# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Tn1
_audit_block_doi                 10.5517/ccdc.csd.cc21zt2y
_database_code_depnum_ccdc_archive 'CCDC 1906440'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9TC04176A 2019
loop_
_audit_author_name
_audit_author_address
'Yosuke Tani'
;Osaka University
Japan
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H44 Br2 O2 S2 Si2'
_chemical_formula_weight         692.75

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   12.0795(9)
_cell_length_b                   9.5698(6)
_cell_length_c                   27.9836(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.019(7)
_cell_angle_gamma                90
_cell_volume                     3232.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    11920
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      54.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.734
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8174
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax RAPID?U'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15261
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.716
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3689
_reflns_number_gt                3025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Rigaku RAPID AUTO'
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_structure_solution    Yadokari-SG
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+3.7827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3689
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0604
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
S1 S -0.16669(4) 0.21079(5) 0.64868(2) 0.01843(11) Uani 1 1 d . . . . .
C1 C -0.28523(15) 0.1115(2) 0.64942(7) 0.0173(4) Uani 1 1 d . . . . .
C2 C -0.28313(17) 0.0269(2) 0.68909(7) 0.0216(4) Uani 1 1 d . . . . .
H1 H -0.3404 -0.0373 0.6959 0.026 Uiso 1 1 calc R U . . .
C3 C -0.18740(17) 0.0450(2) 0.71868(7) 0.0196(4) Uani 1 1 d . . . . .
C4 C -0.11529(16) 0.1428(2) 0.70230(7) 0.0173(4) Uani 1 1 d . . . . .
C5 C -0.01060(17) 0.1962(2) 0.72260(7) 0.0208(4) Uani 1 1 d . . . . .
O1 O 0.05461(13) 0.26180(18) 0.69936(6) 0.0367(4) Uani 1 1 d . . . . .
Br1 Br -0.16138(2) -0.06507(3) 0.77340(2) 0.03282(8) Uani 1 1 d . . . . .
Si1 Si -0.39778(4) 0.11402(6) 0.60067(2) 0.01590(12) Uani 1 1 d . . . . .
C6 C -0.39218(17) 0.2864(2) 0.56775(7) 0.0216(4) Uani 1 1 d . . . . .
H2 H -0.3124 0.3040 0.5614 0.026 Uiso 1 1 calc R U . . .
C7 C -0.4323(2) 0.4126(2) 0.59590(9) 0.0325(6) Uani 1 1 d . . . . .
H3 H -0.4194 0.4982 0.5777 0.049 Uiso 1 1 calc R U . . .
H4 H -0.3916 0.4175 0.6268 0.049 Uiso 1 1 calc R U . . .
H5 H -0.5117 0.4029 0.6012 0.049 Uiso 1 1 calc R U . . .
C8 C -0.45350(19) 0.2813(2) 0.51852(7) 0.0262(5) Uani 1 1 d . . . . .
H6 H -0.5318 0.2595 0.5228 0.039 Uiso 1 1 calc R U . . .
H7 H -0.4204 0.2088 0.4988 0.039 Uiso 1 1 calc R U . . .
H8 H -0.4473 0.3721 0.5027 0.039 Uiso 1 1 calc R U . . .
C9 C -0.36564(16) -0.0320(2) 0.55803(7) 0.0201(4) Uani 1 1 d . . . . .
H9 H -0.4240 -0.0299 0.5318 0.024 Uiso 1 1 calc R U . . .
C10 C -0.25395(18) -0.0109(3) 0.53473(8) 0.0305(5) Uani 1 1 d . . . . .
H10 H -0.1943 -0.0133 0.5594 0.046 Uiso 1 1 calc R U . . .
H11 H -0.2536 0.0798 0.5184 0.046 Uiso 1 1 calc R U . . .
H12 H -0.2425 -0.0855 0.5114 0.046 Uiso 1 1 calc R U . . .
C11 C -0.3705(2) -0.1771(2) 0.58126(8) 0.0284(5) Uani 1 1 d . . . . .
H13 H -0.3529 -0.2486 0.5576 0.043 Uiso 1 1 calc R U . . .
H14 H -0.4450 -0.1935 0.5928 0.043 Uiso 1 1 calc R U . . .
H15 H -0.3165 -0.1818 0.6082 0.043 Uiso 1 1 calc R U . . .
C12 C -0.53131(16) 0.0739(2) 0.63076(7) 0.0203(4) Uani 1 1 d . . . . .
H16 H -0.5217 -0.0215 0.6448 0.024 Uiso 1 1 calc R U . . .
C13 C -0.62947(17) 0.0626(2) 0.59449(8) 0.0276(5) Uani 1 1 d . . . . .
H17 H -0.6954 0.0314 0.6109 0.041 Uiso 1 1 calc R U . . .
H18 H -0.6118 -0.0049 0.5696 0.041 Uiso 1 1 calc R U . . .
H19 H -0.6438 0.1542 0.5799 0.041 Uiso 1 1 calc R U . . .
C14 C -0.5610(2) 0.1698(3) 0.67254(9) 0.0367(6) Uani 1 1 d . . . . .
H20 H -0.5802 0.2629 0.6602 0.055 Uiso 1 1 calc R U . . .
H21 H -0.4973 0.1770 0.6951 0.055 Uiso 1 1 calc R U . . .
H22 H -0.6243 0.1306 0.6889 0.055 Uiso 1 1 calc R U . . .


_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
S1 C1 1.719(2) . ?
S1 C4 1.7305(18) . ?
C1 C2 1.374(3) . ?
C1 Si1 1.8919(19) . ?
C2 C3 1.409(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.369(3) . ?
C3 Br1 1.8760(19) . ?
C4 C5 1.460(3) . ?
C5 O1 1.214(3) . ?
C5 C5 1.546(4) 2_556 ?
Si1 C12 1.885(2) . ?
Si1 C9 1.887(2) . ?
Si1 C6 1.892(2) . ?
C6 C7 1.530(3) . ?
C6 C8 1.542(3) . ?
C6 H2 1.0000 . ?
C7 H3 0.9800 . ?
C7 H4 0.9800 . ?
C7 H5 0.9800 . ?
C8 H6 0.9800 . ?
C8 H7 0.9800 . ?
C8 H8 0.9800 . ?
C9 C10 1.533(3) . ?
C9 C11 1.535(3) . ?
C9 H9 1.0000 . ?
C10 H10 0.9800 . ?
C10 H11 0.9800 . ?
C10 H12 0.9800 . ?
C11 H13 0.9800 . ?
C11 H14 0.9800 . ?
C11 H15 0.9800 . ?
C12 C13 1.537(3) . ?
C12 C14 1.538(3) . ?
C12 H16 1.0000 . ?
C13 H17 0.9800 . ?
C13 H18 0.9800 . ?
C13 H19 0.9800 . ?
C14 H20 0.9800 . ?
C14 H21 0.9800 . ?
C14 H22 0.9800 . ?

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
C1 S1 C4 93.18(9) . . ?
C2 C1 S1 110.11(14) . . ?
C2 C1 Si1 125.63(15) . . ?
S1 C1 Si1 124.19(11) . . ?
C1 C2 C3 113.20(18) . . ?
C1 C2 H1 123.4 . . ?
C3 C2 H1 123.4 . . ?
C4 C3 C2 113.96(17) . . ?
C4 C3 Br1 124.55(14) . . ?
C2 C3 Br1 121.41(15) . . ?
C3 C4 C5 131.41(18) . . ?
C3 C4 S1 109.53(14) . . ?
C5 C4 S1 119.04(15) . . ?
O1 C5 C4 122.81(18) . . ?
O1 C5 C5 116.33(19) . 2_556 ?
C4 C5 C5 119.8(2) . 2_556 ?
C12 Si1 C9 109.27(9) . . ?
C12 Si1 C1 106.25(9) . . ?
C9 Si1 C1 106.73(9) . . ?
C12 Si1 C6 116.15(10) . . ?
C9 Si1 C6 109.06(9) . . ?
C1 Si1 C6 108.96(9) . . ?
C7 C6 C8 109.54(17) . . ?
C7 C6 Si1 114.85(15) . . ?
C8 C6 Si1 112.50(14) . . ?
C7 C6 H2 106.5 . . ?
C8 C6 H2 106.5 . . ?
Si1 C6 H2 106.5 . . ?
C6 C7 H3 109.5 . . ?
C6 C7 H4 109.5 . . ?
H3 C7 H4 109.5 . . ?
C6 C7 H5 109.5 . . ?
H3 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
C6 C8 H6 109.5 . . ?
C6 C8 H7 109.5 . . ?
H6 C8 H7 109.5 . . ?
C6 C8 H8 109.5 . . ?
H6 C8 H8 109.5 . . ?
H7 C8 H8 109.5 . . ?
C10 C9 C11 110.30(18) . . ?
C10 C9 Si1 112.02(15) . . ?
C11 C9 Si1 112.99(14) . . ?
C10 C9 H9 107.1 . . ?
C11 C9 H9 107.1 . . ?
Si1 C9 H9 107.1 . . ?
C9 C10 H10 109.5 . . ?
C9 C10 H11 109.5 . . ?
H10 C10 H11 109.5 . . ?
C9 C10 H12 109.5 . . ?
H10 C10 H12 109.5 . . ?
H11 C10 H12 109.5 . . ?
C9 C11 H13 109.5 . . ?
C9 C11 H14 109.5 . . ?
H13 C11 H14 109.5 . . ?
C9 C11 H15 109.5 . . ?
H13 C11 H15 109.5 . . ?
H14 C11 H15 109.5 . . ?
C13 C12 C14 110.41(18) . . ?
C13 C12 Si1 111.82(14) . . ?
C14 C12 Si1 116.36(15) . . ?
C13 C12 H16 105.8 . . ?
C14 C12 H16 105.8 . . ?
Si1 C12 H16 105.8 . . ?
C12 C13 H17 109.5 . . ?
C12 C13 H18 109.5 . . ?
H17 C13 H18 109.5 . . ?
C12 C13 H19 109.5 . . ?
H17 C13 H19 109.5 . . ?
H18 C13 H19 109.5 . . ?
C12 C14 H20 109.5 . . ?
C12 C14 H21 109.5 . . ?
H20 C14 H21 109.5 . . ?
C12 C14 H22 109.5 . . ?
H20 C14 H22 109.5 . . ?
H21 C14 H22 109.5 . . ?

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
C4 S1 C1 C2 -1.46(17) . . . . ?
C4 S1 C1 Si1 -178.73(13) . . . . ?
S1 C1 C2 C3 1.1(2) . . . . ?
Si1 C1 C2 C3 178.33(15) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 Br1 -176.77(15) . . . . ?
C2 C3 C4 C5 177.4(2) . . . . ?
Br1 C3 C4 C5 -5.9(3) . . . . ?
C2 C3 C4 S1 -1.1(2) . . . . ?
Br1 C3 C4 S1 175.56(12) . . . . ?
C1 S1 C4 C3 1.44(16) . . . . ?
C1 S1 C4 C5 -177.26(17) . . . . ?
C3 C4 C5 O1 164.5(2) . . . . ?
S1 C4 C5 O1 -17.1(3) . . . . ?
C3 C4 C5 C5 -27.8(3) . . . 2_556 ?
S1 C4 C5 C5 150.58(11) . . . 2_556 ?
C2 C1 Si1 C12 33.3(2) . . . . ?
S1 C1 Si1 C12 -149.87(13) . . . . ?
C2 C1 Si1 C9 -83.2(2) . . . . ?
S1 C1 Si1 C9 93.61(15) . . . . ?
C2 C1 Si1 C6 159.14(19) . . . . ?
S1 C1 Si1 C6 -24.02(16) . . . . ?
C12 Si1 C6 C7 47.88(18) . . . . ?
C9 Si1 C6 C7 171.84(15) . . . . ?
C1 Si1 C6 C7 -72.01(17) . . . . ?
C12 Si1 C6 C8 -78.33(18) . . . . ?
C9 Si1 C6 C8 45.63(18) . . . . ?
C1 Si1 C6 C8 161.79(15) . . . . ?
C12 Si1 C9 C10 -176.22(14) . . . . ?
C1 Si1 C9 C10 -61.73(16) . . . . ?
C6 Si1 C9 C10 55.85(16) . . . . ?
C12 Si1 C9 C11 -50.91(17) . . . . ?
C1 Si1 C9 C11 63.59(16) . . . . ?
C6 Si1 C9 C11 -178.84(14) . . . . ?
C9 Si1 C12 C13 -61.29(17) . . . . ?
C1 Si1 C12 C13 -176.10(15) . . . . ?
C6 Si1 C12 C13 62.56(17) . . . . ?
C9 Si1 C12 C14 170.57(16) . . . . ?
C1 Si1 C12 C14 55.76(19) . . . . ?
C6 Si1 C12 C14 -65.59(19) . . . . ?

_refine_diff_density_max         0.739
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.065

