# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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 2027691'
loop_
_audit_author_name
_audit_author_address
'Liu Pei'
;CCDC
China
;
_audit_update_record             
;
2020-09-07 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_audit_creation_date             2020-07-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H23 N O Si'
_chemical_formula_sum            'C14 H23 N O Si'
_chemical_formula_weight         249.42
_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 0.0033 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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.2659(17)
_cell_length_b                   11.991(2)
_cell_length_c                   25.229(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3105.7(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7169
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0689 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.8929.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            31062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.617
_diffrn_reflns_theta_min         1.614
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2460
_reflns_number_total             3245
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.087
_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)+(0.0497P)²+1.0189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1093
_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 Aromatic/amide H refined with riding coordinates:
 N003(H003), C007(H007), C008(H008), C00A(H00A), C00B(H00B)
2.b Idealised Me refined as rotating group:
 C00C(H00C,H00D,H00E), C00D(H00F,H00G,H00H), C00E(H00I,H00J,H00K), C00F(H00L,
 H00M,H00N), C00G(H00O,H00P,H00Q), C00H(H00R,H00S,H00T)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.098
;
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
Si01 Si 0.24878(5) 0.42180(4) 0.45609(2) 0.02925(14) Uani 1 1 d . . . . .
O002 O 0.08612(10) 0.71972(10) 0.23336(4) 0.0328(3) Uani 1 1 d . . . . .
N003 N 0.30161(12) 0.76238(11) 0.23228(5) 0.0270(3) Uani 1 1 d . . . . .
H003 H 0.3753 0.7526 0.2478 0.032 Uiso 1 1 calc R U . . .
C004 C 0.21577(14) 0.64466(13) 0.30290(6) 0.0244(3) Uani 1 1 d . . . . .
C005 C 0.23506(15) 0.51204(13) 0.39550(6) 0.0260(3) Uani 1 1 d . . . . .
C006 C 0.19629(14) 0.71229(13) 0.25321(6) 0.0246(3) Uani 1 1 d . . . . .
C007 C 0.33671(15) 0.58215(13) 0.37927(6) 0.0276(3) Uani 1 1 d . . . . .
H007 H 0.4123 0.5852 0.3996 0.033 Uiso 1 1 calc R U . . .
C008 C 0.32830(14) 0.64706(13) 0.33399(6) 0.0274(4) Uani 1 1 d . . . . .
H008 H 0.3978 0.6924 0.3243 0.033 Uiso 1 1 calc R U . . .
C009 C 0.29915(16) 0.83329(14) 0.18417(7) 0.0303(4) Uani 1 1 d . . . . .
C00A C 0.11306(16) 0.57678(15) 0.31877(7) 0.0345(4) Uani 1 1 d . . . . .
H00A H 0.0368 0.5751 0.2989 0.041 Uiso 1 1 calc R U . . .
C00B C 0.12316(17) 0.51172(15) 0.36387(7) 0.0357(4) Uani 1 1 d . . . . .
H00B H 0.0535 0.4664 0.3734 0.043 Uiso 1 1 calc R U . . .
C00C C 0.20056(19) 0.92825(15) 0.19105(8) 0.0420(4) Uani 1 1 d . . . . .
H00C H 0.1142 0.8978 0.1931 0.063 Uiso 1 1 calc R U . . .
H00D H 0.2062 0.9780 0.1613 0.063 Uiso 1 1 calc R U . . .
H00E H 0.2196 0.9684 0.2230 0.063 Uiso 1 1 calc R U . . .
C00D C 0.43522(18) 0.88363(17) 0.17864(8) 0.0457(5) Uani 1 1 d . . . . .
H00F H 0.4559 0.9255 0.2100 0.068 Uiso 1 1 calc R U . . .
H00G H 0.4374 0.9321 0.1484 0.068 Uiso 1 1 calc R U . . .
H00H H 0.4978 0.8249 0.1741 0.068 Uiso 1 1 calc R U . . .
C00E C 0.37211(18) 0.31015(16) 0.44469(8) 0.0414(4) Uani 1 1 d . . . . .
H00I H 0.3468 0.2660 0.4147 0.062 Uiso 1 1 calc R U . . .
H00J H 0.3775 0.2634 0.4755 0.062 Uiso 1 1 calc R U . . .
H00K H 0.4555 0.3435 0.4380 0.062 Uiso 1 1 calc R U . . .
C00F C 0.2665(2) 0.76173(16) 0.13588(7) 0.0437(5) Uani 1 1 d . . . . .
H00L H 0.3308 0.7042 0.1320 0.066 Uiso 1 1 calc R U . . .
H00M H 0.2659 0.8076 0.1047 0.066 Uiso 1 1 calc R U . . .
H00N H 0.1822 0.7285 0.1406 0.066 Uiso 1 1 calc R U . . .
C00G C 0.08813(19) 0.35511(18) 0.47005(8) 0.0475(5) Uani 1 1 d . . . . .
H00O H 0.0226 0.4118 0.4736 0.071 Uiso 1 1 calc R U . . .
H00P H 0.0936 0.3131 0.5024 0.071 Uiso 1 1 calc R U . . .
H00Q H 0.0655 0.3062 0.4414 0.071 Uiso 1 1 calc R U . . .
C00H C 0.2988(2) 0.51057(18) 0.51339(8) 0.0483(5) Uani 1 1 d . . . . .
H00R H 0.3805 0.5459 0.5056 0.072 Uiso 1 1 calc R U . . .
H00S H 0.3079 0.4649 0.5444 0.072 Uiso 1 1 calc R U . . .
H00T H 0.2336 0.5665 0.5196 0.072 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
Si01 C005 1.8782(16) . ?
Si01 C00E 1.8649(19) . ?
Si01 C00G 1.8664(19) . ?
Si01 C00H 1.867(2) . ?
O002 C006 1.2401(19) . ?
N003 H003 0.8600 . ?
N003 C006 1.345(2) . ?
N003 C009 1.482(2) . ?
C004 C006 1.506(2) . ?
C004 C008 1.397(2) . ?
C004 C00A 1.391(2) . ?
C005 C007 1.401(2) . ?
C005 C00B 1.399(2) . ?
C007 H007 0.9300 . ?
C007 C008 1.385(2) . ?
C008 H008 0.9300 . ?
C009 C00C 1.533(2) . ?
C009 C00D 1.528(2) . ?
C009 C00F 1.527(3) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.384(2) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9600 . ?
C00C H00D 0.9600 . ?
C00C H00E 0.9600 . ?
C00D H00F 0.9600 . ?
C00D H00G 0.9600 . ?
C00D H00H 0.9600 . ?
C00E H00I 0.9600 . ?
C00E H00J 0.9600 . ?
C00E H00K 0.9600 . ?
C00F H00L 0.9600 . ?
C00F H00M 0.9600 . ?
C00F H00N 0.9600 . ?
C00G H00O 0.9600 . ?
C00G H00P 0.9600 . ?
C00G H00Q 0.9600 . ?
C00H H00R 0.9600 . ?
C00H H00S 0.9600 . ?
C00H H00T 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
C00E Si01 C005 109.82(8) . . ?
C00E Si01 C00G 108.75(9) . . ?
C00E Si01 C00H 110.01(10) . . ?
C00G Si01 C005 109.52(8) . . ?
C00G Si01 C00H 109.94(10) . . ?
C00H Si01 C005 108.80(9) . . ?
C006 N003 H003 117.8 . . ?
C006 N003 C009 124.34(13) . . ?
C009 N003 H003 117.8 . . ?
C008 C004 C006 124.48(14) . . ?
C00A C004 C006 116.99(14) . . ?
C00A C004 C008 118.52(15) . . ?
C007 C005 Si01 121.85(12) . . ?
C00B C005 Si01 121.62(12) . . ?
C00B C005 C007 116.53(14) . . ?
O002 C006 N003 122.86(15) . . ?
O002 C006 C004 119.73(14) . . ?
N003 C006 C004 117.42(13) . . ?
C005 C007 H007 118.9 . . ?
C008 C007 C005 122.13(14) . . ?
C008 C007 H007 118.9 . . ?
C004 C008 H008 119.9 . . ?
C007 C008 C004 120.21(14) . . ?
C007 C008 H008 119.9 . . ?
N003 C009 C00C 110.15(14) . . ?
N003 C009 C00D 106.61(13) . . ?
N003 C009 C00F 109.55(14) . . ?
C00D C009 C00C 108.68(15) . . ?
C00F C009 C00C 111.25(15) . . ?
C00F C009 C00D 110.48(15) . . ?
C004 C00A H00A 119.7 . . ?
C00B C00A C004 120.66(15) . . ?
C00B C00A H00A 119.7 . . ?
C005 C00B H00B 119.0 . . ?
C00A C00B C005 121.95(15) . . ?
C00A C00B H00B 119.0 . . ?
C009 C00C H00C 109.5 . . ?
C009 C00C H00D 109.5 . . ?
C009 C00C H00E 109.5 . . ?
H00C C00C H00D 109.5 . . ?
H00C C00C H00E 109.5 . . ?
H00D C00C H00E 109.5 . . ?
C009 C00D H00F 109.5 . . ?
C009 C00D H00G 109.5 . . ?
C009 C00D H00H 109.5 . . ?
H00F C00D H00G 109.5 . . ?
H00F C00D H00H 109.5 . . ?
H00G C00D H00H 109.5 . . ?
Si01 C00E H00I 109.5 . . ?
Si01 C00E H00J 109.5 . . ?
Si01 C00E H00K 109.5 . . ?
H00I C00E H00J 109.5 . . ?
H00I C00E H00K 109.5 . . ?
H00J C00E H00K 109.5 . . ?
C009 C00F H00L 109.5 . . ?
C009 C00F H00M 109.5 . . ?
C009 C00F H00N 109.5 . . ?
H00L C00F H00M 109.5 . . ?
H00L C00F H00N 109.5 . . ?
H00M C00F H00N 109.5 . . ?
Si01 C00G H00O 109.5 . . ?
Si01 C00G H00P 109.5 . . ?
Si01 C00G H00Q 109.5 . . ?
H00O C00G H00P 109.5 . . ?
H00O C00G H00Q 109.5 . . ?
H00P C00G H00Q 109.5 . . ?
Si01 C00H H00R 109.5 . . ?
Si01 C00H H00S 109.5 . . ?
Si01 C00H H00T 109.5 . . ?
H00R C00H H00S 109.5 . . ?
H00R C00H H00T 109.5 . . ?
H00S C00H H00T 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
Si01 C005 C007 C008 178.55(12) . . . . ?
Si01 C005 C00B C00A -179.07(14) . . . . ?
C004 C00A C00B C005 0.7(3) . . . . ?
C005 C007 C008 C004 0.3(2) . . . . ?
C006 N003 C009 C00C 55.6(2) . . . . ?
C006 N003 C009 C00D 173.35(15) . . . . ?
C006 N003 C009 C00F -67.1(2) . . . . ?
C006 C004 C008 C007 179.62(14) . . . . ?
C006 C004 C00A C00B 179.81(16) . . . . ?
C007 C005 C00B C00A 0.2(3) . . . . ?
C008 C004 C006 O002 -167.53(15) . . . . ?
C008 C004 C006 N003 12.5(2) . . . . ?
C008 C004 C00A C00B -1.1(3) . . . . ?
C009 N003 C006 O002 1.1(2) . . . . ?
C009 N003 C006 C004 -178.94(14) . . . . ?
C00A C004 C006 O002 11.5(2) . . . . ?
C00A C004 C006 N003 -168.41(15) . . . . ?
C00A C004 C008 C007 0.6(2) . . . . ?
C00B C005 C007 C008 -0.7(2) . . . . ?
C00E Si01 C005 C007 -68.04(15) . . . . ?
C00E Si01 C005 C00B 111.22(15) . . . . ?
C00G Si01 C005 C007 172.60(14) . . . . ?
C00G Si01 C005 C00B -8.14(17) . . . . ?
C00H Si01 C005 C007 52.41(16) . . . . ?
C00H Si01 C005 C00B -128.33(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
