# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 2324350'
loop_
_audit_author_name
_audit_author_address
'Makoto Sako'
;Osaka University
Japan
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H20 O3 S Si'
_chemical_formula_moiety         'C18 H20 O3 S Si'
_chemical_formula_weight         344.50
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.1061(7)
_cell_length_b                   8.2101(4)
_cell_length_c                   16.7736(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.719(6)
_cell_angle_gamma                90.0000
_cell_volume                     1804.73(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9544
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    143
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728.00
_exptl_absorpt_coefficient_mu    2.324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_T_max  0.793

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      143
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12077
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_min         4.255
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3259
_reflns_number_gt                2831
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3259
_refine_ls_number_parameters     208
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0495P)²+1.1650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Si Si 0.2541 0.3302
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.12202(5) 0.10106(7) 0.31989(3) 0.02872(18) Uani 1 1 d . . . . .
Si1 Si 0.88572(5) 0.21661(8) 0.00380(4) 0.0287(2) Uani 1 1 d . . . . .
O1 O 0.96601(13) 0.1524(2) 0.07491(9) 0.0341(4) Uani 1 1 d . . . . .
O2 O 1.07527(16) 0.2249(2) 0.36814(10) 0.0425(5) Uani 1 1 d . . . . .
O3 O 1.23157(14) 0.1009(2) 0.31332(11) 0.0450(5) Uani 1 1 d . . . . .
C1 C 0.9563(2) 0.2761(3) -0.08573(15) 0.0380(6) Uani 1 1 d . . . . .
H1A H 0.908115 0.313594 -0.126952 0.046 Uiso 1 1 calc R U . . .
H1B H 1.003884 0.364309 -0.072273 0.046 Uiso 1 1 calc R U . . .
H1C H 0.994461 0.182249 -0.105646 0.046 Uiso 1 1 calc R U . . .
C2 C 0.7906(2) 0.0569(3) -0.01880(17) 0.0409(6) Uani 1 1 d . . . . .
H2A H 0.743691 0.095479 -0.060642 0.049 Uiso 1 1 calc R U . . .
H2B H 0.825543 -0.041542 -0.037143 0.049 Uiso 1 1 calc R U . . .
H2C H 0.752095 0.031801 0.029375 0.049 Uiso 1 1 calc R U . . .
C3 C 0.83653(18) 0.3874(3) 0.06547(15) 0.0310(6) Uani 1 1 d . . . . .
C4 C 0.7698(2) 0.5177(3) 0.05168(17) 0.0400(6) Uani 1 1 d . . . . .
H4 H 0.737225 0.529257 0.001089 0.048 Uiso 1 1 calc R U . . .
C5 C 0.7510(2) 0.6301(3) 0.11147(19) 0.0461(7) Uani 1 1 d . . . . .
H5 H 0.706047 0.718716 0.101424 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7972(2) 0.6140(3) 0.18550(18) 0.0441(7) Uani 1 1 d . . . . .
H6 H 0.783024 0.690648 0.226322 0.053 Uiso 1 1 calc R U . . .
C7 C 0.8641(2) 0.4867(3) 0.20055(15) 0.0381(6) Uani 1 1 d . . . . .
H7 H 0.895861 0.475974 0.251487 0.046 Uiso 1 1 calc R U . . .
C8 C 0.88438(18) 0.3746(3) 0.14047(15) 0.0309(6) Uani 1 1 d . . . . .
C9 C 0.96031(19) 0.2379(3) 0.14913(14) 0.0290(5) Uani 1 1 d . . . . .
C10 C 1.06986(18) 0.2759(3) 0.17948(14) 0.0298(5) Uani 1 1 d . . . . .
H10A H 1.074387 0.370993 0.215639 0.036 Uiso 1 1 calc R U . . .
H10B H 1.121117 0.282732 0.136760 0.036 Uiso 1 1 calc R U . . .
C11 C 0.95033(19) 0.1128(3) 0.21767(14) 0.0322(6) Uani 1 1 d . . . . .
H11A H 0.917185 0.156588 0.265857 0.039 Uiso 1 1 calc R U . . .
H11B H 0.919317 0.007953 0.201133 0.039 Uiso 1 1 calc R U . . .
C12 C 1.06765(18) 0.1094(3) 0.22303(13) 0.0269(5) Uani 1 1 d . . . . .
H12 H 1.095885 0.021326 0.188548 0.032 Uiso 1 1 calc R U . . .
C13 C 1.08114(18) -0.0909(3) 0.35398(13) 0.0255(5) Uani 1 1 d . . . . .
C14 C 1.13064(19) -0.2292(3) 0.32697(14) 0.0311(6) Uani 1 1 d . . . . .
H14 H 1.187070 -0.219994 0.292253 0.037 Uiso 1 1 calc R U . . .
C15 C 0.9991(2) -0.1011(3) 0.40519(15) 0.0349(6) Uani 1 1 d . . . . .
H15 H 0.966125 -0.005425 0.423611 0.042 Uiso 1 1 calc R U . . .
C16 C 1.0972(2) -0.3790(3) 0.35093(15) 0.0373(6) Uani 1 1 d . . . . .
H16 H 1.130103 -0.474719 0.332475 0.045 Uiso 1 1 calc R U . . .
C17 C 0.9666(2) -0.2532(3) 0.42878(16) 0.0465(7) Uani 1 1 d . . . . .
H17 H 0.910251 -0.262814 0.463575 0.056 Uiso 1 1 calc R U . . .
C18 C 1.0152(2) -0.3912(3) 0.40221(16) 0.0435(7) Uani 1 1 d . . . . .
H18 H 0.992549 -0.495453 0.419063 0.052 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O3 1.4414(19) . ?
S1 O2 1.4413(18) . ?
S1 C13 1.762(2) . ?
S1 C12 1.767(2) . ?
Si1 O1 1.6662(17) . ?
Si1 C1 1.840(3) . ?
Si1 C2 1.846(3) . ?
Si1 C3 1.862(3) . ?
O1 C9 1.432(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.399(3) . ?
C3 C8 1.403(3) . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.506(3) . ?
C9 C11 1.549(3) . ?
C9 C10 1.549(3) . ?
C10 C12 1.550(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.539(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C13 C14 1.387(3) . ?
C13 C15 1.387(3) . ?
C14 C16 1.368(3) . ?
C14 H14 0.9500 . ?
C15 C17 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C18 1.388(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(4) . ?
C17 H17 0.9500 . ?
C18 H18 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
O3 S1 O2 118.33(12) . . ?
O3 S1 C13 109.34(11) . . ?
O2 S1 C13 108.41(11) . . ?
O3 S1 C12 108.68(11) . . ?
O2 S1 C12 108.63(11) . . ?
C13 S1 C12 102.26(11) . . ?
O1 Si1 C1 110.43(11) . . ?
O1 Si1 C2 109.93(11) . . ?
C1 Si1 C2 111.49(13) . . ?
O1 Si1 C3 93.48(10) . . ?
C1 Si1 C3 115.75(11) . . ?
C2 Si1 C3 114.30(12) . . ?
C9 O1 Si1 115.31(14) . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C8 118.5(2) . . ?
C4 C3 Si1 134.7(2) . . ?
C8 C3 Si1 106.73(17) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 119.5(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C3 120.8(2) . . ?
C7 C8 C9 123.7(2) . . ?
C3 C8 C9 115.5(2) . . ?
O1 C9 C8 108.86(19) . . ?
O1 C9 C11 109.00(19) . . ?
C8 C9 C11 120.3(2) . . ?
O1 C9 C10 109.03(19) . . ?
C8 C9 C10 119.4(2) . . ?
C11 C9 C10 88.63(18) . . ?
C9 C10 C12 87.41(18) . . ?
C9 C10 H10A 114.1 . . ?
C12 C10 H10A 114.1 . . ?
C9 C10 H10B 114.1 . . ?
C12 C10 H10B 114.1 . . ?
H10A C10 H10B 111.3 . . ?
C12 C11 C9 87.80(17) . . ?
C12 C11 H11A 114.0 . . ?
C9 C11 H11A 114.0 . . ?
C12 C11 H11B 114.0 . . ?
C9 C11 H11B 114.0 . . ?
H11A C11 H11B 111.2 . . ?
C11 C12 C10 88.92(17) . . ?
C11 C12 S1 116.45(16) . . ?
C10 C12 S1 117.24(16) . . ?
C11 C12 H12 110.8 . . ?
C10 C12 H12 110.8 . . ?
S1 C12 H12 110.8 . . ?
C14 C13 C15 121.5(2) . . ?
C14 C13 S1 118.74(18) . . ?
C15 C13 S1 119.73(18) . . ?
C16 C14 C13 119.2(2) . . ?
C16 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C17 C15 C13 118.5(2) . . ?
C17 C15 H15 120.8 . . ?
C13 C15 H15 120.8 . . ?
C14 C16 C18 120.0(2) . . ?
C14 C16 H16 120.0 . . ?
C18 C16 H16 120.0 . . ?
C18 C17 C15 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C15 C17 H17 119.8 . . ?
C17 C18 C16 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C16 C18 H18 119.8 . . ?

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
C1 Si1 O1 C9 123.06(17) . . . . ?
C2 Si1 O1 C9 -113.51(17) . . . . ?
C3 Si1 O1 C9 3.92(17) . . . . ?
O1 Si1 C3 C4 174.2(3) . . . . ?
C1 Si1 C3 C4 59.5(3) . . . . ?
C2 Si1 C3 C4 -72.1(3) . . . . ?
O1 Si1 C3 C8 -3.19(18) . . . . ?
C1 Si1 C3 C8 -117.87(18) . . . . ?
C2 Si1 C3 C8 110.52(18) . . . . ?
C8 C3 C4 C5 -0.7(4) . . . . ?
Si1 C3 C4 C5 -177.9(2) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C3 -1.2(4) . . . . ?
C6 C7 C8 C9 176.3(2) . . . . ?
C4 C3 C8 C7 1.6(4) . . . . ?
Si1 C3 C8 C7 179.48(19) . . . . ?
C4 C3 C8 C9 -176.1(2) . . . . ?
Si1 C3 C8 C9 1.8(2) . . . . ?
Si1 O1 C9 C8 -3.4(2) . . . . ?
Si1 O1 C9 C11 129.50(17) . . . . ?
Si1 O1 C9 C10 -135.22(16) . . . . ?
C7 C8 C9 O1 -176.8(2) . . . . ?
C3 C8 C9 O1 0.8(3) . . . . ?
C7 C8 C9 C11 56.5(3) . . . . ?
C3 C8 C9 C11 -125.9(2) . . . . ?
C7 C8 C9 C10 -50.8(3) . . . . ?
C3 C8 C9 C10 126.8(2) . . . . ?
O1 C9 C10 C12 -89.6(2) . . . . ?
C8 C9 C10 C12 144.5(2) . . . . ?
C11 C9 C10 C12 20.05(18) . . . . ?
O1 C9 C11 C12 89.5(2) . . . . ?
C8 C9 C11 C12 -143.9(2) . . . . ?
C10 C9 C11 C12 -20.19(18) . . . . ?
C9 C11 C12 C10 20.17(18) . . . . ?
C9 C11 C12 S1 140.31(17) . . . . ?
C9 C10 C12 C11 -20.18(18) . . . . ?
C9 C10 C12 S1 -139.61(17) . . . . ?
O3 S1 C12 C11 -179.26(17) . . . . ?
O2 S1 C12 C11 -49.3(2) . . . . ?
C13 S1 C12 C11 65.20(19) . . . . ?
O3 S1 C12 C10 -75.8(2) . . . . ?
O2 S1 C12 C10 54.2(2) . . . . ?
C13 S1 C12 C10 168.64(18) . . . . ?
O3 S1 C13 C14 -37.6(2) . . . . ?
O2 S1 C13 C14 -167.89(19) . . . . ?
C12 S1 C13 C14 77.5(2) . . . . ?
O3 S1 C13 C15 144.1(2) . . . . ?
O2 S1 C13 C15 13.8(2) . . . . ?
C12 S1 C13 C15 -100.9(2) . . . . ?
C15 C13 C14 C16 0.5(4) . . . . ?
S1 C13 C14 C16 -177.77(19) . . . . ?
C14 C13 C15 C17 -0.5(4) . . . . ?
S1 C13 C15 C17 177.8(2) . . . . ?
C13 C14 C16 C18 -0.5(4) . . . . ?
C13 C15 C17 C18 0.4(4) . . . . ?
C15 C17 C18 C16 -0.4(4) . . . . ?
C14 C16 C18 C17 0.5(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


