# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a
_database_code_depnum_ccdc_archive 'CCDC 2269293'
loop_
_audit_author_name
_audit_author_address
'Man-Yi Han'
;Huaibei Normal University
China
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H30 O2 Si'
_chemical_formula_weight         390.58

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3035(2)
_cell_length_b                   9.3843(8)
_cell_length_c                   19.8035(6)
_cell_angle_alpha                89.16(2)
_cell_angle_beta                 83.61(2)
_cell_angle_gamma                88.49(2)
_cell_volume                     1163.68(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    361
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      17.67

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5685
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_sigmaI/netI    0.2166
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4034
_reflns_number_gt                1212
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0180P)²+0.5000P] 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_number_reflns         4034
_refine_ls_number_parameters     253
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.2597
_refine_ls_R_factor_gt           0.0915
_refine_ls_wR_factor_ref         0.1995
_refine_ls_wR_factor_gt          0.1511
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.256
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.9937(3) 0.0131(2) 0.32809(10) 0.0689(7) Uani 1 1 d . . .
O1 O 0.3893(11) 0.2112(7) 0.5008(3) 0.153(3) Uani 1 1 d . . .
O2 O 0.4506(10) 0.3447(8) 0.4098(3) 0.152(3) Uani 1 1 d . . .
C1 C 0.637(2) 0.8946(10) -0.0796(4) 0.094(3) Uani 1 1 d . . .
H1A H 0.6270 0.9588 -0.1155 0.113 Uiso 1 1 calc R . .
C2 C 0.4725(17) 0.8086(12) -0.0592(5) 0.103(3) Uani 1 1 d . . .
H2A H 0.3507 0.8117 -0.0818 0.123 Uiso 1 1 calc R . .
C3 C 0.4855(13) 0.7159(9) -0.0048(5) 0.084(3) Uani 1 1 d . . .
H3A H 0.3683 0.6612 0.0103 0.101 Uiso 1 1 calc R . .
C4 C 0.6657(15) 0.7027(9) 0.0273(4) 0.069(2) Uani 1 1 d . . .
C5 C 0.8310(14) 0.7924(10) 0.0057(4) 0.083(3) Uani 1 1 d . . .
H5A H 0.9543 0.7888 0.0275 0.099 Uiso 1 1 calc R . .
C6 C 0.8167(16) 0.8861(10) -0.0470(5) 0.098(3) Uani 1 1 d . . .
H6A H 0.9305 0.9448 -0.0608 0.117 Uiso 1 1 calc R . .
C7 C 0.6826(12) 0.6070(8) 0.0864(4) 0.062(2) Uani 1 1 d . . .
C8 C 0.8701(12) 0.5320(8) 0.0954(4) 0.074(2) Uani 1 1 d . . .
H8A H 0.9884 0.5423 0.0633 0.089 Uiso 1 1 calc R . .
C9 C 0.8858(12) 0.4432(8) 0.1501(4) 0.077(2) Uani 1 1 d . . .
H9A H 1.0159 0.3972 0.1549 0.092 Uiso 1 1 calc R . .
C10 C 0.7134(12) 0.4194(8) 0.1989(4) 0.067(2) Uani 1 1 d . . .
C11 C 0.5223(13) 0.4932(8) 0.1889(4) 0.082(3) Uani 1 1 d . . .
H11A H 0.4027 0.4815 0.2203 0.098 Uiso 1 1 calc R . .
C12 C 0.5084(12) 0.5825(8) 0.1337(4) 0.077(2) Uani 1 1 d . . .
H12A H 0.3782 0.6275 0.1280 0.092 Uiso 1 1 calc R . .
C13 C 0.7259(11) 0.3289(9) 0.2570(4) 0.070(2) Uani 1 1 d . . .
C14 C 0.7341(10) 0.2534(9) 0.3044(4) 0.063(2) Uani 1 1 d . . .
C15 C 0.7716(9) 0.1492(8) 0.3553(4) 0.059(2) Uani 1 1 d . . .
C16 C 1.2083(10) 0.1107(8) 0.2775(4) 0.095(3) Uani 1 1 d . . .
H16A H 1.3242 0.0458 0.2631 0.142 Uiso 1 1 calc R . .
H16B H 1.2583 0.1839 0.3047 0.142 Uiso 1 1 calc R . .
H16C H 1.1539 0.1533 0.2383 0.142 Uiso 1 1 calc R . .
C17 C 1.0889(11) -0.0695(8) 0.4044(3) 0.095(3) Uani 1 1 d . . .
H17A H 1.2027 -0.1367 0.3911 0.143 Uiso 1 1 calc R . .
H17B H 0.9736 -0.1178 0.4301 0.143 Uiso 1 1 calc R . .
H17C H 1.1400 0.0030 0.4318 0.143 Uiso 1 1 calc R . .
C18 C 0.8904(12) -0.1286(8) 0.2743(4) 0.073(2) Uani 1 1 d . . .
C19 C 0.7107(14) -0.2063(9) 0.3136(4) 0.116(3) Uani 1 1 d . . .
H19A H 0.6601 -0.2775 0.2854 0.173 Uiso 1 1 calc R . .
H19B H 0.5964 -0.1399 0.3277 0.173 Uiso 1 1 calc R . .
H19C H 0.7606 -0.2513 0.3530 0.173 Uiso 1 1 calc R . .
C20 C 1.0727(12) -0.2355(9) 0.2518(4) 0.124(4) Uani 1 1 d . . .
H20A H 1.0209 -0.3075 0.2243 0.187 Uiso 1 1 calc R . .
H20B H 1.1240 -0.2793 0.2912 0.187 Uiso 1 1 calc R . .
H20C H 1.1869 -0.1864 0.2260 0.187 Uiso 1 1 calc R . .
C21 C 0.8097(13) -0.0595(9) 0.2098(4) 0.115(3) Uani 1 1 d . . .
H21A H 0.7577 -0.1322 0.1827 0.172 Uiso 1 1 calc R . .
H21B H 0.9251 -0.0119 0.1838 0.172 Uiso 1 1 calc R . .
H21C H 0.6965 0.0082 0.2230 0.172 Uiso 1 1 calc R . .
C22 C 0.6612(10) 0.1391(8) 0.4167(3) 0.073(2) Uani 1 1 d . . .
H22A H 0.6971 0.0619 0.4435 0.088 Uiso 1 1 calc R . .
C23 C 0.4884(14) 0.2359(11) 0.4474(5) 0.096(3) Uani 1 1 d . . .
C24 C 0.2777(19) 0.4448(13) 0.4400(6) 0.199(5) Uani 1 1 d DU . .
H24A H 0.2077 0.4029 0.4814 0.239 Uiso 1 1 calc R . .
H24B H 0.3405 0.5331 0.4517 0.239 Uiso 1 1 calc R . .
C25 C 0.134(2) 0.4726(15) 0.3972(6) 0.217(6) Uani 1 1 d DU . .
H25A H 0.0171 0.5270 0.4199 0.326 Uiso 1 1 calc R . .
H25B H 0.0833 0.3847 0.3817 0.326 Uiso 1 1 calc R . .
H25C H 0.1989 0.5263 0.3591 0.326 Uiso 1 1 calc R . .


_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 C16 1.846(7) . ?
Si1 C17 1.840(6) . ?
Si1 C18 1.889(8) . ?
Si1 C15 1.908(6) . ?
O1 C23 1.190(8) . ?
O2 C23 1.287(9) . ?
O2 C24 1.498(9) . ?
C1 C2 1.351(11) . ?
C1 C6 1.368(10) . ?
C1 H1A 0.9300 . ?
C2 C3 1.383(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.364(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(10) . ?
C4 C7 1.478(9) . ?
C5 C6 1.363(9) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.386(8) . ?
C7 C12 1.383(8) . ?
C8 C9 1.368(8) . ?
C8 H8A 0.9300 . ?
C9 C10 1.392(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.405(8) . ?
C10 C13 1.428(10) . ?
C11 C12 1.377(9) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.172(9) . ?
C14 C15 1.429(9) . ?
C15 C22 1.337(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.500(10) . ?
C18 C20 1.537(8) . ?
C18 C21 1.554(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.482(9) . ?
C22 H22A 0.9300 . ?
C24 C25 1.324(11) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C16 Si1 C17 111.3(3) . . ?
C16 Si1 C18 109.7(4) . . ?
C17 Si1 C18 109.8(4) . . ?
C16 Si1 C15 106.9(3) . . ?
C17 Si1 C15 109.0(3) . . ?
C18 Si1 C15 110.1(3) . . ?
C23 O2 C24 114.9(7) . . ?
C2 C1 C6 119.2(9) . . ?
C2 C1 H1A 120.4 . . ?
C6 C1 H1A 120.4 . . ?
C1 C2 C3 120.1(9) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 121.7(9) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C3 C4 C5 117.0(8) . . ?
C3 C4 C7 122.9(9) . . ?
C5 C4 C7 119.8(9) . . ?
C6 C5 C4 121.3(8) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C1 120.6(9) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
C8 C7 C12 116.8(7) . . ?
C8 C7 C4 121.8(7) . . ?
C12 C7 C4 121.3(7) . . ?
C9 C8 C7 121.8(7) . . ?
C9 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
C8 C9 C10 122.2(7) . . ?
C8 C9 H9A 118.9 . . ?
C10 C9 H9A 118.9 . . ?
C9 C10 C11 115.9(7) . . ?
C9 C10 C13 123.4(7) . . ?
C11 C10 C13 120.7(7) . . ?
C12 C11 C10 121.4(7) . . ?
C12 C11 H11A 119.3 . . ?
C10 C11 H11A 119.3 . . ?
C11 C12 C7 121.8(7) . . ?
C11 C12 H12A 119.1 . . ?
C7 C12 H12A 119.1 . . ?
C14 C13 C10 179.1(10) . . ?
C13 C14 C15 170.5(7) . . ?
C22 C15 C14 125.4(6) . . ?
C22 C15 Si1 120.1(6) . . ?
C14 C15 Si1 114.4(5) . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C20 109.2(7) . . ?
C19 C18 C21 109.1(7) . . ?
C20 C18 C21 108.5(6) . . ?
C19 C18 Si1 110.7(5) . . ?
C20 C18 Si1 109.2(5) . . ?
C21 C18 Si1 110.0(6) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 C22 C23 128.0(7) . . ?
C15 C22 H22A 116.0 . . ?
C23 C22 H22A 116.0 . . ?
O1 C23 O2 123.6(8) . . ?
O1 C23 C22 122.4(9) . . ?
O2 C23 C22 113.9(8) . . ?
C25 C24 O2 111.5(10) . . ?
C25 C24 H24A 109.3 . . ?
O2 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
O2 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2269294'
loop_
_audit_author_name
_audit_author_address
'Man-Yi Han'
;Huaibei Normal University
China
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 O4 Si'
_chemical_formula_weight         392.60

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.450(11)
_cell_length_b                   6.749(5)
_cell_length_c                   24.159(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.04(4)
_cell_angle_gamma                90.00
_cell_volume                     2335(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    488
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      16.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10905
_diffrn_reflns_av_R_equivalents  0.1501
_diffrn_reflns_av_sigmaI/netI    0.1840
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4099
_reflns_number_gt                1420
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.1000P] 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_number_reflns         4099
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2179
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.61931(8) 0.5715(2) -0.07242(6) 0.0508(4) Uani 1 1 d . . .
O1 O 0.75341(19) 0.3171(4) 0.06322(15) 0.0566(9) Uani 1 1 d . . .
O2 O 0.7695(2) 0.1696(5) -0.01631(13) 0.0604(10) Uani 1 1 d . . .
O3 O 0.9594(2) 0.7833(5) 0.04551(14) 0.0653(10) Uani 1 1 d . . .
O4 O 0.9400(2) 0.4599(5) 0.05764(15) 0.0801(12) Uani 1 1 d . . .
C1 C 0.7602(4) 0.1266(7) 0.0939(2) 0.0617(15) Uani 1 1 d . . .
H1A H 0.7336 0.0217 0.0643 0.074 Uiso 1 1 calc R . .
C2 C 0.7029(3) 0.1466(9) 0.1331(3) 0.0804(19) Uani 1 1 d . . .
H2A H 0.6383 0.1824 0.1087 0.097 Uiso 1 1 calc R . .
C3 C 0.7063(4) -0.0580(10) 0.1625(2) 0.113(2) Uani 1 1 d . . .
H3A H 0.6685 -0.0552 0.1867 0.136 Uiso 1 1 calc R . .
H3B H 0.6808 -0.1580 0.1318 0.136 Uiso 1 1 calc R . .
C4 C 0.8071(4) -0.1107(8) 0.2015(2) 0.0818(17) Uani 1 1 d . . .
H4A H 0.8084 -0.2396 0.2205 0.098 Uiso 1 1 calc R . .
C5 C 0.8630(4) -0.1228(8) 0.1617(2) 0.101(2) Uani 1 1 d . . .
H5A H 0.8376 -0.2259 0.1320 0.121 Uiso 1 1 calc R . .
H5B H 0.9274 -0.1560 0.1854 0.121 Uiso 1 1 calc R . .
C6 C 0.8589(3) 0.0793(8) 0.1301(2) 0.0666(15) Uani 1 1 d . . .
H6A H 0.8949 0.0720 0.1043 0.080 Uiso 1 1 calc R . .
C7 C 0.9007(3) 0.2350(8) 0.1780(2) 0.0796(18) Uani 1 1 d . . .
H7A H 0.9652 0.2019 0.2013 0.095 Uiso 1 1 calc R . .
H7B H 0.8994 0.3628 0.1594 0.095 Uiso 1 1 calc R . .
C8 C 0.8467(4) 0.2473(9) 0.2188(2) 0.0786(17) Uani 1 1 d . . .
H8A H 0.8742 0.3492 0.2493 0.094 Uiso 1 1 calc R . .
C9 C 0.7464(4) 0.3019(9) 0.1812(3) 0.0914(19) Uani 1 1 d . . .
H9A H 0.7448 0.4302 0.1628 0.110 Uiso 1 1 calc R . .
H9B H 0.7105 0.3113 0.2066 0.110 Uiso 1 1 calc R . .
C10 C 0.8468(4) 0.0465(9) 0.2493(2) 0.0868(18) Uani 1 1 d . . .
H10A H 0.9100 0.0115 0.2750 0.104 Uiso 1 1 calc R . .
H10B H 0.8092 0.0553 0.2736 0.104 Uiso 1 1 calc R . .
C11 C 0.7601(3) 0.3155(8) 0.0096(2) 0.0480(13) Uani 1 1 d . . .
C12 C 0.7423(3) 0.5206(7) -0.01710(18) 0.0404(12) Uani 1 1 d . . .
C13 C 0.8111(3) 0.6551(7) -0.00349(17) 0.0498(13) Uani 1 1 d . . .
H13A H 0.7961 0.7807 -0.0202 0.060 Uiso 1 1 calc R . .
C14 C 0.9093(3) 0.6182(8) 0.0362(2) 0.0521(14) Uani 1 1 d . . .
C15 C 1.0578(3) 0.7673(8) 0.0831(2) 0.0884(19) Uani 1 1 d . . .
H15A H 1.0657 0.6780 0.1162 0.106 Uiso 1 1 calc R . .
H15B H 1.0923 0.7143 0.0602 0.106 Uiso 1 1 calc R . .
C16 C 1.0932(3) 0.9625(8) 0.1058(2) 0.097(2) Uani 1 1 d . . .
H16A H 1.1587 0.9536 0.1297 0.145 Uiso 1 1 calc R . .
H16B H 1.0605 1.0120 0.1298 0.145 Uiso 1 1 calc R . .
H16C H 1.0840 1.0509 0.0730 0.145 Uiso 1 1 calc R . .
C17 C 0.5395(3) 0.3818(6) -0.06020(19) 0.0712(16) Uani 1 1 d . . .
H17A H 0.5574 0.2522 -0.0684 0.107 Uiso 1 1 calc R . .
H17B H 0.4764 0.4084 -0.0865 0.107 Uiso 1 1 calc R . .
H17C H 0.5440 0.3878 -0.0195 0.107 Uiso 1 1 calc R . .
C18 C 0.5855(3) 0.8266(6) -0.0568(2) 0.0743(16) Uani 1 1 d . . .
H18A H 0.5870 0.8318 -0.0168 0.112 Uiso 1 1 calc R . .
H18B H 0.5236 0.8566 -0.0844 0.112 Uiso 1 1 calc R . .
H18C H 0.6286 0.9217 -0.0613 0.112 Uiso 1 1 calc R . .
C19 C 0.6175(3) 0.5530(8) -0.1511(2) 0.0600(14) Uani 1 1 d . . .
C20 C 0.6791(4) 0.7115(8) -0.1635(2) 0.107(2) Uani 1 1 d . . .
H20A H 0.6767 0.6969 -0.2036 0.161 Uiso 1 1 calc R . .
H20B H 0.7424 0.6962 -0.1359 0.161 Uiso 1 1 calc R . .
H20C H 0.6568 0.8407 -0.1588 0.161 Uiso 1 1 calc R . .
C21 C 0.5153(3) 0.5795(8) -0.1962(2) 0.111(2) Uani 1 1 d . . .
H21A H 0.5137 0.5694 -0.2362 0.166 Uiso 1 1 calc R . .
H21B H 0.4926 0.7074 -0.1906 0.166 Uiso 1 1 calc R . .
H21C H 0.4766 0.4782 -0.1897 0.166 Uiso 1 1 calc R . .
C22 C 0.6508(3) 0.3491(8) -0.1619(2) 0.0876(18) Uani 1 1 d . . .
H22A H 0.6494 0.3424 -0.2019 0.131 Uiso 1 1 calc R . .
H22B H 0.6105 0.2490 -0.1565 0.131 Uiso 1 1 calc R . .
H22C H 0.7135 0.3274 -0.1341 0.131 Uiso 1 1 calc R . .


_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 C17 1.876(4) . ?
Si1 C18 1.878(4) . ?
Si1 C19 1.894(5) . ?
Si1 C12 1.900(4) . ?
O1 C11 1.337(5) . ?
O1 C1 1.468(5) . ?
O2 C11 1.205(5) . ?
O3 C14 1.327(5) . ?
O3 C15 1.453(4) . ?
O4 C14 1.205(5) . ?
C1 C6 1.480(5) . ?
C1 C2 1.526(6) . ?
C1 H1A 0.9800 . ?
C2 C9 1.522(6) . ?
C2 C3 1.545(6) . ?
C2 H2A 0.9800 . ?
C3 C4 1.530(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C10 1.518(6) . ?
C4 C5 1.517(6) . ?
C4 H4A 0.9800 . ?
C5 C6 1.552(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.516(6) . ?
C6 H6A 0.9800 . ?
C7 C8 1.513(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.518(6) . ?
C8 C10 1.542(6) . ?
C8 H8A 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.508(6) . ?
C12 C13 1.342(5) . ?
C13 C14 1.479(5) . ?
C13 H13A 0.9300 . ?
C15 C16 1.452(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C22 1.526(6) . ?
C19 C20 1.535(6) . ?
C19 C21 1.556(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 Si1 C18 110.2(2) . . ?
C17 Si1 C19 110.5(2) . . ?
C18 Si1 C19 111.2(2) . . ?
C17 Si1 C12 108.0(2) . . ?
C18 Si1 C12 107.75(19) . . ?
C19 Si1 C12 109.2(2) . . ?
C11 O1 C1 117.7(4) . . ?
C14 O3 C15 116.8(4) . . ?
O1 C1 C6 110.5(4) . . ?
O1 C1 C2 106.7(4) . . ?
C6 C1 C2 111.2(4) . . ?
O1 C1 H1A 109.5 . . ?
C6 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C9 C2 C1 110.1(4) . . ?
C9 C2 C3 109.6(5) . . ?
C1 C2 C3 106.2(5) . . ?
C9 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
C4 C3 C2 110.0(4) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C10 C4 C5 110.9(5) . . ?
C10 C4 C3 109.5(5) . . ?
C5 C4 C3 108.2(5) . . ?
C10 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C4 C5 C6 109.7(4) . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C1 C6 C7 110.5(4) . . ?
C1 C6 C5 108.8(4) . . ?
C7 C6 C5 107.8(4) . . ?
C1 C6 H6A 109.9 . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C8 C7 C6 110.8(4) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 108.2(4) . . ?
C7 C8 C10 111.1(5) . . ?
C9 C8 C10 108.5(5) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C10 C8 H8A 109.7 . . ?
C8 C9 C2 110.4(4) . . ?
C8 C9 H9A 109.6 . . ?
C2 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C2 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C4 C10 C8 108.9(4) . . ?
C4 C10 H10A 109.9 . . ?
C8 C10 H10A 109.9 . . ?
C4 C10 H10B 109.9 . . ?
C8 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O2 C11 O1 125.4(5) . . ?
O2 C11 C12 124.4(5) . . ?
O1 C11 C12 109.8(4) . . ?
C13 C12 C11 121.1(4) . . ?
C13 C12 Si1 122.8(4) . . ?
C11 C12 Si1 116.1(3) . . ?
C12 C13 C14 124.8(4) . . ?
C12 C13 H13A 117.6 . . ?
C14 C13 H13A 117.6 . . ?
O4 C14 O3 124.1(4) . . ?
O4 C14 C13 124.8(5) . . ?
O3 C14 C13 111.1(4) . . ?
C16 C15 O3 109.1(4) . . ?
C16 C15 H15A 109.9 . . ?
O3 C15 H15A 109.9 . . ?
C16 C15 H15B 109.9 . . ?
O3 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C19 C20 108.8(4) . . ?
C22 C19 C21 107.6(4) . . ?
C20 C19 C21 108.9(4) . . ?
C22 C19 Si1 110.7(3) . . ?
C20 C19 Si1 111.9(3) . . ?
C21 C19 Si1 109.0(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C11 O1 C1 C6 88.0(5) . . . . ?
C11 O1 C1 C2 -151.0(4) . . . . ?
O1 C1 C2 C9 -64.5(5) . . . . ?
C6 C1 C2 C9 56.1(6) . . . . ?
O1 C1 C2 C3 177.0(4) . . . . ?
C6 C1 C2 C3 -62.4(5) . . . . ?
C9 C2 C3 C4 -57.1(6) . . . . ?
C1 C2 C3 C4 61.7(6) . . . . ?
C2 C3 C4 C10 59.1(6) . . . . ?
C2 C3 C4 C5 -61.8(6) . . . . ?
C10 C4 C5 C6 -60.7(6) . . . . ?
C3 C4 C5 C6 59.3(6) . . . . ?
O1 C1 C6 C7 61.8(5) . . . . ?
C2 C1 C6 C7 -56.4(6) . . . . ?
O1 C1 C6 C5 -180.0(4) . . . . ?
C2 C1 C6 C5 61.8(5) . . . . ?
C4 C5 C6 C1 -59.6(6) . . . . ?
C4 C5 C6 C7 60.3(6) . . . . ?
C1 C6 C7 C8 59.2(6) . . . . ?
C5 C6 C7 C8 -59.6(5) . . . . ?
C6 C7 C8 C9 -59.9(6) . . . . ?
C6 C7 C8 C10 59.1(5) . . . . ?
C7 C8 C9 C2 59.5(6) . . . . ?
C10 C8 C9 C2 -61.1(6) . . . . ?
C1 C2 C9 C8 -57.7(6) . . . . ?
C3 C2 C9 C8 58.7(6) . . . . ?
C5 C4 C10 C8 57.8(6) . . . . ?
C3 C4 C10 C8 -61.5(6) . . . . ?
C7 C8 C10 C4 -56.6(6) . . . . ?
C9 C8 C10 C4 62.2(6) . . . . ?
C1 O1 C11 O2 1.4(7) . . . . ?
C1 O1 C11 C12 174.6(3) . . . . ?
O2 C11 C12 C13 -102.1(5) . . . . ?
O1 C11 C12 C13 84.6(5) . . . . ?
O2 C11 C12 Si1 75.8(5) . . . . ?
O1 C11 C12 Si1 -97.5(4) . . . . ?
C17 Si1 C12 C13 -162.6(4) . . . . ?
C18 Si1 C12 C13 -43.6(4) . . . . ?
C19 Si1 C12 C13 77.3(4) . . . . ?
C17 Si1 C12 C11 19.5(4) . . . . ?
C18 Si1 C12 C11 138.5(4) . . . . ?
C19 Si1 C12 C11 -100.6(4) . . . . ?
C11 C12 C13 C14 2.0(7) . . . . ?
Si1 C12 C13 C14 -175.8(3) . . . . ?
C15 O3 C14 O4 1.4(7) . . . . ?
C15 O3 C14 C13 -179.1(4) . . . . ?
C12 C13 C14 O4 5.2(8) . . . . ?
C12 C13 C14 O3 -174.4(4) . . . . ?
C14 O3 C15 C16 -159.8(4) . . . . ?
C17 Si1 C19 C22 -60.8(4) . . . . ?
C18 Si1 C19 C22 176.6(3) . . . . ?
C12 Si1 C19 C22 57.8(4) . . . . ?
C17 Si1 C19 C20 177.8(3) . . . . ?
C18 Si1 C19 C20 55.1(4) . . . . ?
C12 Si1 C19 C20 -63.7(4) . . . . ?
C17 Si1 C19 C21 57.3(4) . . . . ?
C18 Si1 C19 C21 -65.4(4) . . . . ?
C12 Si1 C19 C21 175.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 2269295'
loop_
_audit_author_name
_audit_author_address
'Man-Yi Han'
;Huaibei Normal University
China
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N2 O7 Si'
_chemical_formula_weight         436.53

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0411(16)
_cell_length_b                   24.0685(12)
_cell_length_c                   10.800(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.45(3)
_cell_angle_gamma                90.00
_cell_volume                     2285.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    555
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      16.33

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9594
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11192
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_sigmaI/netI    0.1435
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4026
_reflns_number_gt                1717
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0005P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0043(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4026
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1638
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.78301(12) 0.31195(4) 0.80181(10) 0.0496(3) Uani 1 1 d . . .
C1 C 1.0520(5) 0.58955(17) 0.7185(4) 0.0565(11) Uani 1 1 d . . .
C2 C 1.0973(5) 0.53555(18) 0.7380(4) 0.0683(12) Uani 1 1 d . . .
H2A H 1.1929 0.5267 0.7876 0.082 Uiso 1 1 calc R . .
C3 C 0.9973(6) 0.49436(17) 0.6820(4) 0.0758(13) Uani 1 1 d . . .
H3A H 1.0265 0.4573 0.6945 0.091 Uiso 1 1 calc R . .
C4 C 0.8553(5) 0.50694(16) 0.6083(4) 0.0594(11) Uani 1 1 d . . .
C5 C 0.8162(5) 0.56199(17) 0.5904(4) 0.0717(12) Uani 1 1 d . . .
H5A H 0.7214 0.5714 0.5401 0.086 Uiso 1 1 calc R . .
C6 C 0.9147(6) 0.60353(17) 0.6455(4) 0.0707(12) Uani 1 1 d . . .
H6A H 0.8870 0.6407 0.6326 0.085 Uiso 1 1 calc R . .
C7 C 0.7463(5) 0.46262(16) 0.5464(4) 0.0766(13) Uani 1 1 d . . .
H7A H 0.6510 0.4792 0.5017 0.092 Uiso 1 1 calc R . .
H7B H 0.7885 0.4420 0.4855 0.092 Uiso 1 1 calc R . .
C8 C 0.6151(4) 0.38654(15) 0.6073(4) 0.0526(10) Uani 1 1 d . . .
C9 C 0.6012(4) 0.35148(13) 0.7205(3) 0.0460(10) Uani 1 1 d . . .
C10 C 0.5299(4) 0.38381(14) 0.8201(4) 0.0574(11) Uani 1 1 d . . .
H10A H 0.5932 0.3781 0.9060 0.069 Uiso 1 1 calc R . .
C11 C 0.3713(5) 0.31962(19) 0.7296(5) 0.0824(15) Uani 1 1 d . . .
H11A H 0.2843 0.2976 0.7104 0.099 Uiso 1 1 calc R . .
C12 C 0.5094(5) 0.44533(17) 0.7938(5) 0.0614(12) Uani 1 1 d . . .
C13 C 0.6021(6) 0.53534(16) 0.8586(5) 0.0856(14) Uani 1 1 d . . .
H13A H 0.5138 0.5515 0.8814 0.103 Uiso 1 1 calc R . .
H13B H 0.5973 0.5435 0.7698 0.103 Uiso 1 1 calc R . .
C14 C 0.7444(6) 0.55821(18) 0.9409(5) 0.1133(18) Uani 1 1 d . . .
H14A H 0.7464 0.5978 0.9302 0.170 Uiso 1 1 calc R . .
H14B H 0.8307 0.5419 0.9171 0.170 Uiso 1 1 calc R . .
H14C H 0.7477 0.5497 1.0283 0.170 Uiso 1 1 calc R . .
C15 C 0.9229(4) 0.36309(15) 0.8909(4) 0.0695(12) Uani 1 1 d . . .
H15A H 1.0144 0.3441 0.9321 0.104 Uiso 1 1 calc R . .
H15B H 0.8805 0.3814 0.9537 0.104 Uiso 1 1 calc R . .
H15C H 0.9457 0.3901 0.8327 0.104 Uiso 1 1 calc R . .
C16 C 0.7206(4) 0.26456(14) 0.9153(4) 0.0678(12) Uani 1 1 d . . .
H16A H 0.8057 0.2431 0.9602 0.102 Uiso 1 1 calc R . .
H16B H 0.6431 0.2401 0.8694 0.102 Uiso 1 1 calc R . .
H16C H 0.6806 0.2860 0.9750 0.102 Uiso 1 1 calc R . .
C17 C 0.8616(4) 0.27183(15) 0.6824(4) 0.0587(11) Uani 1 1 d . . .
C18 C 0.9163(5) 0.30969(17) 0.5885(4) 0.0940(16) Uani 1 1 d . . .
H18A H 0.9551 0.2874 0.5294 0.141 Uiso 1 1 calc R . .
H18B H 0.9954 0.3336 0.6342 0.141 Uiso 1 1 calc R . .
H18C H 0.8329 0.3318 0.5430 0.141 Uiso 1 1 calc R . .
C19 C 0.9988(5) 0.23814(18) 0.7556(5) 0.0922(15) Uani 1 1 d . . .
H19A H 1.0405 0.2169 0.6965 0.138 Uiso 1 1 calc R . .
H19B H 0.9667 0.2134 0.8140 0.138 Uiso 1 1 calc R . .
H19C H 1.0749 0.2630 0.8019 0.138 Uiso 1 1 calc R . .
C20 C 0.7439(5) 0.23107(18) 0.6054(5) 0.0998(16) Uani 1 1 d . . .
H20A H 0.7884 0.2112 0.5460 0.150 Uiso 1 1 calc R . .
H20B H 0.6568 0.2514 0.5599 0.150 Uiso 1 1 calc R . .
H20C H 0.7133 0.2052 0.6623 0.150 Uiso 1 1 calc R . .
O1 O 1.2813(4) 0.62086(14) 0.8438(3) 0.1045(12) Uani 1 1 d . . .
O2 O 1.1153(4) 0.68187(14) 0.7592(3) 0.1057(12) Uani 1 1 d . . .
O3 O 0.7212(3) 0.42591(9) 0.6459(2) 0.0561(7) Uani 1 1 d . . .
O4 O 0.5466(3) 0.38050(11) 0.4985(3) 0.0753(9) Uani 1 1 d . . .
O5 O 0.4845(3) 0.30993(10) 0.6707(2) 0.0600(7) Uani 1 1 d . . .
O6 O 0.6061(3) 0.47512(11) 0.8797(3) 0.0688(8) Uani 1 1 d . . .
O7 O 0.4153(4) 0.46440(12) 0.7063(3) 0.0882(10) Uani 1 1 d . . .
N1 N 1.1577(5) 0.63376(18) 0.7777(4) 0.0720(11) Uani 1 1 d . . .
N2 N 0.3812(4) 0.35780(16) 0.8100(4) 0.0923(13) Uani 1 1 d . . .


_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 C16 1.855(3) . ?
Si1 C15 1.864(4) . ?
Si1 C17 1.878(4) . ?
Si1 C9 1.925(4) . ?
C1 C6 1.349(5) . ?
C1 C2 1.364(5) . ?
C1 N1 1.473(5) . ?
C2 C3 1.383(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(5) . ?
C4 C7 1.500(5) . ?
C5 C6 1.379(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 O3 1.450(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O4 1.202(4) . ?
C8 O3 1.344(4) . ?
C8 C9 1.515(5) . ?
C9 O5 1.463(4) . ?
C9 C10 1.581(4) . ?
C10 N2 1.464(5) . ?
C10 C12 1.511(5) . ?
C10 H10A 0.9800 . ?
C11 N2 1.253(5) . ?
C11 O5 1.346(4) . ?
C11 H11A 0.9300 . ?
C12 O7 1.206(5) . ?
C12 O6 1.328(5) . ?
C13 O6 1.466(4) . ?
C13 C14 1.489(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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 1.528(5) . ?
C17 C19 1.538(5) . ?
C17 C20 1.541(5) . ?
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 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1 N1 1.218(4) . ?
O2 N1 1.222(4) . ?

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
C16 Si1 C15 109.82(18) . . ?
C16 Si1 C17 111.06(17) . . ?
C15 Si1 C17 112.00(18) . . ?
C16 Si1 C9 104.26(16) . . ?
C15 Si1 C9 108.28(16) . . ?
C17 Si1 C9 111.12(17) . . ?
C6 C1 C2 122.0(4) . . ?
C6 C1 N1 119.3(4) . . ?
C2 C1 N1 118.7(4) . . ?
C1 C2 C3 118.2(4) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C5 C4 C3 117.9(4) . . ?
C5 C4 C7 120.2(4) . . ?
C3 C4 C7 121.9(4) . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
O3 C7 C4 107.6(3) . . ?
O3 C7 H7A 110.2 . . ?
C4 C7 H7A 110.2 . . ?
O3 C7 H7B 110.2 . . ?
C4 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
O4 C8 O3 123.8(4) . . ?
O4 C8 C9 127.0(4) . . ?
O3 C8 C9 109.2(3) . . ?
O5 C9 C8 105.7(3) . . ?
O5 C9 C10 102.3(2) . . ?
C8 C9 C10 113.5(3) . . ?
O5 C9 Si1 107.2(2) . . ?
C8 C9 Si1 114.9(2) . . ?
C10 C9 Si1 111.9(2) . . ?
N2 C10 C12 109.6(3) . . ?
N2 C10 C9 104.6(3) . . ?
C12 C10 C9 114.0(3) . . ?
N2 C10 H10A 109.5 . . ?
C12 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N2 C11 O5 121.0(4) . . ?
N2 C11 H11A 119.5 . . ?
O5 C11 H11A 119.5 . . ?
O7 C12 O6 124.9(4) . . ?
O7 C12 C10 123.6(4) . . ?
O6 C12 C10 111.5(4) . . ?
O6 C13 C14 106.6(4) . . ?
O6 C13 H13A 110.4 . . ?
C14 C13 H13A 110.4 . . ?
O6 C13 H13B 110.4 . . ?
C14 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C19 108.0(3) . . ?
C18 C17 C20 108.1(4) . . ?
C19 C17 C20 108.4(3) . . ?
C18 C17 Si1 112.4(3) . . ?
C19 C17 Si1 107.9(3) . . ?
C20 C17 Si1 112.0(3) . . ?
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 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 O3 C7 115.0(3) . . ?
C11 O5 C9 105.7(3) . . ?
C12 O6 C13 115.9(4) . . ?
O1 N1 O2 123.2(4) . . ?
O1 N1 C1 119.0(4) . . ?
O2 N1 C1 117.8(4) . . ?
C11 N2 C10 106.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048
