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_1574127
_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         '0.471(C20 H12 O4 S3), 0.235(H2 O)'
_chemical_formula_sum            'C9.41 H6.12 O2.12 S1.41'
_chemical_formula_weight         198.35
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-19
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.894(3)
_cell_angle_gamma                90
_cell_formula_units_Z            17
_cell_length_a                   16.4453(6)
_cell_length_b                   11.4878(5)
_cell_length_c                   20.1149(8)
_cell_measurement_reflns_used    21036
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8000
_cell_measurement_theta_min      2.0060
_cell_volume                     3798.0(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   11.32    --   10.60  82.00-180.00  234
  2  \w    -15.00 100.00   0.50   11.32    --   10.60  77.00 -30.00  230
  3  \w    -17.00 100.00   0.50   11.32    --   10.60  82.00-150.00  234
  4  \w    -17.00 100.00   0.50   11.32    --   10.60  82.00-120.00  234
  5  \w    -79.00  36.00   0.50   11.32    --   10.60 -77.00   0.00  230
  6  \w    -17.00 100.00   0.50   11.32    --   10.60  82.00 150.00  234
  7  \w    -37.00  78.00   0.50   11.32    --  -10.90  80.00-172.05  230
  8  \w   -100.00  20.00   0.50   11.32    --  -10.90 -57.00   0.00  240
  9  \w    -79.00   1.00   0.50   11.32    --   10.60 -82.00 150.00  160
 10  \w    -79.00  41.00   0.50   11.32    --   10.60 -57.00 -90.00  240
 11  \w    -36.00  79.00   0.50   11.32    --  -10.90  77.00 -90.00  230
 12  \w    -38.00  79.00   0.50   11.32    --  -10.90  82.00  90.00  234
;
_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      -0.0030625000
_diffrn_orient_matrix_UB_12      0.0520429000
_diffrn_orient_matrix_UB_13      0.0187264000
_diffrn_orient_matrix_UB_21      0.0021332000
_diffrn_orient_matrix_UB_22      -0.0327723000
_diffrn_orient_matrix_UB_23      0.0298940000
_diffrn_orient_matrix_UB_31      0.0429848000
_diffrn_orient_matrix_UB_32      0.0053568000
_diffrn_orient_matrix_UB_33      0.0009877000
_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  0.4948
_diffrn_reflns_av_unetI/netI     0.1251
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            56326
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.026
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11451
_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    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.844
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         6662
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.1004
_refine_ls_shift/su_max          1.322
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2934
_refine_ls_wR_factor_ref         0.3212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4917
_reflns_number_total             6662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00198f2.cif
_cod_data_source_block           k11301-myc-a(lys0509)_auto
_cod_depositor_comments
'Adding full bibliography for 1574120--1574127.cif.'
_cod_database_code               1574127
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.885
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
S5 \\sim S2 \\sim S4 \\sim S3 \\sim S6 \\sim S1 \\sim O007 \\sim O7 \\sim O8
\\sim O3 \\sim O2 \\sim O6 \\sim O5 \\sim O4 \\sim O1: within 2A with sigma of
0.001 and sigma for terminal atoms of 3.8 within 2A
3.a Free rotating group:
 O007(H00a,H00b)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H00N), C29(H00P), C34(H00S), C14(H00T), C32(H00X), C27(H00Y), C23(H00Z),
 C3(H010), C30(H012), C22(H013), C31(H015), C12(H016), C38(H017), C9(H018),
 C21(H01A), C39(H01B), C11(H01C), C18(H01D), C2(H01E), C40(H01F), C1(H01G),
 C10(H01H), C19(H01I), C20(H01J)
;
_shelx_res_checksum              74068
_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 6.151
_oxdiff_exptl_absorpt_empirical_full_min 0.339