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_1574122
_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         'C16 H10 Cl2 N2'
_chemical_formula_sum            'C16 H10 Cl2 N2'
_chemical_formula_weight         301.16
_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             2023-09-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 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                 100.168(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4787(3)
_cell_length_b                   13.8797(4)
_cell_length_c                   6.2389(2)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8750
_cell_measurement_theta_min      1.9780
_cell_volume                     1319.31(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 0.963
_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    -79.00 100.00   0.50    7.69    --   10.60   0.00 120.00  358
  2  \w    -15.00 100.00   0.50    7.69    --   10.60  77.00 -90.00  230
  3  \w    -79.00  38.00   0.50    7.69    --   10.60 -82.00-180.00  234
  4  \w    -15.00 100.00   0.50    7.69    --   10.60  77.00 -30.00  230
  5  \w    -17.00 100.00   0.50    7.69    --   10.60  82.00 150.00  234
  6  \w    -38.00   8.00   0.50    7.69    --  -10.90  82.00 -90.00   92
  7  \w    -41.00  79.00   0.50    7.69    --  -10.90  57.00  30.00  240
;
_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      -0.0405506000
_diffrn_orient_matrix_UB_12      -0.0233490000
_diffrn_orient_matrix_UB_13      -0.0381745000
_diffrn_orient_matrix_UB_21      0.0223940000
_diffrn_orient_matrix_UB_22      -0.0443713000
_diffrn_orient_matrix_UB_23      -0.0038159000
_diffrn_orient_matrix_UB_31      -0.0047509000
_diffrn_orient_matrix_UB_32      -0.0097529000
_diffrn_orient_matrix_UB_33      0.1089564000
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            18065
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.975
_diffrn_reflns_theta_min         1.985
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40803
_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    1.516
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0410P)^2^+0.2720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2290
_reflns_number_total             2758
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00198f2.cif
_cod_data_source_block           k11208-myc-d(lysh0821)_auto
_cod_depositor_comments
'Adding full bibliography for 1574120--1574127.cif.'
_cod_database_code               1574122
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.831
_shelx_estimated_absorpt_t_min   0.795
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H008), C5(H00A), C4(H00B), C1(H00C), C9(H00D), C16(H00E), C2(H00F),
 C12(H00G), C15(H00I), C13(H00J)
;
_shelx_res_checksum              232
_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 1.585
_oxdiff_exptl_absorpt_empirical_full_min 0.464