Arylsulfone-driven divergence in base-mediated [3 + 3] benzannulation reactions of aurones: facile synthesis of substituted dibenzofurans.
Husni P, Farooqe; Andrews P, Alex; Menon, Rajeev S.; Organic & biomolecular chemistry 24 (2026) 1352–1357; doi:10.1039/d5ob01723h

data_7160953
_publ_section_title
;
 Arylsulfone-driven divergence in base-mediated [3 + 3] benzannulation
 reactions of aurones: facile synthesis of substituted dibenzofurans.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1352
_journal_page_last               1357
_journal_paper_doi               10.1039/d5ob01723h
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C25 H18 O3 S'
_chemical_formula_sum            'C25 H18 O3 S'
_chemical_formula_weight         398.45
_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
_audit_creation_method
;FinalCif 2024.9-0 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-06-01 deposited with the CCDC.	2026-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                102.714(2)
_cell_angle_beta                 96.3410(10)
_cell_angle_gamma                90.4280(10)
_cell_formula_units_Z            4
_cell_length_a                   10.5477(4)
_cell_length_b                   13.6992(6)
_cell_length_c                   13.9449(6)
_cell_measurement_reflns_used    9238
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.2661
_cell_measurement_theta_min      2.3704
_cell_measurement_wavelength     0.71073
_cell_volume                     1952.49(14)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.27 Release'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.391
_diffrn_detector_type            'Bruker PHOTON III C14'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;<Phi   scan: start= 360.0; len= 180.0; end= 540.0 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   0.000 deg omega=   0.000 deg chi=  54.740 deg] 
		measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 180.0; len= 180.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   0.000 deg omega=   0.000 deg chi=  54.740 deg] 
		measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 180.0; len= 180.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   0.000 deg omega=   0.000 deg chi=  54.740 deg] 
		measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 360.0; len= 180.0; end= 540.0 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   0.000 deg omega=   0.000 deg chi=  54.740 deg] 
		measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start=   0.0; len= 360.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   4.921 deg omega= 268.711 deg chi=  24.000 deg] 
		measure for 3.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 324.6; len=  61.0; end= 385.6 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   7.383 deg phi= 360.000 deg chi=  68.500 deg] 
		measure for 3.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 324.6; len=  65.5; end= 390.1 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   9.665 deg phi= 180.000 deg chi=  68.500 deg] 
		measure for 3.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start=   5.2; len= 114.5; end= 119.7 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   4.921 deg phi= 288.000 deg chi= -44.500 deg] 
		measure for 3.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 324.6; len=  65.5; end= 390.1 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   9.665 deg phi= 108.000 deg chi=  68.500 deg] 
		measure for 3.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Phi   scan: start= 360.0; len=   0.5; end= 360.5 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   4.921 deg omega=   3.663 deg chi= -24.000 deg] 
		measure for 3.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start=   5.2; len= 114.5; end= 119.7 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   4.921 deg phi=   0.000 deg chi= -44.500 deg] 
		measure for 3.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Phi   scan: start=   0.0; len= 360.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   4.921 deg omega=   4.261 deg chi= -44.500 deg] 
		measure for 3.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
;
_diffrn_measurement_device       'Bruker D8 QUEST'
_diffrn_measurement_device_type  'Four-circle Kappa diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support Fibre-loop
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            103135
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_reduction_process narrow-frame
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.268
_diffrn_reflns_theta_min         1.891
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.404
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.19
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      1.354
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         9640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0611P)^2^+0.3791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8257
_reflns_number_total             9640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01723h2.cif
_cod_data_source_block           FH78_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7160953
_shelx_shelxl_version_number     2019/3
_exptl_bruker_absorpt_correction_t_ratio 0.957
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.979
_diffrn_measurement_bruker_total_exposure_time 9726.0
_diffrn_reflns_bruker_av_norm_i  2386.095
_diffrn_reflns_bruker_number_gt  90255
_computing_bruker_data_scaling
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_geom_details
; All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
_shelx_res_checksum              99943