#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:16:20 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288725 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/01/1570153.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_1570153
loop_
_publ_author_name
'Yasuo, Eisuke'
'Aikawa, Kohsuke'
'Nozaki, Kyoko'
'Okazoe, Takashi'
_publ_section_title
;
 Fluoroalkylated hypervalent sulfur fluorides: radical addition of
 arylchlorotetrafluoro-λ⁶-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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  56.00   0.50    6.98    --   20.00  54.00  60.00   66
  2  ω     85.00 110.00   0.50    6.98    --   20.00  54.00  60.00   50
  3  ω    -73.00  67.00   0.50    6.98    --   20.00  54.00-180.00  280
  4  ω     73.00 110.00   0.50    6.98    --   20.00  54.00-180.00   74
  5  ω    -33.00  49.00   0.50    6.98    --   20.00  54.00 -60.00  164
  6  ω     82.00 107.00   0.50    6.98    --   20.00  54.00 -60.00   50
  7  ω    -61.00 -35.00   0.50    6.98    --   20.00  54.00-150.00   52
  8  ω     35.00  67.00   0.50    6.98    --   20.00  54.00-150.00   64
  9  ω    -68.00 -43.00   0.50    6.98    --   20.00  54.00 -30.00   50
 10  ω     11.00  36.00   0.50    6.98    --   20.00  54.00 -30.00   50
 11  ω    -20.00   5.00   0.50    6.98    --   20.00  54.00   0.00   50
 12  ω    -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       'ω 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/[σ²(Fo²)+(0.0540P)²+2.0655P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.853
_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)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S001 S 0.32569(10) 0.37801(9) 0.65672(6) 0.0509(3) Uani 1 1 d . . . . .
F003 F 0.2864(2) 0.5183(2) 0.68116(16) 0.0598(6) Uani 1 1 d . . . . .
F004 F 0.4731(2) 0.4251(2) 0.61572(17) 0.0646(6) Uani 1 1 d . . . . .
F005 F 0.1806(3) 0.3314(2) 0.70336(16) 0.0750(7) Uani 1 1 d . . . . .
F006 F 0.3709(3) 0.2377(2) 0.63878(18) 0.0763(7) Uani 1 1 d . . . . .
O008 O -0.1159(3) 0.3104(2) 0.17953(19) 0.0560(6) Uani 1 1 d . . . . .
N1 N -0.0282(3) 0.3959(3) 0.2114(2) 0.0456(6) Uani 1 1 d . . . . .
O00C O 0.0000(4) 0.4809(3) 0.1557(2) 0.0690(8) Uani 1 1 d . . . . .
C00E C 0.2105(3) 0.3862(3) 0.5249(2) 0.0354(6) Uani 1 1 d . . . . .
C00F C 0.2205(3) 0.4911(3) 0.4651(2) 0.0403(7) Uani 1 1 d . . . . .
H00F H 0.281740 0.559637 0.494518 0.048 Uiso 1 1 calc R U . . .
C00G C 0.0512(3) 0.3944(3) 0.3230(2) 0.0368(6) Uani 1 1 d . . . . .
C00H C 0.1404(4) 0.4952(3) 0.3621(2) 0.0422(7) Uani 1 1 d . . . . .
H00H H 0.146735 0.565979 0.319121 0.051 Uiso 1 1 calc R U . . .
C00I C 0.0362(4) 0.2914(3) 0.3828(2) 0.0398(7) Uani 1 1 d . . . . .
H00I H -0.028537 0.224496 0.353953 0.048 Uiso 1 1 calc R U . . .
C00J C 0.1173(4) 0.2867(3) 0.4857(2) 0.0409(7) Uani 1 1 d . . . . .
H00J H 0.109287 0.216451 0.528823 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4211(8) 0.3529(9) 0.8061(6) 0.053(2) Uani 0.527(11) 1 d D U P A 1
C1 C 0.5909(9) 0.3734(7) 0.8288(7) 0.063(3) Uani 0.527(11) 1 d D U P A 1
F1 F 0.3490(13) 0.4056(16) 0.8815(10) 0.077(4) Uani 0.527(11) 1 d D . P A 1
F3 F 0.4019(11) 0.2269(9) 0.8344(7) 0.0572(19) Uani 0.527(11) 1 d D U P A 1
Cl2 Cl 0.6688(9) 0.3463(9) 0.9619(6) 0.0610(13) Uani 0.527(11) 1 d . U P A 1
F9 F 0.6100(11) 0.4919(7) 0.8040(6) 0.0651(18) Uani 0.527(11) 1 d . . P A 1
F7 F 0.6410(16) 0.3028(15) 0.7687(12) 0.058(2) Uani 0.527(11) 1 d . . P A 1
F1A F 0.5353(11) 0.5023(8) 0.8006(7) 0.065(2) Uani 0.473(11) 1 d . . P A 2
C7A C 0.4680(16) 0.3972(10) 0.7865(8) 0.081(3) Uani 0.473(11) 1 d D . P A 2
C1A C 0.5195(14) 0.2980(9) 0.8508(8) 0.089(3) Uani 0.473(11) 1 d D . P A 2
F9A F 0.646(2) 0.2725(19) 0.7714(16) 0.084(5) Uani 0.473(11) 1 d . . P A 2
F7A F 0.4414(13) 0.1978(9) 0.8532(9) 0.061(2) Uani 0.473(11) 1 d . . P A 2
Cl2A Cl 0.6306(10) 0.3311(9) 0.9776(7) 0.0600(14) Uani 0.473(11) 1 d . . P A 2
F3A F 0.3538(19) 0.4332(17) 0.8614(10) 0.067(3) Uani 0.473(11) 1 d . . 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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
F003 S001 F004 89.83(13) . . ?
F003 S001 F005 89.55(14) . . ?
F003 S001 C00E 92.02(12) . . ?
F003 S001 C7 90.2(3) . . ?
F003 S001 C7A 81.8(4) . . ?
F004 S001 F005 177.51(12) . . ?
F004 S001 C00E 91.21(12) . . ?
F004 S001 C7 98.5(2) . . ?
F004 S001 C7A 79.1(4) . . ?
F005 S001 C00E 91.22(12) . . ?
F005 S001 C7 79.1(2) . . ?
F005 S001 C7A 98.4(4) . . ?
F006 S001 F003 176.76(12) . . ?
F006 S001 F004 89.96(15) . . ?
F006 S001 F005 90.51(15) . . ?
F006 S001 C00E 91.22(12) . . ?
F006 S001 C7 86.6(3) . . ?
F006 S001 C7A 95.0(4) . . ?
C00E S001 C7 170.0(3) . . ?
C00E S001 C7A 168.4(3) . . ?
O008 N1 C00G 118.1(3) . . ?
O00C N1 O008 123.9(3) . . ?
O00C N1 C00G 118.1(3) . . ?
C00F C00E S001 118.7(2) . . ?
C00F C00E C00J 121.8(3) . . ?
C00J C00E S001 119.5(2) . . ?
C00E C00F H00F 120.4 . . ?
C00E C00F C00H 119.3(3) . . ?
C00H C00F H00F 120.4 . . ?
C00H C00G N1 118.6(3) . . ?
C00I C00G N1 118.6(3) . . ?
C00I C00G C00H 122.8(3) . . ?
C00F C00H H00H 120.7 . . ?
C00G C00H C00F 118.5(3) . . ?
C00G C00H H00H 120.7 . . ?
C00G C00I H00I 120.6 . . ?
C00G C00I C00J 118.7(3) . . ?
C00J C00I H00I 120.6 . . ?
C00E C00J H00J 120.5 . . ?
C00I C00J C00E 118.9(3) . . ?
C00I C00J H00J 120.5 . . ?
C1 C7 S001 113.0(6) . . ?
F1 C7 S001 117.6(7) . . ?
F1 C7 C1 113.4(8) . . ?
F1 C7 F3 96.2(9) . . ?
F3 C7 S001 109.5(6) . . ?
F3 C7 C1 105.0(7) . . ?
C7 C1 Cl2 110.7(6) . . ?
F9 C1 C7 105.5(8) . . ?
F9 C1 Cl2 110.6(7) . . ?
F7 C1 C7 105.6(10) . . ?
F7 C1 Cl2 113.4(9) . . ?
F7 C1 F9 110.7(10) . . ?
F1A C7A S001 115.7(7) . . ?
F1A C7A C1A 120.7(9) . . ?
F1A C7A F3A 92.3(12) . . ?
C1A C7A S001 122.3(7) . . ?
C1A C7A F3A 89.8(11) . . ?
F3A C7A S001 99.7(9) . . ?
C7A C1A F9A 86.6(11) . . ?
C7A C1A Cl2A 117.5(8) . . ?
F9A C1A Cl2A 106.0(10) . . ?
F7A C1A C7A 123.1(10) . . ?
F7A C1A F9A 108.2(13) . . ?
F7A C1A Cl2A 110.5(8) . . ?
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
S001 F003 1.593(2) . ?
S001 F004 1.600(2) . ?
S001 F005 1.618(2) . ?
S001 F006 1.589(2) . ?
S001 C00E 1.808(3) . ?
S001 C7 1.968(8) . ?
S001 C7A 1.902(10) . ?
O008 N1 1.223(4) . ?
N1 O00C 1.221(4) . ?
N1 C00G 1.475(4) . ?
C00E C00F 1.379(4) . ?
C00E C00J 1.386(4) . ?
C00F H00F 0.9500 . ?
C00F C00H 1.381(4) . ?
C00G C00H 1.378(4) . ?
C00G C00I 1.372(4) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00I C00J 1.383(4) . ?
C00J H00J 0.9500 . ?
C7 C1 1.504(11) . ?
C7 F1 1.395(12) . ?
C7 F3 1.420(12) . ?
C1 Cl2 1.747(11) . ?
C1 F9 1.331(11) . ?
C1 F7 1.235(16) . ?
F1A C7A 1.275(13) . ?
C7A C1A 1.372(12) . ?
C7A F3A 1.593(19) . ?
C1A F9A 1.70(2) . ?
C1A F7A 1.286(13) . ?
C1A Cl2A 1.774(13) . ?
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
S001 C00E C00F C00H 176.0(2) . . . . ?
S001 C00E C00J C00I -176.5(2) . . . . ?
S001 C7 C1 Cl2 -178.7(5) . . . . ?
S001 C7 C1 F9 61.7(8) . . . . ?
S001 C7 C1 F7 -55.6(10) . . . . ?
S001 C7A C1A F9A 82.4(13) . . . . ?
S001 C7A C1A F7A -27(2) . . . . ?
S001 C7A C1A Cl2A -171.3(8) . . . . ?
F003 S001 C00E C00F 43.6(2) . . . . ?
F003 S001 C00E C00J -137.7(2) . . . . ?
F004 S001 C00E C00F -46.3(2) . . . . ?
F004 S001 C00E C00J 132.4(3) . . . . ?
F005 S001 C00E C00F 133.2(2) . . . . ?
F005 S001 C00E C00J -48.1(3) . . . . ?
F006 S001 C00E C00F -136.3(3) . . . . ?
F006 S001 C00E C00J 42.4(3) . . . . ?
O008 N1 C00G C00H -174.7(3) . . . . ?
O008 N1 C00G C00I 7.0(4) . . . . ?
N1 C00G C00H C00F -176.9(3) . . . . ?
N1 C00G C00I C00J 176.4(3) . . . . ?
O00C N1 C00G C00H 6.8(4) . . . . ?
O00C N1 C00G C00I -171.5(3) . . . . ?
C00E C00F C00H C00G 0.9(4) . . . . ?
C00F C00E C00J C00I 2.1(5) . . . . ?
C00G C00I C00J C00E 0.1(4) . . . . ?
C00H C00G C00I C00J -1.8(5) . . . . ?
C00I C00G C00H C00F 1.3(5) . . . . ?
C00J C00E C00F C00H -2.6(5) . . . . ?
F1 C7 C1 Cl2 44.3(11) . . . . ?
F1 C7 C1 F9 -75.3(11) . . . . ?
F1 C7 C1 F7 167.4(11) . . . . ?
F3 C7 C1 Cl2 -59.5(8) . . . . ?
F3 C7 C1 F9 -179.1(7) . . . . ?
F3 C7 C1 F7 63.6(11) . . . . ?
F1A C7A C1A F9A -83.7(17) . . . . ?
F1A C7A C1A F7A 166.7(14) . . . . ?
F1A C7A C1A Cl2A 23(2) . . . . ?
C7A S001 C00E C00F -14(2) . . . . ?
C7A S001 C00E C00J 165(2) . . . . ?
F3A C7A C1A F9A -176.3(11) . . . . ?
F3A C7A C1A F7A 74.1(16) . . . . ?
F3A C7A C1A Cl2A -70.0(13) . . . . ?
