# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_12627_auto
_database_code_depnum_ccdc_archive 'CCDC 2168339'
loop_
_audit_author_name
_audit_author_address
'Hao Xu'
;HZNU
China
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-08-22 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         ?
_chemical_formula_sum            'C21 H20 F2 Si'
_chemical_formula_weight         338.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   11.3006(6)
_cell_length_b                   6.0667(3)
_cell_length_c                   13.5359(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.061(5)
_cell_angle_gamma                90
_cell_volume                     903.98(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1939
_cell_measurement_theta_min      4.6070
_cell_measurement_theta_max      70.8280

_exptl_crystal_description       block
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.298
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_T_min  0.85598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3122
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.352
_diffrn_reflns_theta_max         67.244
_diffrn_reflns_theta_full        67.244
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.670
_diffrn_reflns_point_group_measured_fraction_full 0.670
_reflns_number_total             2178
_reflns_number_gt                1969
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.222
_reflns_Friedel_fraction_max     0.272
_reflns_Friedel_fraction_full    0.272

_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       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)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_abs_structure_details 
;
 Flack x determined using 341 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         2178
_refine_ls_number_parameters     219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.77992(7) 0.04125(14) 0.36831(6) 0.0410(2) Uani 1 1 d . . . . .
F1 F 0.87509(18) 0.5482(4) 0.20110(15) 0.0687(6) Uani 1 1 d . . . . .
F2 F 0.70471(16) 0.3670(4) 0.17610(15) 0.0704(6) Uani 1 1 d . . . . .
C1 C 0.7259(3) 0.2335(5) 0.4568(2) 0.0424(7) Uani 1 1 d . . . . .
C2 C 0.7819(3) 0.2470(6) 0.5595(2) 0.0557(9) Uani 1 1 d . . . . .
H2 H 0.846070 0.152781 0.586132 0.067 Uiso 1 1 calc R U . . .
C3 C 0.7439(4) 0.3979(7) 0.6228(3) 0.0690(11) Uani 1 1 d . . . . .
H3 H 0.783880 0.406029 0.690778 0.083 Uiso 1 1 calc R U . . .
C4 C 0.6474(3) 0.5357(8) 0.5856(3) 0.0703(10) Uani 1 1 d . . . . .
H4 H 0.621625 0.635812 0.628366 0.084 Uiso 1 1 calc R U . . .
C5 C 0.5889(3) 0.5248(7) 0.4846(3) 0.0658(9) Uani 1 1 d . . . . .
H5 H 0.523047 0.615997 0.458848 0.079 Uiso 1 1 calc R U . . .
C6 C 0.6295(3) 0.3766(6) 0.4219(2) 0.0532(9) Uani 1 1 d . . . . .
H6 H 0.590593 0.372561 0.353632 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8805(3) -0.1752(6) 0.4396(3) 0.0585(9) Uani 1 1 d . . . . .
H7A H 0.952596 -0.108017 0.479414 0.088 Uiso 1 1 calc R U . . .
H7B H 0.902408 -0.277718 0.392728 0.088 Uiso 1 1 calc R U . . .
H7C H 0.838520 -0.251737 0.483524 0.088 Uiso 1 1 calc R U . . .
C8 C 0.6480(3) -0.0837(6) 0.2778(2) 0.0562(9) Uani 1 1 d . . . . .
H8A H 0.600913 -0.169344 0.314594 0.084 Uiso 1 1 calc R U . . .
H8B H 0.676870 -0.177216 0.231021 0.084 Uiso 1 1 calc R U . . .
H8C H 0.598276 0.031041 0.241004 0.084 Uiso 1 1 calc R U . . .
C9 C 0.8744(3) 0.2087(5) 0.2980(2) 0.0427(7) Uani 1 1 d . . . . .
H9 H 0.949694 0.264771 0.341564 0.051 Uiso 1 1 calc R U . . .
C10 C 0.8274(3) 0.3469(6) 0.2112(2) 0.0507(8) Uani 1 1 d . . . . .
C11 C 0.8874(3) 0.1468(6) 0.1880(2) 0.0443(7) Uani 1 1 d . . . . .
H11 H 0.830948 0.031640 0.155682 0.053 Uiso 1 1 calc R U . . .
C12 C 1.0065(3) 0.1412(5) 0.1584(2) 0.0401(7) Uani 1 1 d . . . . .
C13 C 1.0942(3) 0.2983(5) 0.1849(2) 0.0471(7) Uani 1 1 d . . . . .
H13 H 1.081545 0.414829 0.225960 0.056 Uiso 1 1 calc R U . . .
C14 C 1.2042(3) 0.2881(6) 0.1513(2) 0.0471(8) Uani 1 1 d . . . . .
C15 C 1.2943(3) 0.4532(7) 0.1754(3) 0.0656(10) Uani 1 1 d . . . . .
H15 H 1.283292 0.570928 0.216400 0.079 Uiso 1 1 calc R U . . .
C16 C 1.3976(3) 0.4411(9) 0.1390(3) 0.0801(13) Uani 1 1 d . . . . .
H16 H 1.455883 0.551535 0.154882 0.096 Uiso 1 1 calc R U . . .
C17 C 1.4162(3) 0.2654(10) 0.0783(3) 0.0847(16) Uani 1 1 d . . . . .
H17 H 1.486425 0.259949 0.053466 0.102 Uiso 1 1 calc R U . . .
C18 C 1.3330(3) 0.1022(8) 0.0552(3) 0.0736(14) Uani 1 1 d . . . . .
H18 H 1.347359 -0.016152 0.015821 0.088 Uiso 1 1 calc R U . . .
C19 C 1.2236(3) 0.1100(6) 0.0906(2) 0.0485(9) Uani 1 1 d . . . . .
C20 C 1.1342(3) -0.0525(7) 0.0665(2) 0.0546(8) Uani 1 1 d . . . . .
H20 H 1.147263 -0.172828 0.027777 0.066 Uiso 1 1 calc R U . . .
C21 C 1.0282(3) -0.0391(6) 0.0983(2) 0.0473(7) Uani 1 1 d . . . . .
H21 H 0.969789 -0.148878 0.080478 0.057 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 C7 1.858(3) . ?
Si1 C8 1.864(3) . ?
Si1 C1 1.870(3) . ?
Si1 C9 1.881(3) . ?
F1 C10 1.354(4) . ?
F2 C10 1.365(4) . ?
C1 C6 1.389(4) . ?
C1 C2 1.394(4) . ?
C2 C3 1.387(5) . ?
C3 C4 1.377(5) . ?
C4 C5 1.379(5) . ?
C5 C6 1.383(5) . ?
C9 C10 1.443(4) . ?
C9 C11 1.575(4) . ?
C10 C11 1.460(5) . ?
C11 C12 1.489(4) . ?
C12 C13 1.363(4) . ?
C12 C21 1.417(4) . ?
C13 C14 1.419(4) . ?
C14 C19 1.404(4) . ?
C14 C15 1.413(5) . ?
C15 C16 1.368(5) . ?
C16 C17 1.390(7) . ?
C17 C18 1.352(6) . ?
C18 C19 1.424(4) . ?
C19 C20 1.396(5) . ?
C20 C21 1.364(4) . ?

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
C7 Si1 C8 111.02(17) . . ?
C7 Si1 C1 111.00(15) . . ?
C8 Si1 C1 110.26(15) . . ?
C7 Si1 C9 107.09(14) . . ?
C8 Si1 C9 110.37(14) . . ?
C1 Si1 C9 106.98(13) . . ?
C6 C1 C2 116.5(3) . . ?
C6 C1 Si1 121.1(2) . . ?
C2 C1 Si1 122.3(3) . . ?
C3 C2 C1 121.4(4) . . ?
C4 C3 C2 120.3(4) . . ?
C3 C4 C5 119.7(4) . . ?
C4 C5 C6 119.2(4) . . ?
C5 C6 C1 122.8(3) . . ?
C10 C9 C11 57.7(2) . . ?
C10 C9 Si1 125.4(2) . . ?
C11 C9 Si1 122.3(2) . . ?
F1 C10 F2 106.3(3) . . ?
F1 C10 C9 121.6(3) . . ?
F2 C10 C9 119.5(3) . . ?
F1 C10 C11 120.9(3) . . ?
F2 C10 C11 118.9(3) . . ?
C9 C10 C11 65.7(2) . . ?
C10 C11 C12 124.7(3) . . ?
C10 C11 C9 56.7(2) . . ?
C12 C11 C9 122.9(2) . . ?
C13 C12 C21 118.8(3) . . ?
C13 C12 C11 124.1(3) . . ?
C21 C12 C11 117.1(3) . . ?
C12 C13 C14 121.5(3) . . ?
C19 C14 C15 118.7(3) . . ?
C19 C14 C13 119.0(3) . . ?
C15 C14 C13 122.2(3) . . ?
C16 C15 C14 120.5(4) . . ?
C15 C16 C17 120.6(4) . . ?
C18 C17 C16 120.5(3) . . ?
C17 C18 C19 120.6(4) . . ?
C20 C19 C14 118.6(3) . . ?
C20 C19 C18 122.4(3) . . ?
C14 C19 C18 119.0(3) . . ?
C21 C20 C19 121.7(3) . . ?
C20 C21 C12 120.3(3) . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_mo211127b
_database_code_depnum_ccdc_archive 'CCDC 2168342'
loop_
_audit_author_name
_audit_author_address
'Hao Xu'
;HZNU
China
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_audit_creation_date             2021-11-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 F2 O Si'
_chemical_formula_sum            'C19 H20 F2 O Si'
_chemical_formula_weight         330.44
_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'
F F 0.0171 0.0103 '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                   10.789(2)
_cell_length_b                   11.963(2)
_cell_length_c                   26.976(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3481.8(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3630
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.753
_cell_measurement_theta_min      2.417
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0797 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.7600.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            34286
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.463
_diffrn_reflns_theta_min         2.417
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_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                2421
_reflns_number_total             5027
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         5027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.8627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.71560(5) 0.35355(5) 0.31996(2) 0.04844(18) Uani 1 1 d . . . . .
F1 F 0.48964(12) 0.17179(11) 0.32865(5) 0.0695(4) Uani 1 1 d . . . . .
F2 F 0.55966(13) 0.08663(10) 0.39433(5) 0.0703(4) Uani 1 1 d . . . . .
O1 O 0.66885(13) 0.44156(11) 0.45706(5) 0.0499(4) Uani 1 1 d . . . . .
C1 C 0.6349(2) 0.48633(18) 0.33640(9) 0.0591(6) Uani 1 1 d . . . . .
H1A H 0.6744 0.5189 0.3653 0.071 Uiso 1 1 calc R U . . .
H1B H 0.6433 0.5388 0.3092 0.071 Uiso 1 1 calc R U . . .
C2 C 0.4987(2) 0.46844(18) 0.34725(8) 0.0512(5) Uani 1 1 d . . . . .
C3 C 0.4113(2) 0.5420(2) 0.32750(9) 0.0659(7) Uani 1 1 d . . . . .
H3 H 0.4381 0.6000 0.3072 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2864(2) 0.5312(2) 0.33712(10) 0.0763(8) Uani 1 1 d . . . . .
H4 H 0.2305 0.5821 0.3237 0.092 Uiso 1 1 calc R U . . .
C5 C 0.2447(2) 0.4459(2) 0.36637(10) 0.0691(7) Uani 1 1 d . . . . .
H5 H 0.1606 0.4386 0.3731 0.083 Uiso 1 1 calc R U . . .
C6 C 0.3287(2) 0.3702(2) 0.38589(8) 0.0560(6) Uani 1 1 d . . . . .
H6 H 0.3001 0.3116 0.4054 0.067 Uiso 1 1 calc R U . . .
C7 C 0.45569(18) 0.38034(17) 0.37682(7) 0.0447(5) Uani 1 1 d . . . . .
C8 C 0.53865(17) 0.29187(16) 0.39958(7) 0.0416(5) Uani 1 1 d . . . . .
C9 C 0.66269(18) 0.26131(16) 0.37171(7) 0.0427(5) Uani 1 1 d . . . . .
H9 H 0.7295 0.2362 0.3937 0.051 Uiso 1 1 calc R U . . .
C10 C 0.5549(2) 0.18749(17) 0.37115(8) 0.0509(5) Uani 1 1 d . . . . .
C11 C 0.53782(18) 0.28586(16) 0.45536(8) 0.0431(5) Uani 1 1 d . . . . .
C12 C 0.4683(2) 0.20574(18) 0.48029(8) 0.0552(6) Uani 1 1 d . . . . .
H12 H 0.4231 0.1537 0.4621 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4647(2) 0.2016(2) 0.53144(9) 0.0656(7) Uani 1 1 d . . . . .
H13 H 0.4186 0.1468 0.5475 0.079 Uiso 1 1 calc R U . . .
C14 C 0.5298(2) 0.2791(2) 0.55821(9) 0.0647(7) Uani 1 1 d . . . . .
H14 H 0.5274 0.2766 0.5927 0.078 Uiso 1 1 calc R U . . .
C15 C 0.5990(2) 0.36083(19) 0.53493(8) 0.0539(5) Uani 1 1 d . . . . .
H15 H 0.6424 0.4133 0.5535 0.065 Uiso 1 1 calc R U . . .
C16 C 0.60320(17) 0.36399(17) 0.48356(7) 0.0424(5) Uani 1 1 d . . . . .
C17 C 0.7237(2) 0.53169(18) 0.48372(8) 0.0581(6) Uani 1 1 d . . . . .
H17A H 0.7600 0.5836 0.4608 0.087 Uiso 1 1 calc R U . . .
H17B H 0.7867 0.5032 0.5054 0.087 Uiso 1 1 calc R U . . .
H17C H 0.6613 0.5691 0.5029 0.087 Uiso 1 1 calc R U . . .
C18 C 0.6710(3) 0.2981(2) 0.25850(9) 0.0954(10) Uani 1 1 d . . . . .
H18A H 0.7031 0.2237 0.2547 0.143 Uiso 1 1 calc R U . . .
H18B H 0.7045 0.3452 0.2330 0.143 Uiso 1 1 calc R U . . .
H18C H 0.5823 0.2965 0.2558 0.143 Uiso 1 1 calc R U . . .
C19 C 0.8862(2) 0.3683(2) 0.32336(9) 0.0683(7) Uani 1 1 d . . . . .
H19A H 0.9094 0.3933 0.3559 0.102 Uiso 1 1 calc R U . . .
H19B H 0.9134 0.4220 0.2992 0.102 Uiso 1 1 calc R U . . .
H19C H 0.9245 0.2974 0.3167 0.102 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 C1 1.865(2) . ?
Si1 C9 1.869(2) . ?
Si1 C18 1.849(3) . ?
Si1 C19 1.852(2) . ?
F1 C10 1.359(2) . ?
F2 C10 1.360(2) . ?
O1 C16 1.369(2) . ?
O1 C17 1.425(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.513(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.401(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.397(3) . ?
C7 C8 1.516(3) . ?
C8 C9 1.578(3) . ?
C8 C10 1.476(3) . ?
C8 C11 1.506(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.460(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.396(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C1 Si1 C9 100.53(10) . . ?
C18 Si1 C1 113.42(13) . . ?
C18 Si1 C9 112.24(12) . . ?
C18 Si1 C19 109.71(14) . . ?
C19 Si1 C1 111.76(11) . . ?
C19 Si1 C9 108.85(10) . . ?
C16 O1 C17 117.67(16) . . ?
Si1 C1 H1A 109.2 . . ?
Si1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 Si1 112.25(16) . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 C7 117.9(2) . . ?
C7 C2 C1 122.57(19) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C8 124.06(18) . . ?
C6 C7 C2 119.3(2) . . ?
C6 C7 C8 116.60(19) . . ?
C7 C8 C9 118.01(17) . . ?
C10 C8 C7 116.78(17) . . ?
C10 C8 C9 57.01(13) . . ?
C10 C8 C11 118.64(17) . . ?
C11 C8 C7 115.74(16) . . ?
C11 C8 C9 118.03(16) . . ?
Si1 C9 H9 114.0 . . ?
C8 C9 Si1 118.56(14) . . ?
C8 C9 H9 114.0 . . ?
C10 C9 Si1 126.34(15) . . ?
C10 C9 C8 57.97(13) . . ?
C10 C9 H9 114.0 . . ?
F1 C10 F2 106.54(17) . . ?
F1 C10 C8 119.59(18) . . ?
F1 C10 C9 120.34(19) . . ?
F2 C10 C8 121.09(18) . . ?
F2 C10 C9 120.13(19) . . ?
C9 C10 C8 65.02(13) . . ?
C12 C11 C8 121.28(19) . . ?
C12 C11 C16 118.05(19) . . ?
C16 C11 C8 120.62(17) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
O1 C16 C11 115.50(17) . . ?
O1 C16 C15 123.85(19) . . ?
C15 C16 C11 120.65(19) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Si1 C1 C2 C3 -135.6(2) . . . . ?
Si1 C1 C2 C7 44.7(3) . . . . ?
Si1 C9 C10 F1 7.1(3) . . . . ?
Si1 C9 C10 F2 143.27(17) . . . . ?
Si1 C9 C10 C8 -103.89(18) . . . . ?
C1 Si1 C9 C8 23.16(17) . . . . ?
C1 Si1 C9 C10 92.73(19) . . . . ?
C1 C2 C3 C4 -178.4(2) . . . . ?
C1 C2 C7 C6 178.9(2) . . . . ?
C1 C2 C7 C8 -2.2(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C7 C8 C9 -28.8(3) . . . . ?
C2 C7 C8 C10 -93.8(2) . . . . ?
C2 C7 C8 C11 119.2(2) . . . . ?
C3 C2 C7 C6 -0.8(3) . . . . ?
C3 C2 C7 C8 178.1(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C5 C6 C7 C8 -179.3(2) . . . . ?
C6 C7 C8 C9 150.18(18) . . . . ?
C6 C7 C8 C10 85.2(2) . . . . ?
C6 C7 C8 C11 -61.9(2) . . . . ?
C7 C2 C3 C4 1.3(4) . . . . ?
C7 C8 C9 Si1 11.8(2) . . . . ?
C7 C8 C9 C10 -105.3(2) . . . . ?
C7 C8 C10 F1 -4.7(3) . . . . ?
C7 C8 C10 F2 -141.11(19) . . . . ?
C7 C8 C10 C9 107.43(19) . . . . ?
C7 C8 C11 C12 100.0(2) . . . . ?
C7 C8 C11 C16 -77.4(2) . . . . ?
C8 C9 C10 F1 111.0(2) . . . . ?
C8 C9 C10 F2 -112.8(2) . . . . ?
C8 C11 C12 C13 -178.4(2) . . . . ?
C8 C11 C16 O1 -1.9(3) . . . . ?
C8 C11 C16 C15 177.77(18) . . . . ?
C9 Si1 C1 C2 -49.28(18) . . . . ?
C9 C8 C10 F1 -112.1(2) . . . . ?
C9 C8 C10 F2 111.5(2) . . . . ?
C9 C8 C11 C12 -112.1(2) . . . . ?
C9 C8 C11 C16 70.5(2) . . . . ?
C10 C8 C9 Si1 117.08(18) . . . . ?
C10 C8 C11 C12 -46.5(3) . . . . ?
C10 C8 C11 C16 136.2(2) . . . . ?
C11 C8 C9 Si1 -135.35(16) . . . . ?
C11 C8 C9 C10 107.6(2) . . . . ?
C11 C8 C10 F1 141.41(19) . . . . ?
C11 C8 C10 F2 5.0(3) . . . . ?
C11 C8 C10 C9 -106.49(19) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C11 C16 O1 -179.29(17) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 O1 179.9(2) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C17 O1 C16 C11 171.91(17) . . . . ?
C17 O1 C16 C15 -7.7(3) . . . . ?
C18 Si1 C1 C2 70.7(2) . . . . ?
C18 Si1 C9 C8 -97.69(18) . . . . ?
C18 Si1 C9 C10 -28.1(2) . . . . ?
C19 Si1 C1 C2 -164.61(16) . . . . ?
C19 Si1 C9 C8 140.67(15) . . . . ?
C19 Si1 C9 C10 -149.76(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_12628_auto
_database_code_depnum_ccdc_archive 'CCDC 2168341'
loop_
_audit_author_name
_audit_author_address
'Hao Xu'
;HZNU
China
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-08-22 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         ?
_chemical_formula_sum            'C20 H20 F2 O2 Si'
_chemical_formula_weight         358.45

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.4695(2)
_cell_length_b                   15.7802(4)
_cell_length_c                   14.2929(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.538(3)
_cell_angle_gamma                90
_cell_volume                     1840.44(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2741
_cell_measurement_theta_min      3.1810
_cell_measurement_theta_max      70.8030

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.388
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.862
_exptl_absorpt_correction_T_min  0.90222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6732
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.261
_diffrn_reflns_theta_max         67.247
_diffrn_reflns_theta_full        67.247
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3284
_reflns_number_gt                2515
_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       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.2798P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0131(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3284
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 -0.06195(7) 0.21971(4) 0.46213(4) 0.0431(2) Uani 1 1 d . . . . .
F1 F 0.33141(17) 0.18337(9) 0.34228(10) 0.0590(4) Uani 1 1 d . . . . .
F2 F 0.08404(17) 0.22406(9) 0.27215(9) 0.0561(4) Uani 1 1 d . . . . .
O1 O 0.5149(2) 0.30596(15) 0.45729(15) 0.0841(7) Uani 1 1 d . . . . .
O2 O 0.38664(18) 0.38598(11) 0.53980(12) 0.0568(5) Uani 1 1 d . . . . .
C1 C -0.0622(3) 0.33187(15) 0.50259(18) 0.0525(6) Uani 1 1 d . . . . .
H1A H -0.167725 0.345634 0.513079 0.063 Uiso 1 1 calc R U . . .
H1B H 0.021228 0.339699 0.563421 0.063 Uiso 1 1 calc R U . . .
C2 C -0.0286(3) 0.38910(14) 0.42684(16) 0.0457(5) Uani 1 1 d . . . . .
C3 C -0.1308(3) 0.45723(15) 0.3912(2) 0.0598(7) Uani 1 1 d . . . . .
H3 H -0.218887 0.467770 0.416839 0.072 Uiso 1 1 calc R U . . .
C4 C -0.1069(3) 0.50934(17) 0.3200(2) 0.0679(8) Uani 1 1 d . . . . .
H4 H -0.177631 0.554541 0.298066 0.081 Uiso 1 1 calc R U . . .
C5 C 0.0223(4) 0.49462(16) 0.28087(19) 0.0669(7) Uani 1 1 d . . . . .
H5 H 0.039894 0.530226 0.232800 0.080 Uiso 1 1 calc R U . . .
C6 C 0.1263(3) 0.42651(15) 0.31324(17) 0.0529(6) Uani 1 1 d . . . . .
H6 H 0.212608 0.416030 0.286019 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1021(2) 0.37393(13) 0.38619(15) 0.0417(5) Uani 1 1 d . . . . .
C8 C 0.2215(2) 0.30175(13) 0.41878(15) 0.0390(5) Uani 1 1 d . . . . .
C9 C 0.1575(2) 0.21409(13) 0.45045(14) 0.0384(5) Uani 1 1 d . . . . .
C10 C 0.2011(3) 0.22463(14) 0.35781(15) 0.0440(5) Uani 1 1 d . . . . .
C11 C 0.2715(2) 0.16288(14) 0.52847(15) 0.0435(5) Uani 1 1 d . . . . .
C12 C 0.2984(3) 0.07860(16) 0.51163(19) 0.0603(7) Uani 1 1 d . . . . .
H12 H 0.249049 0.055099 0.451191 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3971(4) 0.0288(2) 0.5829(2) 0.0783(9) Uani 1 1 d . . . . .
H13 H 0.413058 -0.028040 0.570723 0.094 Uiso 1 1 calc R U . . .
C14 C 0.4725(3) 0.0634(2) 0.6726(2) 0.0822(10) Uani 1 1 d . . . . .
H14 H 0.541443 0.030389 0.720337 0.099 Uiso 1 1 calc R U . . .
C15 C 0.4452(3) 0.1467(2) 0.6909(2) 0.0763(9) Uani 1 1 d . . . . .
H15 H 0.495144 0.169985 0.751353 0.092 Uiso 1 1 calc R U . . .
C16 C 0.3434(3) 0.19617(17) 0.61967(16) 0.0561(6) Uani 1 1 d . . . . .
H16 H 0.323096 0.252155 0.633169 0.067 Uiso 1 1 calc R U . . .
C17 C 0.3921(3) 0.32937(14) 0.47180(15) 0.0434(5) Uani 1 1 d . . . . .
C18 C 0.5429(3) 0.4149(2) 0.5995(2) 0.0762(9) Uani 1 1 d . . . . .
H18A H 0.606200 0.367200 0.630266 0.114 Uiso 1 1 calc R U . . .
H18B H 0.525684 0.452989 0.648241 0.114 Uiso 1 1 calc R U . . .
H18C H 0.600826 0.443867 0.559728 0.114 Uiso 1 1 calc R U . . .
C19 C -0.2187(3) 0.20065(17) 0.34582(18) 0.0608(7) Uani 1 1 d . . . . .
H19A H -0.203867 0.145062 0.322247 0.091 Uiso 1 1 calc R U . . .
H19B H -0.207483 0.242244 0.299007 0.091 Uiso 1 1 calc R U . . .
H19C H -0.326015 0.204784 0.355957 0.091 Uiso 1 1 calc R U . . .
C20 C -0.0888(3) 0.14363(19) 0.5555(2) 0.0710(8) Uani 1 1 d . . . . .
H20A H -0.198211 0.148079 0.562298 0.106 Uiso 1 1 calc R U . . .
H20B H -0.011668 0.156370 0.616488 0.106 Uiso 1 1 calc R U . . .
H20C H -0.070343 0.087059 0.536094 0.106 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 C19 1.853(2) . ?
Si1 C20 1.854(3) . ?
Si1 C1 1.862(2) . ?
Si1 C9 1.912(2) . ?
F1 C10 1.350(2) . ?
F2 C10 1.354(2) . ?
O1 C17 1.173(3) . ?
O2 C17 1.330(3) . ?
O2 C18 1.444(3) . ?
C1 C2 1.494(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.365(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.388(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.512(3) . ?
C8 C10 1.480(3) . ?
C8 C17 1.505(3) . ?
C8 C9 1.595(3) . ?
C9 C10 1.476(3) . ?
C9 C11 1.501(3) . ?
C11 C12 1.381(3) . ?
C11 C16 1.386(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.382(5) . ?
C14 C15 1.371(5) . ?
C15 C16 1.386(4) . ?

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
C19 Si1 C20 110.14(13) . . ?
C19 Si1 C1 111.89(12) . . ?
C20 Si1 C1 112.42(13) . . ?
C19 Si1 C9 113.19(11) . . ?
C20 Si1 C9 110.02(11) . . ?
C1 Si1 C9 98.80(9) . . ?
C17 O2 C18 116.03(19) . . ?
C2 C1 Si1 109.46(15) . . ?
C3 C2 C7 117.6(2) . . ?
C3 C2 C1 120.9(2) . . ?
C7 C2 C1 121.4(2) . . ?
C4 C3 C2 122.5(3) . . ?
C3 C4 C5 119.6(2) . . ?
C4 C5 C6 119.9(3) . . ?
C5 C6 C7 120.3(2) . . ?
C6 C7 C2 120.0(2) . . ?
C6 C7 C8 117.4(2) . . ?
C2 C7 C8 122.6(2) . . ?
C10 C8 C17 118.66(18) . . ?
C10 C8 C7 118.38(17) . . ?
C17 C8 C7 114.19(17) . . ?
C10 C8 C9 57.25(13) . . ?
C17 C8 C9 117.51(17) . . ?
C7 C8 C9 119.37(17) . . ?
C10 C9 C11 117.46(18) . . ?
C10 C9 C8 57.44(13) . . ?
C11 C9 C8 118.55(17) . . ?
C10 C9 Si1 123.77(15) . . ?
C11 C9 Si1 114.02(14) . . ?
C8 C9 Si1 113.39(13) . . ?
F1 C10 F2 106.33(16) . . ?
F1 C10 C9 120.35(18) . . ?
F2 C10 C9 120.77(18) . . ?
F1 C10 C8 121.47(18) . . ?
F2 C10 C8 118.68(18) . . ?
C9 C10 C8 65.31(14) . . ?
C12 C11 C16 118.5(2) . . ?
C12 C11 C9 119.5(2) . . ?
C16 C11 C9 121.9(2) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 C14 119.9(3) . . ?
C15 C14 C13 119.8(3) . . ?
C14 C15 C16 120.2(3) . . ?
C15 C16 C11 120.5(3) . . ?
O1 C17 O2 123.1(2) . . ?
O1 C17 C8 126.6(2) . . ?
O2 C17 C8 110.25(17) . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038

