Selenium dioxide-mediated oxidative annulation of sulfonyl <i>o</i>-hydroxyacetophenones with acetophenones. One-pot synthesis of aurone analogs.
Chang, Meng-Yang; Liu, Yu-Hsuan; Organic & biomolecular chemistry 23 (2025) 6986–6991; doi:10.1039/d5ob00989h

data_7160627
_publ_section_title
;
 Selenium dioxide-mediated oxidative annulation of sulfonyl
 <i>o</i>-hydroxyacetophenones with acetophenones. One-pot synthesis of
 aurone analogs.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6986
_journal_page_last               6991
_journal_paper_doi               10.1039/d5ob00989h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H16 N2 O2'
_chemical_formula_sum            'C23 H16 N2 O2'
_chemical_formula_weight         352.38
_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             2023-05-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-12-27 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                96.863(5)
_cell_angle_beta                 90.517(9)
_cell_angle_gamma                93.533(9)
_cell_formula_units_Z            2
_cell_length_a                   3.8702(6)
_cell_length_b                   13.0697(10)
_cell_length_c                   16.8646(8)
_cell_measurement_reflns_used    7994
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9760
_cell_measurement_theta_min      1.8640
_cell_volume                     845.21(15)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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   23.04    --   10.60  77.00 -30.00  230
  2  \w    -20.00 100.00   0.50   23.04    --   10.60  57.00-120.00  240
  3  \w    -17.00 100.00   0.50   23.04    --   10.60  82.00  90.00  234
  4  \w    -79.00  38.00   0.50   23.04    --   10.60 -82.00  30.00  234
  5  \w    -17.00 100.00   0.50   23.04    --   10.60  82.00 -90.00  234
  6  \w    -17.00 100.00   0.50   23.04    --   10.60  82.00 150.00  234
  7  \w    -79.00  48.00   0.50   23.04    --   10.60 -37.00 120.00  254
  8  \w    -15.00 100.00   0.50   23.04    --   10.60  77.00  90.00  230
  9  \w    -15.00 100.00   0.50   23.04    --   10.60  77.00-150.00  230
 10  \w    -17.00 100.00   0.50   23.04    --   10.60  82.00  30.00  234
 11  \w    -79.00  48.00   0.50   23.04    --   10.60 -37.00  60.00  254
 12  \w    -79.00  36.00   0.50   23.04    --   10.60 -77.00-150.00  230
 13  \w    -79.00 -54.00   0.50   23.04    --   10.60 -82.00 -30.00   50
 14  \w    -41.00  79.00   0.50   23.04    --  -10.90  57.00 -60.00  240
;
_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      0.0510522000
_diffrn_orient_matrix_UB_12      0.0121154000
_diffrn_orient_matrix_UB_13      0.0407064000
_diffrn_orient_matrix_UB_21      0.0006062000
_diffrn_orient_matrix_UB_22      0.0534147000
_diffrn_orient_matrix_UB_23      -0.0040256000
_diffrn_orient_matrix_UB_31      -0.1764060000
_diffrn_orient_matrix_UB_32      0.0000887000
_diffrn_orient_matrix_UB_33      0.0110370000
_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  0.1676
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20747
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.572
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57562
_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    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0975
_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^)+(0.1770P)^2^+0.5848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2493
_refine_ls_wR_factor_ref         0.2751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2191
_reflns_number_total             2962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00989h2.cif
_cod_data_source_block           k11205-myc-b_auto
_cod_depositor_comments
'Adding full bibliography for 7160623--7160627.cif.'
_cod_database_code               7160627
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(C17) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C23) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.005
2.a Aromatic/amide H refined with riding coordinates:
 C17(H18), C3(H4), C16(H17), C23(H12), C21(H10), C15(H16), C7(H22), C22(H11),
 C14(H15), C13(H14), C20(H9), C19(H8), C10(H25), C9(H24), C8(H23)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H27)
;
_shelx_res_checksum              53040
_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 3.226
_oxdiff_exptl_absorpt_empirical_full_min 0.375