#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:56:51 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301156 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/41/1574126.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1574126
loop_
_publ_author_name
'Chang, Meng-Yang'
'Hsueh, Nai-Chen'
_publ_section_title
;
 One-pot synthesis of diaroyl benzothiepine-1,1-dioxides.
;
_journal_issue                   15
_journal_name_full               'Organic & 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -131.00 -87.00   0.50    0.23    --  -77.71 -30.00 -60.00   88
  2  ω   -124.00 -87.00   0.50    0.23    --  -77.71 -30.00 -90.00   74
  3  ω   -121.00 -95.00   0.50    0.23    --  -77.71 -30.00-120.00   52
  4  ω   -127.00 -86.00   0.50    0.23    --  -77.71 -30.00-150.00   82
  5  ω    -88.00 -30.00   0.50    0.23    --  -77.71 111.00-180.00  116
  6  ω    -69.00 -30.00   0.50    0.23    --  -77.71 111.00-120.00   78
  7  ω    -90.00 -36.00   0.50    0.23    --  -77.71 111.00  30.00  108
  8  ω    -85.00 -42.00   0.50    0.23    --  -77.71 111.00  90.00   86
  9  ω    -63.00 -37.00   0.50    0.23    --  -77.71 111.00 120.00   52
 10  ω    -65.00 -18.00   0.50    0.23    --  -57.29 125.00  90.00   94
 11  ω     67.00  93.00   0.50    0.23    --   55.92  30.00  90.00   52
 12  ω     90.00 129.00   0.50    0.23    --   83.05  30.00  60.00   78
 13  ω     75.00 120.00   0.50    0.23    --   67.81  30.00 -60.00   90
 14  ω    111.00 136.00   0.50    0.23    --   83.05  30.00 -60.00   50
 15  ω     67.00  94.00   0.50    0.23    --   55.92  30.00-120.00   54
 16  ω     91.00 132.00   0.50    0.23    --   83.05  30.00-150.00   82
 17  ω     55.00 134.00   0.50    0.23    --   83.05  15.00-180.00  158
 18  ω     33.00  66.00   0.50    0.23    --   55.92 -95.00-120.00   66
 19  ω     40.00  82.00   0.50    0.23    --   83.05 -95.00  60.00   84
 20  ω     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       'ω 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/[σ²(Fo²)+(0.1712P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.44579(19) 0.18167(18) 0.26888(15) 0.0533(7) Uani 1 1 d . . . . .
C2 C 0.3902(2) 0.2979(2) 0.28869(17) 0.0509(7) Uani 1 1 d . . . . .
C3 C 0.2716(2) 0.2871(2) 0.33103(17) 0.0506(7) Uani 1 1 d . . . . .
C4 C 0.2403(2) 0.1700(2) 0.37900(18) 0.0533(7) Uani 1 1 d . . . . .
H4 H 0.297093 0.096928 0.384285 0.064 Uiso 1 1 calc R U . . .
C5 C 0.1297(3) 0.1603(2) 0.41791(17) 0.0542(7) Uani 1 1 d . . . . .
H5 H 0.110660 0.080586 0.450302 0.065 Uiso 1 1 calc R U . . .
C6 C 0.0433(2) 0.2660(2) 0.41090(17) 0.0516(7) Uani 1 1 d . . . . .
C7 C 0.0736(2) 0.3822(2) 0.36392(18) 0.0540(7) Uani 1 1 d . . . . .
H7 H 0.016503 0.455104 0.358667 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1849(2) 0.3924(2) 0.32523(17) 0.0538(7) Uani 1 1 d . . . . .
H8 H 0.203902 0.472759 0.293650 0.065 Uiso 1 1 calc R U . . .
C9 C -0.0783(3) 0.2544(2) 0.45042(17) 0.0561(7) Uani 1 1 d D . . . .
C13 C 0.4452(2) 0.4214(2) 0.26935(16) 0.0526(7) Uani 1 1 d . . . . .
H13 H 0.405809 0.503278 0.283300 0.063 Uiso 1 1 calc R U . . .
F10 F -0.1202(3) 0.3700(2) 0.4792(2) 0.0923(11) Uani 0.821(4) 1 d D U P A 1
F11 F -0.16655(19) 0.2051(3) 0.38761(15) 0.0787(9) Uani 0.821(4) 1 d D U P A 1
F12 F -0.0738(2) 0.1721(3) 0.52559(16) 0.0775(9) Uani 0.821(4) 1 d D U P A 1
F10A F -0.1689(9) 0.3329(12) 0.4090(8) 0.075(3) Uani 0.179(4) 1 d D U P A 2
F11A F -0.1304(12) 0.1341(10) 0.4427(10) 0.087(4) Uani 0.179(4) 1 d D U P A 2
F12A F -0.0715(11) 0.2883(14) 0.5397(7) 0.088(4) Uani 0.179(4) 1 d D U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C2 120.53(15) 2_655 . ?
N1 C2 C3 116.3(2) . . ?
N1 C2 C13 120.8(3) . . ?
C13 C2 C3 122.9(2) . . ?
C4 C3 C2 121.1(2) . . ?
C8 C3 C2 121.5(2) . . ?
C8 C3 C4 117.5(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C9 121.3(2) . . ?
C7 C6 C5 118.5(3) . . ?
C7 C6 C9 120.2(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 H8 119.2 . . ?
C7 C8 C3 121.6(2) . . ?
C7 C8 H8 119.2 . . ?
F10 C9 C6 113.0(2) . . ?
F10 C9 F11 106.7(3) . . ?
F10 C9 F12 106.3(3) . . ?
F11 C9 C6 112.2(2) . . ?
F11 C9 F12 105.5(2) . . ?
F12 C9 C6 112.5(2) . . ?
F10A C9 C6 115.0(5) . . ?
F11A C9 C6 115.0(5) . . ?
F11A C9 F10A 102.2(8) . . ?
F12A C9 C6 112.3(5) . . ?
F12A C9 F10A 103.8(8) . . ?
F12A C9 F11A 107.4(8) . . ?
C2 C13 H13 120.7 . . ?
C13 C13 C2 118.70(15) 2_655 . ?
C13 C13 H13 120.7 2_655 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.329(4) 2_655 ?
N1 C2 1.348(3) . ?
C2 C3 1.465(4) . ?
C2 C13 1.406(3) . ?
C3 C4 1.408(3) . ?
C3 C8 1.402(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(3) . ?
C6 C7 1.391(3) . ?
C6 C9 1.477(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.367(4) . ?
C8 H8 0.9500 . ?
C9 F10 1.318(3) . ?
C9 F11 1.327(3) . ?
C9 F12 1.339(3) . ?
C9 F10A 1.338(9) . ?
C9 F11A 1.326(9) . ?
C9 F12A 1.299(9) . ?
C13 C13 1.347(5) 2_655 ?
C13 H13 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C2 C3 -179.4(2) 2_655 . . . ?
N1 N1 C2 C13 0.4(4) 2_655 . . . ?
N1 C2 C3 C4 21.9(3) . . . . ?
N1 C2 C3 C8 -157.9(2) . . . . ?
N1 C2 C13 C13 -0.1(4) . . . 2_655 ?
C2 C3 C4 C5 -179.7(2) . . . . ?
C2 C3 C8 C7 179.4(2) . . . . ?
C3 C2 C13 C13 179.7(2) . . . 2_655 ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C4 C5 C6 C9 178.1(2) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C5 C6 C9 F10 149.6(3) . . . . ?
C5 C6 C9 F11 -89.6(3) . . . . ?
C5 C6 C9 F12 29.2(3) . . . . ?
C5 C6 C9 F10A -154.6(7) . . . . ?
C5 C6 C9 F11A -36.2(8) . . . . ?
C5 C6 C9 F12A 87.0(7) . . . . ?
C6 C7 C8 C3 0.2(4) . . . . ?
C7 C6 C9 F10 -31.7(4) . . . . ?
C7 C6 C9 F11 89.1(3) . . . . ?
C7 C6 C9 F12 -152.0(2) . . . . ?
C7 C6 C9 F10A 24.1(7) . . . . ?
C7 C6 C9 F11A 142.5(8) . . . . ?
C7 C6 C9 F12A -94.3(7) . . . . ?
C8 C3 C4 C5 0.1(3) . . . . ?
C9 C6 C7 C8 -178.5(2) . . . . ?
C13 C2 C3 C4 -157.9(2) . . . . ?
C13 C2 C3 C8 22.3(3) . . . . ?
