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

data_7160668
_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         'C17 H12 O3 S'
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_weight         296.33
_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
_audit_creation_date             2022-11-24
_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                 94.811(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5989(3)
_cell_length_b                   7.2926(2)
_cell_length_c                   13.6091(3)
_cell_measurement_reflns_used    18950
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9840
_cell_measurement_theta_min      2.0480
_cell_volume                     1344.88(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -15.00 100.00   0.50    7.51    --   10.60  77.00 -90.00  230
  2  \w    -79.00  36.00   0.50    7.51    --   10.60 -77.00-150.00  230
  3  \w    -17.00 100.00   0.50    7.51    --   10.60  82.00   0.00  234
  4  \w    -79.00 100.00   0.50    7.51    --   10.60  19.00 -90.00  358
  5  \w    -17.00 100.00   0.50    7.51    --   10.60  82.00  30.00  234
  6  \w    -79.00  36.00   0.50    7.51    --   10.60 -77.00-180.00  230
  7  \w    -17.00 100.00   0.50    7.51    --   10.60  82.00 120.00  234
  8  \w   -100.00  17.00   0.50    7.51    --  -10.90 -82.00-180.00  234
  9  \w   -100.00  20.00   0.50    7.51    --  -10.90 -57.00   0.00  240
 10  \w   -100.00  17.00   0.50    7.51    --  -10.90 -82.00  90.00  234
 11  \w    -42.00  20.00   0.50    7.51    --  -10.90 -57.00-120.00  124
;
_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      0.0419940000
_diffrn_orient_matrix_UB_12      0.0031660000
_diffrn_orient_matrix_UB_13      0.0345898000
_diffrn_orient_matrix_UB_21      0.0311990000
_diffrn_orient_matrix_UB_22      -0.0053008000
_diffrn_orient_matrix_UB_23      -0.0390904000
_diffrn_orient_matrix_UB_31      0.0003653000
_diffrn_orient_matrix_UB_32      0.0971307000
_diffrn_orient_matrix_UB_33      -0.0032780000
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26545
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46998
_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    1.464
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0551P)^2^+0.7917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2176
_reflns_number_total             2371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01123j2.cif
_cod_data_source_block           k11111-myc-i(chvn3540)_auto
_cod_depositor_comments
'Adding full bibliography for 7160667--7160674.cif.'
_cod_database_code               7160668
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.886
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C9(H9), C3(H3), C17(H17), C4(H4), C14(H14), C6(H6),
 C16(H16), C15(H15), C7(H7), C8(H8)
;
_shelx_res_checksum              47193
_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 1.663
_oxdiff_exptl_absorpt_empirical_full_min 0.609