# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_LD
_database_code_depnum_ccdc_archive 'CCDC 2340332'
loop_
_audit_author_name
_audit_author_address
'Liliana Dobrzanska'
;Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-17 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         'C27 H38 N2 O5 S Si'
_chemical_formula_sum            'C27 H38 N2 O5 S Si'
_chemical_formula_weight         530.74

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.9560(1)
_cell_length_b                   12.4093(1)
_cell_length_c                   12.9018(1)
_cell_angle_alpha                90
_cell_angle_beta                 95.349(1)
_cell_angle_gamma                90
_cell_volume                     1427.63(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    31738
_cell_measurement_theta_min      3.4370
_cell_measurement_theta_max      77.9750

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.717
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  1.284
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            42196
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.441
_diffrn_reflns_theta_max         78.993
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5911
_reflns_number_gt                5848
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.923
_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       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_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)+(0.0373P)²+0.3770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5911
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_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 0.31533(5) 0.69693(4) 0.93353(3) 0.01783(11) Uani 1 1 d . . . . .
N2 N 0.38196(19) 0.82139(14) 0.94239(13) 0.0204(3) Uani 1 1 d . . . . .
C3 C 0.4953(2) 0.84435(16) 0.87642(16) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.6171(2) 0.90997(17) 0.90920(18) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.626481 0.938852 0.977686 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7243(2) 0.93292(18) 0.8418(2) 0.0281(5) Uani 1 1 d . . . . .
H5 H 0.805968 0.978805 0.864076 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7142(2) 0.88985(18) 0.74217(19) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.789666 0.904615 0.697097 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5927(2) 0.82501(17) 0.70887(17) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.585795 0.795452 0.640668 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4805(2) 0.80252(17) 0.77416(15) 0.0182(4) Uani 1 1 d . . . . .
C9 C 0.3487(2) 0.73866(16) 0.73676(15) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.2570(2) 0.69135(17) 0.80056(14) 0.0171(4) Uani 1 1 d . . . . .
O11 O 0.43431(16) 0.62111(13) 0.95824(11) 0.0227(3) Uani 1 1 d . . . . .
O12 O 0.18929(16) 0.69201(14) 0.99423(11) 0.0250(3) Uani 1 1 d . . . . .
C13 C 0.3877(3) 0.87153(19) 1.04620(17) 0.0264(5) Uani 1 1 d . . . . .
H13A H 0.474076 0.843293 1.090115 0.040 Uiso 1 1 calc R U . . .
H13B H 0.295328 0.854842 1.078112 0.040 Uiso 1 1 calc R U . . .
H13C H 0.397540 0.949810 1.039430 0.040 Uiso 1 1 calc R U . . .
O14 O 0.32529(15) 0.72365(11) 0.63213(10) 0.0179(3) Uani 1 1 d . . . . .
Si15 Si 0.24124(6) 0.80509(4) 0.53943(4) 0.01788(12) Uani 1 1 d . . . . .
C16 C 0.2217(2) 0.71586(17) 0.42135(15) 0.0213(4) Uani 1 1 d . . . . .
C17 C 0.0573(3) 0.8488(2) 0.58110(19) 0.0297(5) Uani 1 1 d . . . . .
H17A H -0.006484 0.785583 0.588286 0.045 Uiso 1 1 calc R U . . .
H17B H 0.008295 0.897711 0.528825 0.045 Uiso 1 1 calc R U . . .
H17C H 0.073176 0.886183 0.648141 0.045 Uiso 1 1 calc R U . . .
C18 C 0.3592(3) 0.92577(19) 0.52182(18) 0.0281(5) Uani 1 1 d . . . . .
H18A H 0.304698 0.975713 0.473082 0.042 Uiso 1 1 calc R U . . .
H18B H 0.452608 0.903631 0.493995 0.042 Uiso 1 1 calc R U . . .
H18C H 0.382429 0.961581 0.589085 0.042 Uiso 1 1 calc R U . . .
C19 C 0.1189(4) 0.6207(2) 0.4379(2) 0.0431(7) Uani 1 1 d . . . . .
H19A H 0.105668 0.577543 0.374098 0.065 Uiso 1 1 calc R U . . .
H19B H 0.021158 0.647458 0.454955 0.065 Uiso 1 1 calc R U . . .
H19C H 0.163718 0.576071 0.495218 0.065 Uiso 1 1 calc R U . . .
C20 C 0.3751(3) 0.6744(3) 0.3986(2) 0.0496(8) Uani 1 1 d . . . . .
H20A H 0.364364 0.627921 0.336961 0.074 Uiso 1 1 calc R U . . .
H20B H 0.419528 0.632982 0.458465 0.074 Uiso 1 1 calc R U . . .
H20C H 0.440282 0.735451 0.385873 0.074 Uiso 1 1 calc R U . . .
C21 C 0.1535(4) 0.7808(2) 0.32772(19) 0.0413(6) Uani 1 1 d . . . . .
H21A H 0.218499 0.842340 0.315980 0.062 Uiso 1 1 calc R U . . .
H21B H 0.054043 0.806960 0.341512 0.062 Uiso 1 1 calc R U . . .
H21C H 0.144456 0.734785 0.265742 0.062 Uiso 1 1 calc R U . . .
C22 C 0.1222(2) 0.62205(16) 0.76405(15) 0.0170(4) Uani 1 1 d . . . . .
H22 H 0.111284 0.628047 0.686419 0.020 Uiso 1 1 calc R U . . .
C23 C 0.1484(2) 0.50240(16) 0.78743(15) 0.0182(4) Uani 1 1 d . . . . .
C24 C 0.0881(2) 0.44754(17) 0.86803(15) 0.0196(4) Uani 1 1 d . . . . .
H24 H 0.029371 0.486218 0.913152 0.024 Uiso 1 1 calc R U . . .
C25 C 0.1112(2) 0.33796(17) 0.88427(15) 0.0210(4) Uani 1 1 d . . . . .
H25 H 0.068657 0.303490 0.940307 0.025 Uiso 1 1 calc R U . . .
C26 C 0.1965(2) 0.27710(17) 0.81933(16) 0.0217(4) Uani 1 1 d . . . . .
C27 C 0.2614(2) 0.33358(18) 0.73995(17) 0.0242(4) Uani 1 1 d . . . . .
H27 H 0.323535 0.296139 0.696184 0.029 Uiso 1 1 calc R U . . .
C28 C 0.2361(2) 0.44245(18) 0.72487(16) 0.0216(4) Uani 1 1 d . . . . .
H28 H 0.280033 0.477736 0.669849 0.026 Uiso 1 1 calc R U . . .
N29 N 0.2115(2) 0.16649(16) 0.82996(15) 0.0291(4) Uani 1 1 d . . . . .
C30 C 0.1648(3) 0.1149(2) 0.9228(2) 0.0341(5) Uani 1 1 d . . . . .
H30A H 0.227668 0.140606 0.984042 0.051 Uiso 1 1 calc R U . . .
H30B H 0.175614 0.036605 0.916757 0.051 Uiso 1 1 calc R U . . .
H30C H 0.059715 0.132648 0.930131 0.051 Uiso 1 1 calc R U . . .
C31 C 0.3271(3) 0.1119(2) 0.7786(2) 0.0416(6) Uani 1 1 d . . . . .
H31A H 0.312676 0.126181 0.703583 0.062 Uiso 1 1 calc R U . . .
H31B H 0.320866 0.034124 0.790796 0.062 Uiso 1 1 calc R U . . .
H31C H 0.425790 0.138340 0.806492 0.062 Uiso 1 1 calc R U . . .
C32 C -0.0251(2) 0.66563(17) 0.79987(16) 0.0196(4) Uani 1 1 d . . . . .
H32A H -0.029218 0.649911 0.874780 0.024 Uiso 1 1 calc R U . . .
H32B H -0.029238 0.744778 0.790427 0.024 Uiso 1 1 calc R U . . .
C33 C -0.1571(2) 0.61439(17) 0.73803(15) 0.0189(4) Uani 1 1 d . . . . .
O34 O -0.16704(17) 0.60179(15) 0.64476(12) 0.0279(4) Uani 1 1 d . . . . .
O35 O -0.26456(15) 0.58642(13) 0.79829(11) 0.0207(3) Uani 1 1 d . . . . .
C36 C -0.3993(2) 0.54131(18) 0.74509(17) 0.0221(4) Uani 1 1 d . . . . .
H36A H -0.430496 0.584940 0.683540 0.033 Uiso 1 1 calc R U . . .
H36B H -0.479224 0.541058 0.792056 0.033 Uiso 1 1 calc R U . . .
H36C H -0.379615 0.467314 0.723566 0.033 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 O12 1.4339(15) . ?
S1 O11 1.4349(15) . ?
S1 N2 1.6559(18) . ?
S1 C10 1.7476(18) . ?
N2 C3 1.413(3) . ?
N2 C13 1.473(3) . ?
C3 C4 1.395(3) . ?
C3 C8 1.413(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.387(4) . ?
C6 C7 1.388(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.466(3) . ?
C9 C10 1.350(3) . ?
C9 O14 1.359(2) . ?
C10 C22 1.521(3) . ?
O14 Si15 1.6884(14) . ?
Si15 C18 1.859(2) . ?
Si15 C17 1.861(2) . ?
Si15 C16 1.878(2) . ?
C16 C20 1.521(3) . ?
C16 C19 1.524(3) . ?
C16 C21 1.531(3) . ?
C22 C23 1.529(3) . ?
C22 C32 1.536(3) . ?
C23 C28 1.393(3) . ?
C23 C24 1.393(3) . ?
C24 C25 1.389(3) . ?
C25 C26 1.405(3) . ?
C26 N29 1.385(3) . ?
C26 C27 1.410(3) . ?
C27 C28 1.381(3) . ?
N29 C31 1.448(3) . ?
N29 C30 1.453(3) . ?
C32 C33 1.504(3) . ?
C33 O34 1.209(3) . ?
C33 O35 1.338(2) . ?
O35 C36 1.444(2) . ?

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
O12 S1 O11 117.19(9) . . ?
O12 S1 N2 107.40(9) . . ?
O11 S1 N2 109.93(9) . . ?
O12 S1 C10 110.85(9) . . ?
O11 S1 C10 109.87(9) . . ?
N2 S1 C10 100.22(9) . . ?
C3 N2 C13 119.75(17) . . ?
C3 N2 S1 114.90(14) . . ?
C13 N2 S1 116.00(14) . . ?
C4 C3 C8 120.01(19) . . ?
C4 C3 N2 121.37(19) . . ?
C8 C3 N2 118.58(17) . . ?
C5 C4 C3 119.9(2) . . ?
C4 C5 C6 120.9(2) . . ?
C5 C6 C7 119.5(2) . . ?
C6 C7 C8 121.0(2) . . ?
C7 C8 C3 118.64(18) . . ?
C7 C8 C9 120.78(18) . . ?
C3 C8 C9 120.57(17) . . ?
C10 C9 O14 119.98(18) . . ?
C10 C9 C8 123.47(18) . . ?
O14 C9 C8 116.47(17) . . ?
C9 C10 C22 124.58(17) . . ?
C9 C10 S1 115.98(15) . . ?
C22 C10 S1 118.85(14) . . ?
C9 O14 Si15 129.69(13) . . ?
O14 Si15 C18 110.36(9) . . ?
O14 Si15 C17 108.55(9) . . ?
C18 Si15 C17 109.21(12) . . ?
O14 Si15 C16 102.91(8) . . ?
C18 Si15 C16 112.76(10) . . ?
C17 Si15 C16 112.84(11) . . ?
C20 C16 C19 109.5(2) . . ?
C20 C16 C21 109.1(2) . . ?
C19 C16 C21 108.5(2) . . ?
C20 C16 Si15 109.77(15) . . ?
C19 C16 Si15 110.78(15) . . ?
C21 C16 Si15 109.24(16) . . ?
C10 C22 C23 112.65(16) . . ?
C10 C22 C32 112.77(16) . . ?
C23 C22 C32 113.76(16) . . ?
C28 C23 C24 116.78(19) . . ?
C28 C23 C22 119.26(17) . . ?
C24 C23 C22 123.96(18) . . ?
C25 C24 C23 121.88(19) . . ?
C24 C25 C26 121.21(19) . . ?
N29 C26 C25 121.8(2) . . ?
N29 C26 C27 121.4(2) . . ?
C25 C26 C27 116.72(19) . . ?
C28 C27 C26 121.00(19) . . ?
C27 C28 C23 122.35(19) . . ?
C26 N29 C31 119.0(2) . . ?
C26 N29 C30 119.06(19) . . ?
C31 N29 C30 116.3(2) . . ?
C33 C32 C22 110.26(16) . . ?
O34 C33 O35 123.72(19) . . ?
O34 C33 C32 124.32(18) . . ?
O35 C33 C32 111.94(16) . . ?
C33 O35 C36 116.01(16) . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.040



