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

data_7160667
_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         'C31 H32 O5 S2'
_chemical_formula_sum            'C31 H32 O5 S2'
_chemical_formula_weight         548.68
_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
_audit_creation_date             2022-10-31
_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                 92.616(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4021(2)
_cell_length_b                   7.89070(10)
_cell_length_c                   36.9561(7)
_cell_measurement_reflns_used    27339
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9450
_cell_measurement_theta_min      2.1580
_cell_volume                     2738.88(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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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   30.49    --   10.60  82.00 -90.00  234
  2  \w    -79.00  36.00   0.50   30.49    --   10.60 -77.00 150.00  230
  3  \w    -17.00 100.00   0.50   30.49    --   10.60  82.00 120.00  234
  4  \w    -17.00 100.00   0.50   30.49    --   10.60  82.00 -30.00  234
  5  \w    -17.00 100.00   0.50   30.49    --   10.60  82.00-120.00  234
  6  \w    -79.00  41.00   0.50   30.49    --   10.60 -57.00  60.00  240
  7  \w    -79.00  41.00   0.50   30.49    --   10.60 -57.00 -30.00  240
  8  \w    -17.00  70.00   0.50   30.49    --   10.60  82.00  30.00  174
  9  \w    -18.00  18.00   0.50   30.49    --   10.60  57.00 -90.00   72
 10  \w     57.00  99.00   0.50   30.49    --   10.60  57.00 -90.00   84
 11  \w    -15.00  47.00   0.50   30.49    --   10.60  77.00   0.00  124
 12  \w   -100.00  13.00   0.50   30.49    --  -10.90 -82.00  60.00  226
 13  \w     25.00  66.00   0.50   30.49    --  -10.90  77.00-120.00   82
 14  \w    -15.00  11.00   0.50   30.49    --  -10.90 -82.00-180.00   52
 15  \w    -85.00 -47.00   0.50   30.49    --  -10.90 -82.00-180.00   76
 16  \w      0.00  46.00   0.50   30.49    --  -10.90  76.00 171.46   92
;
_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      -0.0546852000
_diffrn_orient_matrix_UB_12      0.0250550000
_diffrn_orient_matrix_UB_13      0.0114670000
_diffrn_orient_matrix_UB_21      0.0426366000
_diffrn_orient_matrix_UB_22      -0.0256888000
_diffrn_orient_matrix_UB_23      0.0153520000
_diffrn_orient_matrix_UB_31      0.0299333000
_diffrn_orient_matrix_UB_32      0.0824452000
_diffrn_orient_matrix_UB_33      0.0012951000
_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  0.0513
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            54331
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.168
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49989
_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    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4786
_refine_ls_number_restraints     209
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0648
_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^)+(0.0579P)^2^+6.6936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4220
_reflns_number_total             4786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01123j2.cif
_cod_data_source_block           k11110-myc-g(chv914)_auto
_cod_depositor_comments
'Adding full bibliography for 7160667--7160674.cif.'
_cod_database_code               7160667
_shelx_shelxl_version_number     2018/3
_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 C(H,H,H) groups
2. Restrained distances
 C25-C28 \\sim C25-C35A
 with sigma of 0.02
 C31-C29 \\sim C38A-C36A
 with sigma of 0.04
 C31-C30 \\sim C38A-C37A
 with sigma of 0.02
 C30-C28 \\sim C37A-C35A
 with sigma of 0.04
 C25-C29 \\sim C25-C36A
 with sigma of 0.04
 C30-C29 \\sim C37A-C36A
 with sigma of 0.02
 C28-C29 \\sim C35A-C36A
 with sigma of 0.02
3. Rigid bond restraints
 C38A, C37A, C36A, C35A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C31, C29, C28, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C38A, C35A, C36A, C37A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C2) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C27) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(C14) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C24) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C38A) \\sim Ueq, Uanis(C37A)
\\sim Ueq, Uanis(C36A) \\sim Ueq, Uanis(C35A) \\sim Ueq: with sigma of 0.005
and sigma for terminal atoms of 0.005
Uanis(C29) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
5. Others
 Sof(C38A)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C37A)=Sof(H37A)=Sof(H37B)=
 Sof(C36A)=Sof(H36A)=Sof(H36B)=Sof(C35A)=Sof(H35A)=Sof(H35B)=1-FVAR(1)
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C28)=
 Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C18(H18A,H18B), C20(H20A,H20B), C30(H30A,H30B), C28(H28A,
 H28B), C29(H29A,H29B), C37A(H37A,H37B), C36A(H36A,H36B), C35A(H35A,H35B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C5(H5), C6(H6), C8(H8), C7(H7), C27(H27), C23(H23),
 C17(H17), C13(H13), C14(H14), C16(H16), C26(H26), C24(H24)
6.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C31(H31A,H31B,H31C), C38A(H38A,H38B,H38C)
;
_shelx_res_checksum              40235
_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 1.723
_oxdiff_exptl_absorpt_empirical_full_min 0.621