# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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. 
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data_230508sjt
_database_code_depnum_ccdc_archive 'CCDC 2268745'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-08-04 downloaded from the CCDC.
;
_audit_creation_date             2023-05-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H26 N2 O3 Si'
_chemical_formula_sum            'C17 H26 N2 O3 Si'
_chemical_formula_weight         334.49
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2153 0.2529 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.3045(2)
_cell_length_b                   11.4846(2)
_cell_length_c                   10.1085(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.1230(10)
_cell_angle_gamma                90
_cell_volume                     977.99(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8215
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.911
_cell_measurement_theta_min      5.378
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1399 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.7501.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11863
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.886
_diffrn_reflns_theta_min         4.203
_diffrn_ambient_temperature      213.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3499
_reflns_number_total             3679
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1566 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.0593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C12(H12A,H12B,H12C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5890(2) 0.5780(2) 0.4839(2) 0.0283(4) Uani 1 1 d . . . . .
H1 H 0.606019 0.658389 0.457969 0.034 Uiso 1 1 calc R U . . .
N1 N 0.4443(2) 0.53476(17) 0.3701(2) 0.0326(4) Uani 1 1 d . . . . .
H1A H 0.415534 0.463031 0.372673 0.039 Uiso 1 1 calc R U . . .
O1 O 0.3795(3) 0.70728(17) 0.2516(2) 0.0603(6) Uani 1 1 d . . . . .
Si1 Si 0.97806(7) 0.33977(6) 0.49456(8) 0.03637(18) Uani 1 1 d . . . . .
C2 C 0.7258(3) 0.5067(2) 0.4961(2) 0.0318(5) Uani 1 1 d . . . . .
N2 N 0.5801(2) 0.58189(17) 0.62697(18) 0.0267(4) Uani 1 1 d . . . . .
O2 O 0.23104(18) 0.54494(14) 0.16188(17) 0.0354(4) Uani 1 1 d . . . . .
C3 C 0.8324(3) 0.4453(2) 0.5015(3) 0.0364(6) Uani 1 1 d . . . . .
O3 O 0.5842(2) 0.78079(14) 0.62289(19) 0.0404(4) Uani 1 1 d . . . . .
C4 C 1.0287(5) 0.3831(3) 0.3434(4) 0.0677(10) Uani 1 1 d . . . . .
H4A H 0.932771 0.386299 0.252988 0.102 Uiso 1 1 calc R U . . .
H4B H 1.101287 0.326585 0.333986 0.102 Uiso 1 1 calc R U . . .
H4C H 1.078707 0.459195 0.363911 0.102 Uiso 1 1 calc R U . . .
C5 C 0.8773(3) 0.1963(3) 0.4611(3) 0.0519(7) Uani 1 1 d . . . . .
H5A H 0.847017 0.178968 0.539738 0.078 Uiso 1 1 calc R U . . .
H5B H 0.948922 0.136526 0.457017 0.078 Uiso 1 1 calc R U . . .
H5C H 0.783210 0.198421 0.369067 0.078 Uiso 1 1 calc R U . . .
C6 C 1.1575(3) 0.3408(4) 0.6697(3) 0.0635(8) Uani 1 1 d . . . . .
H6A H 1.203041 0.418392 0.688046 0.095 Uiso 1 1 calc R U . . .
H6B H 1.234441 0.286055 0.664760 0.095 Uiso 1 1 calc R U . . .
H6C H 1.129210 0.318580 0.748129 0.095 Uiso 1 1 calc R U . . .
C7 C 0.5727(3) 0.4784(2) 0.6919(3) 0.0327(5) Uani 1 1 d . . . . .
H7 H 0.573693 0.407810 0.645315 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5641(3) 0.4770(2) 0.8206(3) 0.0394(6) Uani 1 1 d . . . . .
H8 H 0.559904 0.406046 0.865201 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5615(3) 0.5844(3) 0.8884(3) 0.0403(5) Uani 1 1 d . . . . .
H9 H 0.556544 0.583951 0.979363 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5661(3) 0.6880(2) 0.8258(3) 0.0347(5) Uani 1 1 d . . . . .
C11 C 0.5765(2) 0.6904(2) 0.6863(2) 0.0293(5) Uani 1 1 d . . . . .
C12 C 0.5610(4) 0.8035(3) 0.8922(3) 0.0511(7) Uani 1 1 d . . . . .
H12A H 0.656480 0.847090 0.908635 0.077 Uiso 1 1 calc R U . . .
H12B H 0.554632 0.791667 0.984530 0.077 Uiso 1 1 calc R U . . .
H12C H 0.468754 0.846741 0.826400 0.077 Uiso 1 1 calc R U . . .
C13 C 0.3531(3) 0.6051(2) 0.2593(2) 0.0329(5) Uani 1 1 d . . . . .
C14 C 0.1115(3) 0.6022(2) 0.0321(3) 0.0405(6) Uani 1 1 d . . . . .
C15 C 0.0019(3) 0.5035(3) -0.0473(3) 0.0523(7) Uani 1 1 d . . . . .
H15A H 0.062514 0.441801 -0.065369 0.079 Uiso 1 1 calc R U . . .
H15B H -0.078505 0.531468 -0.139579 0.079 Uiso 1 1 calc R U . . .
H15C H -0.048875 0.473581 0.012071 0.079 Uiso 1 1 calc R U . . .
C16 C 0.1881(4) 0.6497(4) -0.0612(4) 0.0849(13) Uani 1 1 d . . . . .
H16A H 0.246212 0.720158 -0.017013 0.127 Uiso 1 1 calc R U . . .
H16B H 0.106912 0.667325 -0.157909 0.127 Uiso 1 1 calc R U . . .
H16C H 0.260716 0.592239 -0.068681 0.127 Uiso 1 1 calc R U . . .
C17 C 0.0242(4) 0.6912(4) 0.0792(5) 0.0898(15) Uani 1 1 d . . . . .
H17A H -0.020251 0.654198 0.139661 0.135 Uiso 1 1 calc R U . . .
H17B H -0.060615 0.724892 -0.006391 0.135 Uiso 1 1 calc R U . . .
H17C H 0.097234 0.752105 0.134629 0.135 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 H1 0.9900 . ?
C1 N1 1.438(3) . ?
C1 C2 1.473(3) . ?
C1 N2 1.485(3) . ?
N1 H1A 0.8700 . ?
N1 C13 1.349(3) . ?
O1 C13 1.208(3) . ?
Si1 C3 1.842(2) . ?
Si1 C4 1.848(3) . ?
Si1 C5 1.854(3) . ?
Si1 C6 1.847(3) . ?
C2 C3 1.199(3) . ?
N2 C7 1.373(3) . ?
N2 C11 1.390(3) . ?
O2 C13 1.337(3) . ?
O2 C14 1.467(3) . ?
O3 C11 1.238(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 H7 0.9400 . ?
C7 C8 1.337(4) . ?
C8 H8 0.9400 . ?
C8 C9 1.417(4) . ?
C9 H9 0.9400 . ?
C9 C10 1.356(4) . ?
C10 C11 1.454(3) . ?
C10 C12 1.497(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C14 C15 1.509(4) . ?
C14 C16 1.506(4) . ?
C14 C17 1.503(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?

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
N1 C1 H1 108.1 . . ?
N1 C1 C2 110.91(18) . . ?
N1 C1 N2 111.64(16) . . ?
C2 C1 H1 108.1 . . ?
C2 C1 N2 109.79(17) . . ?
N2 C1 H1 108.1 . . ?
C1 N1 H1A 119.9 . . ?
C13 N1 C1 120.15(19) . . ?
C13 N1 H1A 119.9 . . ?
C3 Si1 C4 107.73(15) . . ?
C3 Si1 C5 105.57(12) . . ?
C3 Si1 C6 109.85(14) . . ?
C4 Si1 C5 112.04(15) . . ?
C6 Si1 C4 110.27(17) . . ?
C6 Si1 C5 111.22(17) . . ?
C3 C2 C1 177.1(2) . . ?
C7 N2 C1 118.35(19) . . ?
C7 N2 C11 123.69(18) . . ?
C11 N2 C1 117.94(19) . . ?
C13 O2 C14 120.76(18) . . ?
C2 C3 Si1 173.3(2) . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7 119.6 . . ?
C8 C7 N2 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.7(2) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 C12 123.7(2) . . ?
C11 C10 C12 116.5(2) . . ?
N2 C11 C10 115.1(2) . . ?
O3 C11 N2 120.8(2) . . ?
O3 C11 C10 124.1(2) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 N1 124.2(2) . . ?
O1 C13 O2 125.9(2) . . ?
O2 C13 N1 109.88(19) . . ?
O2 C14 C15 102.9(2) . . ?
O2 C14 C16 109.9(2) . . ?
O2 C14 C17 109.2(2) . . ?
C16 C14 C15 109.4(3) . . ?
C17 C14 C15 110.3(3) . . ?
C17 C14 C16 114.5(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C1 N1 C13 O1 -4.4(4) . . . . ?
C1 N1 C13 O2 175.88(18) . . . . ?
C1 N2 C7 C8 -179.9(2) . . . . ?
C1 N2 C11 O3 -1.6(3) . . . . ?
C1 N2 C11 C10 179.41(16) . . . . ?
N1 C1 N2 C7 67.6(2) . . . . ?
N1 C1 N2 C11 -111.2(2) . . . . ?
C2 C1 N1 C13 -123.0(2) . . . . ?
C2 C1 N2 C7 -55.8(2) . . . . ?
C2 C1 N2 C11 125.4(2) . . . . ?
N2 C1 N1 C13 114.2(2) . . . . ?
N2 C7 C8 C9 0.5(4) . . . . ?
C7 N2 C11 O3 179.7(2) . . . . ?
C7 N2 C11 C10 0.7(3) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C8 C9 C10 C12 179.0(2) . . . . ?
C9 C10 C11 N2 0.4(3) . . . . ?
C9 C10 C11 O3 -178.6(2) . . . . ?
C11 N2 C7 C8 -1.2(3) . . . . ?
C12 C10 C11 N2 -179.7(2) . . . . ?
C12 C10 C11 O3 1.4(3) . . . . ?
C13 O2 C14 C15 178.4(2) . . . . ?
C13 O2 C14 C16 61.9(3) . . . . ?
C13 O2 C14 C17 -64.5(3) . . . . ?
C14 O2 C13 N1 178.54(19) . . . . ?
C14 O2 C13 O1 -1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
