# 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_i17962
_database_code_depnum_ccdc_archive 'CCDC 2083039'
loop_
_audit_author_name
_audit_author_address
'Prof. Rong-Jie Chein'
;Institute of Chemistry, Academia Sinica, Taiwan
Taiwan
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H33 N O3 Si'
_chemical_formula_sum            'C23 H33 N O3 Si'
_chemical_formula_weight         399.59

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.3096(2)
_cell_length_b                   12.9213(4)
_cell_length_c                   26.6212(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2170.38(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      72.27

_exptl_crystal_description       niddle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    1.132
_shelx_estimated_absorpt_T_min   0.769
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8054
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            46023
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.1278
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.802
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_full        66.583
_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             3844
_reflns_number_gt                3550
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0467P)²+0.0435P] 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_abs_structure_details 
;
 Flack x determined using 1418 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3844
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.37574(11) 0.56614(5) 0.36618(2) 0.01713(17) Uani 1 1 d . . . . .
O1 O 0.5425(3) 0.60045(13) 0.23693(6) 0.0259(4) Uani 1 1 d . . . . .
O2 O 1.0483(3) 0.85303(14) 0.23678(6) 0.0250(4) Uani 1 1 d . . . . .
O3 O 0.5374(3) 0.66615(12) 0.35912(6) 0.0184(4) Uani 1 1 d . . . . .
N1 N 0.8238(3) 0.71364(15) 0.23107(7) 0.0183(4) Uani 1 1 d . . . . .
C1 C 0.6234(4) 0.68300(19) 0.24709(8) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.5267(4) 0.77062(18) 0.27664(8) 0.0171(5) Uani 1 1 d . . . . .
H2 H 0.391174 0.797835 0.262346 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5302(4) 0.76375(18) 0.33557(8) 0.0160(5) Uani 1 1 d . . . . .
C4 C 0.3557(4) 0.83318(18) 0.35706(8) 0.0186(5) Uani 1 1 d . . . . .
H4A H 0.314761 0.885187 0.331541 0.022 Uiso 1 1 calc R U . . .
H4AB H 0.229367 0.790516 0.364632 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4269(4) 0.8888(2) 0.40486(9) 0.0235(6) Uani 1 1 d . . . . .
H5A H 0.308658 0.930791 0.418338 0.028 Uiso 1 1 calc R U . . .
H5AB H 0.467661 0.837309 0.430657 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6149(4) 0.9584(2) 0.39306(9) 0.0248(6) Uani 1 1 d . . . . .
H6A H 0.652433 0.999449 0.423188 0.030 Uiso 1 1 calc R U . . .
H6AB H 0.576409 1.007150 0.365845 0.030 Uiso 1 1 calc R U . . .
C7 C 0.8045(4) 0.8937(2) 0.37689(9) 0.0212(6) Uani 1 1 d . . . . .
H7A H 0.860095 0.855555 0.406338 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.917987 0.940162 0.364624 0.025 Uiso 1 1 calc R U . . .
C8 C 0.7480(4) 0.81665(18) 0.33568(8) 0.0169(5) Uani 1 1 d . . . . .
H8 H 0.859108 0.761463 0.335251 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7069(4) 0.85167(19) 0.27994(9) 0.0180(5) Uani 1 1 d . . . . .
H9 H 0.664310 0.925540 0.275078 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8792(4) 0.81279(19) 0.24668(8) 0.0190(5) Uani 1 1 d . . . . .
C11 C 0.9693(4) 0.6458(2) 0.20347(9) 0.0215(5) Uani 1 1 d . . . . .
H11A H 0.922316 0.573218 0.207741 0.026 Uiso 1 1 calc R U . . .
H11B H 1.112395 0.651974 0.218404 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9836(4) 0.66940(18) 0.14802(8) 0.0186(5) Uani 1 1 d . . . . .
C13 C 1.1664(4) 0.7119(2) 0.12836(9) 0.0243(6) Uani 1 1 d . . . . .
H13 H 1.279919 0.729962 0.150104 0.029 Uiso 1 1 calc R U . . .
C14 C 1.1855(5) 0.7284(2) 0.07700(10) 0.0335(7) Uani 1 1 d . . . . .
H14 H 1.311479 0.758284 0.063875 0.040 Uiso 1 1 calc R U . . .
C15 C 1.0244(5) 0.7021(2) 0.04528(10) 0.0316(7) Uani 1 1 d . . . . .
H15 H 1.038949 0.712148 0.010100 0.038 Uiso 1 1 calc R U . . .
C16 C 0.8394(5) 0.6605(2) 0.06481(10) 0.0353(7) Uani 1 1 d . . . . .
H16 H 0.726366 0.642375 0.042942 0.042 Uiso 1 1 calc R U . . .
C17 C 0.8187(4) 0.6452(2) 0.11601(10) 0.0273(6) Uani 1 1 d . . . . .
H17 H 0.690504 0.617874 0.129210 0.033 Uiso 1 1 calc R U . . .
C18 C 0.5332(5) 0.4503(2) 0.34787(10) 0.0293(6) Uani 1 1 d . . . . .
H18A H 0.585080 0.458845 0.313422 0.044 Uiso 1 1 calc R U . . .
H18B H 0.443555 0.388539 0.349811 0.044 Uiso 1 1 calc R U . . .
H18C H 0.653871 0.442681 0.370749 0.044 Uiso 1 1 calc R U . . .
C19 C 0.1381(5) 0.5761(2) 0.32544(9) 0.0274(6) Uani 1 1 d . . . . .
H19A H 0.172423 0.617113 0.295555 0.041 Uiso 1 1 calc R U . . .
H19B H 0.023224 0.609902 0.344043 0.041 Uiso 1 1 calc R U . . .
H19C H 0.092958 0.506692 0.315216 0.041 Uiso 1 1 calc R U . . .
C20 C 0.2958(5) 0.5573(2) 0.43476(9) 0.0270(6) Uani 1 1 d . . . . .
C21 C 0.1830(5) 0.4536(2) 0.44292(10) 0.0371(7) Uani 1 1 d . . . . .
H21A H 0.057049 0.450207 0.421442 0.056 Uiso 1 1 calc R U . . .
H21B H 0.140462 0.447529 0.478198 0.056 Uiso 1 1 calc R U . . .
H21C H 0.279387 0.396849 0.434329 0.056 Uiso 1 1 calc R U . . .
C22 C 0.4948(6) 0.5620(3) 0.46807(10) 0.0462(9) Uani 1 1 d . . . . .
H22A H 0.591596 0.505890 0.458721 0.069 Uiso 1 1 calc R U . . .
H22B H 0.453796 0.554340 0.503376 0.069 Uiso 1 1 calc R U . . .
H22C H 0.565850 0.628738 0.463320 0.069 Uiso 1 1 calc R U . . .
C23 C 0.1433(6) 0.6442(2) 0.44951(11) 0.0427(8) Uani 1 1 d . . . . .
H23A H 0.211506 0.711305 0.443807 0.064 Uiso 1 1 calc R U . . .
H23B H 0.106233 0.637436 0.485107 0.064 Uiso 1 1 calc R U . . .
H23C H 0.014514 0.639442 0.429069 0.064 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 O3 1.6571(17) . ?
Si1 C19 1.855(3) . ?
Si1 C18 1.861(3) . ?
Si1 C20 1.897(3) . ?
O1 C1 1.213(3) . ?
O2 C10 1.216(3) . ?
O3 C3 1.409(3) . ?
N1 C10 1.391(3) . ?
N1 C1 1.392(3) . ?
N1 C11 1.467(3) . ?
C1 C2 1.507(3) . ?
C2 C9 1.548(3) . ?
C2 C3 1.571(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.531(3) . ?
C3 C8 1.535(3) . ?
C4 C5 1.529(3) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.522(4) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.524(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.573(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.489(3) . ?
C9 H9 1.0000 . ?
C11 C12 1.510(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.380(4) . ?
C12 C17 1.381(4) . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.364(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C23 1.529(4) . ?
C20 C21 1.533(4) . ?
C20 C22 1.538(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
O3 Si1 C19 112.15(11) . . ?
O3 Si1 C18 105.58(11) . . ?
C19 Si1 C18 109.54(13) . . ?
O3 Si1 C20 108.63(10) . . ?
C19 Si1 C20 110.59(13) . . ?
C18 Si1 C20 110.23(12) . . ?
C3 O3 Si1 136.77(16) . . ?
C10 N1 C1 113.5(2) . . ?
C10 N1 C11 122.9(2) . . ?
C1 N1 C11 123.5(2) . . ?
O1 C1 N1 124.3(2) . . ?
O1 C1 C2 127.3(2) . . ?
N1 C1 C2 108.3(2) . . ?
C1 C2 C9 103.9(2) . . ?
C1 C2 C3 118.21(19) . . ?
C9 C2 C3 88.35(17) . . ?
C1 C2 H2 114.3 . . ?
C9 C2 H2 114.3 . . ?
C3 C2 H2 114.3 . . ?
O3 C3 C4 112.41(19) . . ?
O3 C3 C8 111.65(19) . . ?
C4 C3 C8 112.47(19) . . ?
O3 C3 C2 119.68(19) . . ?
C4 C3 C2 109.26(19) . . ?
C8 C3 C2 89.39(18) . . ?
C5 C4 C3 112.0(2) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4AB 109.2 . . ?
C3 C4 H4AB 109.2 . . ?
H4A C4 H4AB 107.9 . . ?
C6 C5 C4 109.6(2) . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5AB 109.8 . . ?
C4 C5 H5AB 109.8 . . ?
H5A C5 H5AB 108.2 . . ?
C5 C6 C7 110.2(2) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6AB 109.6 . . ?
C7 C6 H6AB 109.6 . . ?
H6A C6 H6AB 108.1 . . ?
C6 C7 C8 112.3(2) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7AB 109.2 . . ?
C8 C7 H7AB 109.2 . . ?
H7A C7 H7AB 107.9 . . ?
C7 C8 C3 120.1(2) . . ?
C7 C8 C9 122.0(2) . . ?
C3 C8 C9 88.77(17) . . ?
C7 C8 H8 108.1 . . ?
C3 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C10 C9 C2 105.9(2) . . ?
C10 C9 C8 110.1(2) . . ?
C2 C9 C8 88.86(17) . . ?
C10 C9 H9 116.2 . . ?
C2 C9 H9 116.2 . . ?
C8 C9 H9 116.2 . . ?
O2 C10 N1 123.3(2) . . ?
O2 C10 C9 128.7(2) . . ?
N1 C10 C9 107.8(2) . . ?
N1 C11 C12 114.0(2) . . ?
N1 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C17 119.1(2) . . ?
C13 C12 C11 120.1(2) . . ?
C17 C12 C11 120.8(2) . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C12 C17 C16 120.3(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C20 C21 108.2(2) . . ?
C23 C20 C22 109.7(3) . . ?
C21 C20 C22 109.4(2) . . ?
C23 C20 Si1 111.74(18) . . ?
C21 C20 Si1 108.19(17) . . ?
C22 C20 Si1 109.59(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_i18031
_database_code_depnum_ccdc_archive 'CCDC 2083040'
loop_
_audit_author_name
_audit_author_address
'Prof. Rong-Jie Chein'
;Institute of Chemistry, Academia Sinica, Taiwan
Taiwan
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H35 N O3 Si'
_chemical_formula_sum            'C24 H35 N O3 Si'
_chemical_formula_weight         413.62

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.5874(3)
_cell_length_b                   6.3337(2)
_cell_length_c                   15.8579(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.1940(10)
_cell_angle_gamma                90
_cell_volume                     1162.98(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.1

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(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            34193
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5088
_reflns_number_gt                4813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.997

_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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0334P)²+0.2248P] 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_abs_structure_details 
;
 Flack x determined using 2076 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5088
_refine_ls_number_parameters     268
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.68149(4) 0.23929(7) 0.85619(3) 0.01851(12) Uani 1 1 d . . . . .
O1 O 0.60078(10) 0.42962(19) 0.81286(7) 0.0173(3) Uani 1 1 d . . . . .
O2 O 0.49476(11) 0.9253(2) 0.54833(8) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.77691(11) 0.4920(3) 0.65545(9) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.65363(12) 0.7303(3) 0.59173(8) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.52205(14) 0.4253(3) 0.74289(10) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.43174(15) 0.2496(3) 0.74837(10) 0.0186(3) Uani 1 1 d . . . . .
H2A H 0.401018 0.215669 0.690842 0.022 Uiso 1 1 calc R U . . .
H2AB H 0.469321 0.120972 0.771916 0.022 Uiso 1 1 calc R U . . .
C3 C 0.33167(17) 0.3113(3) 0.80338(12) 0.0228(4) Uani 1 1 d . . . . .
H3A H 0.361504 0.345557 0.861095 0.027 Uiso 1 1 calc R U . . .
H3AB H 0.277192 0.191569 0.807158 0.027 Uiso 1 1 calc R U . . .
C4 C 0.26882(16) 0.5036(3) 0.76482(12) 0.0228(4) Uani 1 1 d . . . . .
H4 H 0.245347 0.469463 0.705026 0.027 Uiso 1 1 calc R U . . .
C5 C 0.35114(15) 0.6910(3) 0.76462(12) 0.0202(4) Uani 1 1 d . . . . .
H5A H 0.313451 0.808573 0.732994 0.024 Uiso 1 1 calc R U . . .
H5AB H 0.365989 0.738901 0.823456 0.024 Uiso 1 1 calc R U . . .
C6 C 0.46543(15) 0.6421(3) 0.72574(10) 0.0152(3) Uani 1 1 d . . . . .
H6 H 0.522024 0.755078 0.742638 0.018 Uiso 1 1 calc R U . . .
C7 C 0.47497(15) 0.5979(3) 0.62828(10) 0.0157(3) Uani 1 1 d . . . . .
H7 H 0.403119 0.542970 0.599004 0.019 Uiso 1 1 calc R U . . .
C8 C 0.53562(15) 0.7709(3) 0.58288(10) 0.0162(4) Uani 1 1 d . . . . .
C9 C 0.67943(15) 0.5448(3) 0.63599(11) 0.0180(4) Uani 1 1 d . . . . .
C10 C 0.56789(15) 0.4297(3) 0.65091(11) 0.0164(3) Uani 1 1 d . . . . .
H10 H 0.558452 0.293746 0.619342 0.020 Uiso 1 1 calc R U . . .
C11 C 0.16007(17) 0.5561(4) 0.81224(14) 0.0326(5) Uani 1 1 d . . . . .
H11A H 0.121570 0.678584 0.785933 0.049 Uiso 1 1 calc R U . . .
H11B H 0.181343 0.588693 0.871214 0.049 Uiso 1 1 calc R U . . .
H11C H 0.107579 0.434761 0.809960 0.049 Uiso 1 1 calc R U . . .
C12 C 0.74287(16) 0.8738(3) 0.56437(12) 0.0209(4) Uani 1 1 d . . . . .
H12A H 0.799073 0.896709 0.612091 0.025 Uiso 1 1 calc R U . . .
H12B H 0.706681 1.011765 0.550530 0.025 Uiso 1 1 calc R U . . .
C13 C 0.80815(15) 0.7995(3) 0.48853(11) 0.0188(4) Uani 1 1 d . . . . .
C14 C 0.89595(16) 0.9304(4) 0.46057(12) 0.0248(4) Uani 1 1 d . . . . .
H14 H 0.909896 1.062878 0.487148 0.030 Uiso 1 1 calc R U . . .
C15 C 0.96275(17) 0.8683(4) 0.39436(13) 0.0317(5) Uani 1 1 d . . . . .
H15 H 1.021912 0.958479 0.375413 0.038 Uiso 1 1 calc R U . . .
C16 C 0.94331(17) 0.6743(4) 0.35571(12) 0.0313(5) Uani 1 1 d . . . . .
H16 H 0.989762 0.630936 0.310777 0.038 Uiso 1 1 calc R U . . .
C17 C 0.85625(17) 0.5443(4) 0.38266(12) 0.0280(4) Uani 1 1 d . . . . .
H17 H 0.842757 0.411670 0.356121 0.034 Uiso 1 1 calc R U . . .
C18 C 0.78816(16) 0.6079(3) 0.44884(11) 0.0214(4) Uani 1 1 d . . . . .
H18 H 0.727755 0.518933 0.466696 0.026 Uiso 1 1 calc R U . . .
C19 C 0.59623(19) 0.0725(4) 0.92873(13) 0.0305(5) Uani 1 1 d . . . . .
H19A H 0.549911 -0.029459 0.895562 0.046 Uiso 1 1 calc R U . . .
H19B H 0.545047 0.162891 0.960768 0.046 Uiso 1 1 calc R U . . .
H19C H 0.649075 -0.003139 0.967843 0.046 Uiso 1 1 calc R U . . .
C20 C 0.74316(19) 0.0747(3) 0.77168(13) 0.0286(4) Uani 1 1 d . . . . .
H20A H 0.681216 -0.006016 0.742855 0.043 Uiso 1 1 calc R U . . .
H20B H 0.800461 -0.022808 0.796770 0.043 Uiso 1 1 calc R U . . .
H20C H 0.780268 0.166314 0.730928 0.043 Uiso 1 1 calc R U . . .
C21 C 0.79917(16) 0.3819(3) 0.91901(12) 0.0221(4) Uani 1 1 d . . . . .
C22 C 0.85194(19) 0.5531(4) 0.86469(14) 0.0345(5) Uani 1 1 d . . . . .
H22A H 0.878975 0.489858 0.812605 0.052 Uiso 1 1 calc R U . . .
H22B H 0.917203 0.618529 0.895918 0.052 Uiso 1 1 calc R U . . .
H22C H 0.793511 0.660623 0.850690 0.052 Uiso 1 1 calc R U . . .
C23 C 0.89425(18) 0.2257(4) 0.94718(13) 0.0338(5) Uani 1 1 d . . . . .
H23A H 0.934839 0.176558 0.897763 0.051 Uiso 1 1 calc R U . . .
H23B H 0.859530 0.104823 0.975278 0.051 Uiso 1 1 calc R U . . .
H23C H 0.949108 0.296004 0.986478 0.051 Uiso 1 1 calc R U . . .
C24 C 0.74913(19) 0.4853(4) 0.99708(14) 0.0328(5) Uani 1 1 d . . . . .
H24A H 0.688156 0.584832 0.979317 0.049 Uiso 1 1 calc R U . . .
H24B H 0.810485 0.561084 1.028740 0.049 Uiso 1 1 calc R U . . .
H24C H 0.716772 0.376182 1.033060 0.049 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 O1 1.6585(13) . ?
Si1 C20 1.862(2) . ?
Si1 C19 1.871(2) . ?
Si1 C21 1.888(2) . ?
O1 C1 1.410(2) . ?
O2 C8 1.208(2) . ?
O3 C9 1.207(2) . ?
N1 C8 1.393(2) . ?
N1 C9 1.395(2) . ?
N1 C12 1.456(2) . ?
C1 C2 1.533(2) . ?
C1 C6 1.542(2) . ?
C1 C10 1.572(2) . ?
C2 C3 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.534(3) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.523(3) . ?
C4 C11 1.529(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.514(2) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.579(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.501(2) . ?
C7 C10 1.547(2) . ?
C7 H7 1.0000 . ?
C9 C10 1.510(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.520(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.383(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.527(3) . ?
C21 C24 1.534(3) . ?
C21 C23 1.534(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
O1 Si1 C20 109.55(8) . . ?
O1 Si1 C19 111.25(9) . . ?
C20 Si1 C19 110.65(10) . . ?
O1 Si1 C21 104.80(8) . . ?
C20 Si1 C21 110.99(9) . . ?
C19 Si1 C21 109.47(9) . . ?
C1 O1 Si1 130.53(11) . . ?
C8 N1 C9 113.38(14) . . ?
C8 N1 C12 124.08(16) . . ?
C9 N1 C12 122.34(15) . . ?
O1 C1 C2 113.09(14) . . ?
O1 C1 C6 112.33(14) . . ?
C2 C1 C6 111.72(14) . . ?
O1 C1 C10 119.91(14) . . ?
C2 C1 C10 108.74(14) . . ?
C6 C1 C10 88.70(12) . . ?
C3 C2 C1 112.41(15) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2AB 109.1 . . ?
C1 C2 H2AB 109.1 . . ?
H2A C2 H2AB 107.9 . . ?
C2 C3 C4 109.55(15) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3AB 109.8 . . ?
C4 C3 H3AB 109.8 . . ?
H3A C3 H3AB 108.2 . . ?
C5 C4 C11 111.08(17) . . ?
C5 C4 C3 109.37(15) . . ?
C11 C4 C3 111.38(17) . . ?
C5 C4 H4 108.3 . . ?
C11 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
C6 C5 C4 113.54(15) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5AB 108.9 . . ?
C4 C5 H5AB 108.9 . . ?
H5A C5 H5AB 107.7 . . ?
C5 C6 C1 118.89(14) . . ?
C5 C6 C7 122.01(14) . . ?
C1 C6 C7 88.23(12) . . ?
C5 C6 H6 108.6 . . ?
C1 C6 H6 108.6 . . ?
C7 C6 H6 108.6 . . ?
C8 C7 C10 106.23(14) . . ?
C8 C7 C6 113.05(14) . . ?
C10 C7 C6 88.25(12) . . ?
C8 C7 H7 115.3 . . ?
C10 C7 H7 115.3 . . ?
C6 C7 H7 115.3 . . ?
O2 C8 N1 124.14(16) . . ?
O2 C8 C7 128.74(16) . . ?
N1 C8 C7 107.01(14) . . ?
O3 C9 N1 122.84(17) . . ?
O3 C9 C10 128.66(18) . . ?
N1 C9 C10 108.48(15) . . ?
C9 C10 C7 102.93(14) . . ?
C9 C10 C1 118.40(14) . . ?
C7 C10 C1 88.31(13) . . ?
C9 C10 H10 114.5 . . ?
C7 C10 H10 114.5 . . ?
C1 C10 H10 114.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 115.03(15) . . ?
N1 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
N1 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C18 C13 C14 119.19(17) . . ?
C18 C13 C12 123.54(16) . . ?
C14 C13 C12 117.22(17) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.03(19) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.93(19) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.36(18) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C24 108.90(18) . . ?
C22 C21 C23 108.86(17) . . ?
C24 C21 C23 109.26(16) . . ?
C22 C21 Si1 109.80(13) . . ?
C24 C21 Si1 110.03(13) . . ?
C23 C21 Si1 109.96(15) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_i18225
_database_code_depnum_ccdc_archive 'CCDC 2089102'
loop_
_audit_author_name
_audit_author_address
'Prof. Rong-Jie Chein'
;Institute of Chemistry, Academia Sinica, Taiwan
Taiwan
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H35 N O3 Si'
_chemical_formula_sum            'C24 H35 N O3 Si'
_chemical_formula_weight         413.62

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.43550(10)
_cell_length_b                   11.0753(2)
_cell_length_c                   32.5101(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2317.16(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9831
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      70.21

_exptl_crystal_description       niddle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    1.076
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9093
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56117
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         70.235
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4416
_reflns_number_gt                4217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_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)+(0.0359P)²+0.4175P] 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_abs_structure_details 
;
 Flack x determined using 1744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4416
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.24186(7) 0.58886(4) 0.67826(2) 0.01502(11) Uani 1 1 d . . . . .
O1 O 0.4018(2) 0.49443(11) 0.57337(4) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.86604(19) 0.76479(12) 0.52161(4) 0.0230(3) Uani 1 1 d . . . . .
O3 O 0.41604(18) 0.66725(10) 0.65190(3) 0.0154(3) Uani 1 1 d . . . . .
N1 N 0.6602(2) 0.60928(13) 0.54484(4) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.4724(3) 0.59265(16) 0.56537(5) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.3804(3) 0.71452(15) 0.57507(5) 0.0156(3) Uani 1 1 d . . . . .
H2 H 0.242298 0.731335 0.562170 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4034(3) 0.75621(15) 0.62105(5) 0.0137(3) Uani 1 1 d . . . . .
C4 C 0.2467(3) 0.85624(14) 0.63056(5) 0.0154(3) Uani 1 1 d . . . . .
H4A H 0.119956 0.819724 0.642514 0.018 Uiso 1 1 calc R U . . .
H4AB H 0.206854 0.896773 0.604597 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3329(3) 0.95069(15) 0.66058(5) 0.0165(4) Uani 1 1 d . . . . .
H5 H 0.383737 0.908038 0.685759 0.020 Uiso 1 1 calc R U . . .
C6 C 0.5180(3) 1.01276(16) 0.63994(6) 0.0193(4) Uani 1 1 d . . . . .
H6A H 0.472507 1.049788 0.613727 0.023 Uiso 1 1 calc R U . . .
H6AB H 0.570614 1.077902 0.658006 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6920(3) 0.92247(15) 0.63149(5) 0.0169(4) Uani 1 1 d . . . . .
H7A H 0.798631 0.961900 0.614143 0.020 Uiso 1 1 calc R U . . .
H7AB H 0.758380 0.900428 0.657911 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6193(3) 0.80776(15) 0.61017(5) 0.0137(3) Uani 1 1 d . . . . .
H8 H 0.725090 0.743341 0.615233 0.016 Uiso 1 1 calc R U . . .
C9 C 0.5562(3) 0.80321(15) 0.56333(5) 0.0149(3) Uani 1 1 d . . . . .
H9 H 0.511994 0.881372 0.550649 0.018 Uiso 1 1 calc R U . . .
C10 C 0.7124(3) 0.73053(15) 0.53965(5) 0.0162(3) Uani 1 1 d . . . . .
C11 C 0.1678(3) 1.04207(16) 0.67344(6) 0.0200(4) Uani 1 1 d . . . . .
H11A H 0.108702 1.080250 0.648887 0.030 Uiso 1 1 calc R U . . .
H11B H 0.231096 1.103926 0.690972 0.030 Uiso 1 1 calc R U . . .
H11C H 0.057459 1.000702 0.688710 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7986(3) 0.51007(17) 0.53424(5) 0.0227(4) Uani 1 1 d . . . . .
H12A H 0.803287 0.453435 0.557781 0.027 Uiso 1 1 calc R U . . .
H12B H 0.940323 0.543029 0.530542 0.027 Uiso 1 1 calc R U . . .
C13 C 0.7416(3) 0.43926(14) 0.49598(5) 0.0205(4) Uani 1 1 d . . . . .
C14 C 0.5485(3) 0.44701(16) 0.47703(5) 0.0222(4) Uani 1 1 d . . . . .
H14 H 0.449358 0.504285 0.486399 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5004(4) 0.37083(17) 0.44432(6) 0.0274(4) Uani 1 1 d . . . . .
H15 H 0.367735 0.375779 0.431619 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6447(4) 0.28792(17) 0.43018(6) 0.0309(5) Uani 1 1 d . . . . .
H16 H 0.610296 0.235458 0.408087 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8391(4) 0.28151(17) 0.44827(6) 0.0311(5) Uani 1 1 d . . . . .
H17 H 0.939260 0.225776 0.438253 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8875(3) 0.35664(16) 0.48107(6) 0.0248(4) Uani 1 1 d . . . . .
H18 H 1.020893 0.351880 0.493489 0.030 Uiso 1 1 calc R U . . .
C19 C 0.0343(3) 0.52890(18) 0.64397(6) 0.0237(4) Uani 1 1 d . . . . .
H19A H -0.058648 0.594820 0.635846 0.036 Uiso 1 1 calc R U . . .
H19B H -0.045384 0.466991 0.658647 0.036 Uiso 1 1 calc R U . . .
H19C H 0.097579 0.493320 0.619381 0.036 Uiso 1 1 calc R U . . .
C20 C 0.1262(3) 0.68387(17) 0.71989(6) 0.0244(4) Uani 1 1 d . . . . .
H20A H 0.037759 0.746248 0.707611 0.037 Uiso 1 1 calc R U . . .
H20B H 0.237648 0.722250 0.735729 0.037 Uiso 1 1 calc R U . . .
H20C H 0.042540 0.632942 0.738145 0.037 Uiso 1 1 calc R U . . .
C21 C 0.3994(3) 0.46269(16) 0.70189(5) 0.0185(4) Uani 1 1 d . . . . .
C22 C 0.5840(3) 0.51745(18) 0.72534(6) 0.0260(4) Uani 1 1 d . . . . .
H22A H 0.666810 0.567233 0.706565 0.039 Uiso 1 1 calc R U . . .
H22B H 0.670780 0.452437 0.736450 0.039 Uiso 1 1 calc R U . . .
H22C H 0.532311 0.567598 0.747969 0.039 Uiso 1 1 calc R U . . .
C23 C 0.2651(4) 0.38975(17) 0.73213(6) 0.0308(4) Uani 1 1 d . . . . .
H23A H 0.143407 0.357678 0.717685 0.046 Uiso 1 1 calc R U . . .
H23B H 0.219508 0.442327 0.754626 0.046 Uiso 1 1 calc R U . . .
H23C H 0.346986 0.322774 0.743331 0.046 Uiso 1 1 calc R U . . .
C24 C 0.4819(3) 0.37752(17) 0.66846(6) 0.0243(4) Uani 1 1 d . . . . .
H24A H 0.364815 0.339446 0.654207 0.036 Uiso 1 1 calc R U . . .
H24B H 0.568701 0.315063 0.681138 0.036 Uiso 1 1 calc R U . . .
H24C H 0.564949 0.423655 0.648672 0.036 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 O3 1.6566(12) . ?
Si1 C19 1.862(2) . ?
Si1 C20 1.8690(18) . ?
Si1 C21 1.8897(18) . ?
O1 C1 1.207(2) . ?
O2 C10 1.211(2) . ?
O3 C3 1.4084(19) . ?
N1 C1 1.393(2) . ?
N1 C10 1.394(2) . ?
N1 C12 1.455(2) . ?
C1 C2 1.508(2) . ?
C2 C9 1.546(2) . ?
C2 C3 1.571(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.530(2) . ?
C3 C8 1.543(2) . ?
C4 C5 1.534(2) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C11 1.526(2) . ?
C5 C6 1.530(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.526(2) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.577(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.500(2) . ?
C9 H9 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.516(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.389(3) . ?
C13 C18 1.398(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C24 1.534(2) . ?
C21 C22 1.537(3) . ?
C21 C23 1.538(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
O3 Si1 C19 111.28(8) . . ?
O3 Si1 C20 110.42(8) . . ?
C19 Si1 C20 110.39(9) . . ?
O3 Si1 C21 103.58(7) . . ?
C19 Si1 C21 111.38(8) . . ?
C20 Si1 C21 109.60(8) . . ?
C3 O3 Si1 134.11(11) . . ?
C1 N1 C10 113.21(14) . . ?
C1 N1 C12 122.98(15) . . ?
C10 N1 C12 123.45(15) . . ?
O1 C1 N1 123.30(17) . . ?
O1 C1 C2 127.86(16) . . ?
N1 C1 C2 108.84(14) . . ?
C1 C2 C9 103.27(14) . . ?
C1 C2 C3 115.15(14) . . ?
C9 C2 C3 88.80(12) . . ?
C1 C2 H2 115.4 . . ?
C9 C2 H2 115.4 . . ?
C3 C2 H2 115.4 . . ?
O3 C3 C4 113.61(13) . . ?
O3 C3 C8 111.74(13) . . ?
C4 C3 C8 111.83(13) . . ?
O3 C3 C2 118.52(13) . . ?
C4 C3 C2 110.05(13) . . ?
C8 C3 C2 88.62(12) . . ?
C3 C4 C5 112.58(14) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4AB 109.1 . . ?
C5 C4 H4AB 109.1 . . ?
H4A C4 H4AB 107.8 . . ?
C11 C5 C6 111.36(14) . . ?
C11 C5 C4 111.99(14) . . ?
C6 C5 C4 107.99(14) . . ?
C11 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
C4 C5 H5 108.5 . . ?
C7 C6 C5 110.82(14) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6AB 109.5 . . ?
C5 C6 H6AB 109.5 . . ?
H6A C6 H6AB 108.1 . . ?
C8 C7 C6 113.81(14) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7AB 108.8 . . ?
C6 C7 H7AB 108.8 . . ?
H7A C7 H7AB 107.7 . . ?
C7 C8 C3 118.79(14) . . ?
C7 C8 C9 123.09(14) . . ?
C3 C8 C9 88.73(12) . . ?
C7 C8 H8 108.1 . . ?
C3 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C10 C9 C2 106.03(13) . . ?
C10 C9 C8 109.89(13) . . ?
C2 C9 C8 88.29(12) . . ?
C10 C9 H9 116.3 . . ?
C2 C9 H9 116.3 . . ?
C8 C9 H9 116.3 . . ?
O2 C10 N1 123.85(16) . . ?
O2 C10 C9 128.87(16) . . ?
N1 C10 C9 107.07(14) . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 115.92(15) . . ?
N1 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
N1 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C18 119.18(16) . . ?
C14 C13 C12 123.25(16) . . ?
C18 C13 C12 117.43(18) . . ?
C13 C14 C15 120.01(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.94(18) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 119.90(18) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.5(2) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 C21 C22 109.05(15) . . ?
C24 C21 C23 108.93(15) . . ?
C22 C21 C23 108.95(15) . . ?
C24 C21 Si1 110.63(12) . . ?
C22 C21 Si1 108.95(12) . . ?
C23 C21 Si1 110.30(13) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.032

