# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_COSi
_database_code_depnum_ccdc_archive 'CCDC 1581784'
_audit_update_record             
;
2017-10-24 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 F O2 Si'
_chemical_formula_weight         196.25

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'
O O 0.0106 0.0060 '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'
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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   17.2067(7)
_cell_length_b                   7.1378(3)
_cell_length_c                   7.5388(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.265(4)
_cell_angle_gamma                90
_cell_volume                     911.08(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5712
_cell_measurement_theta_min      2.4390
_cell_measurement_theta_max      32.9840

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_min  0.75827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195
_diffrn_reflns_number            10042
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.097
_diffrn_reflns_theta_max         33.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1797
_reflns_number_gt                1584
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0831P)²+0.3748P] 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_number_reflns         1797
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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
Si Si 0.10379(2) 0.0000 0.20607(5) 0.01320(13) Uani 1 2 d S T P . .
O2 O 0.07888(6) 0.0000 -0.02322(14) 0.0165(2) Uani 1 2 d S T P . .
O1 O 0.12991(7) 0.0000 -0.27675(15) 0.0210(2) Uani 1 2 d S T P . .
F1 F 0.27849(6) 0.0000 0.49440(12) 0.0258(2) Uani 1 2 d S T P . .
C4 C 0.35510(9) 0.0000 0.2648(2) 0.0177(3) Uani 1 2 d S T P . .
H4 H 0.4021 0.0000 0.3528 0.021 Uiso 1 2 calc R U P . .
C7 C 0.14038(8) 0.0000 -0.11456(19) 0.0149(3) Uani 1 2 d S T P . .
C8 C 0.06856(6) 0.21344(14) 0.30355(14) 0.0182(2) Uani 1 1 d . . . . .
H8A H 0.0882 0.3239 0.2482 0.027 Uiso 1 1 calc R U . . .
H8B H 0.0881 0.2153 0.4339 0.027 Uiso 1 1 calc R U . . .
H8C H 0.0107 0.2147 0.2805 0.027 Uiso 1 1 calc R U . . .
C6 C 0.29001(9) 0.0000 -0.0483(2) 0.0163(3) Uani 1 2 d S T P . .
H6 H 0.2925 0.0000 -0.1732 0.020 Uiso 1 2 calc R U P . .
C2 C 0.21152(8) 0.0000 0.19340(18) 0.0141(2) Uani 1 2 d S T P . .
C5 C 0.35850(9) 0.0000 0.0816(2) 0.0175(3) Uani 1 2 d S T P . .
H5 H 0.4085 0.0000 0.0446 0.021 Uiso 1 2 calc R U P . .
C3 C 0.28138(9) 0.0000 0.31625(19) 0.0167(3) Uani 1 2 d S T P . .
C1 C 0.21761(8) 0.0000 0.01058(18) 0.0135(2) Uani 1 2 d S T P . .


_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
Si O2 1.7051(11) . ?
Si C8 1.8404(10) . ?
Si C8 1.8405(10) 6 ?
Si C2 1.8731(14) . ?
O2 C7 1.3615(16) . ?
O1 C7 1.2038(17) . ?
F1 C3 1.3528(16) . ?
C4 C5 1.393(2) . ?
C4 C3 1.391(2) . ?
C4 H4 0.9500 . ?
C7 C1 1.486(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 C5 1.392(2) . ?
C6 C1 1.3951(19) . ?
C6 H6 0.9500 . ?
C2 C3 1.381(2) . ?
C2 C1 1.4007(18) . ?
C5 H5 0.9500 . ?

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
O2 Si C8 111.32(4) . . ?
O2 Si C8 111.32(4) . 6 ?
C8 Si C8 111.75(6) . 6 ?
O2 Si C2 91.17(5) . . ?
C8 Si C2 114.82(4) . . ?
C8 Si C2 114.82(4) 6 . ?
C7 O2 Si 115.80(9) . . ?
C5 C4 C3 118.55(13) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
O1 C7 O2 121.64(13) . . ?
O1 C7 C1 126.86(13) . . ?
O2 C7 C1 111.50(11) . . ?
Si C8 H8A 109.5 . . ?
Si C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6 C1 117.92(13) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
C3 C2 C1 116.82(12) . . ?
C3 C2 Si 135.81(10) . . ?
C1 C2 Si 107.36(10) . . ?
C6 C5 C4 121.19(13) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
F1 C3 C2 118.96(12) . . ?
F1 C3 C4 118.26(13) . . ?
C2 C3 C4 122.78(13) . . ?
C6 C1 C2 122.74(13) . . ?
C6 C1 C7 123.09(12) . . ?
C2 C1 C7 114.16(11) . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_Spiro
_database_code_depnum_ccdc_archive 'CCDC 1581785'
_audit_update_record             
;
2017-10-24 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H38 B2 F4 O4 Si4'
_chemical_formula_sum            'C32 H38 B2 F4 O4 Si4'
_chemical_formula_weight         696.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   20.3719(4)
_cell_length_b                   8.5430(2)
_cell_length_c                   20.6238(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.992(2)
_cell_angle_gamma                90
_cell_volume                     3588.77(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12986
_cell_measurement_theta_min      2.5780
_cell_measurement_theta_max      32.3860

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_min  0.93923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0026
_diffrn_reflns_number            24087
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_max         32.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6060
_reflns_number_gt                5362
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+3.2249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6060
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Si2 Si 0.08791(2) 0.42389(3) 0.33525(2) 0.01379(8) Uani 1 1 d . . . . .
Si1 Si -0.10724(2) 0.00152(3) 0.30966(2) 0.01387(8) Uani 1 1 d . . . . .
O1 O -0.03122(4) 0.07827(9) 0.29982(4) 0.01380(14) Uani 1 1 d . . . . .
O2 O 0.01623(4) 0.34633(9) 0.30702(4) 0.01408(14) Uani 1 1 d . . . . .
F2 F 0.21047(3) 0.32356(9) 0.43149(4) 0.02371(16) Uani 1 1 d . . . . .
F1 F -0.24762(3) 0.10803(10) 0.37133(4) 0.02655(17) Uani 1 1 d . . . . .
C10 C 0.16048(6) 0.09647(13) 0.47295(5) 0.0179(2) Uani 1 1 d . . . . .
H10 H 0.1982 0.0762 0.4994 0.021 Uiso 1 1 calc R U . . .
C8 C 0.10327(5) 0.26275(12) 0.39395(5) 0.01388(18) Uani 1 1 d . . . . .
C7 C 0.04842(5) 0.16095(12) 0.39461(5) 0.01299(18) Uani 1 1 d . . . . .
C2 C -0.13423(5) 0.16226(12) 0.36353(5) 0.01389(18) Uani 1 1 d . . . . .
C1 C -0.08020(5) 0.25845(12) 0.38037(5) 0.01359(18) Uani 1 1 d . . . . .
C9 C 0.15713(5) 0.22646(13) 0.43308(5) 0.01588(19) Uani 1 1 d . . . . .
C4 C -0.20595(6) 0.32622(14) 0.42822(6) 0.0224(2) Uani 1 1 d . . . . .
H4 H -0.2486 0.3491 0.4436 0.027 Uiso 1 1 calc R U . . .
C3 C -0.19512(5) 0.19998(13) 0.38828(6) 0.0177(2) Uani 1 1 d . . . . .
C13 C 0.14631(6) 0.44477(15) 0.26785(6) 0.0216(2) Uani 1 1 d . . . . .
H13A H 0.1331 0.5334 0.2404 0.032 Uiso 1 1 calc R U . . .
H13B H 0.1462 0.3487 0.2419 0.032 Uiso 1 1 calc R U . . .
H13C H 0.1906 0.4633 0.2856 0.032 Uiso 1 1 calc R U . . .
C6 C -0.08982(6) 0.38574(13) 0.42207(6) 0.0187(2) Uani 1 1 d . . . . .
H6 H -0.0536 0.4496 0.4346 0.022 Uiso 1 1 calc R U . . .
C15 C -0.10229(6) -0.19064(13) 0.35147(7) 0.0231(2) Uani 1 1 d . . . . .
H15A H -0.0793 -0.1781 0.3933 0.035 Uiso 1 1 calc R U . . .
H15B H -0.0783 -0.2650 0.3245 0.035 Uiso 1 1 calc R U . . .
H15C H -0.1467 -0.2303 0.3587 0.035 Uiso 1 1 calc R U . . .
B1 B -0.01169(5) 0.21039(13) 0.34726(6) 0.01324(19) Uani 1 1 d . . . . .
C5 C -0.15208(6) 0.41945(14) 0.44537(6) 0.0231(2) Uani 1 1 d . . . . .
H5 H -0.1579 0.5068 0.4732 0.028 Uiso 1 1 calc R U . . .
C14 C 0.07337(6) 0.61695(13) 0.37384(6) 0.0220(2) Uani 1 1 d . . . . .
H14A H 0.0424 0.6046 0.4093 0.033 Uiso 1 1 calc R U . . .
H14B H 0.0551 0.6897 0.3415 0.033 Uiso 1 1 calc R U . . .
H14C H 0.1150 0.6585 0.3911 0.033 Uiso 1 1 calc R U . . .
C11 C 0.10633(6) -0.00408(13) 0.47286(6) 0.0181(2) Uani 1 1 d . . . . .
H11 H 0.1072 -0.0952 0.4993 0.022 Uiso 1 1 calc R U . . .
C12 C 0.05097(5) 0.02798(13) 0.43439(5) 0.01612(19) Uani 1 1 d . . . . .
H12 H 0.0145 -0.0413 0.4352 0.019 Uiso 1 1 calc R U . . .
C16 C -0.15074(6) -0.02068(15) 0.23042(6) 0.0219(2) Uani 1 1 d . . . . .
H16A H -0.1532 0.0811 0.2086 0.033 Uiso 1 1 calc R U . . .
H16B H -0.1952 -0.0603 0.2375 0.033 Uiso 1 1 calc R U . . .
H16C H -0.1268 -0.0947 0.2033 0.033 Uiso 1 1 calc R U . . .
H1A H 0.0000 0.075(3) 0.2500 0.026 Uiso 1 2 d S U P . .
H1B H 0.0000 0.345(3) 0.2500 0.026 Uiso 1 2 d S U P . .


_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
Si2 O2 1.6974(8) . ?
Si2 C13 1.8538(12) . ?
Si2 C8 1.8562(11) . ?
Si2 C14 1.8574(12) . ?
Si1 O1 1.6971(8) . ?
Si1 C16 1.8552(12) . ?
Si1 C2 1.8557(11) . ?
Si1 C15 1.8563(12) . ?
O1 B1 1.5415(13) . ?
O1 H1A 1.2180(10) . ?
O2 B1 1.5419(14) . ?
O2 H1B 1.2161(8) . ?
F2 C9 1.3680(12) . ?
F1 C3 1.3675(13) . ?
C10 C9 1.3829(16) . ?
C10 C11 1.3982(16) . ?
C10 H10 0.9500 . ?
C8 C9 1.3858(14) . ?
C8 C7 1.4161(14) . ?
C7 C12 1.4017(15) . ?
C7 B1 1.6095(15) . ?
C2 C3 1.3874(14) . ?
C2 C1 1.4122(14) . ?
C1 C6 1.4022(15) . ?
C1 B1 1.6173(15) . ?
C4 C3 1.3773(16) . ?
C4 C5 1.3965(18) . ?
C4 H4 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C6 C5 1.3942(16) . ?
C6 H6 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C5 H5 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C11 C12 1.3947(15) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O2 Si2 C13 109.87(5) . . ?
O2 Si2 C8 93.93(4) . . ?
C13 Si2 C8 117.22(5) . . ?
O2 Si2 C14 110.54(5) . . ?
C13 Si2 C14 110.19(6) . . ?
C8 Si2 C14 113.91(5) . . ?
O1 Si1 C16 110.92(5) . . ?
O1 Si1 C2 93.79(4) . . ?
C16 Si1 C2 117.46(5) . . ?
O1 Si1 C15 110.79(5) . . ?
C16 Si1 C15 109.88(6) . . ?
C2 Si1 C15 112.99(5) . . ?
B1 O1 Si1 115.66(6) . . ?
B1 O1 H1A 114.8(9) . . ?
Si1 O1 H1A 125.7(6) . . ?
B1 O2 Si2 115.63(6) . . ?
B1 O2 H1B 114.5(10) . . ?
Si2 O2 H1B 123.7(5) . . ?
C9 C10 C11 117.49(10) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C9 C8 C7 118.29(9) . . ?
C9 C8 Si2 131.95(8) . . ?
C7 C8 Si2 109.73(7) . . ?
C12 C7 C8 118.82(9) . . ?
C12 C7 B1 126.01(9) . . ?
C8 C7 B1 115.16(9) . . ?
C3 C2 C1 118.19(10) . . ?
C3 C2 Si1 131.93(8) . . ?
C1 C2 Si1 109.89(7) . . ?
C6 C1 C2 119.05(10) . . ?
C6 C1 B1 125.92(9) . . ?
C2 C1 B1 115.03(9) . . ?
F2 C9 C10 118.04(9) . . ?
F2 C9 C8 118.14(10) . . ?
C10 C9 C8 123.81(10) . . ?
C3 C4 C5 117.69(10) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
F1 C3 C4 118.03(10) . . ?
F1 C3 C2 118.22(10) . . ?
C4 C3 C2 123.74(10) . . ?
Si2 C13 H13A 109.5 . . ?
Si2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C6 C1 120.61(11) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 B1 O2 107.66(8) . . ?
O1 B1 C7 112.23(8) . . ?
O2 B1 C7 103.91(8) . . ?
O1 B1 C1 103.82(8) . . ?
O2 B1 C1 111.42(8) . . ?
C7 B1 C1 117.62(9) . . ?
C6 C5 C4 120.70(11) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
Si2 C14 H14A 109.5 . . ?
Si2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 C10 120.69(10) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.90(10) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4

