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_7160311
_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 H13 N O2 S'
_chemical_formula_sum            'C16 H13 N O2 S'
_chemical_formula_weight         283.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-20
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3209(4)
_cell_length_b                   11.0345(5)
_cell_length_c                   16.7334(9)
_cell_measurement_reflns_used    3907
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9460
_cell_measurement_theta_min      1.9700
_cell_volume                     1351.77(12)
_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 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 0.999
_diffrn_measured_fraction_theta_max 0.946
_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    -27.00  62.00   0.50   89.80    --   10.60  38.00 119.00  178
  2  \w      2.00  28.00   0.50   89.80    --  -10.90  38.00 119.00   52
  3  \w    -49.00 -18.00   0.50   89.80    --  -10.90 -38.00 -35.00   62
  4  \w     28.00 100.00   0.50   89.80    --   10.60  77.00-180.00  144
  5  \w    -15.00  34.00   0.50   89.80    --   10.60  77.00 -60.00   98
  6  \w    -20.00  64.00   0.50   89.80    --   10.60  57.00 120.00  168
  7  \w    -15.00  21.00   0.50   89.80    --   10.60  77.00-180.00   72
;
_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      -0.0340147000
_diffrn_orient_matrix_UB_12      0.0120467000
_diffrn_orient_matrix_UB_13      0.0388236000
_diffrn_orient_matrix_UB_21      -0.0295924000
_diffrn_orient_matrix_UB_22      -0.0608945000
_diffrn_orient_matrix_UB_23      0.0031375000
_diffrn_orient_matrix_UB_31      0.0860146000
_diffrn_orient_matrix_UB_32      -0.0164577000
_diffrn_orient_matrix_UB_33      0.0165714000
_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  0.0599
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8961
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.094
_diffrn_reflns_theta_min         2.434
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25846
_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    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0731
_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^)+(0.0252P)^2^+2.0642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                2071
_reflns_number_total             2701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01916d2.cif
_cod_data_source_block           k11212-myc-a(ynn9296)_auto
_cod_depositor_comments
'Adding full bibliography for 7160310--7160313.cif.'
_cod_database_code               7160311
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(C10) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C3) \\sim Ueq,
Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 N1(H004), C12(H006), C16(H007), C14(H008), C15(H009), C1(H00D), C13(H00E),
 C2(H00F), C5(H00G), C8(H00H), C3(H00I), C9(H00J), C4(H00K)
;
_shelx_res_checksum              17350
_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 3.334
_oxdiff_exptl_absorpt_empirical_full_min 0.768