# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mdl-03-18c-220223_auto
_database_code_depnum_ccdc_archive 'CCDC 2158719'
loop_
_audit_author_name
_audit_author_address
'Delong Mu'
;Shenzhen Bay Laboratory
China
;
_audit_update_record             
;
2022-03-15 deposited with the CCDC.	2022-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 S2 Si0.25'
_chemical_formula_weight         357.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.21480(10)
_cell_length_b                   7.6293(2)
_cell_length_c                   38.5427(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1827.49(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             758
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.774
_shelx_estimated_absorpt_T_min   0.490
_shelx_estimated_absorpt_T_max   0.607
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9046
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         76.900
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3650
_reflns_number_gt                3635
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_max     0.914
_reflns_Friedel_fraction_full    0.993

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0894P)²+2.6449P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0020(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1432 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3650
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          4.010
_refine_ls_shift/su_mean         0.040

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
Si11 Si 0.83368(16) 0.63987(13) 0.37083(2) 0.0135(3) Uani 1 1 d . . . . .
H11 H 0.983583 0.629922 0.361608 0.016 Uiso 1 1 calc R U . . .
S16 S 1.06598(19) 0.47064(15) 0.43318(3) 0.0271(3) Uani 1 1 d . . . . .
C18 C 0.6620(10) 0.6238(5) 0.44579(9) 0.0353(14) Uani 1 1 d . . . . .
H18A H 0.637455 0.751712 0.447609 0.042 Uiso 1 1 calc R U . . .
H18B H 0.523996 0.564435 0.440623 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6851(6) 0.4399(5) 0.30990(10) 0.0148(7) Uani 1 1 d . . . . .
C1 C 0.6565(6) 0.4843(5) 0.34593(10) 0.0155(7) Uani 1 1 d . . . . .
C2 C 0.4749(6) 0.4215(5) 0.36264(10) 0.0181(8) Uani 1 1 d . . . . .
H2 H 0.456460 0.446146 0.386619 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8370(7) 0.5798(5) 0.41815(10) 0.0160(7) Uani 1 1 d . . . . .
C9 C 0.8688(6) 0.4938(5) 0.29071(10) 0.0170(8) Uani 1 1 d . . . . .
H9 H 0.975943 0.563415 0.301635 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3171(7) 0.3227(5) 0.34537(11) 0.0196(8) Uani 1 1 d . . . . .
H3 H 0.192895 0.284806 0.357622 0.024 Uiso 1 1 calc R U . . .
C24 C 0.9664(6) 0.4702(5) 0.47523(10) 0.0160(8) Uani 1 1 d . . . . .
C5 C 0.5263(6) 0.3381(5) 0.29272(10) 0.0162(8) Uani 1 1 d . . . . .
C4 C 0.3407(7) 0.2804(5) 0.31105(11) 0.0192(8) Uani 1 1 d . . . . .
H4 H 0.233737 0.213052 0.299561 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8935(7) 0.4460(6) 0.25626(10) 0.0204(8) Uani 1 1 d . . . . .
H8 H 1.018010 0.482014 0.243859 0.024 Uiso 1 1 calc R U . . .
C15 C 0.8592(7) 0.9962(5) 0.38910(11) 0.0204(8) Uani 1 1 d . . . . .
H15A H 0.822962 0.966105 0.413122 0.031 Uiso 1 1 calc R U . . .
H15B H 0.817509 1.117813 0.384461 0.031 Uiso 1 1 calc R U . . .
H15C H 1.014524 0.982861 0.385573 0.031 Uiso 1 1 calc R U . . .
C23 C 1.0723(7) 0.3974(6) 0.50397(11) 0.0207(8) Uani 1 1 d . . . . .
H23 H 1.209066 0.342977 0.501647 0.025 Uiso 1 1 calc R U . . .
C19 C 0.7658(7) 0.5512(5) 0.47824(10) 0.0181(8) Uani 1 1 d . . . . .
C12 C 0.7380(6) 0.8735(5) 0.36427(9) 0.0145(7) Uani 1 1 d . . . . .
C6 C 0.5577(7) 0.2914(6) 0.25715(11) 0.0210(8) Uani 1 1 d . . . . .
H6 H 0.452742 0.222207 0.245602 0.025 Uiso 1 1 calc R U . . .
C13 C 0.7880(7) 0.9285(6) 0.32690(10) 0.0212(9) Uani 1 1 d . . . . .
H13A H 0.942919 0.917968 0.322663 0.032 Uiso 1 1 calc R U . . .
H13B H 0.743256 1.050384 0.323356 0.032 Uiso 1 1 calc R U . . .
H13C H 0.709713 0.852361 0.310774 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4955(6) 0.8862(5) 0.37091(11) 0.0204(8) Uani 1 1 d . . . . .
H14A H 0.418478 0.814319 0.353880 0.031 Uiso 1 1 calc R U . . .
H14B H 0.449398 1.008533 0.368754 0.031 Uiso 1 1 calc R U . . .
H14C H 0.463417 0.843751 0.394346 0.031 Uiso 1 1 calc R U . . .
C20 C 0.6680(8) 0.5614(6) 0.51088(12) 0.0276(10) Uani 1 1 d . . . . .
H20 H 0.532444 0.617417 0.513476 0.033 Uiso 1 1 calc R U . . .
C22 C 0.9707(8) 0.4078(6) 0.53567(11) 0.0267(10) Uani 1 1 d . . . . .
H22 H 1.037911 0.358489 0.555548 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7364(8) 0.3451(6) 0.23961(10) 0.0235(9) Uani 1 1 d . . . . .
H7 H 0.754406 0.313867 0.215932 0.028 Uiso 1 1 calc R U . . .
C21 C 0.7700(8) 0.4897(7) 0.53913(11) 0.0301(11) Uani 1 1 d . . . . .
H21 H 0.703607 0.495741 0.561298 0.036 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
Si11 C17 1.881(4) . ?
Si11 C1 1.882(4) . ?
Si11 C12 1.896(4) . ?
Si11 H11 1.0000 . ?
S16 C24 1.735(4) . ?
S16 C17 1.747(4) . ?
C18 C19 1.513(5) . ?
C18 C17 1.559(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C10 C5 1.420(5) . ?
C10 C9 1.421(5) . ?
C10 C1 1.440(5) . ?
C1 C2 1.385(6) . ?
C2 C3 1.405(6) . ?
C2 H2 0.9500 . ?
C9 C8 1.385(6) . ?
C9 H9 0.9500 . ?
C3 C4 1.369(6) . ?
C3 H3 0.9500 . ?
C24 C19 1.396(6) . ?
C24 C23 1.403(6) . ?
C5 C4 1.422(6) . ?
C5 C6 1.429(6) . ?
C4 H4 0.9500 . ?
C8 C7 1.399(6) . ?
C8 H8 0.9500 . ?
C15 C12 1.536(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C23 C22 1.378(6) . ?
C23 H23 0.9500 . ?
C19 C20 1.399(6) . ?
C12 C14 1.532(5) . ?
C12 C13 1.532(5) . ?
C6 C7 1.363(7) . ?
C6 H6 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C20 C21 1.373(7) . ?
C20 H20 0.9500 . ?
C22 C21 1.402(7) . ?
C22 H22 0.9500 . ?
C7 H7 0.9500 . ?
C21 H21 0.9500 . ?

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
C17 Si11 C1 110.31(17) . . ?
C17 Si11 C12 111.23(17) . . ?
C1 Si11 C12 109.96(17) . . ?
C17 Si11 H11 108.4 . . ?
C1 Si11 H11 108.4 . . ?
C12 Si11 H11 108.4 . . ?
C24 S16 C17 91.15(19) . . ?
C19 C18 C17 100.9(4) . . ?
C19 C18 H18A 111.6 . . ?
C17 C18 H18A 111.6 . . ?
C19 C18 H18B 111.6 . . ?
C17 C18 H18B 111.6 . . ?
H18A C18 H18B 109.4 . . ?
C5 C10 C9 118.3(3) . . ?
C5 C10 C1 119.5(4) . . ?
C9 C10 C1 122.2(4) . . ?
C2 C1 C10 117.9(4) . . ?
C2 C1 Si11 117.2(3) . . ?
C10 C1 Si11 124.6(3) . . ?
C1 C2 C3 122.3(4) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C18 C17 S16 116.4(3) . . ?
C18 C17 Si11 127.0(3) . . ?
S16 C17 Si11 116.5(2) . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C19 C24 C23 121.9(4) . . ?
C19 C24 S16 113.3(3) . . ?
C23 C24 S16 124.8(3) . . ?
C10 C5 C4 120.1(4) . . ?
C10 C5 C6 119.2(4) . . ?
C4 C5 C6 120.7(4) . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C23 C24 117.5(4) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C24 C19 C20 119.2(4) . . ?
C24 C19 C18 118.3(4) . . ?
C20 C19 C18 122.5(4) . . ?
C14 C12 C13 109.8(3) . . ?
C14 C12 C15 109.9(3) . . ?
C13 C12 C15 108.6(3) . . ?
C14 C12 Si11 110.2(3) . . ?
C13 C12 Si11 108.6(3) . . ?
C15 C12 Si11 109.6(3) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C20 C19 119.3(4) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C23 C22 C21 121.2(4) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C6 C7 C8 120.4(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C20 C21 C22 120.9(4) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?

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
C5 C10 C1 C2 1.4(5) . . . . ?
C9 C10 C1 C2 -178.2(4) . . . . ?
C5 C10 C1 Si11 -172.3(3) . . . . ?
C9 C10 C1 Si11 8.1(5) . . . . ?
C17 Si11 C1 C2 34.7(3) . . . . ?
C12 Si11 C1 C2 -88.3(3) . . . . ?
C17 Si11 C1 C10 -151.6(3) . . . . ?
C12 Si11 C1 C10 85.3(3) . . . . ?
C10 C1 C2 C3 -2.2(6) . . . . ?
Si11 C1 C2 C3 171.9(3) . . . . ?
C19 C18 C17 S16 0.7(4) . . . . ?
C19 C18 C17 Si11 -176.5(3) . . . . ?
C24 S16 C17 C18 -0.2(3) . . . . ?
C24 S16 C17 Si11 177.2(2) . . . . ?
C1 Si11 C17 C18 -79.8(4) . . . . ?
C12 Si11 C17 C18 42.5(4) . . . . ?
C1 Si11 C17 S16 103.1(3) . . . . ?
C12 Si11 C17 S16 -134.6(2) . . . . ?
C5 C10 C9 C8 -0.9(6) . . . . ?
C1 C10 C9 C8 178.7(4) . . . . ?
C1 C2 C3 C4 1.8(6) . . . . ?
C17 S16 C24 C19 -0.4(3) . . . . ?
C17 S16 C24 C23 179.7(4) . . . . ?
C9 C10 C5 C4 179.6(3) . . . . ?
C1 C10 C5 C4 -0.1(5) . . . . ?
C9 C10 C5 C6 0.9(5) . . . . ?
C1 C10 C5 C6 -178.7(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C10 C5 C4 C3 -0.5(6) . . . . ?
C6 C5 C4 C3 178.2(4) . . . . ?
C10 C9 C8 C7 0.7(6) . . . . ?
C19 C24 C23 C22 0.2(6) . . . . ?
S16 C24 C23 C22 -179.9(3) . . . . ?
C23 C24 C19 C20 0.5(6) . . . . ?
S16 C24 C19 C20 -179.4(3) . . . . ?
C23 C24 C19 C18 -179.1(4) . . . . ?
S16 C24 C19 C18 1.0(5) . . . . ?
C17 C18 C19 C24 -1.0(5) . . . . ?
C17 C18 C19 C20 179.3(4) . . . . ?
C17 Si11 C12 C14 -72.6(3) . . . . ?
C1 Si11 C12 C14 49.9(3) . . . . ?
C17 Si11 C12 C13 167.0(3) . . . . ?
C1 Si11 C12 C13 -70.5(3) . . . . ?
C17 Si11 C12 C15 48.4(3) . . . . ?
C1 Si11 C12 C15 170.9(3) . . . . ?
C10 C5 C6 C7 -0.7(6) . . . . ?
C4 C5 C6 C7 -179.4(4) . . . . ?
C24 C19 C20 C21 -0.8(6) . . . . ?
C18 C19 C20 C21 178.8(4) . . . . ?
C24 C23 C22 C21 -0.7(6) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C9 C8 C7 C6 -0.5(6) . . . . ?
C19 C20 C21 C22 0.4(7) . . . . ?
C23 C22 C21 C20 0.4(7) . . . . ?

_refine_diff_density_max         1.350
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.087

