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_1574126
_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         'C18 H10 F6 N2'
_chemical_formula_sum            'C18 H10 F6 N2'
_chemical_formula_weight         368.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-06 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.720(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7515(16)
_cell_length_b                   9.9866(15)
_cell_length_c                   14.1041(19)
_cell_measurement_reflns_used    2195
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      72.3600
_cell_measurement_theta_min      6.2670
_cell_volume                     1506.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -131.00 -87.00   0.50    0.23    --  -77.71 -30.00 -60.00   88
  2  \w   -124.00 -87.00   0.50    0.23    --  -77.71 -30.00 -90.00   74
  3  \w   -121.00 -95.00   0.50    0.23    --  -77.71 -30.00-120.00   52
  4  \w   -127.00 -86.00   0.50    0.23    --  -77.71 -30.00-150.00   82
  5  \w    -88.00 -30.00   0.50    0.23    --  -77.71 111.00-180.00  116
  6  \w    -69.00 -30.00   0.50    0.23    --  -77.71 111.00-120.00   78
  7  \w    -90.00 -36.00   0.50    0.23    --  -77.71 111.00  30.00  108
  8  \w    -85.00 -42.00   0.50    0.23    --  -77.71 111.00  90.00   86
  9  \w    -63.00 -37.00   0.50    0.23    --  -77.71 111.00 120.00   52
 10  \w    -65.00 -18.00   0.50    0.23    --  -57.29 125.00  90.00   94
 11  \w     67.00  93.00   0.50    0.23    --   55.92  30.00  90.00   52
 12  \w     90.00 129.00   0.50    0.23    --   83.05  30.00  60.00   78
 13  \w     75.00 120.00   0.50    0.23    --   67.81  30.00 -60.00   90
 14  \w    111.00 136.00   0.50    0.23    --   83.05  30.00 -60.00   50
 15  \w     67.00  94.00   0.50    0.23    --   55.92  30.00-120.00   54
 16  \w     91.00 132.00   0.50    0.23    --   83.05  30.00-150.00   82
 17  \w     55.00 134.00   0.50    0.23    --   83.05  15.00-180.00  158
 18  \w     33.00  66.00   0.50    0.23    --   55.92 -95.00-120.00   66
 19  \w     40.00  82.00   0.50    0.23    --   83.05 -95.00  60.00   84
 20  \w     56.00  87.00   0.50    0.23    --   83.05 -95.00 150.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0372340000
_diffrn_orient_matrix_UB_12      0.0986334000
_diffrn_orient_matrix_UB_13      -0.0818897000
_diffrn_orient_matrix_UB_21      -0.1076725000
_diffrn_orient_matrix_UB_22      -0.0935801000
_diffrn_orient_matrix_UB_23      -0.0378411000
_diffrn_orient_matrix_UB_31      -0.0880654000
_diffrn_orient_matrix_UB_32      0.0727127000
_diffrn_orient_matrix_UB_33      0.0627169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4122
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         6.062
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
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    1.623
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1346
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0694
_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^)+(0.1712P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2092
_refine_ls_wR_factor_ref         0.2225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1061
_reflns_number_total             1346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00198f2.cif
_cod_data_source_block           2501053lt_auto
_cod_depositor_comments
'Adding full bibliography for 1574120--1574127.cif.'
_cod_database_code               1574126
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.848
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F10-C9 \\sim F10A-C9
 with sigma of 0.02
 F12-C9 \\sim F12A-C9
 with sigma of 0.02
 F11-C9 \\sim F11A-C9
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F10 \\sim F11 \\sim F12 \\sim F10A \\sim F11A \\sim F12A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(1)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C13(H13)
;
_shelx_res_checksum              49811
_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 1.474
_oxdiff_exptl_absorpt_empirical_full_min 0.680