# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_zxm324_0m
_database_code_depnum_ccdc_archive 'CCDC 1955948'
loop_
_audit_author_name
_audit_author_address
wenguang
;Hunan Normal University
China
;
_audit_update_record             
;
2019-09-25 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 N O2 Si2'
_chemical_formula_weight         369.60

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'
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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.5803(9)
_cell_length_b                   11.5718(8)
_cell_length_c                   15.1255(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.0500(10)
_cell_angle_gamma                90
_cell_volume                     2170.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5854
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.58

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10933
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.642
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3817
_reflns_number_gt                3220
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0622P)²+0.3647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0125(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3817
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
C4 C 0.43973(16) 0.79669(19) 0.52302(15) 0.0703(5) Uani 1 1 d . . . . .
H4 H 0.4370 0.7799 0.5821 0.084 Uiso 1 1 calc R U . . .
O2 O 1.07012(12) 0.79185(15) 0.81710(11) 0.0953(5) Uani 1 1 d . . . . .
C3 C 0.34639(15) 0.79787(17) 0.44031(16) 0.0672(5) Uani 1 1 d . . . . .
H3 H 0.2805 0.7815 0.4428 0.081 Uiso 1 1 calc R U . . .
C5 C 0.53788(14) 0.82018(17) 0.51955(13) 0.0584(4) Uani 1 1 d . . . . .
H5 H 0.6004 0.8181 0.5763 0.070 Uiso 1 1 calc R U . . .
C6 C 0.54465(12) 0.84679(13) 0.43277(11) 0.0432(3) Uani 1 1 d . . . . .
C7 C 0.65025(11) 0.87540(13) 0.42981(10) 0.0411(3) Uani 1 1 d . . . . .
N1 N 1.03044(11) 0.72555(14) 0.74925(11) 0.0607(4) Uani 1 1 d . . . . .
C1 C 0.44898(13) 0.84713(16) 0.34976(13) 0.0577(4) Uani 1 1 d . . . . .
H1 H 0.4507 0.8636 0.2902 0.069 Uiso 1 1 calc R U . . .
C2 C 0.35169(14) 0.82342(18) 0.35423(15) 0.0674(5) Uani 1 1 d . . . . .
H2 H 0.2887 0.8248 0.2978 0.081 Uiso 1 1 calc R U . . .
Si1 Si 0.72037(4) 0.59975(4) 0.41728(3) 0.05679(18) Uani 1 1 d . . . . .
O1 O 1.06781(11) 0.63092(14) 0.74624(12) 0.0881(5) Uani 1 1 d . . . . .
Si2 Si 0.77919(4) 0.99596(4) 0.34234(3) 0.05356(17) Uani 1 1 d . . . . .
C8 C 0.74862(11) 0.82910(12) 0.51125(10) 0.0380(3) Uani 1 1 d . . . . .
C13 C 0.78620(11) 0.71511(12) 0.51307(10) 0.0402(3) Uani 1 1 d . . . . .
C12 C 0.88023(12) 0.68443(13) 0.59261(11) 0.0449(4) Uani 1 1 d . . . . .
H12 H 0.9085 0.6106 0.5958 0.054 Uiso 1 1 calc R U . . .
C11 C 0.93190(11) 0.76192(13) 0.66661(10) 0.0441(4) Uani 1 1 d . . . . .
C14 C 0.5985(2) 0.5407(2) 0.42888(18) 0.0976(8) Uani 1 1 d . . . . .
H14A H 0.5465 0.6013 0.4177 0.146 Uiso 1 1 calc R U . . .
H14B H 0.5678 0.4804 0.3821 0.146 Uiso 1 1 calc R U . . .
H14C H 0.6185 0.5100 0.4928 0.146 Uiso 1 1 calc R U . . .
C16 C 0.6788(3) 0.6543(2) 0.29221(15) 0.1002(9) Uani 1 1 d . . . . .
H16A H 0.6277 0.7159 0.2809 0.150 Uiso 1 1 calc R U . . .
H16B H 0.7409 0.6825 0.2838 0.150 Uiso 1 1 calc R U . . .
H16C H 0.6462 0.5928 0.2471 0.150 Uiso 1 1 calc R U . . .
C15 C 0.8186(3) 0.4812(3) 0.4392(3) 0.1417(15) Uani 1 1 d . . . . .
H15A H 0.8402 0.4529 0.5040 0.213 Uiso 1 1 calc R U . . .
H15B H 0.7860 0.4197 0.3941 0.213 Uiso 1 1 calc R U . . .
H15C H 0.8807 0.5094 0.4307 0.213 Uiso 1 1 calc R U . . .
C10 C 0.89498(13) 0.87238(14) 0.66544(11) 0.0493(4) Uani 1 1 d . . . . .
H10 H 0.9307 0.9234 0.7159 0.059 Uiso 1 1 calc R U . . .
C9 C 0.80335(13) 0.90525(13) 0.58713(11) 0.0470(4) Uani 1 1 d . . . . .
H9 H 0.7772 0.9800 0.5847 0.056 Uiso 1 1 calc R U . . .
C17 C 0.65964(13) 0.94416(15) 0.36261(12) 0.0505(4) Uani 1 1 d . . . . .
C20 C 0.7362(2) 0.9993(2) 0.20873(15) 0.0818(6) Uani 1 1 d . . . . .
H20A H 0.6734 1.0470 0.1798 0.123 Uiso 1 1 calc R U . . .
H20B H 0.7935 1.0303 0.1941 0.123 Uiso 1 1 calc R U . . .
H20C H 0.7198 0.9222 0.1834 0.123 Uiso 1 1 calc R U . . .
C19 C 0.81111(18) 1.14523(18) 0.39247(16) 0.0762(6) Uani 1 1 d . . . . .
H19A H 0.7480 1.1928 0.3643 0.114 Uiso 1 1 calc R U . . .
H19B H 0.8339 1.1428 0.4614 0.114 Uiso 1 1 calc R U . . .
H19C H 0.8678 1.1769 0.3775 0.114 Uiso 1 1 calc R U . . .
C18 C 0.90100(15) 0.90302(18) 0.39645(16) 0.0699(5) Uani 1 1 d . . . . .
H18A H 0.9241 0.9005 0.4654 0.105 Uiso 1 1 calc R U . . .
H18B H 0.8841 0.8263 0.3706 0.105 Uiso 1 1 calc R U . . .
H18C H 0.9577 0.9343 0.3813 0.105 Uiso 1 1 calc R U . . .
H17 H 0.5947(15) 0.9758(16) 0.3194(14) 0.061(5) Uiso 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
C4 C3 1.371(3) . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
O2 N1 1.217(2) . ?
C3 C2 1.365(3) . ?
C3 H3 0.9300 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
C6 C1 1.391(2) . ?
C6 C7 1.490(2) . ?
C7 C17 1.337(2) . ?
C7 C8 1.499(2) . ?
N1 O1 1.216(2) . ?
N1 C11 1.472(2) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
Si1 C15 1.847(3) . ?
Si1 C16 1.851(2) . ?
Si1 C14 1.863(2) . ?
Si1 C13 1.9039(15) . ?
Si2 C18 1.860(2) . ?
Si2 C20 1.861(2) . ?
Si2 C19 1.865(2) . ?
Si2 C17 1.8695(17) . ?
C8 C9 1.397(2) . ?
C8 C13 1.411(2) . ?
C13 C12 1.397(2) . ?
C12 C11 1.382(2) . ?
C12 H12 0.9300 . ?
C11 C10 1.370(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C10 C9 1.376(2) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C17 H17 0.933(19) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
C3 C4 C5 120.72(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C2 C3 C4 118.94(17) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C4 C5 C6 121.09(17) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 117.19(15) . . ?
C5 C6 C7 120.89(14) . . ?
C1 C6 C7 121.91(14) . . ?
C17 C7 C6 123.09(14) . . ?
C17 C7 C8 120.54(14) . . ?
C6 C7 C8 116.24(12) . . ?
O1 N1 O2 123.45(16) . . ?
O1 N1 C11 118.34(16) . . ?
O2 N1 C11 118.21(16) . . ?
C2 C1 C6 121.12(17) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.94(17) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C15 Si1 C16 109.49(16) . . ?
C15 Si1 C14 108.38(17) . . ?
C16 Si1 C14 107.98(13) . . ?
C15 Si1 C13 107.66(10) . . ?
C16 Si1 C13 113.06(9) . . ?
C14 Si1 C13 110.18(9) . . ?
C18 Si2 C20 108.57(11) . . ?
C18 Si2 C19 109.82(10) . . ?
C20 Si2 C19 109.90(10) . . ?
C18 Si2 C17 114.74(8) . . ?
C20 Si2 C17 106.01(9) . . ?
C19 Si2 C17 107.69(9) . . ?
C9 C8 C13 120.45(13) . . ?
C9 C8 C7 116.57(13) . . ?
C13 C8 C7 122.98(13) . . ?
C12 C13 C8 116.80(13) . . ?
C12 C13 Si1 117.26(11) . . ?
C8 C13 Si1 125.94(11) . . ?
C11 C12 C13 121.12(14) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C10 C11 C12 122.17(14) . . ?
C10 C11 N1 118.61(14) . . ?
C12 C11 N1 119.21(15) . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 . . ?
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 . . ?
C11 C10 C9 117.81(14) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C9 C8 121.63(14) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C7 C17 Si2 132.34(13) . . ?
C7 C17 H17 114.2(12) . . ?
Si2 C17 H17 113.3(11) . . ?
Si2 C20 H20A 109.5 . . ?
Si2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si2 C19 H19A 109.5 . . ?
Si2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si2 C18 H18A 109.5 . . ?
Si2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si2 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
C5 C4 C3 C2 -0.4(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 C7 178.21(17) . . . . ?
C5 C6 C7 C17 -151.96(17) . . . . ?
C1 C6 C7 C17 27.1(2) . . . . ?
C5 C6 C7 C8 24.0(2) . . . . ?
C1 C6 C7 C8 -156.96(15) . . . . ?
C5 C6 C1 C2 0.8(3) . . . . ?
C7 C6 C1 C2 -178.28(17) . . . . ?
C4 C3 C2 C1 0.4(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C17 C7 C8 C9 77.88(19) . . . . ?
C6 C7 C8 C9 -98.18(16) . . . . ?
C17 C7 C8 C13 -101.89(18) . . . . ?
C6 C7 C8 C13 82.06(17) . . . . ?
C9 C8 C13 C12 -1.1(2) . . . . ?
C7 C8 C13 C12 178.71(13) . . . . ?
C9 C8 C13 Si1 178.85(11) . . . . ?
C7 C8 C13 Si1 -1.4(2) . . . . ?
C8 C13 C12 C11 1.4(2) . . . . ?
Si1 C13 C12 C11 -178.49(12) . . . . ?
C13 C12 C11 C10 -0.9(2) . . . . ?
C13 C12 C11 N1 179.67(13) . . . . ?
O1 N1 C11 C10 -174.05(16) . . . . ?
O2 N1 C11 C10 6.0(2) . . . . ?
O1 N1 C11 C12 5.4(2) . . . . ?
O2 N1 C11 C12 -174.49(16) . . . . ?
C12 C11 C10 C9 -0.1(2) . . . . ?
N1 C11 C10 C9 179.36(14) . . . . ?
C11 C10 C9 C8 0.5(2) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
C7 C8 C9 C10 -179.65(14) . . . . ?
C6 C7 C17 Si2 178.98(13) . . . . ?
C8 C7 C17 Si2 3.2(3) . . . . ?
C18 Si2 C17 C7 23.1(2) . . . . ?
C20 Si2 C17 C7 142.94(18) . . . . ?
C19 Si2 C17 C7 -99.47(19) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036

_shelxl_version_number           2014-3



