# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_y2-8_auto
_database_code_depnum_ccdc_archive 'CCDC 2282789'
loop_
_audit_author_name
_audit_author_address
'Eisuke Yasuo'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-04-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_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
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.9467(4)
_cell_length_b                   10.7344(4)
_cell_length_c                   12.9509(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.742(4)
_cell_angle_gamma                90
_cell_volume                     1217.74(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4496
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      30.4020
_cell_measurement_theta_min      2.3440
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.745
_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_absorpt_special_details   ?
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.277
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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
_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_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2091
_reflns_number_total             2487
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.111
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
