# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_202111296
_database_code_depnum_ccdc_archive 'CCDC 2120950'
loop_
_audit_author_name
_audit_author_address
'yingying xue'
;Zhengzhou University
China
;
_audit_update_record             
;
2021-11-06 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H29 N O Si'
_chemical_formula_weight         303.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.3463(8)
_cell_length_b                   7.5222(3)
_cell_length_c                   22.4194(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.133(4)
_cell_angle_gamma                90
_cell_volume                     3684.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.104
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12393
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.034
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_full        67.070
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3274
_reflns_number_gt                2592
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0835P)²+0.5109P] 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         3274
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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 0.59800(2) 0.74546(7) 0.64723(2) 0.04229(19) Uani 1 1 d . . . . .
O1 O 0.79564(8) 1.0710(2) 0.46018(8) 0.0636(4) Uani 1 1 d . . . . .
N1 N 0.74896(7) 0.9765(2) 0.53443(7) 0.0430(4) Uani 1 1 d . . . . .
C1 C 0.82695(10) 0.8025(3) 0.67918(11) 0.0575(5) Uani 1 1 d . . . . .
H1 H 0.8156 0.7674 0.7150 0.069 Uiso 1 1 calc R U . . .
C2 C 0.88752(11) 0.7901(3) 0.67355(13) 0.0650(6) Uani 1 1 d . . . . .
H2 H 0.9170 0.7463 0.7058 0.078 Uiso 1 1 calc R U . . .
C3 C 0.90408(10) 0.8423(3) 0.62049(13) 0.0618(6) Uani 1 1 d . . . . .
H3 H 0.9448 0.8328 0.6175 0.074 Uiso 1 1 calc R U . . .
C4 C 0.86163(9) 0.9086(3) 0.57129(11) 0.0522(5) Uani 1 1 d . . . . .
H4 H 0.8733 0.9447 0.5357 0.063 Uiso 1 1 calc R U . . .
C5 C 0.80090(9) 0.9191(2) 0.57716(9) 0.0431(4) Uani 1 1 d . . . . .
C6 C 0.78378(9) 0.8675(3) 0.63088(9) 0.0441(4) Uani 1 1 d . . . . .
C7 C 0.71628(9) 0.9028(3) 0.62738(9) 0.0422(4) Uani 1 1 d . . . . .
C8 C 0.69350(9) 0.9406(3) 0.55834(9) 0.0483(5) Uani 1 1 d . . . . .
H8A H 0.6717 0.8386 0.5380 0.058 Uiso 1 1 calc R U . . .
H8B H 0.6663 1.0426 0.5522 0.058 Uiso 1 1 calc R U . . .
C9 C 0.71032(11) 1.0702(3) 0.66481(11) 0.0590(6) Uani 1 1 d . . . . .
H9A H 0.7322 1.1663 0.6510 0.089 Uiso 1 1 calc R U . . .
H9B H 0.7271 1.0474 0.7072 0.089 Uiso 1 1 calc R U . . .
H9C H 0.6679 1.1017 0.6597 0.089 Uiso 1 1 calc R U . . .
C10 C 0.68268(9) 0.7426(2) 0.64849(9) 0.0427(4) Uani 1 1 d . . . . .
H10A H 0.7033 0.7170 0.6902 0.051 Uiso 1 1 calc R U . . .
H10B H 0.6900 0.6417 0.6241 0.051 Uiso 1 1 calc R U . . .
C11 C 0.74833(10) 1.0430(3) 0.47765(9) 0.0464(5) Uani 1 1 d . . . . .
C12 C 0.68700(11) 1.0824(3) 0.43842(10) 0.0574(6) Uani 1 1 d . . . . .
H12A H 0.6627 0.9761 0.4331 0.086 Uiso 1 1 calc R U . . .
H12B H 0.6920 1.1247 0.3994 0.086 Uiso 1 1 calc R U . . .
H12C H 0.6669 1.1718 0.4576 0.086 Uiso 1 1 calc R U . . .
C13 C 0.57953(11) 0.8711(4) 0.71360(11) 0.0623(6) Uani 1 1 d . . . . .
H13A H 0.5898 0.9953 0.7096 0.075 Uiso 1 1 calc R U . . .
H13B H 0.5357 0.8644 0.7111 0.075 Uiso 1 1 calc R U . . .
C14 C 0.61164(18) 0.8079(5) 0.77590(13) 0.0957(10) Uani 1 1 d . . . . .
H14A H 0.6551 0.8174 0.7797 0.144 Uiso 1 1 calc R U . . .
H14B H 0.6010 0.6861 0.7812 0.144 Uiso 1 1 calc R U . . .
H14C H 0.5993 0.8798 0.8066 0.144 Uiso 1 1 calc R U . . .
C15 C 0.57539(11) 0.5065(3) 0.65425(12) 0.0604(6) Uani 1 1 d . . . . .
H15A H 0.6054 0.4512 0.6865 0.072 Uiso 1 1 calc R U . . .
H15B H 0.5364 0.5040 0.6667 0.072 Uiso 1 1 calc R U . . .
C16 C 0.56993(13) 0.3958(4) 0.59680(16) 0.0779(8) Uani 1 1 d . . . . .
H16A H 0.5387 0.4450 0.5651 0.117 Uiso 1 1 calc R U . . .
H16B H 0.5594 0.2759 0.6050 0.117 Uiso 1 1 calc R U . . .
H16C H 0.6083 0.3966 0.5840 0.117 Uiso 1 1 calc R U . . .
C17 C 0.55130(10) 0.8403(3) 0.57460(11) 0.0557(5) Uani 1 1 d . . . . .
H17A H 0.5643 0.9617 0.5702 0.067 Uiso 1 1 calc R U . . .
H17B H 0.5597 0.7726 0.5404 0.067 Uiso 1 1 calc R U . . .
C18 C 0.48214(12) 0.8392(5) 0.57149(14) 0.0835(9) Uani 1 1 d . . . . .
H18A H 0.4612 0.8833 0.5325 0.125 Uiso 1 1 calc R U . . .
H18B H 0.4730 0.9137 0.6032 0.125 Uiso 1 1 calc R U . . .
H18C H 0.4689 0.7200 0.5769 0.125 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 C17 1.880(2) . ?
Si1 C13 1.880(2) . ?
Si1 C15 1.882(2) . ?
Si1 C10 1.887(2) . ?
O1 C11 1.220(3) . ?
N1 C11 1.365(3) . ?
N1 C5 1.408(3) . ?
N1 C8 1.475(2) . ?
C1 C6 1.380(3) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C6 C7 1.517(3) . ?
C7 C9 1.534(3) . ?
C7 C10 1.545(3) . ?
C7 C8 1.551(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.494(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.507(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.517(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.532(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 C13 108.69(11) . . ?
C17 Si1 C15 108.95(11) . . ?
C13 Si1 C15 107.85(11) . . ?
C17 Si1 C10 112.93(9) . . ?
C13 Si1 C10 112.33(10) . . ?
C15 Si1 C10 105.90(10) . . ?
C11 N1 C5 126.30(17) . . ?
C11 N1 C8 124.15(17) . . ?
C5 N1 C8 109.40(16) . . ?
C6 C1 C2 119.1(2) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 117.5(2) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 N1 129.29(19) . . ?
C6 C5 N1 109.66(17) . . ?
C1 C6 C5 120.24(19) . . ?
C1 C6 C7 128.76(19) . . ?
C5 C6 C7 110.92(17) . . ?
C6 C7 C9 108.34(16) . . ?
C6 C7 C10 112.93(16) . . ?
C9 C7 C10 111.64(16) . . ?
C6 C7 C8 101.41(15) . . ?
C9 C7 C8 110.33(18) . . ?
C10 C7 C8 111.70(16) . . ?
N1 C8 C7 105.77(16) . . ?
N1 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
N1 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 Si1 122.48(14) . . ?
C7 C10 H10A 106.7 . . ?
Si1 C10 H10A 106.7 . . ?
C7 C10 H10B 106.7 . . ?
Si1 C10 H10B 106.7 . . ?
H10A C10 H10B 106.6 . . ?
O1 C11 N1 121.5(2) . . ?
O1 C11 C12 121.7(2) . . ?
N1 C11 C12 116.75(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 Si1 115.7(2) . . ?
C14 C13 H13A 108.4 . . ?
Si1 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
Si1 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
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 . . ?
C16 C15 Si1 115.36(18) . . ?
C16 C15 H15A 108.4 . . ?
Si1 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
Si1 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
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 . . ?
C18 C17 Si1 114.10(16) . . ?
C18 C17 H17A 108.7 . . ?
Si1 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
Si1 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
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 . . ?

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
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 N1 -178.3(2) . . . . ?
C11 N1 C5 C4 -3.3(3) . . . . ?
C8 N1 C5 C4 172.23(19) . . . . ?
C11 N1 C5 C6 177.29(18) . . . . ?
C8 N1 C5 C6 -7.2(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 -176.3(2) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
N1 C5 C6 C1 178.60(19) . . . . ?
C4 C5 C6 C7 176.30(17) . . . . ?
N1 C5 C6 C7 -4.2(2) . . . . ?
C1 C6 C7 C9 73.7(3) . . . . ?
C5 C6 C7 C9 -103.2(2) . . . . ?
C1 C6 C7 C10 -50.6(3) . . . . ?
C5 C6 C7 C10 132.58(17) . . . . ?
C1 C6 C7 C8 -170.2(2) . . . . ?
C5 C6 C7 C8 12.9(2) . . . . ?
C11 N1 C8 C7 -169.16(17) . . . . ?
C5 N1 C8 C7 15.2(2) . . . . ?
C6 C7 C8 N1 -16.4(2) . . . . ?
C9 C7 C8 N1 98.29(19) . . . . ?
C10 C7 C8 N1 -136.90(17) . . . . ?
C6 C7 C10 Si1 -178.39(13) . . . . ?
C9 C7 C10 Si1 59.2(2) . . . . ?
C8 C7 C10 Si1 -64.8(2) . . . . ?
C17 Si1 C10 C7 44.61(19) . . . . ?
C13 Si1 C10 C7 -78.76(19) . . . . ?
C15 Si1 C10 C7 163.76(17) . . . . ?
C5 N1 C11 O1 -5.4(3) . . . . ?
C8 N1 C11 O1 179.69(19) . . . . ?
C5 N1 C11 C12 175.48(18) . . . . ?
C8 N1 C11 C12 0.6(3) . . . . ?
C17 Si1 C13 C14 178.0(2) . . . . ?
C15 Si1 C13 C14 60.1(3) . . . . ?
C10 Si1 C13 C14 -56.3(3) . . . . ?
C17 Si1 C15 C16 45.7(2) . . . . ?
C13 Si1 C15 C16 163.5(2) . . . . ?
C10 Si1 C15 C16 -76.1(2) . . . . ?
C13 Si1 C17 C18 -56.3(2) . . . . ?
C15 Si1 C17 C18 60.9(2) . . . . ?
C10 Si1 C17 C18 178.3(2) . . . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.045

