# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 
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data_dy240602_0m
_database_code_depnum_ccdc_archive 'CCDC 2360226'
loop_
_audit_author_name
_audit_author_address
'Yang Ding'
;Grubbs
China
;
_audit_update_record             
;
2024-06-03 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2024-06-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 O S Si'
_chemical_formula_sum            'C19 H22 O S Si'
_chemical_formula_weight         326.51
_chemical_absolute_configuration ad
_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 0.0181 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'
O O 0.0492 0.0322 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.0130(2)
_cell_length_b                   16.5709(4)
_cell_length_c                   17.6278(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1756.45(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      68.48
_cell_measurement_theta_min      3.66
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.495
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1445 before and 0.0840 after correction.
The Ratio of minimum to maximum transmission is 0.5921.
The λ/2 correction factor is Not present.
;
_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    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15680
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.472
_diffrn_reflns_theta_min         3.661
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3187
_reflns_number_total             3213
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.077(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.125
_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)+(0.0367P)²+0.4280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0759
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All Si(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 Si1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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
Si1 Si 0.98817(9) 0.63115(3) 0.79927(3) 0.01394(15) Uani 1 1 d . . . . .
H1 H 1.152650 0.639065 0.795404 0.017 Uiso 1 1 calc R U . . .
S2 S 0.39091(9) 0.88250(3) 0.64543(3) 0.01978(15) Uani 1 1 d . . . . .
O1 O 0.8618(3) 0.71071(9) 0.76314(8) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.7889(4) 0.40577(14) 0.65523(13) 0.0216(5) Uani 1 1 d . . . . .
H1A H 0.749765 0.360455 0.625039 0.026 Uiso 1 1 calc R U . . .
C2 C 0.9907(4) 0.40688(13) 0.69308(13) 0.0215(5) Uani 1 1 d . . . . .
H2 H 1.088889 0.362146 0.689283 0.026 Uiso 1 1 calc R U . . .
C3 C 1.0499(4) 0.47378(13) 0.73685(13) 0.0174(5) Uani 1 1 d . . . . .
H3 H 1.188424 0.474080 0.762755 0.021 Uiso 1 1 calc R U . . .
C4 C 0.9082(4) 0.54022(13) 0.74305(12) 0.0156(4) Uani 1 1 d . . . . .
C5 C 0.9125(4) 0.73504(13) 0.68736(12) 0.0176(5) Uani 1 1 d . . . . .
H5A H 0.920103 0.686909 0.654195 0.021 Uiso 1 1 calc R U . . .
H5B H 1.059498 0.761932 0.686344 0.021 Uiso 1 1 calc R U . . .
C6 C 0.7390(4) 0.79164(13) 0.65819(12) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.7503(4) 0.82565(12) 0.58256(12) 0.0139(4) Uani 1 1 d . . . . .
C8 C 0.9099(4) 0.81360(13) 0.52595(13) 0.0174(4) Uani 1 1 d . . . . .
H8 H 1.034267 0.779580 0.535037 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8851(4) 0.85158(13) 0.45676(13) 0.0203(5) Uani 1 1 d . . . . .
H9 H 0.993660 0.843751 0.418303 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7017(4) 0.90156(13) 0.44258(13) 0.0209(5) Uani 1 1 d . . . . .
H10 H 0.687694 0.927042 0.394542 0.025 Uiso 1 1 calc R U . . .
C11 C 0.7034(4) 0.53730(13) 0.70494(13) 0.0177(5) Uani 1 1 d . . . . .
H11 H 0.603772 0.581581 0.709016 0.021 Uiso 1 1 calc R U . . .
C12 C 0.6434(4) 0.47064(14) 0.66120(13) 0.0212(5) Uani 1 1 d . . . . .
H12 H 0.504206 0.469574 0.635705 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5576(4) 0.81666(13) 0.69650(13) 0.0170(5) Uani 1 1 d . . . . .
H13 H 0.524306 0.799812 0.746745 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5664(4) 0.87617(13) 0.56754(12) 0.0165(4) Uani 1 1 d . . . . .
C15 C 0.5410(4) 0.91438(13) 0.49719(13) 0.0193(5) Uani 1 1 d . . . . .
H15 H 0.416730 0.948185 0.487350 0.023 Uiso 1 1 calc R U . . .
C16 C 0.9086(4) 0.62606(13) 0.90188(12) 0.0161(4) Uani 1 1 d . . . . .
C17 C 1.0157(5) 0.55101(14) 0.93736(13) 0.0219(5) Uani 1 1 d . . . . .
H17A H 1.177771 0.554584 0.932557 0.033 Uiso 1 1 calc R U . . .
H17B H 0.962468 0.502622 0.911060 0.033 Uiso 1 1 calc R U . . .
H17C H 0.975301 0.547875 0.991142 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6543(4) 0.62110(15) 0.91023(14) 0.0217(5) Uani 1 1 d . . . . .
H18A H 0.615337 0.617763 0.964122 0.033 Uiso 1 1 calc R U . . .
H18B H 0.599319 0.573017 0.883856 0.033 Uiso 1 1 calc R U . . .
H18C H 0.586228 0.669372 0.888032 0.033 Uiso 1 1 calc R U . . .
C19 C 0.9947(5) 0.70180(13) 0.94275(13) 0.0227(5) Uani 1 1 d . . . . .
H19A H 0.923516 0.749785 0.921169 0.034 Uiso 1 1 calc R U . . .
H19B H 1.156209 0.705736 0.936238 0.034 Uiso 1 1 calc R U . . .
H19C H 0.959344 0.698163 0.996916 0.034 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 H1 1.0000 . ?
Si1 O1 1.6497(15) . ?
Si1 C4 1.866(2) . ?
Si1 C16 1.873(2) . ?
S2 C13 1.734(2) . ?
S2 C14 1.735(2) . ?
O1 C5 1.428(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.385(4) . ?
C1 C12 1.390(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 C11 1.404(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.494(3) . ?
C6 C7 1.449(3) . ?
C6 C13 1.348(3) . ?
C7 C8 1.399(3) . ?
C7 C14 1.412(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.402(4) . ?
C10 H10 0.9500 . ?
C10 C15 1.380(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.401(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.534(3) . ?
C16 C18 1.538(3) . ?
C16 C19 1.537(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O1 Si1 H1 108.9 . . ?
O1 Si1 C4 108.75(9) . . ?
O1 Si1 C16 106.92(9) . . ?
C4 Si1 H1 108.9 . . ?
C4 Si1 C16 114.25(10) . . ?
C16 Si1 H1 108.9 . . ?
C13 S2 C14 91.21(11) . . ?
C5 O1 Si1 119.22(13) . . ?
C2 C1 H1A 119.8 . . ?
C2 C1 C12 120.3(2) . . ?
C12 C1 H1A 119.8 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 Si1 121.39(18) . . ?
C3 C4 C11 118.1(2) . . ?
C11 C4 Si1 120.53(17) . . ?
O1 C5 H5A 109.6 . . ?
O1 C5 H5B 109.6 . . ?
O1 C5 C6 110.48(18) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C7 C6 C5 121.9(2) . . ?
C13 C6 C5 125.8(2) . . ?
C13 C6 C7 112.3(2) . . ?
C8 C7 C6 129.3(2) . . ?
C8 C7 C14 119.2(2) . . ?
C14 C7 C6 111.49(19) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.4 . . ?
C15 C10 C9 121.1(2) . . ?
C15 C10 H10 119.4 . . ?
C4 C11 H11 119.4 . . ?
C12 C11 C4 121.3(2) . . ?
C12 C11 H11 119.4 . . ?
C1 C12 C11 119.4(2) . . ?
C1 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
S2 C13 H13 123.2 . . ?
C6 C13 S2 113.65(17) . . ?
C6 C13 H13 123.2 . . ?
C7 C14 S2 111.34(16) . . ?
C15 C14 S2 127.37(17) . . ?
C15 C14 C7 121.3(2) . . ?
C10 C15 C14 118.1(2) . . ?
C10 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C17 C16 Si1 108.84(15) . . ?
C17 C16 C18 109.6(2) . . ?
C17 C16 C19 109.23(18) . . ?
C18 C16 Si1 110.41(15) . . ?
C19 C16 Si1 109.26(15) . . ?
C19 C16 C18 109.5(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Si1 O1 C5 C6 163.87(15) . . . . ?
Si1 C4 C11 C12 178.44(18) . . . . ?
S2 C14 C15 C10 179.64(18) . . . . ?
O1 Si1 C4 C3 151.98(17) . . . . ?
O1 Si1 C4 C11 -27.3(2) . . . . ?
O1 Si1 C16 C17 177.96(15) . . . . ?
O1 Si1 C16 C18 57.64(19) . . . . ?
O1 Si1 C16 C19 -62.84(17) . . . . ?
O1 C5 C6 C7 179.93(18) . . . . ?
O1 C5 C6 C13 -0.5(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C1 C12 C11 0.7(3) . . . . ?
C2 C3 C4 Si1 -178.39(17) . . . . ?
C2 C3 C4 C11 0.9(3) . . . . ?
C3 C4 C11 C12 -0.9(3) . . . . ?
C4 Si1 O1 C5 -63.35(18) . . . . ?
C4 Si1 C16 C17 57.60(18) . . . . ?
C4 Si1 C16 C18 -62.7(2) . . . . ?
C4 Si1 C16 C19 176.80(16) . . . . ?
C4 C11 C12 C1 0.1(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C14 179.0(2) . . . . ?
C5 C6 C13 S2 179.99(18) . . . . ?
C6 C7 C8 C9 178.9(2) . . . . ?
C6 C7 C14 S2 1.3(2) . . . . ?
C6 C7 C14 C15 -178.84(19) . . . . ?
C7 C6 C13 S2 -0.4(2) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C14 C15 C10 -0.2(3) . . . . ?
C8 C7 C14 S2 -179.90(16) . . . . ?
C8 C7 C14 C15 0.0(3) . . . . ?
C8 C9 C10 C15 0.1(3) . . . . ?
C9 C10 C15 C14 0.2(3) . . . . ?
C12 C1 C2 C3 -0.7(3) . . . . ?
C13 S2 C14 C7 -1.31(17) . . . . ?
C13 S2 C14 C15 178.8(2) . . . . ?
C13 C6 C7 C8 -179.2(2) . . . . ?
C13 C6 C7 C14 -0.6(3) . . . . ?
C14 S2 C13 C6 1.01(18) . . . . ?
C14 C7 C8 C9 0.3(3) . . . . ?
C16 Si1 O1 C5 172.83(16) . . . . ?
C16 Si1 C4 C3 -88.68(19) . . . . ?
C16 Si1 C4 C11 92.03(18) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
