# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2126544'
loop_
_audit_author_name
_audit_author_address
'Lichuan Liu'
;Tsinghua university
China
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2026-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 F2 O Si'
_chemical_formula_weight         306.42

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'
O O 0.0492 0.0322 '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                   9.5297(2)
_cell_length_b                   8.1356(2)
_cell_length_c                   11.0854(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.274(2)
_cell_angle_gamma                90
_cell_volume                     816.11(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    10313
_cell_measurement_theta_min      4.1650
_cell_measurement_theta_max      74.7360

_exptl_crystal_description       rod-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.424
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.65541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18716
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.200
_diffrn_reflns_theta_max         76.432
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3298
_reflns_number_gt                3105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.940
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0495P)²+0.1034P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3298
_refine_ls_number_parameters     197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.15550(7) 0.63937(8) 0.68213(5) 0.03841(17) Uani 1 1 d . . . . .
H1 H 0.053(3) 0.761(4) 0.692(3) 0.046 Uiso 1 1 d . U . . .
F1 F 0.26675(19) 0.7480(2) 0.95854(15) 0.0560(4) Uani 1 1 d . . . . .
F2 F 0.6863(2) 0.8642(2) 0.7350(2) 0.0652(5) Uani 1 1 d . . . . .
O1 O 0.31634(18) 0.3425(2) 0.70258(16) 0.0382(4) Uani 1 1 d . . . . .
C1 C 0.1474(3) 0.6169(4) 0.5127(2) 0.0528(7) Uani 1 1 d . . . . .
H1A H 0.1494 0.7236 0.4764 0.079 Uiso 1 1 calc R U . . .
H1B H 0.0578 0.5613 0.4664 0.079 Uiso 1 1 calc R U . . .
H1C H 0.2308 0.5541 0.5080 0.079 Uiso 1 1 calc R U . . .
C2 C 0.3420(3) 0.7249(3) 0.7768(2) 0.0385(5) Uani 1 1 d . . . . .
C3 C 0.3730(3) 0.7717(3) 0.9024(2) 0.0428(6) Uani 1 1 d . . . . .
C4 C 0.5040(3) 0.8434(4) 0.9742(2) 0.0511(7) Uani 1 1 d . . . . .
H4 H 0.5191 0.8714 1.0587 0.061 Uiso 1 1 calc R U . . .
C5 C 0.6120(3) 0.8728(4) 0.9181(3) 0.0516(7) Uani 1 1 d . . . . .
H5 H 0.7015 0.9208 0.9637 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5835(3) 0.8291(3) 0.7933(3) 0.0466(6) Uani 1 1 d . . . . .
C7 C 0.4533(3) 0.7561(3) 0.7226(2) 0.0427(6) Uani 1 1 d . . . . .
H7 H 0.4394 0.7274 0.6384 0.051 Uiso 1 1 calc R U . . .
C8 C 0.1125(2) 0.4431(3) 0.7522(2) 0.0352(5) Uani 1 1 d . . . . .
C9 C -0.0026(3) 0.4201(4) 0.8053(2) 0.0430(6) Uani 1 1 d . . . . .
C10 C -0.0261(3) 0.2642(4) 0.8478(3) 0.0515(7) Uani 1 1 d . . . . .
H10 H -0.1017 0.2493 0.8832 0.062 Uiso 1 1 calc R U . . .
C11 C 0.0593(3) 0.1334(4) 0.8388(2) 0.0515(6) Uani 1 1 d . . . . .
H11 H 0.0398 0.0303 0.8661 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1751(3) 0.1529(4) 0.7891(2) 0.0432(5) Uani 1 1 d . . . . .
H12 H 0.2344 0.0641 0.7839 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2004(2) 0.3062(3) 0.7478(2) 0.0340(5) Uani 1 1 d . . . . .
C14 C -0.1013(3) 0.5601(5) 0.8175(3) 0.0582(8) Uani 1 1 d . . . . .
H14A H -0.0417 0.6495 0.8623 0.087 Uiso 1 1 calc R U . . .
H14B H -0.1657 0.5234 0.8635 0.087 Uiso 1 1 calc R U . . .
H14C H -0.1594 0.5963 0.7344 0.087 Uiso 1 1 calc R U . . .
C15 C 0.4002(3) 0.2115(4) 0.6716(3) 0.0457(6) Uani 1 1 d . . . . .
H15 H 0.4264 0.1309 0.7408 0.055 Uiso 1 1 calc R U . . .
C16 C 0.3109(4) 0.1284(5) 0.5495(3) 0.0631(8) Uani 1 1 d . . . . .
H16A H 0.2252 0.0778 0.5613 0.095 Uiso 1 1 calc R U . . .
H16B H 0.3704 0.0460 0.5269 0.095 Uiso 1 1 calc R U . . .
H16C H 0.2807 0.2086 0.4828 0.095 Uiso 1 1 calc R U . . .
C17 C 0.5390(4) 0.2922(5) 0.6615(4) 0.0722(10) Uani 1 1 d . . . . .
H17A H 0.5135 0.3684 0.5918 0.108 Uiso 1 1 calc R U . . .
H17B H 0.6040 0.2096 0.6472 0.108 Uiso 1 1 calc R U . . .
H17C H 0.5877 0.3498 0.7389 0.108 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 1.864(3) . ?
Si1 C8 1.877(3) . ?
Si1 C2 1.891(3) . ?
Si1 H1 1.42(3) . ?
F1 C3 1.359(3) . ?
F2 C6 1.362(3) . ?
O1 C13 1.381(3) . ?
O1 C15 1.436(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.382(3) . ?
C2 C7 1.397(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.404(3) . ?
C8 C9 1.410(4) . ?
C9 C10 1.396(4) . ?
C9 C14 1.510(4) . ?
C10 C11 1.362(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(4) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C17 1.512(5) . ?
C15 C16 1.514(4) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 C8 112.84(12) . . ?
C1 Si1 C2 109.29(13) . . ?
C8 Si1 C2 111.87(10) . . ?
C1 Si1 H1 109.4(12) . . ?
C8 Si1 H1 108.6(12) . . ?
C2 Si1 H1 104.5(13) . . ?
C13 O1 C15 119.77(19) . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 115.6(2) . . ?
C3 C2 Si1 121.8(2) . . ?
C7 C2 Si1 122.43(19) . . ?
F1 C3 C4 117.7(2) . . ?
F1 C3 C2 117.9(2) . . ?
C4 C3 C2 124.5(3) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 118.1(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
F2 C6 C5 118.7(3) . . ?
F2 C6 C7 118.3(3) . . ?
C5 C6 C7 123.0(3) . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C13 C8 C9 117.4(2) . . ?
C13 C8 Si1 116.76(17) . . ?
C9 C8 Si1 125.80(19) . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 C14 119.0(2) . . ?
C8 C9 C14 121.7(3) . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 O1 123.9(2) . . ?
C12 C13 C8 122.6(2) . . ?
O1 C13 C8 113.4(2) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C17 105.2(2) . . ?
O1 C15 C16 110.3(2) . . ?
C17 C15 C16 112.7(3) . . ?
O1 C15 H15 109.5 . . ?
C17 C15 H15 109.5 . . ?
C16 C15 H15 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C1 Si1 C2 C3 172.6(2) . . . . ?
C8 Si1 C2 C3 -61.7(2) . . . . ?
C1 Si1 C2 C7 -2.7(2) . . . . ?
C8 Si1 C2 C7 123.0(2) . . . . ?
C7 C2 C3 F1 178.3(2) . . . . ?
Si1 C2 C3 F1 2.7(3) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
Si1 C2 C3 C4 -176.2(2) . . . . ?
F1 C3 C4 C5 -178.3(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 F2 177.0(2) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
F2 C6 C7 C2 -177.0(2) . . . . ?
C5 C6 C7 C2 0.8(4) . . . . ?
C3 C2 C7 C6 -0.1(3) . . . . ?
Si1 C2 C7 C6 175.44(19) . . . . ?
C1 Si1 C8 C13 56.7(2) . . . . ?
C2 Si1 C8 C13 -67.02(19) . . . . ?
C1 Si1 C8 C9 -121.3(2) . . . . ?
C2 Si1 C8 C9 115.0(2) . . . . ?
C13 C8 C9 C10 -1.4(3) . . . . ?
Si1 C8 C9 C10 176.61(19) . . . . ?
C13 C8 C9 C14 178.5(2) . . . . ?
Si1 C8 C9 C14 -3.5(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C14 C9 C10 C11 179.8(3) . . . . ?
C9 C10 C11 C12 1.5(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 O1 176.6(2) . . . . ?
C11 C12 C13 C8 -0.9(3) . . . . ?
C15 O1 C13 C12 13.1(3) . . . . ?
C15 O1 C13 C8 -169.2(2) . . . . ?
C9 C8 C13 C12 2.0(3) . . . . ?
Si1 C8 C13 C12 -176.16(18) . . . . ?
C9 C8 C13 O1 -175.77(19) . . . . ?
Si1 C8 C13 O1 6.1(2) . . . . ?
C13 O1 C15 C17 -164.8(2) . . . . ?
C13 O1 C15 C16 73.4(3) . . . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_3_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2126543'
loop_
_audit_author_name
_audit_author_address
'Lichuan Liu'
;Tsinghua university
China
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2026-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 F2 O Si'
_chemical_formula_weight         292.39

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'
O O 0.0492 0.0322 '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      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                   7.21200(10)
_cell_length_b                   9.48880(10)
_cell_length_c                   22.3464(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1529.24(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    17509
_cell_measurement_theta_min      3.9520
_cell_measurement_theta_max      73.1270

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.496
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31476
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.956
_diffrn_reflns_theta_max         73.224
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2984
_reflns_number_gt                2815
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_max     0.955
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0420P)²+0.0725P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2984
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.37278(6) 0.40502(5) 0.68413(2) 0.03303(12) Uani 1 1 d . . . . .
H1 H 0.275(3) 0.413(2) 0.7375(9) 0.040 Uiso 1 1 d . U . . .
F1 F 0.04397(14) 0.21276(12) 0.66242(5) 0.0453(3) Uani 1 1 d . . . . .
F2 F 0.68123(17) -0.07923(15) 0.63023(6) 0.0554(3) Uani 1 1 d . . . . .
O1 O 0.48433(16) 0.42379(13) 0.56219(5) 0.0348(3) Uani 1 1 d . . . . .
C1 C 0.2562(2) 0.51418(17) 0.62511(7) 0.0303(3) Uani 1 1 d . . . . .
C2 C 0.1007(2) 0.60091(19) 0.63450(8) 0.0377(4) Uani 1 1 d . . . . .
C3 C 0.0153(3) 0.6652(2) 0.58564(10) 0.0433(4) Uani 1 1 d . . . . .
H3 H -0.0903 0.7195 0.5917 0.052 Uiso 1 1 calc R U . . .
C4 C 0.0848(3) 0.6498(2) 0.52845(9) 0.0431(4) Uani 1 1 d . . . . .
H4 H 0.0242 0.6922 0.4964 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2441(3) 0.57138(19) 0.51839(8) 0.0372(4) Uani 1 1 d . . . . .
H5 H 0.2941 0.5637 0.4802 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3274(2) 0.50451(17) 0.56687(7) 0.0303(3) Uani 1 1 d . . . . .
C7 C 0.0302(3) 0.6317(2) 0.69691(10) 0.0513(5) Uani 1 1 d . . . . .
H7A H -0.0007 0.5449 0.7165 0.077 Uiso 1 1 calc R U . . .
H7B H -0.0780 0.6903 0.6945 0.077 Uiso 1 1 calc R U . . .
H7C H 0.1248 0.6796 0.7193 0.077 Uiso 1 1 calc R U . . .
C8 C 0.5907(2) 0.4305(2) 0.50808(8) 0.0366(4) Uani 1 1 d . . . . .
H8A H 0.6278 0.5269 0.5000 0.044 Uiso 1 1 calc R U . . .
H8B H 0.5179 0.3966 0.4745 0.044 Uiso 1 1 calc R U . . .
C9 C 0.7583(3) 0.3392(2) 0.51702(9) 0.0460(5) Uani 1 1 d . . . . .
H9A H 0.8333 0.3410 0.4815 0.069 Uiso 1 1 calc R U . . .
H9B H 0.7197 0.2442 0.5250 0.069 Uiso 1 1 calc R U . . .
H9C H 0.8292 0.3739 0.5503 0.069 Uiso 1 1 calc R U . . .
C10 C 0.6145(3) 0.4617(2) 0.69895(9) 0.0500(5) Uani 1 1 d . . . . .
H10A H 0.6862 0.4534 0.6629 0.075 Uiso 1 1 calc R U . . .
H10B H 0.6675 0.4029 0.7295 0.075 Uiso 1 1 calc R U . . .
H10C H 0.6148 0.5579 0.7121 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3702(2) 0.21362(18) 0.66174(7) 0.0317(3) Uani 1 1 d . . . . .
C12 C 0.2056(3) 0.1404(2) 0.65487(7) 0.0339(4) Uani 1 1 d . . . . .
C13 C 0.1925(3) -0.0007(2) 0.64057(8) 0.0406(4) Uani 1 1 d . . . . .
H13 H 0.0776 -0.0443 0.6369 0.049 Uiso 1 1 calc R U . . .
C14 C 0.3551(3) -0.0756(2) 0.63183(8) 0.0428(4) Uani 1 1 d . . . . .
H14 H 0.3526 -0.1708 0.6219 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5196(3) -0.0054(2) 0.63832(8) 0.0393(4) Uani 1 1 d . . . . .
C16 C 0.5320(3) 0.1350(2) 0.65285(7) 0.0356(4) Uani 1 1 d . . . . .
H16 H 0.6475 0.1776 0.6568 0.043 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 C10 1.854(2) . ?
Si1 C1 1.8760(18) . ?
Si1 C11 1.8838(18) . ?
Si1 H1 1.39(2) . ?
F1 C12 1.363(2) . ?
F2 C15 1.372(2) . ?
O1 C6 1.370(2) . ?
O1 C8 1.4335(19) . ?
C1 C6 1.402(2) . ?
C1 C2 1.407(2) . ?
C2 C3 1.394(3) . ?
C2 C7 1.513(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.501(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.384(3) . ?
C11 C16 1.400(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(3) . ?
C16 H16 0.9300 . ?

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
C10 Si1 C1 112.76(9) . . ?
C10 Si1 C11 109.65(9) . . ?
C1 Si1 C11 109.94(7) . . ?
C10 Si1 H1 108.0(9) . . ?
C1 Si1 H1 110.3(9) . . ?
C11 Si1 H1 105.9(10) . . ?
C6 O1 C8 118.78(13) . . ?
C6 C1 C2 117.96(16) . . ?
C6 C1 Si1 116.88(13) . . ?
C2 C1 Si1 125.13(13) . . ?
C3 C2 C1 119.41(16) . . ?
C3 C2 C7 119.30(18) . . ?
C1 C2 C7 121.21(17) . . ?
C4 C3 C2 121.25(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.49(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 118.42(17) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
O1 C6 C5 123.49(15) . . ?
O1 C6 C1 114.21(15) . . ?
C5 C6 C1 122.30(16) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C9 107.04(14) . . ?
O1 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O1 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 115.58(15) . . ?
C12 C11 Si1 121.48(14) . . ?
C16 C11 Si1 122.91(13) . . ?
F1 C12 C13 117.32(17) . . ?
F1 C12 C11 117.81(16) . . ?
C13 C12 C11 124.87(18) . . ?
C12 C13 C14 118.22(18) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C15 C14 C13 117.96(17) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 F2 118.28(17) . . ?
C14 C15 C16 123.63(18) . . ?
F2 C15 C16 118.09(18) . . ?
C15 C16 C11 119.74(17) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?

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
C10 Si1 C1 C6 65.98(15) . . . . ?
C11 Si1 C1 C6 -56.72(14) . . . . ?
C10 Si1 C1 C2 -116.01(15) . . . . ?
C11 Si1 C1 C2 121.29(15) . . . . ?
C6 C1 C2 C3 4.7(2) . . . . ?
Si1 C1 C2 C3 -173.33(13) . . . . ?
C6 C1 C2 C7 -172.16(16) . . . . ?
Si1 C1 C2 C7 9.9(2) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C7 C2 C3 C4 174.37(18) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 2.5(3) . . . . ?
C8 O1 C6 C5 13.3(2) . . . . ?
C8 O1 C6 C1 -166.94(15) . . . . ?
C4 C5 C6 O1 179.60(15) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 O1 176.81(14) . . . . ?
Si1 C1 C6 O1 -5.03(19) . . . . ?
C2 C1 C6 C5 -3.4(2) . . . . ?
Si1 C1 C6 C5 174.77(13) . . . . ?
C6 O1 C8 C9 176.69(15) . . . . ?
C10 Si1 C11 C12 172.41(14) . . . . ?
C1 Si1 C11 C12 -63.07(15) . . . . ?
C10 Si1 C11 C16 -5.48(16) . . . . ?
C1 Si1 C11 C16 119.04(14) . . . . ?
C16 C11 C12 F1 -179.28(15) . . . . ?
Si1 C11 C12 F1 2.7(2) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
Si1 C11 C12 C13 -177.73(14) . . . . ?
F1 C12 C13 C14 179.05(15) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 F2 179.45(16) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
F2 C15 C16 C11 -179.68(15) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
Si1 C11 C16 C15 178.02(12) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031

