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

data_7160669
_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         'C23 H22 O5 S2'
_chemical_formula_sum            'C23 H22 O5 S2'
_chemical_formula_weight         442.52
_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
_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                 102.284(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1705(3)
_cell_length_b                   12.7063(3)
_cell_length_c                   14.9419(4)
_cell_measurement_reflns_used    27204
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.0250
_cell_measurement_theta_min      2.0730
_cell_volume                     2072.23(9)
_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 0.999
_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    -27.00 100.00   0.50    4.43    --   10.60  38.00 146.00  254
  2  \w    -57.00   9.00   0.50    4.43    --   10.60 -38.00  -7.00  132
  3  \w    -61.00 -36.00   0.50    4.43    --  -10.90 -38.00  -7.00   50
  4  \w     -5.00  25.00   0.50    4.43    --  -10.90  38.00 146.00   60
  5  \w     37.00  63.00   0.50    4.43    --   10.60  82.00-120.00   52
  6  \w    -12.00  27.00   0.50    4.43    --   10.60  82.00  90.00   78
  7  \w     19.00  51.00   0.50    4.43    --   10.60  77.00-180.00   64
  8  \w     62.00  90.00   0.50    4.43    --   10.60  77.00-180.00   56
  9  \w    -17.00  92.00   0.50    4.43    --   10.60  82.00  60.00  218
 10  \w     -4.00  22.00   0.50    4.43    --   10.60  82.00-120.00   52
 11  \w    -16.00  68.00   0.50    4.43    --   10.60  82.00 -60.00  168
 12  \w     73.00 100.00   0.50    4.43    --   10.60  82.00 -60.00   54
 13  \w    -17.00 100.00   0.50    4.43    --   10.60  82.00 150.00  234
 14  \w    -12.00  97.00   0.50    4.43    --   10.60  82.00-150.00  218
 15  \w     -3.00  23.00   0.50    4.43    --   10.60  57.00  60.00   52
 16  \w     42.00  68.00   0.50    4.43    --   10.60  57.00  60.00   52
 17  \w    -27.00  98.00   0.50    4.43    --   10.60  37.00 -30.00  250
 18  \w     -7.00  40.00   0.50    4.43    --   10.60  57.00  90.00   94
 19  \w     56.00  99.00   0.50    4.43    --   10.60  57.00  90.00   86
 20  \w     -4.00  21.00   0.50    4.43    --   10.60  77.00 -30.00   50
 21  \w     22.00  99.00   0.50    4.43    --   10.60  77.00 -30.00  154
 22  \w      9.00  35.00   0.50    4.43    --   10.60  77.00 120.00   52
 23  \w    -41.00  17.00   0.50    4.43    --  -10.90 -82.00-120.00  116
 24  \w    -66.00 -40.00   0.50    4.43    --  -10.90 -77.00 -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      -0.0638734000
_diffrn_orient_matrix_UB_12      0.0101699000
_diffrn_orient_matrix_UB_13      -0.0080182000
_diffrn_orient_matrix_UB_21      -0.0119747000
_diffrn_orient_matrix_UB_22      -0.0494336000
_diffrn_orient_matrix_UB_23      -0.0221101000
_diffrn_orient_matrix_UB_31      -0.0024290000
_diffrn_orient_matrix_UB_32      -0.0238307000
_diffrn_orient_matrix_UB_33      0.0424892000
_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  0.0912
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40297
_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         2.078
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59916
_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    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0653P)^2^+0.5982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3301
_reflns_number_total             3652
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01123j2.cif
_cod_data_source_block           chv2629_auto
_cod_depositor_comments
'Adding full bibliography for 7160667--7160674.cif.'
_cod_database_code               7160669
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C23(H23), C14(H14), C22(H22), C17(H17), C8(H8), C15(H15), C19(H19),
 C11(H11), C21(H21), C20(H20), C16(H16), C10(H10), C9(H9)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              85995
_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 3.825
_oxdiff_exptl_absorpt_empirical_full_min 0.715