One-pot synthesis of sulfonyl 3,6-diarylpyridazines <i>via</i> tandem condensation of α-sulfonyl ketones with methyl ketones.
Chang, Meng-Yang; Ou, Chen-Yo; Organic & biomolecular chemistry 23 (2025) 7314–7319; doi:10.1039/d5ob01051a

data_7160636
_publ_section_title
;
 One-pot synthesis of sulfonyl 3,6-diarylpyridazines <i>via</i> tandem
 condensation of &#x3b1;-sulfonyl ketones with methyl ketones.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7314
_journal_page_last               7319
_journal_paper_doi               10.1039/d5ob01051a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H18 N2 O2 S'
_chemical_formula_sum            'C23 H18 N2 O2 S'
_chemical_formula_weight         386.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-04-18 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.462(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3268(5)
_cell_length_b                   15.1541(6)
_cell_length_c                   14.1675(7)
_cell_measurement_reflns_used    8413
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8740
_cell_measurement_theta_min      2.0050
_cell_volume                     1899.37(17)
_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 0.958
_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  41.00   0.50   18.01    --   10.60 -57.00 120.00  240
  2  \w    -15.00 100.00   0.50   18.01    --   10.60  77.00   0.00  230
  3  \w    -79.00  36.00   0.50   18.01    --   10.60 -77.00  30.00  230
  4  \w    -17.00 100.00   0.50   18.01    --   10.60  82.00 120.00  234
  5  \w    -79.00  36.00   0.50   18.01    --   10.60 -77.00 -90.00  230
  6  \w    -15.00 100.00   0.50   18.01    --   10.60  77.00-120.00  230
  7  \w   -100.00  14.00   0.50   18.01    --  -10.90 -82.00  60.00  228
;
_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      -0.0164566000
_diffrn_orient_matrix_UB_12      0.0074674000
_diffrn_orient_matrix_UB_13      -0.0517585000
_diffrn_orient_matrix_UB_21      -0.0134408000
_diffrn_orient_matrix_UB_22      -0.0457634000
_diffrn_orient_matrix_UB_23      -0.0091026000
_diffrn_orient_matrix_UB_31      -0.0773371000
_diffrn_orient_matrix_UB_32      0.0063987000
_diffrn_orient_matrix_UB_33      -0.0047474000
_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  0.0777
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12473
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.081
_diffrn_reflns_theta_min         2.025
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36021
_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    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1386 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0534P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.917
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                3383
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01051a2.cif
_cod_data_source_block           k11202-myc-a_auto
_cod_depositor_comments
'Adding full bibliography for 7160636--7160639.cif.'
_cod_database_code               7160636
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.910
_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.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C9(H9), C22(H22), C12(H12), C8(H8), C15(H15), C18(H18),
 C19(H19), C14(H14), C21(H21), C6(H6), C7(H7), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              82959
_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 5.139
_oxdiff_exptl_absorpt_empirical_full_min 0.282