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_7160954
_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_sum            'C20 H14 O3'
_chemical_formula_weight         302.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'Intrinsic Phasing'
_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                90
_cell_angle_beta                 121.2430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.6137(9)
_cell_length_b                   7.8287(3)
_cell_length_c                   18.7543(8)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100.14999999999998
_cell_measurement_theta_max      28.2655
_cell_measurement_theta_min      2.3109
_cell_measurement_wavelength     0.71073
_cell_volume                     2838.7(2)
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.27.Release'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_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      100(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.391
_diffrn_detector_type            'Bruker PHOTON III C14'
_diffrn_measured_fraction_theta_full 1.000
_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= 272.0; end= 452.0 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   4.921 deg omega=   4.261 deg chi= -44.500 deg] 
measure for 2.5 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=  36.000 deg chi=  68.500 deg] 
measure for 2.5 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= 144.000 deg chi= -44.500 deg] 
measure for 2.5 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 2.5 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Phi   scan: start= 204.0; len= 224.0; end= 428.0 at [Counterclockwise Eulerian 
angles: dx= 45.00 mm theta=   4.921 deg omega=   3.663 deg chi= -24.000 deg] 
measure for 2.5 seconds; frame angle 0.50 degrees, wavelength=0.71073>
;
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support Fibre-loope
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            44745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_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         28.307
_diffrn_reflns_theta_min         2.107
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.403
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.983
_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            'clear colourless'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0485P)^2^+2.4309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3212
_reflns_number_total             3528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01723h2.cif
_cod_data_source_block           FH79_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_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7160954
_shelx_shelxl_version_number     2019/3
_exptl_bruker_absorpt_correction_t_ratio 0.9281
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.996
_diffrn_measurement_bruker_total_exposure_time 4045.0
_diffrn_reflns_bruker_av_norm_i  5466.614
_diffrn_reflns_bruker_number_gt  39291
_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              51519