One-pot synthesis of sulfonyl benzotropones.
Chang, Meng-Yang; Ho, Chin-Huey; Organic & biomolecular chemistry 23 (2025) 7780–7785; doi:10.1039/d5ob01123j

data_7160671
_publ_section_title
;
 One-pot synthesis of sulfonyl benzotropones.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7780
_journal_page_last               7785
_journal_paper_doi               10.1039/d5ob01123j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C25 H14 F6 O5 S2'
_chemical_formula_sum            'C25 H14 F6 O5 S2'
_chemical_formula_weight         572.48
_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     iterative
_audit_creation_date             2022-10-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-25 deposited with the CCDC.	2025-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.39450(10)
_cell_length_b                   35.2609(6)
_cell_length_c                   14.1439(2)
_cell_measurement_reflns_used    34575
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9660
_cell_measurement_theta_min      1.8550
_cell_volume                     2648.93(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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    'olex2.solve 1.5 (Bourhis et al., 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 0.999
_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  37.00   0.50   14.37    --   10.60 -60.00-152.00  232
  2  \w   -100.00  15.00   0.50   14.37    --  -10.90 -60.00-152.00  230
  3  \w    -37.00  35.00   0.50   14.37    --  -10.90  60.00 -13.00  144
  4  \w    -15.00  98.00   0.50   14.37    --   10.60  77.00  90.00  226
  5  \w    -17.00 100.00   0.50   14.37    --   10.60  57.00-120.00  234
  6  \w     37.00  82.00   0.50   14.37    --   10.60  82.00  30.00   90
  7  \w    -73.00 -14.00   0.50   14.37    --   10.60 -82.00 125.93  118
  8  \w     38.00  63.00   0.50   14.37    --   10.60  60.00 -13.00   50
  9  \w    -15.00  11.00   0.50   14.37    --   10.60  77.00-120.00   52
 10  \w    -15.00 100.00   0.50   14.37    --   10.60  82.00 -60.00  230
 11  \w    -16.00  43.00   0.50   14.37    --   10.60  82.00-120.00  118
 12  \w     54.00  80.00   0.50   14.37    --   10.60  82.00-120.00   52
 13  \w      3.00  29.00   0.50   14.37    --   10.60  77.00   0.00   52
 14  \w     -5.00  33.00   0.50   14.37    --   10.60 -82.00 125.93   76
 15  \w     -8.00  59.00   0.50   14.37    --   10.60  82.00 -30.00  134
 16  \w    -17.00  10.00   0.50   14.37    --   10.60  82.00-180.00   54
 17  \w    -11.00  14.00   0.50   14.37    --   10.60  82.00  60.00   50
 18  \w    -10.00  15.00   0.50   14.37    --  -10.90 -77.00  30.00   50
 19  \w   -100.00 -35.00   0.50   14.37    --  -10.90 -77.00  30.00  130
 20  \w      1.00  78.00   0.50   14.37    --  -10.90  82.00 170.51  154
 21  \w   -100.00 -12.00   0.50   14.37    --  -10.90 -77.00 150.00  176
;
_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      -0.1268492000
_diffrn_orient_matrix_UB_12      -0.0017781000
_diffrn_orient_matrix_UB_13      0.0065944000
_diffrn_orient_matrix_UB_21      0.0206026000
_diffrn_orient_matrix_UB_22      0.0141477000
_diffrn_orient_matrix_UB_23      0.0361654000
_diffrn_orient_matrix_UB_31      -0.0364175000
_diffrn_orient_matrix_UB_32      0.0141822000
_diffrn_orient_matrix_UB_33      -0.0352598000
_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  0.0507
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54158
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.572
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.038
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         4663
_refine_ls_number_restraints     1398
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0809
_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^)+(0.1124P)^2^+8.8095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2155
_refine_ls_wR_factor_ref         0.2191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4217
_reflns_number_total             4663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01123j2.cif
_cod_data_source_block           k11109-myc-j(chv919)_autored
_cod_depositor_comments
'Adding full bibliography for 7160667--7160674.cif.'
_cod_database_code               7160671
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C25-F5
 1.29 with sigma of 0.02
 C25-F6
 1.36 with sigma of 0.02
 C25-F4
 1.27 with sigma of 0.02
 C18-F8
 1.29 with sigma of 0.02
 C18-F9
 1.36 with sigma of 0.02
 C18-F7
 1.27 with sigma of 0.02
 C25-F5 \\sim C25-F6 \\sim C25-F4
 with sigma of 0.02
 F5-F6 \\sim F6-F4 \\sim F4-F5
 with sigma of 0.03
 C18-F8 \\sim C18-F9 \\sim C18-F7
 with sigma of 0.02
 F8-F9 \\sim F9-F7 \\sim F7-F8
 with sigma of 0.03
 C18-F9 \\sim C18-F3
 with sigma of 0.02
 C18-F8 \\sim C18-F2
 with sigma of 0.02
 C18-F7 \\sim C18-F1
 with sigma of 0.02
 C25-F6 \\sim C25-F11
 with sigma of 0.02
 C25-F4 \\sim C25-F12
 with sigma of 0.02
 C25-F5 \\sim C25-F10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim S1 \\sim S2 \\sim F1 \\sim
F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8 \\sim F9 \\sim F10
\\sim F11 \\sim F12: within 3.8A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 3.8A
4. Others
 Sof(F1)=Sof(F2)=Sof(F3)=1-FVAR(1)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(1)
 Sof(F10)=Sof(F11)=Sof(F12)=1-FVAR(2)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14),
 C15(H15), C17(H17), C20(H20), C21(H21), C22(H22), C24(H24)
;
_shelx_res_checksum              58643
_shelx_fab_checksum              90551
_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 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.718