Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ<sup>6</sup>-sulfanes to tetrafluoroethylene.
Yasuo, Eisuke; Aikawa, Kohsuke; Nozaki, Kyoko; Okazoe, Takashi; Chemical science 14 (2023) 12379–12385; doi:10.1039/d3sc04837c

data_1570153
_publ_section_title
;
 Fluoroalkylated hypervalent sulfur fluorides: radical addition of
 arylchlorotetrafluoro-&#x3bb;<sup>6</sup>-sulfanes to
 tetrafluoroethylene.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              12379
_journal_page_last               12385
_journal_paper_doi               10.1039/d3sc04837c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C8 H4 Cl F8 N O2 S'
_chemical_formula_sum            'C8 H4 Cl F8 N O2 S'
_chemical_formula_weight         365.63
_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             2021-04-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-07-19 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.742(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9467(4)
_cell_length_b                   10.7344(4)
_cell_length_c                   12.9509(5)
_cell_measurement_reflns_used    4496
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      30.4020
_cell_measurement_theta_min      2.3440
_cell_volume                     1217.74(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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     23.00  56.00   0.50    6.98    --   20.00  54.00  60.00   66
  2  \w     85.00 110.00   0.50    6.98    --   20.00  54.00  60.00   50
  3  \w    -73.00  67.00   0.50    6.98    --   20.00  54.00-180.00  280
  4  \w     73.00 110.00   0.50    6.98    --   20.00  54.00-180.00   74
  5  \w    -33.00  49.00   0.50    6.98    --   20.00  54.00 -60.00  164
  6  \w     82.00 107.00   0.50    6.98    --   20.00  54.00 -60.00   50
  7  \w    -61.00 -35.00   0.50    6.98    --   20.00  54.00-150.00   52
  8  \w     35.00  67.00   0.50    6.98    --   20.00  54.00-150.00   64
  9  \w    -68.00 -43.00   0.50    6.98    --   20.00  54.00 -30.00   50
 10  \w     11.00  36.00   0.50    6.98    --   20.00  54.00 -30.00   50
 11  \w    -20.00   5.00   0.50    6.98    --   20.00  54.00   0.00   50
 12  \w    -35.00  -8.00   0.50    6.98    --   20.00  54.00  60.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8456
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.325
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.277
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.068
_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     254
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0540P)^2^+2.0655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2091
_reflns_number_total             2487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04837c2.cif
_cod_data_source_block           y2-8_auto
_cod_depositor_comments          'Adding full bibliography for 1570153.cif.'
_cod_database_code               1570153
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.745
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C7-C1
 1.524 with sigma of 0.02
 C7A-C1A
 1.524 with sigma of 0.02
 F1-C7 \\sim C7-F3
 with sigma of 0.02
3. Rigid bond restraints
 C1, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, Cl2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F3, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C7, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 F7A, C1A, F9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3A, C7A, F1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F1A)=Sof(C7A)=Sof(C1A)=Sof(F9A)=Sof(F7A)=Sof(Cl2A)=Sof(F3A)=1-FVAR(1)
 Sof(C7)=Sof(C1)=Sof(F1)=Sof(F3)=Sof(Cl2)=Sof(F9)=Sof(F7)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J)
;
_shelx_res_checksum              68415
_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
;