26.8761(5)
_cell_measurement_reflns_used    23522
_cell_measurement_temperature    130()
_cell_measurement_theta_max      26.9920
_cell_measurement_theta_min      1.8250
_cell_volume                     5306.49(16)
_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      130(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -15.00 100.00   0.50   13.07    --   10.60  77.00 -90.00  230
  2  \w     -3.00  87.00   0.50   13.07    --   10.60  77.00-150.00  180
  3  \w    -17.00  90.00   0.50   13.07    --   10.60  82.00-180.00  214
  4  \w    -15.00  19.00   0.50   13.07    --   10.60  77.00 120.00   68
  5  \w     58.00  92.00   0.50   13.07    --   10.60  77.00 120.00   68
  6  \w     13.00  54.00   0.50   13.07    --  -10.90  57.00 -30.00   82
  7  \w    -40.00 -14.00   0.50   13.07    --  -10.90  57.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            36279
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.827
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71890
_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    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 3314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.070(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         8765
_refine_ls_number_restraints     361
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+7.0473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.877
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                8031
_reflns_number_total             8765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01681e2.cif
_cod_data_source_block           k11109-myc-h(ycm1625)_auto
_cod_depositor_comments
'Adding full bibliography for 7160261--7160263.cif.'
_cod_database_code               7160263
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.912
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
O2 \\sim O7 \\sim O1 \\sim O8 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim C4
\\sim C19 \\sim C53 \\sim C2 \\sim C8 \\sim C3 \\sim C48 \\sim C41 \\sim C1
\\sim C58 \\sim C5 \\sim C33 \\sim C6 \\sim C7 \\sim C22 \\sim C21 \\sim C34
\\sim C11 \\sim C20 \\sim C56 \\sim C57 \\sim C30 \\sim C42 \\sim C35 \\sim C18
\\sim C32 \\sim C12 \\sim C47 \\sim C29 \\sim C54 \\sim C36 \\sim C52 \\sim C23
\\sim C13 \\sim C50 \\sim C31 \\sim C24 \\sim C55 \\sim C28 \\sim C46 \\sim C49
\\sim C45 \\sim C37 \\sim C27 \\sim C44 \\sim C43 \\sim C51 \\sim C15 \\sim C26
\\sim C10 \\sim C9 \\sim C14 \\sim C40 \\sim C38 \\sim C25 \\sim C17 \\sim C39
\\sim C16: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
within 2A
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C8(H8), C3(H3), C48(H48), C58(H58), C7(H7), C22(H22), C21(H21),
 C11(H11), C20(H20), C56(H56), C57(H57), C42(H42), C32(H32), C29(H29), C54(H54),
  C36(H36), C52(H52), C23(H23), C13(H13), C50(H50), C55(H55), C28(H28),
 C46(H46), C49(H49), C45(H45), C37(H37), C27(H27), C44(H44), C43(H43), C51(H51),
  C15(H15), C26(H26), C10(H10), C9(H9), C14(H14), C40(H40), C38(H38), C25(H25),
 C17(H17), C39(H39), C16(H16)
;
_shelx_res_checksum              39753
_shelx_fab_checksum              44090
_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
;