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_7160624
_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         '0.667(C19 H16 O6)'
_chemical_formula_sum            'C12.67 H10.67 O4'
_chemical_formula_weight         226.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-12-27 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.401(3)
_cell_angle_gamma                90
_cell_formula_units_Z            3
_cell_length_a                   12.7257(3)
_cell_length_b                   4.69060(10)
_cell_length_c                   13.7330(5)
_cell_measurement_reflns_used    6132
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8330
_cell_measurement_theta_min      3.0610
_cell_volume                     786.38(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.950
_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    -20.00 100.00   0.50    1.75    --   10.60  57.00  30.00  240
  2  \w    -15.00 100.00   0.50    1.75    --   10.60  77.00 120.00  230
  3  \w    -79.00  48.00   0.50    1.75    --   10.60 -37.00  90.00  254
  4  \w    -15.00 100.00   0.50    1.75    --   10.60  77.00 150.00  230
  5  \w    -79.00  41.00   0.50    1.75    --   10.60 -57.00 -30.00  240
  6  \w   -100.00 -75.00   0.50    1.75    --  -10.90 -82.00-120.00   50
  7  \w    -38.00  79.00   0.50    1.75    --  -10.90  82.00-120.00  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      -0.0532684000
_diffrn_orient_matrix_UB_12      0.0039942000
_diffrn_orient_matrix_UB_13      0.0066570000
_diffrn_orient_matrix_UB_21      0.0062189000
_diffrn_orient_matrix_UB_22      -0.1428755000
_diffrn_orient_matrix_UB_23      0.0175602000
_diffrn_orient_matrix_UB_31      0.0223629000
_diffrn_orient_matrix_UB_32      0.0492293000
_diffrn_orient_matrix_UB_33      0.0504702000
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8968
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.061
_diffrn_reflns_theta_min         1.668
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31845
_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    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0583P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.893
_reflns_Friedel_fraction_max     0.806
_reflns_number_gt                2852
_reflns_number_total             3023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00989h2.cif
_cod_data_source_block           k11109-myc-f(lyk907)_auto
_cod_depositor_comments
'Adding full bibliography for 7160623--7160627.cif.'
_cod_database_code               7160624
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.938
_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:
 C5(H5), C3(H3), C18(H18), C17(H17), C16(H16), C11(H11), C15(H15)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              1002
_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 2.469
_oxdiff_exptl_absorpt_empirical_full_min 0.604