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_7160625
_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         'C17 H12 O4'
_chemical_formula_sum            'C17 H12 O4'
_chemical_formula_weight         280.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-11
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;
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                 92.288(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   8.1869(2)
_cell_length_c                   29.8283(8)
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_cell_measurement_temperature    130(2)
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_cell_measurement_theta_min      2.5700
_cell_volume                     1298.38(7)
_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)'
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_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 0.996
_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   19.25    --   10.60  19.00-120.00  358
  2  \w    -79.00 100.00   0.50   19.25    --   10.60  19.00-120.00  358
  3  \w    -20.00 100.00   0.50   19.25    --   10.60  57.00  30.00  240
  4  \w    -27.00 100.00   0.50   19.25    --   10.60  37.00 -90.00  254
  5  \w   -100.00  20.00   0.50   19.25    --  -10.90 -57.00 -60.00  240
  6  \w    -79.00  41.00   0.50   19.25    --   10.60 -57.00 -90.00  240
  7  \w    -38.00 -13.00   0.50   19.25    --  -10.90  82.00  30.00   50
  8  \w    -41.00  79.00   0.50   19.25    --  -10.90  57.00 150.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
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'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0389828000
_diffrn_orient_matrix_UB_12      -0.0680268000
_diffrn_orient_matrix_UB_13      -0.0126906000
_diffrn_orient_matrix_UB_21      -0.0696483000
_diffrn_orient_matrix_UB_22      0.0301464000
_diffrn_orient_matrix_UB_23      -0.0190187000
_diffrn_orient_matrix_UB_31      0.1068800000
_diffrn_orient_matrix_UB_32      0.0444697000
_diffrn_orient_matrix_UB_33      -0.0065738000
_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  0.0383
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19804
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.580
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64192
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0541P)^2^+0.9108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2010
_reflns_number_total             2288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00989h2.cif
_cod_data_source_block           k11111-myc-d(lyk1018)_auto
_cod_depositor_comments
'Adding full bibliography for 7160623--7160627.cif.'
_cod_database_code               7160625
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.980
_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:
 C14(H14), C2(H2), C16(H16), C13(H13), C5(H5), C9(H9), C7(H7), C8(H8), C6(H6)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              64431
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.506