# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_C17H24O2Si
_database_code_depnum_ccdc_archive 'CCDC 905626'
#TrackingRef '14637_web_deposit_cif_file_0_LinPu_1349970533.C17H24O2Si.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H24 O2 Si'
_chemical_formula_weight         288.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   9.1005(3)
_cell_length_b                   12.8251(5)
_cell_length_c                   13.4859(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1574.0(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9792
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      37.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9401
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38547
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         37.08
_reflns_number_total             7644
_reflns_number_gt                7264
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_number_reflns         7644
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_restrained_S_all      0.874
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 1.000178(19) 0.959782(13) 0.772182(13) 0.02014(5) Uani 1 1 d . . .
O1 O 0.42007(7) 0.73423(5) 0.62152(4) 0.03043(12) Uani 1 1 d . . .
O2 O 0.74561(7) 0.94055(4) 0.93559(4) 0.02520(10) Uani 1 1 d . . .
C1 C 0.82887(6) 0.87857(5) 0.77599(4) 0.01816(9) Uani 1 1 d . . .
C2 C 0.76364(7) 0.81819(5) 0.70669(4) 0.01901(10) Uani 1 1 d . . .
C3 C 0.78101(9) 0.80864(7) 0.59692(5) 0.02985(15) Uani 1 1 d . . .
H3A H 0.8021 0.7360 0.5766 0.036 Uiso 1 1 calc R . .
H3B H 0.8589 0.8554 0.5713 0.036 Uiso 1 1 calc R . .
C4 C 0.62573(10) 0.84416(7) 0.56324(5) 0.02929(14) Uani 1 1 d . . .
H4A H 0.6251 0.9202 0.5504 0.035 Uiso 1 1 calc R . .
H4B H 0.5973 0.8077 0.5015 0.035 Uiso 1 1 calc R . .
C5 C 0.51661(8) 0.81703(5) 0.64782(4) 0.02142(11) Uani 1 1 d . . .
H5 H 0.4594 0.8802 0.6679 0.026 Uiso 1 1 calc R . .
C6 C 0.50540(12) 0.64186(6) 0.63355(6) 0.03239(15) Uani 1 1 d . . .
H6A H 0.5754 0.6336 0.5779 0.039 Uiso 1 1 calc R . .
H6B H 0.4413 0.5796 0.6364 0.039 Uiso 1 1 calc R . .
C7 C 0.58782(8) 0.65658(5) 0.73187(5) 0.02220(11) Uani 1 1 d . . .
H7 H 0.6840 0.6189 0.7300 0.027 Uiso 1 1 calc R . .
C8 C 0.49497(10) 0.61855(5) 0.82018(5) 0.02684(12) Uani 1 1 d . . .
H8A H 0.4353 0.5581 0.7988 0.032 Uiso 1 1 calc R . .
H8B H 0.5617 0.5946 0.8735 0.032 Uiso 1 1 calc R . .
C9 C 0.39216(8) 0.70261(6) 0.86220(5) 0.02584(12) Uani 1 1 d . . .
H9A H 0.3247 0.7279 0.8099 0.031 Uiso 1 1 calc R . .
H9B H 0.3326 0.6735 0.9171 0.031 Uiso 1 1 calc R . .
C10 C 0.48615(7) 0.79101(5) 0.89958(4) 0.01981(10) Uani 1 1 d . . .
C11 C 0.59346(7) 0.82258(5) 0.83806(4) 0.01644(9) Uani 1 1 d . . .
C12 C 0.72498(6) 0.88700(4) 0.86114(4) 0.01714(9) Uani 1 1 d . . .
C13 C 0.46189(8) 0.83043(7) 1.00275(5) 0.02681(13) Uani 1 1 d . . .
H13A H 0.5343 0.8847 1.0178 0.040 Uiso 1 1 calc R . .
H13B H 0.4728 0.7728 1.0499 0.040 Uiso 1 1 calc R . .
H13C H 0.3627 0.8596 1.0081 0.040 Uiso 1 1 calc R . .
C14 C 0.61363(6) 0.77735(4) 0.73608(4) 0.01615(9) Uani 1 1 d . . .
C15 C 1.10803(10) 0.93763(8) 0.88790(7) 0.03538(18) Uani 1 1 d . . .
H15A H 1.1435 0.8655 0.8893 0.053 Uiso 1 1 calc R . .
H15B H 1.0453 0.9504 0.9457 0.053 Uiso 1 1 calc R . .
H15C H 1.1920 0.9854 0.8895 0.053 Uiso 1 1 calc R . .
C16 C 0.94229(9) 1.09901(6) 0.76545(6) 0.02767(12) Uani 1 1 d . . .
H16A H 0.8723 1.1138 0.8189 0.042 Uiso 1 1 calc R . .
H16B H 0.8955 1.1124 0.7012 0.042 Uiso 1 1 calc R . .
H16C H 1.0286 1.1441 0.7727 0.042 Uiso 1 1 calc R . .
C17 C 1.11715(9) 0.92601(7) 0.66300(7) 0.03361(16) Uani 1 1 d . . .
H17A H 1.2136 0.9591 0.6701 0.050 Uiso 1 1 calc R . .
H17B H 1.0698 0.9510 0.6022 0.050 Uiso 1 1 calc R . .
H17C H 1.1294 0.8502 0.6594 0.050 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Si1 0.01573(7) 0.02104(8) 0.02366(8) 0.00285(5) -0.00238(6) -0.00185(5)
O1 0.0311(3) 0.0375(3) 0.0227(2) 0.00076(19) -0.00925(19) -0.0132(2)
O2 0.0281(2) 0.0273(2) 0.02025(19) -0.00761(16) -0.00378(17) -0.00368(18)
C1 0.0165(2) 0.0198(2) 0.0182(2) 0.00058(17) -0.00108(17) -0.00133(17)
C2 0.0184(2) 0.0225(2) 0.0162(2) -0.00121(17) 0.00141(17) -0.00154(19)
C3 0.0287(3) 0.0444(4) 0.0164(2) -0.0048(2) 0.0060(2) -0.0087(3)
C4 0.0357(4) 0.0358(3) 0.0164(2) 0.0049(2) -0.0025(2) -0.0088(3)
C5 0.0239(3) 0.0236(2) 0.0167(2) 0.00126(17) -0.00423(19) -0.0026(2)
C6 0.0476(4) 0.0266(3) 0.0230(3) -0.0065(2) -0.0015(3) -0.0140(3)
C7 0.0281(3) 0.0167(2) 0.0218(2) -0.00201(19) 0.0010(2) -0.00141(19)
C8 0.0357(3) 0.0198(2) 0.0249(3) 0.00320(19) 0.0010(3) -0.0061(3)
C9 0.0236(3) 0.0312(3) 0.0227(2) -0.0002(2) 0.0033(2) -0.0096(2)
C10 0.0190(2) 0.0251(2) 0.01540(19) -0.00022(17) 0.00095(18) -0.00008(19)
C11 0.0175(2) 0.0179(2) 0.01393(18) -0.00103(15) -0.00072(15) -0.00061(17)
C12 0.0182(2) 0.0166(2) 0.0167(2) -0.00070(16) -0.00244(16) -0.00015(17)
C13 0.0256(3) 0.0385(4) 0.0163(2) -0.0025(2) 0.00311(19) 0.0018(2)
C14 0.0177(2) 0.01712(19) 0.01362(18) -0.00107(16) -0.00081(16) -0.00143(16)
C15 0.0260(3) 0.0423(4) 0.0379(4) 0.0132(3) -0.0137(3) -0.0075(3)
C16 0.0282(3) 0.0228(3) 0.0319(3) 0.0028(2) 0.0002(3) -0.0006(2)
C17 0.0234(3) 0.0338(4) 0.0436(4) -0.0036(3) 0.0106(3) -0.0023(3)

_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 C16 1.8640(8) . ?
Si1 C15 1.8654(8) . ?
Si1 C17 1.8678(8) . ?
Si1 C1 1.8756(6) . ?
O1 C5 1.4232(9) . ?
O1 C6 1.4258(12) . ?
O2 C12 1.2308(7) . ?
C1 C2 1.3511(8) . ?
C1 C12 1.4914(8) . ?
C2 C3 1.4937(9) . ?
C2 C14 1.5150(8) . ?
C3 C4 1.5527(12) . ?
C4 C5 1.5518(10) . ?
C5 C14 1.5670(8) . ?
C6 C7 1.5349(11) . ?
C7 C8 1.5395(10) . ?
C7 C14 1.5676(8) . ?
C8 C9 1.5358(12) . ?
C9 C10 1.5070(10) . ?
C10 C11 1.3439(8) . ?
C10 C13 1.4967(9) . ?
C11 C12 1.4873(8) . ?
C11 C14 1.5039(8) . ?

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
C16 Si1 C15 109.59(4) . . ?
C16 Si1 C17 110.17(4) . . ?
C15 Si1 C17 108.92(5) . . ?
C16 Si1 C1 107.36(3) . . ?
C15 Si1 C1 109.26(3) . . ?
C17 Si1 C1 111.50(3) . . ?
C5 O1 C6 104.80(6) . . ?
C2 C1 C12 107.20(5) . . ?
C2 C1 Si1 131.65(5) . . ?
C12 C1 Si1 120.51(4) . . ?
C1 C2 C3 133.32(6) . . ?
C1 C2 C14 114.40(5) . . ?
C3 C2 C14 109.04(5) . . ?
C2 C3 C4 99.76(6) . . ?
C5 C4 C3 107.55(5) . . ?
O1 C5 C4 112.28(5) . . ?
O1 C5 C14 107.14(5) . . ?
C4 C5 C14 105.70(5) . . ?
O1 C6 C7 105.21(5) . . ?
C6 C7 C8 111.16(6) . . ?
C6 C7 C14 103.06(5) . . ?
C8 C7 C14 111.54(5) . . ?
C9 C8 C7 113.42(5) . . ?
C10 C9 C8 107.81(6) . . ?
C11 C10 C13 125.40(6) . . ?
C11 C10 C9 115.63(5) . . ?
C13 C10 C9 118.77(6) . . ?
C10 C11 C12 128.53(5) . . ?
C10 C11 C14 122.48(5) . . ?
C12 C11 C14 107.91(5) . . ?
O2 C12 C11 127.11(6) . . ?
O2 C12 C1 124.88(6) . . ?
C11 C12 C1 107.98(4) . . ?
C11 C14 C2 102.47(4) . . ?
C11 C14 C5 120.04(5) . . ?
C2 C14 C5 101.34(4) . . ?
C11 C14 C7 113.33(5) . . ?
C2 C14 C7 117.85(5) . . ?
C5 C14 C7 102.06(5) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        37.08
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042