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


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_auto
_database_code_depnum_ccdc_archive 'CCDC 898062'
#TrackingRef '13508_web_deposit_cif_file_0_YoshinoriYamanoi_1345809836.cifdoc.cif'


_audit_creation_date             2012-07-19T17:14:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_sum            'C18 H18 O Si'
_chemical_formula_weight         278.41
_chemical_absolute_configuration ad

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_space_group_name_H-M   P21
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.975(3)
_cell_length_b                   8.530(3)
_cell_length_c                   11.592(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.387(4)
_cell_angle_gamma                90
_cell_volume                     748.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2429
_cell_measurement_theta_min      4.409
_cell_measurement_theta_max      27.4719

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.15
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_T_max  0.969

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       
;
Saturn724 (4x4 bin mode)
;
_diffrn_measurement_method       dtintegrate.ref
_diffrn_ambient_temperature      123
_diffrn_reflns_number            5332
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.944
_reflns_number_total             3186
_reflns_number_gt                3050
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    
;
????
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.0470P)^2^+0.0042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3186
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0719
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.003
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(8)
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.16

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
Si01 Si 0.23032(4) 0.74228(4) 0.34906(3) 0.01677(10) Uani 1 d . . .
O002 O 0.35577(13) 0.47261(11) 0.23857(9) 0.0226(2) Uani 1 d . . .
C003 C -0.12577(17) 1.2447(2) 0.08223(12) 0.0264(3) Uani 1 d . . .
C004 C -0.07632(18) 1.09197(19) 0.05770(12) 0.0236(3) Uani 1 d . . .
C005 C 0.39070(15) 0.74381(18) 0.26012(10) 0.0170(2) Uani 1 d . . .
C006 C 0.02488(17) 1.20389(15) 0.29746(12) 0.0188(3) Uani 1 d . . .
C007 C 0.07100(15) 1.04828(15) 0.27373(11) 0.0164(3) Uani 1 d . . .
C008 C 0.01835(17) 0.99718(16) 0.15054(11) 0.0193(3) Uani 1 d . . .
C009 C 0.3934(2) 0.32683(18) 0.19275(15) 0.0289(3) Uani 1 d . . .
C010 C 0.5993(2) 0.88177(19) 0.18042(14) 0.0246(3) Uani 1 d . . .
C011 C 0.17051(16) 0.95046(15) 0.37268(11) 0.0172(2) Uani 1 d . . .
C012 C 0.47301(18) 0.88199(17) 0.24034(13) 0.0202(3) Uani 1 d . . .
C013 C 0.43934(17) 0.60414(16) 0.21571(12) 0.0182(3) Uani 1 d . . .
C014 C 0.22032(18) 1.01352(17) 0.48849(12) 0.0201(3) Uani 1 d . . .
C015 C 0.08079(18) 1.26068(18) 0.41891(13) 0.0232(3) Uani 1 d . . .
C016 C 0.17705(18) 1.16864(18) 0.51209(13) 0.0237(3) Uani 1 d . . .
C017 C -0.07521(19) 1.29896(18) 0.19924(14) 0.0246(3) Uani 1 d . . .
C018 C 0.3315(2) 0.64312(18) 0.49778(13) 0.0253(3) Uani 1 d . . .
C019 C 0.64342(16) 0.7410(2) 0.13764(11) 0.0249(3) Uani 1 d . . .
C020 C 0.56303(18) 0.60110(18) 0.15343(12) 0.0215(3) Uani 1 d . . .
H12 H 0.646(3) 0.979(2) 0.1683(17) 0.038(5) Uiso 1 d . . .
H11 H 0.444(2) 0.979(2) 0.2716(15) 0.024(4) Uiso 1 d . . .
H2 H -0.113(2) 1.062(2) -0.0278(17) 0.030(5) Uiso 1 d . . .
H6 H 0.221(2) 1.206(2) 0.5906(18) 0.032(5) Uiso 1 d . . .
H7 H 0.289(2) 0.952(2) 0.5507(16) 0.030(4) Uiso 1 d . . .
H13 H 0.730(2) 0.740(3) 0.0972(15) 0.032(4) Uiso 1 d . . .
H1 H 0.055(2) 0.888(2) 0.1313(16) 0.025(4) Uiso 1 d . . .
H4 H -0.105(2) 1.396(2) 0.2131(16) 0.024(4) Uiso 1 d . . .
H5 H 0.049(2) 1.362(2) 0.4322(16) 0.025(4) Uiso 1 d . . .
H18 H 0.080(2) 0.664(2) 0.2796(15) 0.024(4) Uiso 1 d . . .
H14 H 0.591(2) 0.505(2) 0.1243(15) 0.026(4) Uiso 1 d . . .
H9 H 0.439(2) 0.690(2) 0.5487(17) 0.029(5) Uiso 1 d . . .
H8 H 0.354(3) 0.527(3) 0.4843(18) 0.045(6) Uiso 1 d . . .
H17 H 0.324(2) 0.241(3) 0.2129(15) 0.033(4) Uiso 1 d . . .
H16 H 0.518(3) 0.301(2) 0.2322(18) 0.035(5) Uiso 1 d . . .
H15 H 0.362(3) 0.340(3) 0.101(2) 0.044(6) Uiso 1 d . . .
H3 H -0.196(3) 1.312(2) 0.0170(18) 0.041(5) Uiso 1 d . . .
H10 H 0.253(3) 0.644(3) 0.549(2) 0.046(6) Uiso 1 d . . .

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
Si01 0.01583(16) 0.01622(16) 0.01913(16) 0.00057(15) 0.00674(12) 0.00038(14)
O002 0.0258(5) 0.0156(5) 0.0294(5) -0.0029(4) 0.0129(4) -0.0016(4)
C003 0.0212(6) 0.0284(7) 0.0276(6) 0.0105(7) 0.0049(5) 0.0046(7)
C004 0.0179(6) 0.0317(7) 0.0194(6) 0.0018(6) 0.0035(5) -0.0012(5)
C005 0.0149(5) 0.0190(5) 0.0157(5) 0.0009(6) 0.0028(4) -0.0002(6)
C006 0.0144(5) 0.0182(7) 0.0250(6) -0.0004(5) 0.0082(5) -0.0007(4)
C007 0.0107(5) 0.0195(6) 0.0200(6) 0.0001(5) 0.0063(5) -0.0007(5)
C008 0.0162(6) 0.0218(7) 0.0210(6) -0.0003(5) 0.0074(5) -0.0006(5)
C009 0.0326(8) 0.0202(7) 0.0359(8) -0.0039(6) 0.0136(7) 0.0012(6)
C010 0.0215(7) 0.0271(8) 0.0261(7) 0.0059(6) 0.0089(6) -0.0034(6)
C011 0.0142(6) 0.0184(6) 0.0207(6) -0.0006(5) 0.0079(5) -0.0016(5)
C012 0.0184(6) 0.0199(7) 0.0208(6) 0.0008(5) 0.0040(5) -0.0006(5)
C013 0.0157(6) 0.0206(7) 0.0160(5) 0.0021(5) 0.0017(5) 0.0006(5)
C014 0.0163(6) 0.0251(7) 0.0186(6) 0.0002(5) 0.0051(5) 0.0003(5)
C015 0.0180(6) 0.0220(7) 0.0313(7) -0.0057(6) 0.0103(5) -0.0006(6)
C016 0.0197(6) 0.0305(7) 0.0213(7) -0.0079(6) 0.0071(5) -0.0036(6)
C017 0.0198(6) 0.0204(6) 0.0336(7) 0.0031(6) 0.0086(6) 0.0035(5)
C018 0.0281(7) 0.0266(7) 0.0242(7) 0.0074(6) 0.0127(6) 0.0077(6)
C019 0.0196(6) 0.0361(7) 0.0209(5) 0.0061(7) 0.0089(5) 0.0010(7)
C020 0.0195(6) 0.0256(7) 0.0186(6) -0.0001(5) 0.0051(5) 0.0037(5)


#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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
Si01 C018 1.8604(15) . ?
Si01 C005 1.8792(13) . ?
Si01 C011 1.8810(15) . ?
Si01 H18 1.388(17) . ?
O002 C013 1.3728(17) . ?
O002 C009 1.4208(17) . ?
C003 C017 1.368(2) . ?
C003 C004 1.416(2) . ?
C003 H3 0.97(2) . ?
C004 C008 1.3673(19) . ?
C004 H2 0.976(18) . ?
C005 C013 1.400(2) . ?
C005 C012 1.403(2) . ?
C006 C017 1.420(2) . ?
C006 C015 1.421(2) . ?
C006 C007 1.4270(18) . ?
C007 C008 1.4238(18) . ?
C007 C011 1.4379(18) . ?
C008 H1 1.020(18) . ?
C009 H17 0.99(2) . ?
C009 H16 0.98(2) . ?
C009 H15 1.02(2) . ?
C010 C019 1.386(2) . ?
C010 C012 1.393(2) . ?
C010 H12 0.93(2) . ?
C011 C014 1.3830(18) . ?
C012 H11 0.959(18) . ?
C013 C020 1.394(2) . ?
C014 C016 1.416(2) . ?
C014 H7 0.919(19) . ?
C015 C016 1.360(2) . ?
C015 H5 0.93(2) . ?
C016 H6 0.922(19) . ?
C017 H4 0.890(19) . ?
C018 H9 0.96(2) . ?
C018 H8 1.03(2) . ?
C018 H10 0.99(2) . ?
C019 C020 1.394(2) . ?
C019 H13 0.948(17) . ?
C020 H14 0.940(19) . ?

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
C018 Si01 C005 109.88(7) . . ?
C018 Si01 C011 110.50(7) . . ?
C005 Si01 C011 108.73(6) . . ?
C018 Si01 H18 111.2(7) . . ?
C005 Si01 H18 107.4(7) . . ?
C011 Si01 H18 109.0(7) . . ?
C013 O002 C009 118.07(11) . . ?
C017 C003 C004 119.80(13) . . ?
C017 C003 H3 119.4(12) . . ?
C004 C003 H3 120.8(12) . . ?
C008 C004 C003 120.38(13) . . ?
C008 C004 H2 123.8(11) . . ?
C003 C004 H2 115.9(11) . . ?
C013 C005 C012 117.17(11) . . ?
C013 C005 Si01 120.74(11) . . ?
C012 C005 Si01 122.02(11) . . ?
C017 C006 C015 121.39(13) . . ?
C017 C006 C007 119.36(12) . . ?
C015 C006 C007 119.25(12) . . ?
C008 C007 C006 117.76(11) . . ?
C008 C007 C011 122.44(12) . . ?
C006 C007 C011 119.79(12) . . ?
C004 C008 C007 121.55(13) . . ?
C004 C008 H1 119.4(10) . . ?
C007 C008 H1 119.0(10) . . ?
O002 C009 H17 111.1(12) . . ?
O002 C009 H16 108.9(11) . . ?
H17 C009 H16 106.6(15) . . ?
O002 C009 H15 106.7(13) . . ?
H17 C009 H15 110.9(16) . . ?
H16 C009 H15 112.7(16) . . ?
C019 C010 C012 118.99(14) . . ?
C019 C010 H12 123.8(12) . . ?
C012 C010 H12 117.2(12) . . ?
C014 C011 C007 117.77(12) . . ?
C014 C011 Si01 120.00(10) . . ?
C007 C011 Si01 122.22(10) . . ?
C010 C012 C005 122.00(13) . . ?
C010 C012 H11 119.5(10) . . ?
C005 C012 H11 118.5(10) . . ?
O002 C013 C020 123.41(12) . . ?
O002 C013 C005 114.63(12) . . ?
C020 C013 C005 121.96(13) . . ?
C011 C014 C016 122.56(13) . . ?
C011 C014 H7 117.3(11) . . ?
C016 C014 H7 120.1(11) . . ?
C016 C015 C006 120.81(14) . . ?
C016 C015 H5 121.4(11) . . ?
C006 C015 H5 117.8(11) . . ?
C015 C016 C014 119.80(13) . . ?
C015 C016 H6 121.9(12) . . ?
C014 C016 H6 118.3(12) . . ?
C003 C017 C006 121.12(14) . . ?
C003 C017 H4 118.8(12) . . ?
C006 C017 H4 120.0(12) . . ?
Si01 C018 H9 114.8(11) . . ?
Si01 C018 H8 110.1(11) . . ?
H9 C018 H8 109.3(16) . . ?
Si01 C018 H10 112.3(13) . . ?
H9 C018 H10 104.1(16) . . ?
H8 C018 H10 105.8(17) . . ?
C010 C019 C020 121.04(11) . . ?
C010 C019 H13 119.4(13) . . ?
C020 C019 H13 119.5(13) . . ?
C019 C020 C013 118.82(13) . . ?
C019 C020 H14 122.1(11) . . ?
C013 C020 H14 119.1(11) . . ?