# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_190405A-19_a
_database_code_depnum_ccdc_archive 'CCDC 2015911'
loop_
_audit_author_name
_audit_author_address
'Hongdong Hao'
;College of Chemistry and Pharmacy, Northwest Agriculture and Forestry University 
China
;
_audit_update_record             
;
2020-07-11 deposited with the CCDC.	2025-05-21 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         'C13 H16 O3'
_chemical_formula_sum            'C13 H16 O3'
_chemical_formula_weight         220.26

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'

_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                   8.4757(17)
_cell_length_b                   11.538(3)
_cell_length_c                   11.708(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1144.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2258
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      19.60
_exptl_crystal_colour            'Pale yellow solid'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13567
_diffrn_reflns_av_unetI/netI     0.1436
_diffrn_reflns_av_R_equivalents  0.1251
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.967
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2345
_reflns_number_gt                1182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2 (Bruker, 2012)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2012)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.0382P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 362 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2345
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1845
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
C1 C 0.5246(5) 0.2946(4) 0.7331(4) 0.0375(11) Uani 1 1 d . . . . .
C2 C 0.5968(5) 0.3653(4) 0.6401(3) 0.0593(14) Uani 1 1 d . . . . .
H2A H 0.662900 0.315295 0.593767 0.071 Uiso 1 1 calc R U . . .
H2B H 0.664267 0.423613 0.674286 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4786(5) 0.4251(5) 0.5630(4) 0.0641(15) Uani 1 1 d . . . . .
H3A H 0.443905 0.372424 0.503475 0.077 Uiso 1 1 calc R U . . .
H3B H 0.526751 0.492088 0.527089 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3390(6) 0.4626(4) 0.6353(4) 0.0628(15) Uani 1 1 d . . . . .
H4A H 0.271648 0.513563 0.590958 0.075 Uiso 1 1 calc R U . . .
H4B H 0.376492 0.505353 0.701209 0.075 Uiso 1 1 calc R U . . .
C5 C 0.2439(5) 0.3579(4) 0.6751(3) 0.0372(11) Uani 1 1 d . . . . .
H5 H 0.179368 0.329415 0.611545 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3519(4) 0.2569(3) 0.7196(3) 0.0299(10) Uani 1 1 d . . . . .
C7 C 0.3614(5) 0.1587(4) 0.6403(3) 0.0402(12) Uani 1 1 d . . . . .
C8 C 0.3747(5) 0.0799(5) 0.5776(4) 0.0613(16) Uani 1 1 d . . . . .
H8 H 0.385142 0.017504 0.527909 0.074 Uiso 1 1 calc R U . . .
C9 C 0.2765(4) 0.2276(3) 0.8348(3) 0.0298(11) Uani 1 1 d . . . . .
H9 H 0.342329 0.180294 0.885423 0.036 Uiso 1 1 calc R U . . .
C10 C 0.1106(4) 0.1803(4) 0.8149(3) 0.0405(11) Uani 1 1 d . . . . .
H10 H 0.110763 0.126445 0.750162 0.049 Uiso 1 1 calc R U . . .
C11 C 0.0117(5) 0.2902(4) 0.7851(3) 0.0405(12) Uani 1 1 d . . . . .
H11 H -0.044217 0.281037 0.712374 0.049 Uiso 1 1 calc R U . . .
C12 C 0.1369(5) 0.3828(4) 0.7777(3) 0.0381(11) Uani 1 1 d . . . . .
H12 H 0.095930 0.462172 0.780567 0.046 Uiso 1 1 calc R U . . .
C13 C 0.2409(5) 0.3496(4) 0.8796(3) 0.0396(12) Uani 1 1 d . . . . .
H13A H 0.334529 0.397463 0.885974 0.047 Uiso 1 1 calc R U . . .
H13B H 0.183656 0.348968 0.951359 0.047 Uiso 1 1 calc R U . . .
O1 O 0.5985(3) 0.2652(3) 0.8165(3) 0.0561(10) Uani 1 1 d . . . . .
O2 O 0.0503(3) 0.1243(3) 0.9140(2) 0.0668(11) Uani 1 1 d . . . . .
H2 H -0.011062 0.175245 0.934399 0.100 Uiso 1 1 d R U . . .
O3 O -0.0942(3) 0.3169(3) 0.8758(2) 0.0595(10) Uani 1 1 d . . . . .
H3 H -0.184434 0.300101 0.856684 0.089 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
C1 O1 1.209(5) . ?
C1 C2 1.492(5) . ?
C1 C6 1.535(5) . ?
C2 C3 1.515(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.518(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.525(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C12 1.532(5) . ?
C5 C6 1.571(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.467(6) . ?
C6 C9 1.531(5) . ?
C7 C8 1.174(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.527(5) . ?
C9 C13 1.531(5) . ?
C9 H9 0.9800 . ?
C10 O2 1.423(4) . ?
C10 C11 1.559(5) . ?
C10 H10 0.9800 . ?
C11 O3 1.424(4) . ?
C11 C12 1.508(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.532(5) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O2 H2 0.8199 . ?
O3 H3 0.8200 . ?

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 C1 C2 122.1(4) . . ?
O1 C1 C6 119.9(4) . . ?
C2 C1 C6 118.1(4) . . ?
C1 C2 C3 114.4(4) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 108.2(4) . . ?
C2 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C3 C4 C5 110.9(4) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C12 113.8(4) . . ?
C4 C5 C6 112.4(3) . . ?
C12 C5 C6 102.9(3) . . ?
C4 C5 H5 109.2 . . ?
C12 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C7 C6 C9 114.2(3) . . ?
C7 C6 C1 103.4(3) . . ?
C9 C6 C1 111.7(3) . . ?
C7 C6 C5 113.3(3) . . ?
C9 C6 C5 102.3(3) . . ?
C1 C6 C5 112.3(3) . . ?
C8 C7 C6 177.6(5) . . ?
C7 C8 H8 180.0 . . ?
C10 C9 C6 109.2(3) . . ?
C10 C9 C13 101.5(3) . . ?
C6 C9 C13 100.5(3) . . ?
C10 C9 H9 114.7 . . ?
C6 C9 H9 114.7 . . ?
C13 C9 H9 114.7 . . ?
O2 C10 C9 111.6(3) . . ?
O2 C10 C11 111.0(3) . . ?
C9 C10 C11 103.8(3) . . ?
O2 C10 H10 110.1 . . ?
C9 C10 H10 110.1 . . ?
C11 C10 H10 110.1 . . ?
O3 C11 C12 109.4(3) . . ?
O3 C11 C10 110.4(3) . . ?
C12 C11 C10 102.2(3) . . ?
O3 C11 H11 111.5 . . ?
C12 C11 H11 111.5 . . ?
C10 C11 H11 111.5 . . ?
C11 C12 C13 100.6(3) . . ?
C11 C12 C5 109.2(3) . . ?
C13 C12 C5 102.9(3) . . ?
C11 C12 H12 114.3 . . ?
C13 C12 H12 114.3 . . ?
C5 C12 H12 114.3 . . ?
C9 C13 C12 94.4(3) . . ?
C9 C13 H13A 112.8 . . ?
C12 C13 H13A 112.8 . . ?
C9 C13 H13B 112.8 . . ?
C12 C13 H13B 112.8 . . ?
H13A C13 H13B 110.3 . . ?
C10 O2 H2 98.0 . . ?
C11 O3 H3 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
O1 C1 C2 C3 -161.7(4) . . . . ?
C6 C1 C2 C3 19.5(6) . . . . ?
C1 C2 C3 C4 35.9(6) . . . . ?
C2 C3 C4 C5 -69.9(5) . . . . ?
C3 C4 C5 C12 161.0(3) . . . . ?
C3 C4 C5 C6 44.4(5) . . . . ?
O1 C1 C6 C7 -100.3(4) . . . . ?
C2 C1 C6 C7 78.5(5) . . . . ?
O1 C1 C6 C9 23.0(5) . . . . ?
C2 C1 C6 C9 -158.2(4) . . . . ?
O1 C1 C6 C5 137.2(4) . . . . ?
C2 C1 C6 C5 -44.0(5) . . . . ?
C4 C5 C6 C7 -106.3(4) . . . . ?
C12 C5 C6 C7 130.8(4) . . . . ?
C4 C5 C6 C9 130.3(4) . . . . ?
C12 C5 C6 C9 7.4(4) . . . . ?
C4 C5 C6 C1 10.4(5) . . . . ?
C12 C5 C6 C1 -112.5(3) . . . . ?
C7 C6 C9 C10 -57.9(4) . . . . ?
C1 C6 C9 C10 -174.8(3) . . . . ?
C5 C6 C9 C10 64.9(4) . . . . ?
C7 C6 C9 C13 -164.1(3) . . . . ?
C1 C6 C9 C13 79.0(4) . . . . ?
C5 C6 C9 C13 -41.3(3) . . . . ?
C6 C9 C10 O2 164.9(3) . . . . ?
C13 C9 C10 O2 -89.6(4) . . . . ?
C6 C9 C10 C11 -75.5(4) . . . . ?
C13 C9 C10 C11 30.0(3) . . . . ?
O2 C10 C11 O3 10.4(5) . . . . ?
C9 C10 C11 O3 -109.6(4) . . . . ?
O2 C10 C11 C12 126.7(3) . . . . ?
C9 C10 C11 C12 6.7(4) . . . . ?
O3 C11 C12 C13 76.0(4) . . . . ?
C10 C11 C12 C13 -41.0(4) . . . . ?
O3 C11 C12 C5 -176.3(3) . . . . ?
C10 C11 C12 C5 66.8(4) . . . . ?
C4 C5 C12 C11 161.1(4) . . . . ?
C6 C5 C12 C11 -76.9(4) . . . . ?
C4 C5 C12 C13 -92.7(4) . . . . ?
C6 C5 C12 C13 29.2(4) . . . . ?
C10 C9 C13 C12 -53.9(3) . . . . ?
C6 C9 C13 C12 58.3(3) . . . . ?
C11 C12 C13 C9 58.9(3) . . . . ?
C5 C12 C13 C9 -53.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.91 2.577(4) 138.0 . yes
O3 H3 O1 0.82 1.94 2.761(4) 177.4 1_455 yes

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_sf190606-1_a
_database_code_depnum_ccdc_archive 'CCDC 2015913'
loop_
_audit_author_name
_audit_author_address
'Hongdong Hao'
;College of Chemistry and Pharmacy, Northwest Agriculture and Forestry University 
China
;
_audit_update_record             
;
2020-07-11 deposited with the CCDC.	2025-05-21 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 H39 O3 Si'
_chemical_formula_weight         379.62

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.2115(14)
_cell_length_b                   8.6473(15)
_cell_length_c                   18.221(3)
_cell_angle_alpha                92.225(4)
_cell_angle_beta                 95.522(4)
_cell_angle_gamma                117.574(4)
_cell_volume                     1136.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4739
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      20.60

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_F_000             418
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34524
_diffrn_reflns_av_unetI/netI     0.2003
_diffrn_reflns_av_R_equivalents  0.1751
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.669
_diffrn_reflns_theta_max         28.610
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5819
_reflns_number_gt                2320
_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       'Bruker APEX2 (Bruker, 2012)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2012)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.0732P)²+0.7268P] 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         5819
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2544
_refine_ls_R_factor_gt           0.0953
_refine_ls_wR_factor_ref         0.2144
_refine_ls_wR_factor_gt          0.1663
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
Si1 Si 0.30805(14) 0.13282(14) 0.65382(6) 0.0440(4) Uani 1 1 d . . . . .
O1 O 0.5142(3) 0.2019(3) 0.93598(13) 0.0525(7) Uani 1 1 d . . . . .
H1 H 0.514445 0.215417 0.980786 0.079 Uiso 1 1 calc R U . . .
O2 O 0.4377(4) 0.7272(4) 0.91319(14) 0.0590(8) Uani 1 1 d . . . . .
H2 H 0.375736 0.765744 0.890177 0.089 Uiso 1 1 calc R U . . .
O3 O 1.2365(3) 0.8934(3) 0.86468(16) 0.0560(8) Uani 1 1 d . . . . .
H3 H 1.327887 0.988745 0.876803 0.084 Uiso 1 1 calc R U . . .
C1 C 0.6887(5) 0.3252(4) 0.91617(19) 0.0359(9) Uani 1 1 d . . . . .
H1A H 0.765739 0.396566 0.961452 0.043 Uiso 1 1 calc R U . . .
C2 C 0.7855(5) 0.2320(5) 0.8844(2) 0.0497(11) Uani 1 1 d . . . . .
H2A H 0.709712 0.157056 0.840352 0.060 Uiso 1 1 calc R U . . .
H2B H 0.801624 0.158551 0.920202 0.060 Uiso 1 1 calc R U . . .
C3 C 0.9740(5) 0.3628(5) 0.8646(2) 0.0493(11) Uani 1 1 d . . . . .
H3A H 1.054131 0.429877 0.909332 0.059 Uiso 1 1 calc R U . . .
H3B H 1.030912 0.300038 0.841676 0.059 Uiso 1 1 calc R U . . .
C4 C 0.9542(5) 0.4866(4) 0.81165(19) 0.0397(10) Uani 1 1 d . . . . .
H4A H 1.076514 0.574319 0.803283 0.048 Uiso 1 1 calc R U . . .
H4B H 0.889150 0.420783 0.764448 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8505(4) 0.5775(4) 0.84040(18) 0.0305(8) Uani 1 1 d . . . . .
H5 H 0.826037 0.638721 0.800068 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6610(4) 0.4479(4) 0.86355(17) 0.0293(8) Uani 1 1 d . . . . .
C7 C 0.6027(4) 0.5669(4) 0.90702(18) 0.0337(9) Uani 1 1 d . . . . .
H7 H 0.531243 0.500922 0.945456 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7863(5) 0.7166(5) 0.9453(2) 0.0457(10) Uani 1 1 d . . . . .
H8A H 0.787408 0.828275 0.940148 0.055 Uiso 1 1 calc R U . . .
H8B H 0.800930 0.702338 0.997691 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9448(4) 0.7117(4) 0.90881(18) 0.0329(8) Uani 1 1 d . . . . .
H9 H 1.009371 0.667612 0.943131 0.039 Uiso 1 1 calc R U . . .
C10 C 0.4898(5) 0.6336(5) 0.8628(2) 0.0493(11) Uani 1 1 d . . . . .
H10A H 0.561809 0.710210 0.827714 0.059 Uiso 1 1 calc R U . . .
H10B H 0.380494 0.536650 0.835555 0.059 Uiso 1 1 calc R U . . .
C11 C 1.0819(5) 0.8929(4) 0.8922(2) 0.0451(10) Uani 1 1 d . . . . .
H11A H 1.021198 0.935204 0.856031 0.054 Uiso 1 1 calc R U . . .
H11B H 1.123083 0.972072 0.937085 0.054 Uiso 1 1 calc R U . . .
C12 C 0.5303(4) 0.3422(4) 0.79798(19) 0.0340(9) Uani 1 1 d . . . . .
C13 C 0.4331(5) 0.2569(5) 0.74300(19) 0.0412(9) Uani 1 1 d . . . . .
C14 C 0.0871(6) 0.1439(6) 0.6362(2) 0.0643(13) Uani 1 1 d . . . . .
H14 H 0.027826 0.083755 0.586872 0.077 Uiso 1 1 calc R U . . .
C15 C 0.1154(9) 0.3305(8) 0.6348(3) 0.125(2) Uani 1 1 d . . . . .
H15A H -0.002649 0.328124 0.624436 0.188 Uiso 1 1 calc R U . . .
H15B H 0.190823 0.386406 0.597058 0.188 Uiso 1 1 calc R U . . .
H15C H 0.175759 0.394616 0.682095 0.188 Uiso 1 1 calc R U . . .
C16 C -0.0469(7) 0.0499(9) 0.6903(3) 0.124(2) Uani 1 1 d . . . . .
H16A H 0.004645 0.107774 0.739273 0.187 Uiso 1 1 calc R U . . .
H16B H -0.068546 -0.069238 0.689663 0.187 Uiso 1 1 calc R U . . .
H16C H -0.161904 0.051363 0.676416 0.187 Uiso 1 1 calc R U . . .
C17 C 0.2517(8) -0.1010(6) 0.6625(3) 0.0956(19) Uani 1 1 d . . . . .
H17 H 0.168577 -0.137143 0.700704 0.115 Uiso 1 1 calc R U . . .
C18 C 0.4039(7) -0.1345(6) 0.6907(3) 0.0857(16) Uani 1 1 d . . . . .
H18A H 0.356388 -0.256705 0.697315 0.129 Uiso 1 1 calc R U . . .
H18B H 0.462780 -0.066336 0.737334 0.129 Uiso 1 1 calc R U . . .
H18C H 0.492465 -0.102295 0.655975 0.129 Uiso 1 1 calc R U . . .
C19 C 0.1342(8) -0.2245(6) 0.5931(3) 0.126(3) Uani 1 1 d . . . . .
H19A H 0.205482 -0.195615 0.552272 0.189 Uiso 1 1 calc R U . . .
H19B H 0.025167 -0.211254 0.581150 0.189 Uiso 1 1 calc R U . . .
H19C H 0.098758 -0.343555 0.602710 0.189 Uiso 1 1 calc R U . . .
C20 C 0.4601(7) 0.2350(9) 0.5829(3) 0.119(3) Uani 1 1 d . . . . .
H20 H 0.518223 0.158352 0.583012 0.143 Uiso 1 1 calc R U . . .
C21 C 0.3680(8) 0.1845(9) 0.5033(3) 0.119(2) Uani 1 1 d . . . . .
H21A H 0.285132 0.233708 0.494628 0.179 Uiso 1 1 calc R U . . .
H21B H 0.299490 0.059126 0.494528 0.179 Uiso 1 1 calc R U . . .
H21C H 0.460863 0.228534 0.470514 0.179 Uiso 1 1 calc R U . . .
C22 C 0.6211(9) 0.3916(9) 0.5949(3) 0.174(4) Uani 1 1 d . . . . .
H22A H 0.665756 0.457997 0.555608 0.209 Uiso 1 1 calc R U . . .
H22B H 0.685230 0.431052 0.642391 0.209 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 C13 1.836(4) . ?
Si1 C20 1.841(5) . ?
Si1 C14 1.859(4) . ?
Si1 C17 1.871(5) . ?
O1 C1 1.427(4) . ?
O1 H1 0.8200 . ?
O2 C10 1.421(4) . ?
O2 H2 0.8200 . ?
O3 C11 1.408(4) . ?
O3 H3 0.8200 . ?
C1 C2 1.504(5) . ?
C1 C6 1.535(5) . ?
C1 H1A 0.9800 . ?
C2 C3 1.525(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.521(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.514(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C9 1.539(4) . ?
C5 C6 1.550(4) . ?
C5 H5 0.9800 . ?
C6 C12 1.475(4) . ?
C6 C7 1.543(4) . ?
C7 C10 1.493(5) . ?
C7 C8 1.535(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.534(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.511(5) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.195(4) . ?
C14 C16 1.513(7) . ?
C14 C15 1.521(7) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.460(6) . ?
C17 C19 1.541(6) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C22 1.376(7) . ?
C20 C21 1.515(6) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9300 . ?
C22 H22B 0.9300 . ?

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
C13 Si1 C20 106.9(2) . . ?
C13 Si1 C14 108.87(18) . . ?
C20 Si1 C14 111.4(3) . . ?
C13 Si1 C17 107.3(2) . . ?
C20 Si1 C17 113.9(3) . . ?
C14 Si1 C17 108.4(2) . . ?
C1 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C11 O3 H3 109.5 . . ?
O1 C1 C2 110.5(3) . . ?
O1 C1 C6 109.7(3) . . ?
C2 C1 C6 113.0(3) . . ?
O1 C1 H1A 107.8 . . ?
C2 C1 H1A 107.8 . . ?
C6 C1 H1A 107.8 . . ?
C1 C2 C3 110.9(3) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 110.7(3) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 112.8(3) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C9 117.7(3) . . ?
C4 C5 C6 112.9(3) . . ?
C9 C5 C6 103.4(2) . . ?
C4 C5 H5 107.5 . . ?
C9 C5 H5 107.5 . . ?
C6 C5 H5 107.5 . . ?
C12 C6 C1 109.1(3) . . ?
C12 C6 C7 115.0(3) . . ?
C1 C6 C7 108.8(3) . . ?
C12 C6 C5 110.6(3) . . ?
C1 C6 C5 109.3(3) . . ?
C7 C6 C5 103.9(2) . . ?
C10 C7 C8 111.9(3) . . ?
C10 C7 C6 116.2(3) . . ?
C8 C7 C6 104.2(3) . . ?
C10 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
C6 C7 H7 108.1 . . ?
C9 C8 C7 108.2(3) . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C11 C9 C8 111.0(3) . . ?
C11 C9 C5 114.7(3) . . ?
C8 C9 C5 105.5(3) . . ?
C11 C9 H9 108.5 . . ?
C8 C9 H9 108.5 . . ?
C5 C9 H9 108.5 . . ?
O2 C10 C7 107.6(3) . . ?
O2 C10 H10A 110.2 . . ?
C7 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
C7 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
O3 C11 C9 111.7(3) . . ?
O3 C11 H11A 109.3 . . ?
C9 C11 H11A 109.3 . . ?
O3 C11 H11B 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C6 176.1(4) . . ?
C12 C13 Si1 173.5(3) . . ?
C16 C14 C15 109.5(5) . . ?
C16 C14 Si1 112.9(4) . . ?
C15 C14 Si1 113.1(4) . . ?
C16 C14 H14 107.0 . . ?
C15 C14 H14 107.0 . . ?
Si1 C14 H14 107.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C19 112.2(4) . . ?
C18 C17 Si1 117.0(4) . . ?
C19 C17 Si1 113.3(4) . . ?
C18 C17 H17 104.2 . . ?
C19 C17 H17 104.2 . . ?
Si1 C17 H17 104.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C21 115.2(5) . . ?
C22 C20 Si1 124.6(4) . . ?
C21 C20 Si1 115.7(4) . . ?
C22 C20 H20 97.0 . . ?
C21 C20 H20 97.0 . . ?
Si1 C20 H20 97.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 120.0 . . ?
C20 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?

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
O1 C1 C2 C3 -178.8(3) . . . . ?
C6 C1 C2 C3 57.9(4) . . . . ?
C1 C2 C3 C4 -56.0(4) . . . . ?
C2 C3 C4 C5 53.9(4) . . . . ?
C3 C4 C5 C9 67.8(4) . . . . ?
C3 C4 C5 C6 -52.5(4) . . . . ?
O1 C1 C6 C12 -57.2(3) . . . . ?
C2 C1 C6 C12 66.5(3) . . . . ?
O1 C1 C6 C7 69.0(3) . . . . ?
C2 C1 C6 C7 -167.3(3) . . . . ?
O1 C1 C6 C5 -178.2(2) . . . . ?
C2 C1 C6 C5 -54.5(3) . . . . ?
C4 C5 C6 C12 -68.9(4) . . . . ?
C9 C5 C6 C12 162.9(3) . . . . ?
C4 C5 C6 C1 51.2(3) . . . . ?
C9 C5 C6 C1 -77.0(3) . . . . ?
C4 C5 C6 C7 167.2(3) . . . . ?
C9 C5 C6 C7 39.0(3) . . . . ?
C12 C6 C7 C10 -30.5(4) . . . . ?
C1 C6 C7 C10 -153.1(3) . . . . ?
C5 C6 C7 C10 90.5(3) . . . . ?
C12 C6 C7 C8 -154.1(3) . . . . ?
C1 C6 C7 C8 83.2(3) . . . . ?
C5 C6 C7 C8 -33.1(3) . . . . ?
C10 C7 C8 C9 -111.5(3) . . . . ?
C6 C7 C8 C9 14.9(4) . . . . ?
C7 C8 C9 C11 134.0(3) . . . . ?
C7 C8 C9 C5 9.2(4) . . . . ?
C4 C5 C9 C11 83.0(4) . . . . ?
C6 C5 C9 C11 -151.9(3) . . . . ?
C4 C5 C9 C8 -154.7(3) . . . . ?
C6 C5 C9 C8 -29.5(4) . . . . ?
C8 C7 C10 O2 -65.2(4) . . . . ?
C6 C7 C10 O2 175.2(3) . . . . ?
C8 C9 C11 O3 174.8(3) . . . . ?
C5 C9 C11 O3 -65.9(4) . . . . ?
C13 Si1 C14 C16 -66.5(4) . . . . ?
C20 Si1 C14 C16 175.9(4) . . . . ?
C17 Si1 C14 C16 49.9(4) . . . . ?
C13 Si1 C14 C15 58.6(4) . . . . ?
C20 Si1 C14 C15 -59.0(4) . . . . ?
C17 Si1 C14 C15 175.0(4) . . . . ?
C13 Si1 C17 C18 -50.9(5) . . . . ?
C20 Si1 C17 C18 67.1(5) . . . . ?
C14 Si1 C17 C18 -168.3(4) . . . . ?
C13 Si1 C17 C19 176.1(4) . . . . ?
C20 Si1 C17 C19 -65.9(5) . . . . ?
C14 Si1 C17 C19 58.7(5) . . . . ?
C13 Si1 C20 C22 -9.9(8) . . . . ?
C14 Si1 C20 C22 108.9(7) . . . . ?
C17 Si1 C20 C22 -128.2(7) . . . . ?
C13 Si1 C20 C21 -165.1(5) . . . . ?
C14 Si1 C20 C21 -46.3(6) . . . . ?
C17 Si1 C20 C21 76.7(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.93 2.743(3) 169.8 2_667 yes
O2 H2 O3 0.82 1.96 2.755(4) 162.7 1_455 yes
O3 H3 O1 0.82 1.95 2.744(3) 161.6 1_665 yes

_refine_diff_density_max         0.519
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.053

