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_7160639
_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 H15 Cl2 F N2 O2 S'
_chemical_formula_sum            'C23 H15 Cl2 F N2 O2 S'
_chemical_formula_weight         473.33
_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             2023-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-04-18 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                71.447(2)
_cell_angle_beta                 86.430(2)
_cell_angle_gamma                80.166(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7238(2)
_cell_length_b                   10.1366(2)
_cell_length_c                   11.2215(3)
_cell_measurement_reflns_used    41557
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_cell_measurement_theta_min      1.9090
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_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
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_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 0.996
_diffrn_measured_fraction_theta_max 0.964
_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    -79.00 100.00   0.50    2.08    --   10.60  13.00 155.00  358
  2  \w   -100.00  78.00   0.50    2.08    --  -10.90  13.00 155.00  356
  3  \w    -15.00 100.00   0.50    2.08    --   10.60  77.00-120.00  230
  4  \w    -17.00 100.00   0.50    2.08    --   10.60  82.00 120.00  234
  5  \w    -79.00  38.00   0.50    2.08    --   10.60 -82.00 120.00  234
  6  \w    -17.00 100.00   0.50    2.08    --   10.60  82.00-180.00  234
  7  \w    -17.00 100.00   0.50    2.08    --   10.60  82.00  60.00  234
  8  \w    -79.00 100.00   0.50    2.08    --   10.60 -13.00 -16.00  358
  9  \w    -79.00  38.00   0.50    2.08    --   10.60 -82.00 -60.00  234
 10  \w    -79.00  36.00   0.50    2.08    --   10.60 -77.00  30.00  230
 11  \w   -100.00  17.00   0.50    2.08    --  -10.90 -82.00-180.00  234
 12  \w   -100.00  17.00   0.50    2.08    --  -10.90 -82.00-120.00  234
 13  \w    -36.00  79.00   0.50    2.08    --  -10.90  77.00 -90.00  230
 14  \w   -100.00  15.00   0.50    2.08    --  -10.90 -77.00 -30.00  230
 15  \w   -100.00  15.00   0.50    2.08    --  -10.90 -77.00-180.00  230
 16  \w   -100.00  78.00   0.50    2.08    --  -10.90 -13.00 -16.00  356
 17  \w    -79.00  33.00   0.50    2.08    --   10.60 -82.00 -90.00  224
 18  \w    -79.00  36.00   0.50    2.08    --   10.60 -62.00  78.03  230
 19  \w    -79.00  38.00   0.50    2.08    --   10.60 -82.00 -12.01  234
 20  \w    -79.00  36.00   0.50    2.08    --   10.60 -62.00 179.48  230
 21  \w    -79.00  38.00   0.50    2.08    --   10.60 -82.00-180.00  234
 22  \w    -79.00  38.00   0.50    2.08    --   10.60 -82.00 150.00  234
 23  \w    -79.00  38.00   0.50    2.08    --   10.60 -82.00-150.00  234
 24  \w    -79.00  36.00   0.50    2.08    --   10.60 -77.00   0.00  230
 25  \w    -79.00  38.00   0.50    2.08    --   10.60 -82.00-120.00  234
 26  \w    -15.00 100.00   0.50    2.08    --   10.60  77.00 -30.00  230
 27  \w    -79.00  36.00   0.50    2.08    --   10.60 -77.00  90.00  230
 28  \w    -20.00 100.00   0.50    2.08    --   10.60  57.00 -30.00  240
 29  \w    -38.00  78.00   0.50    2.08    --  -10.90  82.00 -46.14  232
 30  \w    -41.00  79.00   0.50    2.08    --  -10.90  57.00 -90.00  240
 31  \w    -38.00  79.00   0.50    2.08    --  -10.90  82.00  60.00  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      -0.0737424000
_diffrn_orient_matrix_UB_12      0.0056384000
_diffrn_orient_matrix_UB_13      0.0040699000
_diffrn_orient_matrix_UB_21      -0.0046230000
_diffrn_orient_matrix_UB_22      0.0659675000
_diffrn_orient_matrix_UB_23      0.0106148000
_diffrn_orient_matrix_UB_31      -0.0046777000
_diffrn_orient_matrix_UB_32      0.0347380000
_diffrn_orient_matrix_UB_33      -0.0657001000
_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  0.0503
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            69896
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.114
_diffrn_reflns_theta_min         2.849
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49692
_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    1.522
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.050
_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     281
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0354P)^2^+0.5699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3925
_reflns_number_total             4400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01051a2.cif
_cod_data_source_block           k11208-myc-a(oyz0710)_auto
_cod_depositor_comments
'Adding full bibliography for 7160636--7160639.cif.'
_cod_original_cell_volume        1033.14(4)
_cod_database_code               7160639
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.841
_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:
 C8(H12), C2(H3), C5(H6), C22(H30), C21(H29), C18(H26), C12(H18), C16(H14),
 C19(H27), C13(H17), C15(H15), C14(H16)
2.b Idealised Me refined as rotating group:
 C23(H31A,H31B,H31C)
;
_shelx_res_checksum              56729
_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 1.664
_oxdiff_exptl_absorpt_empirical_full_min 0.544