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_7160313
_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         'C18 H20 O3 S'
_chemical_formula_sum            'C18 H20 O3 S'
_chemical_formula_weight         316.40
_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             2024-11-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.3990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.49110(10)
_cell_length_b                   17.9817(2)
_cell_length_c                   17.8130(2)
_cell_measurement_reflns_used    10908
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.5400
_cell_measurement_theta_min      3.5210
_cell_volume                     3282.01(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_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     78.00 116.00   0.50    0.06    --   68.01  30.00 -90.00   76
  2  \w     92.00 124.00   0.50    0.06    --   83.08  30.00 -60.00   64
  3  \w     96.00 121.00   0.50    0.06    --   83.08  30.00 -30.00   50
  4  \w     64.00  90.00   0.50    0.06    --   56.11  30.00 150.00   52
  5  \w    109.00 135.00   0.50    0.06    --   83.08  30.00  90.00   52
  6  \w     60.00 122.00   0.50    0.06    --   83.08  15.00-120.00  124
  7  \w     95.00 132.00   0.50    0.06    --   83.08  30.00-120.00   74
  8  \w     40.00  82.00   0.50    0.06    --   83.08 -95.00  30.00   84
  9  \w     50.00  77.00   0.50    0.06    --   68.01 -95.00 -30.00   54
 10  \w     12.00  51.00   0.50    0.06    --   56.11 -95.00 -30.00   78
 11  \w     20.00  62.00   0.50    0.06    --   56.11-125.00-120.00   84
 12  \w     11.00  50.00   0.50    0.06    --   56.11 -95.00-180.00   78
 13  \w     38.00  63.00   0.50    0.06    --   83.08 -95.00-120.00   50
 14  \w     45.00  83.00   0.50    0.06    --   83.08 -95.00-150.00   76
 15  \w     38.00  63.00   0.50    0.06    --   83.08 -95.00   0.00   50
 16  \w     39.00  76.00   0.50    0.06    --   83.08 -95.00 120.00   74
 17  \w     59.00  91.00   0.50    0.06    --   83.08 -95.00 150.00   64
 18  \w   -125.00 -51.00   0.50    0.06    --  -77.69 -15.00 -90.00  148
 19  \w   -131.00 -85.00   0.50    0.06    --  -77.69 -30.00   0.00   92
 20  \w   -128.00 -95.00   0.50    0.06    --  -77.69 -30.00  30.00   66
 21  \w   -110.00 -82.00   0.50    0.06    --  -57.37 -30.00  90.00   56
 22  \w   -127.00 -89.00   0.50    0.06    --  -77.69 -30.00 120.00   76
 23  \w   -112.00 -86.00   0.50    0.06    --  -77.69 -30.00  60.00   52
 24  \w    -74.00 -34.00   0.50    0.06    --  -77.69 111.00-150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0998552000
_diffrn_orient_matrix_UB_12      -0.0639725000
_diffrn_orient_matrix_UB_13      0.0162550000
_diffrn_orient_matrix_UB_21      0.0020663000
_diffrn_orient_matrix_UB_22      0.0058623000
_diffrn_orient_matrix_UB_23      0.0865371000
_diffrn_orient_matrix_UB_31      -0.1123458000
_diffrn_orient_matrix_UB_32      -0.0567074000
_diffrn_orient_matrix_UB_33      -0.0093842000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22177
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.100
_diffrn_reflns_theta_min         3.535
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0563P)^2^+2.7153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5455
_reflns_number_total             6354
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01916d2.cif
_cod_data_source_block           241075lt_auto
_cod_depositor_comments
'Adding full bibliography for 7160310--7160313.cif.'
_cod_database_code               7160313
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.853
_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 Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C23(H23), C24(H24), C26(H26), C27(H27)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C36(H36),
  C37(H37), C38(H38), C39(H39), C40(H40)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C43(H43A,H43B,H43C), C44(H44A,H44B,
 H44C)
;
_shelx_res_checksum              52333
_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 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.912