One-pot synthesis of diaroyl benzothiepine-1,1-dioxides.
Chang, Meng-Yang; Hsueh, Nai-Chen; Organic & biomolecular chemistry 23 (2025) 3572–3582; doi:10.1039/d5ob00198f

data_1574123
_publ_section_title
;
 One-pot synthesis of diaroyl benzothiepine-1,1-dioxides.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3572
_journal_page_last               3582
_journal_paper_doi               10.1039/d5ob00198f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C39 H28 O6 S, C4 H8 O2'
_chemical_formula_sum            'C43 H36 Cl O8 S0.25'
_chemical_formula_weight         724.18
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.809(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5314(3)
_cell_length_b                   13.6665(4)
_cell_length_c                   25.0346(7)
_cell_measurement_reflns_used    12586
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.7760
_cell_measurement_theta_min      1.7030
_cell_volume                     3598.83(18)
_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 0.947
_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    -79.00  48.00   0.50   82.19    --   10.60 -37.00-120.00  254
  2  \w    -17.00 100.00   0.50   82.19    --   10.60  82.00  90.00  234
  3  \w    -17.00 100.00   0.50   82.19    --   10.60  82.00 -60.00  234
  4  \w    -79.00  38.00   0.50   82.19    --   10.60 -82.00  30.00  234
  5  \w    -15.00 100.00   0.50   82.19    --   10.60  77.00-150.00  230
  6  \w    -17.00  41.00   0.50   82.19    --   10.60  82.00   0.00  116
  7  \w    -15.00  10.00   0.50   82.19    --  -10.90 -82.00 -90.00   50
;
_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      0.0167431000
_diffrn_orient_matrix_UB_12      0.0388169000
_diffrn_orient_matrix_UB_13      0.0177761000
_diffrn_orient_matrix_UB_21      0.0077148000
_diffrn_orient_matrix_UB_22      -0.0338374000
_diffrn_orient_matrix_UB_23      0.0213657000
_diffrn_orient_matrix_UB_31      0.0649413000
_diffrn_orient_matrix_UB_32      -0.0059692000
_diffrn_orient_matrix_UB_33      -0.0056789000
_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  0.1160
_diffrn_reflns_av_unetI/netI     0.1912
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            37585
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.069
_diffrn_reflns_theta_min         1.629
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31140
_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    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1516
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1910
_refine_ls_R_factor_gt           0.0769
_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^)+(0.0730P)^2^+5.2674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4658
_reflns_number_total             7507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00198f2.cif
_cod_data_source_block           k11205-myc-i_auto
_cod_depositor_comments
'Adding full bibliography for 1574120--1574127.cif.'
_cod_database_code               1574123
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C5(H00B), C2(H00I), C4(H00N), C1(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C01A(H01I,H01J)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H00E), C14(H00F), C16(H00J), C21(H00L), C24(H00S), C15(H00V), C25(H00W),
 C8(H00X), C23(H00Y), C9(H00Z), C12(H010), C39(H011), C10(H012), C36(H013),
 C37(H014), C35(H015), C22(H016), C38(H017), C11(H018), C30(H01C), C28(H01D),
 C32(H01E), C29(H01F), C31(H01G)
2.d Idealised Me refined as rotating group:
 C019(H01A,H01B,H01H), C01B(H01K,H01L,H01M)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              52656
_shelx_fab_checksum              37766
_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 3.337
_oxdiff_exptl_absorpt_empirical_full_min 0.461