# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_TMSBTO2
_audit_block_doi                 10.5517/ccdc.csd.cc2819rd
_database_code_depnum_ccdc_archive 'CCDC 2086633'
loop_
_audit_author_name
_audit_author_address
'Wataru Setaka'
;Tokyo Metropolitan University
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2,5-is(trimethylsilyl)benzo[b]thiophene dioxide'
_chemical_name_common            TMSBTO2
_chemical_melting_point          '353-354 K'
_chemical_formula_moiety         'C14 H22 O2 S Si2'
_chemical_formula_sum            'C14 H22 O2 S Si2'
_chemical_formula_weight         310.55

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'

_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                   22.436(15)
_cell_length_b                   6.470(4)
_cell_length_c                   23.601(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.711(9)
_cell_angle_gamma                90
_cell_volume                     3386(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4480
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_process_details   'CrystalClear; Rigaku'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean 7.3
_diffrn_reflns_number            16276
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.280
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3888
_reflns_number_gt                3482
_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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SIR2019, IUCr'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'WinGX 2020'
_computing_publication_material  'WinGX 2020'



_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)+(0.0511P)²+6.8952P] 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         3888
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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
Si1 Si 0.35572(2) 0.34578(9) 0.46934(2) 0.02109(15) Uani 1 1 d . . . . .
Si2 Si 0.65164(3) 0.30826(9) 0.29465(2) 0.02235(15) Uani 1 1 d . . . . .
S1 S 0.42486(2) 0.66524(7) 0.39977(2) 0.02260(14) Uani 1 1 d . . . . .
O1 O 0.37243(7) 0.6898(3) 0.35677(7) 0.0338(4) Uani 1 1 d . . . . .
O2 O 0.43866(8) 0.8305(2) 0.44056(7) 0.0339(4) Uani 1 1 d . . . . .
C1 C 0.42308(9) 0.4243(3) 0.43533(8) 0.0217(4) Uani 1 1 d . . . . .
C2 C 0.47109(9) 0.3123(3) 0.42562(9) 0.0228(4) Uani 1 1 d . . . . .
H2 H 0.479631 0.180034 0.442405 0.027 Uiso 1 1 calc R U . . .
C3 C 0.50977(9) 0.4075(3) 0.38722(8) 0.0209(4) Uani 1 1 d . . . . .
C4 C 0.55964(9) 0.3227(3) 0.36719(9) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.574173 0.190541 0.380325 0.026 Uiso 1 1 calc R U . . .
C5 C 0.58865(9) 0.4317(3) 0.32754(8) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.56676(9) 0.6290(3) 0.31010(8) 0.0239(4) Uani 1 1 d . . . . .
H6 H 0.586416 0.704796 0.283817 0.029 Uiso 1 1 calc R U . . .
C7 C 0.51688(9) 0.7175(3) 0.33023(9) 0.0245(4) Uani 1 1 d . . . . .
H7 H 0.502578 0.850985 0.318150 0.029 Uiso 1 1 calc R U . . .
C8 C 0.48944(9) 0.6029(3) 0.36827(8) 0.0208(4) Uani 1 1 d . . . . .
C9 C 0.30385(10) 0.2079(4) 0.41222(10) 0.0299(5) Uani 1 1 d . . . . .
H9A H 0.291121 0.302648 0.380283 0.045 Uiso 1 1 calc R U . . .
H9B H 0.324879 0.089523 0.398487 0.045 Uiso 1 1 calc R U . . .
H9C H 0.268362 0.159190 0.427937 0.045 Uiso 1 1 calc R U . . .
C10 C 0.31971(10) 0.5853(4) 0.49255(10) 0.0314(5) Uani 1 1 d . . . . .
H10A H 0.307000 0.673534 0.459146 0.047 Uiso 1 1 calc R U . . .
H10B H 0.284478 0.547900 0.510344 0.047 Uiso 1 1 calc R U . . .
H10C H 0.348759 0.660261 0.520339 0.047 Uiso 1 1 calc R U . . .
C11 C 0.38095(10) 0.1711(3) 0.53079(9) 0.0275(4) Uani 1 1 d . . . . .
H11A H 0.399560 0.047470 0.517076 0.041 Uiso 1 1 calc R U . . .
H11B H 0.410435 0.243099 0.558858 0.041 Uiso 1 1 calc R U . . .
H11C H 0.346154 0.130738 0.548863 0.041 Uiso 1 1 calc R U . . .
C12 C 0.61519(12) 0.1612(4) 0.23056(10) 0.0341(5) Uani 1 1 d . . . . .
H12A H 0.588646 0.054875 0.242610 0.051 Uiso 1 1 calc R U . . .
H12B H 0.591471 0.256118 0.203682 0.051 Uiso 1 1 calc R U . . .
H12C H 0.646342 0.095481 0.211743 0.051 Uiso 1 1 calc R U . . .
C13 C 0.70264(10) 0.5125(4) 0.27357(10) 0.0346(5) Uani 1 1 d . . . . .
H13A H 0.679705 0.605018 0.245424 0.052 Uiso 1 1 calc R U . . .
H13B H 0.719677 0.592105 0.307522 0.052 Uiso 1 1 calc R U . . .
H13C H 0.735329 0.447897 0.256684 0.052 Uiso 1 1 calc R U . . .
C14 C 0.69403(11) 0.1293(4) 0.34832(10) 0.0370(6) Uani 1 1 d . . . . .
H14A H 0.666607 0.023075 0.358922 0.056 Uiso 1 1 calc R U . . .
H14B H 0.726693 0.063384 0.331684 0.056 Uiso 1 1 calc R U . . .
H14C H 0.711040 0.207592 0.382522 0.056 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
Si1 C11 1.858(2) . ?
Si1 C10 1.868(2) . ?
Si1 C9 1.869(2) . ?
Si1 C1 1.885(2) . ?
Si2 C13 1.864(2) . ?
Si2 C14 1.867(2) . ?
Si2 C12 1.867(2) . ?
Si2 C5 1.889(2) . ?
S1 O2 1.4406(18) . ?
S1 O1 1.4414(18) . ?
S1 C8 1.772(2) . ?
S1 C1 1.774(2) . ?
C1 C2 1.347(3) . ?
C2 C3 1.481(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 C8 1.395(3) . ?
C4 C5 1.408(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(3) . ?
C6 C7 1.403(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C11 Si1 C10 111.71(11) . . ?
C11 Si1 C9 110.83(11) . . ?
C10 Si1 C9 110.97(11) . . ?
C11 Si1 C1 109.10(10) . . ?
C10 Si1 C1 108.14(10) . . ?
C9 Si1 C1 105.86(10) . . ?
C13 Si2 C14 110.52(12) . . ?
C13 Si2 C12 110.86(12) . . ?
C14 Si2 C12 110.44(13) . . ?
C13 Si2 C5 109.71(11) . . ?
C14 Si2 C5 108.63(10) . . ?
C12 Si2 C5 106.57(11) . . ?
O2 S1 O1 117.29(11) . . ?
O2 S1 C8 110.03(10) . . ?
O1 S1 C8 111.21(11) . . ?
O2 S1 C1 110.73(11) . . ?
O1 S1 C1 110.83(10) . . ?
C8 S1 C1 94.42(9) . . ?
C2 C1 S1 108.47(15) . . ?
C2 C1 Si1 129.85(16) . . ?
S1 C1 Si1 121.02(11) . . ?
C1 C2 C3 115.99(19) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 H2 122.0 . . ?
C4 C3 C8 119.29(18) . . ?
C4 C3 C2 128.30(19) . . ?
C8 C3 C2 112.33(18) . . ?
C3 C4 C5 120.30(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.25(18) . . ?
C6 C5 Si2 120.88(15) . . ?
C4 C5 Si2 120.73(15) . . ?
C7 C6 C5 122.17(18) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C8 C7 C6 117.32(19) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C8 C3 122.65(19) . . ?
C7 C8 S1 128.67(16) . . ?
C3 C8 S1 108.67(14) . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si2 C12 H12A 109.5 . . ?
Si2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si2 C13 H13A 109.5 . . ?
Si2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si2 C14 H14A 109.5 . . ?
Si2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O2 S1 C1 C2 -110.09(16) . . . . ?
O1 S1 C1 C2 117.95(16) . . . . ?
C8 S1 C1 C2 3.27(16) . . . . ?
O2 S1 C1 Si1 78.35(14) . . . . ?
O1 S1 C1 Si1 -53.60(15) . . . . ?
C8 S1 C1 Si1 -168.28(12) . . . . ?
C11 Si1 C1 C2 39.3(2) . . . . ?
C10 Si1 C1 C2 161.0(2) . . . . ?
C9 Si1 C1 C2 -80.0(2) . . . . ?
C11 Si1 C1 S1 -151.14(12) . . . . ?
C10 Si1 C1 S1 -29.44(15) . . . . ?
C9 Si1 C1 S1 89.55(14) . . . . ?
S1 C1 C2 C3 -3.0(2) . . . . ?
Si1 C1 C2 C3 167.59(15) . . . . ?
C1 C2 C3 C4 -175.8(2) . . . . ?
C1 C2 C3 C8 1.0(3) . . . . ?
C8 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 175.63(19) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C3 C4 C5 Si2 -174.16(15) . . . . ?
C13 Si2 C5 C6 30.89(19) . . . . ?
C14 Si2 C5 C6 151.81(17) . . . . ?
C12 Si2 C5 C6 -89.19(18) . . . . ?
C13 Si2 C5 C4 -153.57(17) . . . . ?
C14 Si2 C5 C4 -32.6(2) . . . . ?
C12 Si2 C5 C4 86.35(18) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
Si2 C5 C6 C7 174.67(16) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C3 0.7(3) . . . . ?
C6 C7 C8 S1 -177.88(16) . . . . ?
C4 C3 C8 C7 -0.1(3) . . . . ?
C2 C3 C8 C7 -177.26(19) . . . . ?
C4 C3 C8 S1 178.65(15) . . . . ?
C2 C3 C8 S1 1.5(2) . . . . ?
O2 S1 C8 C7 -70.1(2) . . . . ?
O1 S1 C8 C7 61.6(2) . . . . ?
C1 S1 C8 C7 176.0(2) . . . . ?
O2 S1 C8 C3 111.22(16) . . . . ?
O1 S1 C8 C3 -117.10(15) . . . . ?
C1 S1 C8 C3 -2.74(15) . . . . ?

_refine_diff_density_max         0.874
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.064



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_chemical_compound_source        no
_exptl_crystal_preparation       Luminescent
