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

data_7160673
_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         'C38 H28 O7 S2'
_chemical_formula_sum            'C38 H28 O7 S2'
_chemical_formula_weight         660.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-15
_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                108.412(2)
_cell_angle_beta                 97.946(2)
_cell_angle_gamma                92.222(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2954(2)
_cell_length_b                   12.1523(2)
_cell_length_c                   14.4951(3)
_cell_measurement_reflns_used    20557
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9620
_cell_measurement_theta_min      1.9100
_cell_volume                     1532.71(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 0.949
_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    -17.00 100.00   0.50    4.13    --   10.60  82.00 -60.00  234
  2  \w    -79.00 100.00   0.50    4.13    --   10.60   0.00-120.00  358
  3  \w    -17.00 100.00   0.50    4.13    --   10.60  82.00 150.00  234
  4  \w    -15.00 100.00   0.50    4.13    --   10.60  77.00-150.00  230
  5  \w    -17.00  90.00   0.50    4.13    --   10.60  82.00  90.00  214
  6  \w      0.00  82.00   0.50    4.13    --   10.60  82.00   0.00  164
  7  \w    -78.00  37.00   0.50    4.13    --   10.60 -82.00 160.88  230
  8  \w    -72.00 -20.00   0.50    4.13    --   10.60   0.00-120.00  104
  9  \w     -7.00  85.00   0.50    4.13    --   10.60  82.00 -30.00  184
 10  \w     19.00  45.00   0.50    4.13    --   10.60  57.00-180.00   52
 11  \w     62.00  99.00   0.50    4.13    --   10.60  57.00-180.00   74
 12  \w     -8.00  36.00   0.50    4.13    --   10.60  82.00-120.00   88
 13  \w     57.00  83.00   0.50    4.13    --   10.60  82.00-120.00   52
 14  \w     26.00  69.00   0.50    4.13    --   10.60  82.00 -90.00   86
 15  \w    -20.00   9.00   0.50    4.13    --  -10.90 -82.00  60.00   58
 16  \w    -42.00   4.00   0.50    4.13    --  -10.90 -82.00  90.00   92
 17  \w    -99.00 -47.00   0.50    4.13    --  -10.90 -82.00  60.00  104
 18  \w    -10.00  16.00   0.50    4.13    --  -10.90 -82.00 -60.00   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      0.0625306000
_diffrn_orient_matrix_UB_12      0.0384128000
_diffrn_orient_matrix_UB_13      0.0255407000
_diffrn_orient_matrix_UB_21      0.0347954000
_diffrn_orient_matrix_UB_22      -0.0197652000
_diffrn_orient_matrix_UB_23      -0.0421238000
_diffrn_orient_matrix_UB_31      -0.0293503000
_diffrn_orient_matrix_UB_32      0.0441295000
_diffrn_orient_matrix_UB_33      -0.0173737000
_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  0.0313
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34663
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.110
_diffrn_reflns_theta_min         1.773
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73194
_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    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0532P)^2^+0.6048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5442
_reflns_number_total             6416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01123j2.cif
_cod_data_source_block           k11109-myc-e(chvb90)_auto
_cod_depositor_comments
'Adding full bibliography for 7160667--7160674.cif.'
_cod_database_code               7160673
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.914
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C11(H11), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C7(H7), C20(H20), C38(H38), C22(H22), C30(H30),
 C28(H28), C26(H26), C32(H32), C23(H23), C34(H34), C19(H19), C31(H31), C37(H37),
  C29(H29), C36(H36), C25(H25), C24(H24), C16(H16), C35(H35), C18(H18), C17(H17)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              2938
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.707