# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_TSCl_200k
_database_code_depnum_ccdc_archive 'CCDC 2192388'
loop_
_audit_author_name
_audit_author_address
"Megan O'Shaughnessy"
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2022-07-25 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_audit_creation_date             2019-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            TSCl
_chemical_name_systematic        Tetrakis(4-sulfonylchloridephenyl)methane
_chemical_formula_moiety         'C25 H16 Cl4 O8 S4'
_chemical_formula_sum            'C25 H16 Cl4 O8 S4'
_chemical_formula_weight         714.42
_chemical_absolute_configuration ?
_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'
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      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   13.6104(8)
_cell_length_b                   13.6104(8)
_cell_length_c                   9.8000(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1815.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.895
_cell_measurement_theta_min      2.561
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.7145.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10185
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         2.561
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1647
_reflns_number_total             1842
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1842
_refine_ls_number_restraints     209
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.242
_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)+(0.0954P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1345
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.495(10)
 0.505(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Shared sites
{C1B, C1A}
4. Restrained distances
 Cl1B-S1B = Cl1A-S1A
 2.04 with sigma of 0.02
 S1B-O4A = S1A-O2A = S1B-O3A = S1A-O1A
 1.42 with sigma of 0.02
 C1B-C1 = C1A-C1
 1.49 with sigma of 0.005
 C6A-C1A = C6B-C1B = C6A-C5A = C6B-C5B = C5A-C4A = C5B-C4B = C4A-C3A = C4B-C3B
 = C3B-C2B = C3A-C2A = C2A-C1A = C2B-C1B
 1.39 with sigma of 0.01
 O2A-O1A
 2.48 with sigma of 0.02
 Cl1A-O1A \\sim Cl1A-O4A
 with sigma of 0.02
 Cl1B-O3A \\sim Cl1B-O4A
 with sigma of 0.02
5. Restrained planarity
 C1A, C2A, C3A, C4A, C5A, C6A
 with sigma of 0.001
 C1B, C2B, C3B, C4B, C5B, C6B
 with sigma of 0.001
6. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq, Uanis(C1B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(Cl1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1A) = Uanis(C1B)
Uanis(C1B) = Uanis(C1A)
7. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
8. Others
 Fixed Sof: C1A(0.5) C6A(0.5) H6A(0.5) C5A(0.5) H5A(0.5) C4A(0.5) C3A(0.5)
 H3A(0.5) C2A(0.5) H2A(0.5) Cl1A(0.5) O1A(0.5) O2A(0.5) S1A(0.5) C1B(0.5)
 C6B(0.5) H6B(0.5) C5B(0.5) H5B(0.5) C4B(0.5) C3B(0.5) H3B(0.5) C2B(0.5)
 H2B(0.5) Cl1B(0.5) O3A(0.5) O4A(0.5) S1B(0.5)
9.a Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C5A(H5A), C3A(H3A), C2A(H2A), C6B(H6B), C5B(H5B), C3B(H3B), C2B(H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.5000 0.5000 0.0000 0.0332(12) Uani 1 4 d DS TU P . .
C1A C 0.4390(4) 0.4377(4) 0.0984(3) 0.0361(7) Uani 0.5 1 d D U . A 1
C6A C 0.3442(9) 0.4668(13) 0.1323(15) 0.056(5) Uani 0.5 1 d D U . A 1
H6A H 0.3157 0.5214 0.0867 0.067 Uiso 0.5 1 calc R . . A 1
C5A C 0.2903(14) 0.4177(13) 0.2314(15) 0.050(4) Uani 0.5 1 d D U . A 1
H5A H 0.2255 0.4367 0.2556 0.059 Uiso 0.5 1 calc R . . A 1
C4A C 0.3375(12) 0.3394(14) 0.2922(17) 0.054(5) Uani 0.5 1 d D U . A 1
C3A C 0.4322(11) 0.3073(9) 0.2621(11) 0.058(5) Uani 0.5 1 d D U . A 1
H3A H 0.4602 0.2526 0.3081 0.070 Uiso 0.5 1 calc R . . A 1
C2A C 0.4844(9) 0.3580(7) 0.1621(8) 0.040(4) Uani 0.5 1 d D U . A 1
H2A H 0.5492 0.3389 0.1380 0.048 Uiso 0.5 1 calc R . . A 1
Cl1A Cl 0.3456(6) 0.3149(6) 0.5950(4) 0.106(3) Uani 0.5 1 d D U . A 1
O1A O 0.3028(18) 0.1634(13) 0.410(2) 0.108(6) Uani 0.5 1 d D U . A 1
O2A O 0.1787(10) 0.2760(16) 0.422(2) 0.094(5) Uani 0.5 1 d D U . A 1
S1A S 0.2803(7) 0.2667(8) 0.4226(8) 0.072(3) Uani 0.5 1 d D U . A 1
C1B C 0.4390(4) 0.4377(4) 0.0984(3) 0.0361(7) Uani 0.5 1 d D U . A 2
C6B C 0.3576(9) 0.4777(16) 0.1651(14) 0.057(5) Uani 0.5 1 d D U . A 2
H6B H 0.3379 0.5421 0.1395 0.068 Uiso 0.5 1 calc R . . A 2
C5B C 0.3035(15) 0.4312(15) 0.2655(16) 0.059(5) Uani 0.5 1 d D U . A 2
H5B H 0.2489 0.4634 0.3062 0.071 Uiso 0.5 1 calc R . . A 2
C4B C 0.3292(12) 0.3386(15) 0.3055(18) 0.059(5) Uani 0.5 1 d D U . A 2
C3B C 0.4086(9) 0.2948(13) 0.2439(11) 0.063(5) Uani 0.5 1 d D U . A 2
H3B H 0.4275 0.2304 0.2705 0.075 Uiso 0.5 1 calc R . . A 2
C2B C 0.4620(7) 0.3433(8) 0.1428(9) 0.037(3) Uani 0.5 1 d D U . A 2
H2B H 0.5165 0.3106 0.1027 0.045 Uiso 0.5 1 calc R . . A 2
Cl1B Cl 0.3059(10) 0.3596(9) 0.5889(10) 0.140(4) Uani 0.5 1 d D U . A 2
O3A O 0.293(3) 0.1895(16) 0.451(2) 0.141(9) Uani 0.5 1 d D U . A 2
O4A O 0.1699(16) 0.319(2) 0.422(3) 0.153(9) Uani 0.5 1 d D U . A 2
S1B S 0.2649(15) 0.2793(13) 0.4322(11) 0.105(4) Uani 0.5 1 d D U . 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
C1 C1A 1.529(3) . ?
C1 C1A 1.529(3) 4_655 ?
C1 C1A 1.529(3) 3_565 ?
C1 C1A 1.529(3) 2_665 ?
C1 C1B 1.529(3) 4_655 ?
C1 C1B 1.529(3) . ?
C1 C1B 1.529(3) 2_665 ?
C1 C1B 1.529(3) 3_565 ?
C1A C6A 1.389(12) . ?
C1A C2A 1.396(10) . ?
C6A H6A 0.9500 . ?
C6A C5A 1.388(13) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.380(13) . ?
C4A C3A 1.393(13) . ?
C4A S1A 1.79(2) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.394(11) . ?
C2A H2A 0.9500 . ?
Cl1A S1A 2.018(7) . ?
O1A S1A 1.445(19) . ?
O2A S1A 1.389(15) . ?
C1B C6B 1.396(12) . ?
C1B C2B 1.392(10) . ?
C6B H6B 0.9500 . ?
C6B C5B 1.382(13) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.366(13) . ?
C4B C3B 1.374(13) . ?
C4B S1B 1.72(2) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.395(11) . ?
C2B H2B 0.9500 . ?
Cl1B S1B 1.966(14) . ?
O3A S1B 1.29(2) . ?
O4A S1B 1.40(2) . ?

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
C1A C1 C1A 101.8(2) . 2_665 ?
C1A C1 C1A 101.8(2) 4_655 3_565 ?
C1A C1 C1A 113.41(11) 2_665 3_565 ?
C1A C1 C1A 113.41(11) . 4_655 ?
C1A C1 C1A 113.41(11) . 3_565 ?
C1A C1 C1A 113.41(11) 2_665 4_655 ?
C1B C1 C1B 113.41(11) . 4_655 ?
C1B C1 C1B 113.41(11) 2_665 3_565 ?
C1B C1 C1B 113.41(11) . 3_565 ?
C1B C1 C1B 113.41(11) 2_665 4_655 ?
C1B C1 C1B 101.8(2) 4_655 3_565 ?
C1B C1 C1B 101.8(2) . 2_665 ?
C6A C1A C1 119.8(9) . . ?
C6A C1A C2A 121.7(10) . . ?
C2A C1A C1 118.2(6) . . ?
C1A C6A H6A 119.3 . . ?
C5A C6A C1A 121.4(16) . . ?
C5A C6A H6A 119.3 . . ?
C6A C5A H5A 122.3 . . ?
C4A C5A C6A 115.3(18) . . ?
C4A C5A H5A 122.3 . . ?
C5A C4A C3A 125.6(18) . . ?
C5A C4A S1A 122.1(14) . . ?
C3A C4A S1A 112.3(13) . . ?
C4A C3A H3A 121.1 . . ?
C4A C3A C2A 117.7(14) . . ?
C2A C3A H3A 121.1 . . ?
C1A C2A H2A 120.9 . . ?
C3A C2A C1A 118.3(10) . . ?
C3A C2A H2A 120.9 . . ?
C4A S1A Cl1A 103.1(5) . . ?
O1A S1A C4A 112.7(12) . . ?
O1A S1A Cl1A 107.1(11) . . ?
O2A S1A C4A 112.3(13) . . ?
O2A S1A Cl1A 114.3(10) . . ?
O2A S1A O1A 107.4(12) . . ?
C6B C1B C1 120.6(10) . . ?
C2B C1B C1 125.9(6) . . ?
C2B C1B C6B 113.1(10) . . ?
C1B C6B H6B 117.3 . . ?
C5B C6B C1B 125.3(19) . . ?
C5B C6B H6B 117.3 . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B C6B 119(2) . . ?
C4B C5B H5B 120.3 . . ?
C5B C4B C3B 118(2) . . ?
C5B C4B S1B 120.6(16) . . ?
C3B C4B S1B 120.9(17) . . ?
C4B C3B H3B 119.4 . . ?
C4B C3B C2B 121.1(17) . . ?
C2B C3B H3B 119.4 . . ?
C1B C2B C3B 122.8(11) . . ?
C1B C2B H2B 118.6 . . ?
C3B C2B H2B 118.6 . . ?
C4B S1B Cl1B 99.1(8) . . ?
O3A S1B C4B 113.2(19) . . ?
O3A S1B Cl1B 109.4(13) . . ?
O3A S1B O4A 130(2) . . ?
O4A S1B C4B 104.0(17) . . ?
O4A S1B Cl1B 96.0(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.495(10)
2 0.505(10)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,1,2,2-Hexafluoro-2-propanol'
