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

data_7160670
_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_absolute_configuration syn
_chemical_formula_moiety         'C29 H24 O7 S2'
_chemical_formula_sum            'C29 H24 O7 S2'
_chemical_formula_weight         548.60
_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             2022-11-11
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3356(3)
_cell_length_b                   11.7574(3)
_cell_length_c                   19.2696(5)
_cell_measurement_reflns_used    24622
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9380
_cell_measurement_theta_min      2.0150
_cell_volume                     2568.20(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 0.998
_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   14.30    --   10.60  77.00 -30.00  230
  2  \w    -17.00 100.00   0.50   14.30    --   10.60  82.00 -60.00  234
  3  \w    -79.00  36.00   0.50   14.30    --   10.60 -77.00-120.00  230
  4  \w    -17.00 100.00   0.50   14.30    --   10.60  82.00  60.00  234
  5  \w    -17.00 100.00   0.50   14.30    --   10.60  82.00   0.00  234
  6  \w    -17.00 100.00   0.50   14.30    --   10.60  82.00 150.00  234
  7  \w    -17.00 100.00   0.50   14.30    --   10.60  82.00 -90.00  234
  8  \w    -20.00 100.00   0.50   14.30    --   10.60  57.00 150.00  240
  9  \w    -79.00  37.00   0.50   14.30    --   10.60 -78.00-136.72  232
 10  \w    -79.00  37.00   0.50   14.30    --   10.60 -79.00 -49.82  232
 11  \w     -5.00  32.00   0.50   14.30    --   10.60  82.00-150.00   74
 12  \w    -44.00 -18.00   0.50   14.30    --  -10.90 -77.00 150.00   52
 13  \w    -49.00 -23.00   0.50   14.30    --  -10.90 -82.00  90.00   52
 14  \w    -92.00 -66.00   0.50   14.30    --  -10.90 -82.00  90.00   52
;
_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      0.0505577000
_diffrn_orient_matrix_UB_12      0.0244263000
_diffrn_orient_matrix_UB_13      -0.0157277000
_diffrn_orient_matrix_UB_21      0.0167753000
_diffrn_orient_matrix_UB_22      0.0236636000
_diffrn_orient_matrix_UB_23      0.0323771000
_diffrn_orient_matrix_UB_31      0.0328807000
_diffrn_orient_matrix_UB_32      -0.0498126000
_diffrn_orient_matrix_UB_33      0.0076634000
_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  0.0994
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            52781
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.029
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34747
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1662 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0738P)^2^+0.6154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4113
_reflns_number_total             4509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01123j2.cif
_cod_data_source_block           k11111-myc-a(chvb921)_auto
_cod_depositor_comments
'Adding full bibliography for 7160667--7160674.cif.'
_cod_database_code               7160670
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.883
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C3(H3)
1.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C15(H15A,H15B)
1.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C9(H9), C11(H11), C29(H29), C10(H10), C26(H26), C19(H19), C25(H25),
 C27(H27), C21(H21), C23(H23), C28(H28), C20(H20), C22(H22)
1.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              76626
_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 1.994
_oxdiff_exptl_absorpt_empirical_full_min 0.497