Construction of diaryl oxacyclic sulfones <i>via</i> Bi(OTf)<sub>3</sub>-catalyzed intramolecular cyclocondensation of 1,3-diaroylsulfones.
Chang, Meng-Yang; Lin, Chun-Yi; Organic & biomolecular chemistry 23 (2025) 1662–1672; doi:10.1039/d4ob01916d

data_7160312
_publ_section_title
;
 Construction of diaryl oxacyclic sulfones <i>via</i>
 Bi(OTf)<sub>3</sub>-catalyzed intramolecular cyclocondensation of
 1,3-diaroylsulfones.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1662
_journal_page_last               1672
_journal_paper_doi               10.1039/d4ob01916d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H10 Br2 O3 S'
_chemical_formula_sum            'C16 H10 Br2 O3 S'
_chemical_formula_weight         442.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.652(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4471(3)
_cell_length_b                   10.9120(4)
_cell_length_c                   17.0111(6)
_cell_measurement_reflns_used    7663
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.1880
_cell_measurement_theta_min      2.2200
_cell_volume                     1535.68(10)
_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  (Sheldrick, 2015)'
_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 0.953
_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    3.90    --   10.60  19.00 120.00  358
  2  \w    -15.00 100.00   0.50    3.90    --   10.60  77.00 120.00  230
  3  \w    -79.00  36.00   0.50    3.90    --   10.60 -77.00 150.00  230
  4  \w    -79.00  41.00   0.50    3.90    --   10.60 -57.00  30.00  240
  5  \w    -17.00  86.00   0.50    3.90    --   10.60  57.00  90.00  206
  6  \w     23.00  78.00   0.50    3.90    --  -10.90  82.00  30.00  110
;
_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      -0.0249913000
_diffrn_orient_matrix_UB_12      -0.0082335000
_diffrn_orient_matrix_UB_13      -0.0420015000
_diffrn_orient_matrix_UB_21      -0.0231676000
_diffrn_orient_matrix_UB_22      -0.0610727000
_diffrn_orient_matrix_UB_23      0.0063739000
_diffrn_orient_matrix_UB_31      -0.0787960000
_diffrn_orient_matrix_UB_32      0.0205967000
_diffrn_orient_matrix_UB_33      0.0020890000
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.125
_diffrn_reflns_theta_min         2.231
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.423
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10807
_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    1.912
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.603
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0332P)^2^+5.1047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2639
_reflns_number_total             3230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01916d2.cif
_cod_data_source_block           k11212-myc-f(ynp1020)_auto
_cod_depositor_comments
'Adding full bibliography for 7160310--7160313.cif.'
_cod_database_code               7160312
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.410
_shelx_estimated_absorpt_t_min   0.220
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H2), C15(H16), C1(H8), C9(H4), C3(H10), C4(H11), C2(H9), C12(H19),
 C14(H17), C13(H18)
;
_shelx_res_checksum              40572
_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 5.727
_oxdiff_exptl_absorpt_empirical_full_min 0.499