# 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. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2248832'
loop_
_audit_author_name
_audit_author_address
'Hou Zhong-Wei'
;Taizhou University
China
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-06-08 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            'C17 H24 F3 N O Si'
_chemical_formula_weight         343.46

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.990(2)
_cell_length_b                   8.9043(16)
_cell_length_c                   19.578(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.894(3)
_cell_angle_gamma                90
_cell_volume                     1897.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2305
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.64

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9300
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.955
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3336
_reflns_number_gt                1915
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0807P)²] 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         3336
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_restrained_S_all      0.905
_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 0.51458(6) 0.74816(8) 0.36940(3) 0.0569(2) Uani 1 1 d . . . . .
N1 N 0.83917(19) 0.7328(2) 0.49399(10) 0.0584(5) Uani 1 1 d . . . . .
F3 F 0.89009(15) 0.9236(2) 0.31231(10) 0.1210(8) Uani 1 1 d . . . . .
F2 F 0.87740(18) 0.7015(3) 0.27317(10) 0.1221(8) Uani 1 1 d . . . . .
C8 C 0.7874(2) 0.7447(2) 0.37370(11) 0.0496(6) Uani 1 1 d . . . . .
F1 F 0.99979(14) 0.7500(2) 0.36505(10) 0.1168(8) Uani 1 1 d . . . . .
C16 C 0.7978(2) 0.5851(2) 0.39877(12) 0.0492(6) Uani 1 1 d . . . . .
C11 C 0.8272(2) 0.5846(3) 0.46926(12) 0.0505(6) Uani 1 1 d . . . . .
C9 C 0.8140(2) 0.8319(3) 0.44218(14) 0.0633(7) Uani 1 1 d . . . . .
O1 O 0.8107(2) 0.9677(2) 0.44853(11) 0.1076(8) Uani 1 1 d . . . . .
C4 C 0.3973(2) 0.8796(3) 0.32263(13) 0.0674(7) Uani 1 1 d . . . . .
C7 C 0.6625(2) 0.7906(3) 0.33407(11) 0.0554(6) Uani 1 1 d . . . . .
H7A H 0.6563 0.7443 0.2889 0.066 Uiso 1 1 calc R U . . .
H7B H 0.6651 0.8983 0.3270 0.066 Uiso 1 1 calc R U . . .
C15 C 0.7814(2) 0.4514(3) 0.36446(14) 0.0722(8) Uani 1 1 d . . . . .
H15 H 0.7620 0.4502 0.3167 0.087 Uiso 1 1 calc R U . . .
C12 C 0.8402(2) 0.4543(3) 0.50779(14) 0.0703(7) Uani 1 1 d . . . . .
H12 H 0.8597 0.4559 0.5555 0.084 Uiso 1 1 calc R U . . .
C13 C 0.8228(3) 0.3217(3) 0.4714(2) 0.0918(10) Uani 1 1 d . . . . .
H13 H 0.8309 0.2314 0.4955 0.110 Uiso 1 1 calc R U . . .
C14 C 0.7936(3) 0.3180(3) 0.4007(2) 0.0928(10) Uani 1 1 d . . . . .
H14 H 0.7824 0.2267 0.3776 0.111 Uiso 1 1 calc R U . . .
C17 C 0.8891(3) 0.7820(4) 0.33206(18) 0.0840(9) Uani 1 1 d . . . . .
C3 C 0.3919(3) 0.8614(4) 0.24431(14) 0.1028(11) Uani 1 1 d . . . . .
H3A H 0.4677 0.8955 0.2304 0.154 Uiso 1 1 calc R U . . .
H3B H 0.3251 0.9197 0.2213 0.154 Uiso 1 1 calc R U . . .
H3C H 0.3796 0.7575 0.2322 0.154 Uiso 1 1 calc R U . . .
C6 C 0.5283(3) 0.7789(4) 0.46415(13) 0.0987(11) Uani 1 1 d . . . . .
H6A H 0.5608 0.8774 0.4751 0.148 Uiso 1 1 calc R U . . .
H6B H 0.5824 0.7049 0.4875 0.148 Uiso 1 1 calc R U . . .
H6C H 0.4487 0.7702 0.4788 0.148 Uiso 1 1 calc R U . . .
C10 C 0.8651(3) 0.7743(4) 0.56623(14) 0.1015(11) Uani 1 1 d . . . . .
H10A H 0.7919 0.7633 0.5875 0.152 Uiso 1 1 calc R U . . .
H10B H 0.8922 0.8768 0.5700 0.152 Uiso 1 1 calc R U . . .
H10C H 0.9282 0.7101 0.5890 0.152 Uiso 1 1 calc R U . . .
C2 C 0.4287(3) 1.0442(4) 0.34161(16) 0.0968(10) Uani 1 1 d . . . . .
H2A H 0.4265 1.0590 0.3900 0.145 Uiso 1 1 calc R U . . .
H2B H 0.3699 1.1092 0.3156 0.145 Uiso 1 1 calc R U . . .
H2C H 0.5095 1.0671 0.3311 0.145 Uiso 1 1 calc R U . . .
C1 C 0.2689(3) 0.8454(4) 0.34221(18) 0.1109(12) Uani 1 1 d . . . . .
H1A H 0.2486 0.7422 0.3322 0.166 Uiso 1 1 calc R U . . .
H1B H 0.2091 0.9090 0.3161 0.166 Uiso 1 1 calc R U . . .
H1C H 0.2691 0.8637 0.3905 0.166 Uiso 1 1 calc R U . . .
C5 C 0.4671(3) 0.5487(4) 0.3517(2) 0.1147(12) Uani 1 1 d . . . . .
H5A H 0.3870 0.5328 0.3646 0.172 Uiso 1 1 calc R U . . .
H5B H 0.5250 0.4828 0.3778 0.172 Uiso 1 1 calc R U . . .
H5C H 0.4650 0.5280 0.3034 0.172 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 C6 1.861(3) . ?
Si1 C5 1.871(3) . ?
Si1 C4 1.883(3) . ?
Si1 C7 1.890(2) . ?
N1 C9 1.344(3) . ?
N1 C11 1.406(3) . ?
N1 C10 1.452(3) . ?
F3 C17 1.320(3) . ?
F2 C17 1.348(4) . ?
C8 C16 1.503(3) . ?
C8 C17 1.508(3) . ?
C8 C7 1.537(3) . ?
C8 C9 1.542(3) . ?
F1 C17 1.327(3) . ?
C16 C15 1.367(3) . ?
C16 C11 1.373(3) . ?
C11 C12 1.381(3) . ?
C9 O1 1.217(3) . ?
C4 C3 1.535(4) . ?
C4 C2 1.540(4) . ?
C4 C1 1.543(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C15 C14 1.380(4) . ?
C15 H15 0.9300 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 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
C6 Si1 C5 107.88(16) . . ?
C6 Si1 C4 110.48(13) . . ?
C5 Si1 C4 110.18(15) . . ?
C6 Si1 C7 112.32(13) . . ?
C5 Si1 C7 110.71(13) . . ?
C4 Si1 C7 105.28(11) . . ?
C9 N1 C11 110.9(2) . . ?
C9 N1 C10 124.1(2) . . ?
C11 N1 C10 124.8(2) . . ?
C16 C8 C17 110.9(2) . . ?
C16 C8 C7 116.01(19) . . ?
C17 C8 C7 110.23(19) . . ?
C16 C8 C9 101.25(18) . . ?
C17 C8 C9 107.1(2) . . ?
C7 C8 C9 110.78(19) . . ?
C15 C16 C11 119.2(2) . . ?
C15 C16 C8 131.6(2) . . ?
C11 C16 C8 109.17(19) . . ?
C16 C11 C12 123.0(2) . . ?
C16 C11 N1 109.91(19) . . ?
C12 C11 N1 127.1(2) . . ?
O1 C9 N1 125.5(3) . . ?
O1 C9 C8 125.7(2) . . ?
N1 C9 C8 108.7(2) . . ?
C3 C4 C2 108.6(2) . . ?
C3 C4 C1 108.4(2) . . ?
C2 C4 C1 108.1(2) . . ?
C3 C4 Si1 110.50(18) . . ?
C2 C4 Si1 111.01(19) . . ?
C1 C4 Si1 110.2(2) . . ?
C8 C7 Si1 121.06(15) . . ?
C8 C7 H7A 107.1 . . ?
Si1 C7 H7A 107.1 . . ?
C8 C7 H7B 107.1 . . ?
Si1 C7 H7B 107.1 . . ?
H7A C7 H7B 106.8 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C11 C12 C13 116.2(3) . . ?
C11 C12 H12 121.9 . . ?
C13 C12 H12 121.9 . . ?
C14 C13 C12 122.4(3) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
F3 C17 F1 107.7(3) . . ?
F3 C17 F2 105.1(2) . . ?
F1 C17 F2 106.0(3) . . ?
F3 C17 C8 113.9(2) . . ?
F1 C17 C8 112.8(2) . . ?
F2 C17 C8 110.8(3) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
C17 C8 C16 C15 -68.8(3) . . . . ?
C7 C8 C16 C15 57.9(3) . . . . ?
C9 C8 C16 C15 177.9(3) . . . . ?
C17 C8 C16 C11 112.5(2) . . . . ?
C7 C8 C16 C11 -120.8(2) . . . . ?
C9 C8 C16 C11 -0.8(2) . . . . ?
C15 C16 C11 C12 -0.5(4) . . . . ?
C8 C16 C11 C12 178.4(2) . . . . ?
C15 C16 C11 N1 -179.7(2) . . . . ?
C8 C16 C11 N1 -0.8(3) . . . . ?
C9 N1 C11 C16 2.3(3) . . . . ?
C10 N1 C11 C16 177.5(2) . . . . ?
C9 N1 C11 C12 -176.8(2) . . . . ?
C10 N1 C11 C12 -1.6(4) . . . . ?
C11 N1 C9 O1 176.0(3) . . . . ?
C10 N1 C9 O1 0.7(4) . . . . ?
C11 N1 C9 C8 -2.8(3) . . . . ?
C10 N1 C9 C8 -178.1(2) . . . . ?
C16 C8 C9 O1 -176.6(3) . . . . ?
C17 C8 C9 O1 67.3(3) . . . . ?
C7 C8 C9 O1 -53.0(3) . . . . ?
C16 C8 C9 N1 2.2(2) . . . . ?
C17 C8 C9 N1 -113.9(2) . . . . ?
C7 C8 C9 N1 125.8(2) . . . . ?
C6 Si1 C4 C3 176.4(2) . . . . ?
C5 Si1 C4 C3 -64.5(2) . . . . ?
C7 Si1 C4 C3 54.9(2) . . . . ?
C6 Si1 C4 C2 55.9(2) . . . . ?
C5 Si1 C4 C2 174.98(19) . . . . ?
C7 Si1 C4 C2 -65.61(19) . . . . ?
C6 Si1 C4 C1 -63.8(3) . . . . ?
C5 Si1 C4 C1 55.3(3) . . . . ?
C7 Si1 C4 C1 174.7(2) . . . . ?
C16 C8 C7 Si1 49.1(3) . . . . ?
C17 C8 C7 Si1 176.1(2) . . . . ?
C9 C8 C7 Si1 -65.6(2) . . . . ?
C6 Si1 C7 C8 40.3(2) . . . . ?
C5 Si1 C7 C8 -80.4(2) . . . . ?
C4 Si1 C7 C8 160.55(19) . . . . ?
C11 C16 C15 C14 0.4(4) . . . . ?
C8 C16 C15 C14 -178.2(3) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
N1 C11 C12 C13 179.4(2) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C16 C15 C14 C13 -0.2(5) . . . . ?
C16 C8 C17 F3 -175.8(2) . . . . ?
C7 C8 C17 F3 54.4(3) . . . . ?
C9 C8 C17 F3 -66.2(3) . . . . ?
C16 C8 C17 F1 -52.6(4) . . . . ?
C7 C8 C17 F1 177.5(3) . . . . ?
C9 C8 C17 F1 57.0(3) . . . . ?
C16 C8 C17 F2 66.0(3) . . . . ?
C7 C8 C17 F2 -63.8(3) . . . . ?
C9 C8 C17 F2 175.6(2) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034

