# Electronic Supplementary Material (ESI) for Organdic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       13659475258@163.com
loop_
_publ_author_name
'Xian-Liang Qi'
'Jun-Tao Zhang'
'Jian-Peng Feng'
'Xiaoping Cao'

data_p212121
_database_code_depnum_ccdc_archive 'CCDC 784532'
#TrackingRef '13-qxl.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H25 I O2 Si'
_chemical_formula_weight         368.32
_chemical_absolute_configuration none

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'
I I -0.4742 1.8119 '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                   11.5224(12)
_cell_length_b                   11.6757(14)
_cell_length_c                   12.5624(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1690.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4858
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      25.98

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5474
_exptl_absorpt_correction_T_max  0.6102
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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            10387
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3682
_reflns_number_gt                3136
_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^)+(0.0274P)^2^+0.3089P] 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     SHELXL
_refine_ls_extinction_coef       0.0137(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(18)
_refine_ls_number_reflns         3682
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3879(3) 0.7946(3) 0.1562(2) 0.0486(7) Uani 1 1 d . . .
C2 C 0.4401(3) 0.6777(3) 0.1562(3) 0.0518(8) Uani 1 1 d . . .
H2 H 0.3822 0.6245 0.1275 0.062 Uiso 1 1 calc R . .
C3 C 0.5456(3) 0.6750(3) 0.0827(3) 0.0552(8) Uani 1 1 d . . .
H3 H 0.5163 0.6834 0.0098 0.066 Uiso 1 1 calc R . .
C4 C 0.6252(3) 0.7755(2) 0.1030(2) 0.0459(7) Uani 1 1 d . . .
H4 H 0.6921 0.7706 0.0550 0.055 Uiso 1 1 calc R . .
C5 C 0.5625(3) 0.8873(3) 0.0837(3) 0.0553(8) Uani 1 1 d . . .
H5A H 0.6055 0.9488 0.1176 0.066 Uiso 1 1 calc R . .
H5B H 0.5611 0.9026 0.0078 0.066 Uiso 1 1 calc R . .
C6 C 0.4414(3) 0.8877(3) 0.1249(3) 0.0535(8) Uani 1 1 d . . .
H6 H 0.4020 0.9571 0.1285 0.064 Uiso 1 1 calc R . .
C7 C 0.6080(4) 0.5592(3) 0.0876(4) 0.0875(14) Uani 1 1 d . . .
H7A H 0.6716 0.5591 0.0383 0.131 Uiso 1 1 calc R . .
H7B H 0.5546 0.4992 0.0693 0.131 Uiso 1 1 calc R . .
H7C H 0.6368 0.5468 0.1584 0.131 Uiso 1 1 calc R . .
C8 C 0.8891(3) 0.6660(3) 0.1911(3) 0.0687(10) Uani 1 1 d . . .
H8A H 0.8649 0.5959 0.2243 0.103 Uiso 1 1 calc R . .
H8B H 0.9699 0.6787 0.2053 0.103 Uiso 1 1 calc R . .
H8C H 0.8770 0.6608 0.1156 0.103 Uiso 1 1 calc R . .
C9 C 0.8608(3) 0.9226(3) 0.1897(4) 0.0748(11) Uani 1 1 d . . .
H9A H 0.8597 0.9191 0.1134 0.112 Uiso 1 1 calc R . .
H9B H 0.9391 0.9336 0.2138 0.112 Uiso 1 1 calc R . .
H9C H 0.8135 0.9854 0.2133 0.112 Uiso 1 1 calc R . .
C10 C 0.8008(3) 0.7860(3) 0.3948(2) 0.0564(8) Uani 1 1 d . . .
C11 C 0.7306(5) 0.8868(4) 0.4355(4) 0.0896(14) Uani 1 1 d . . .
H11A H 0.6523 0.8810 0.4098 0.134 Uiso 1 1 calc R . .
H11B H 0.7646 0.9569 0.4106 0.134 Uiso 1 1 calc R . .
H11C H 0.7304 0.8862 0.5119 0.134 Uiso 1 1 calc R . .
C12 C 0.7462(4) 0.6751(3) 0.4341(3) 0.0833(13) Uani 1 1 d . . .
H12A H 0.7535 0.6706 0.5101 0.125 Uiso 1 1 calc R . .
H12B H 0.7851 0.6111 0.4020 0.125 Uiso 1 1 calc R . .
H12C H 0.6655 0.6737 0.4149 0.125 Uiso 1 1 calc R . .
C13 C 0.9254(4) 0.7972(5) 0.4365(4) 0.1023(16) Uani 1 1 d . . .
H13A H 0.9579 0.8686 0.4129 0.153 Uiso 1 1 calc R . .
H13B H 0.9715 0.7350 0.4098 0.153 Uiso 1 1 calc R . .
H13C H 0.9249 0.7951 0.5129 0.153 Uiso 1 1 calc R . .
I1 I 0.21838(2) 0.80396(3) 0.21874(2) 0.07868(12) Uani 1 1 d . . .
O2 O 0.66512(16) 0.77039(16) 0.21145(15) 0.0435(4) Uani 1 1 d . . .
O1 O 0.4662(2) 0.6426(2) 0.2618(2) 0.0739(7) Uani 1 1 d . . .
H1 H 0.5180 0.6832 0.2860 0.111 Uiso 1 1 calc R . .
Si1 Si 0.80291(7) 0.78664(7) 0.24525(6) 0.04554(19) Uani 1 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
C1 0.0452(14) 0.0571(18) 0.0435(15) -0.0055(15) -0.0088(12) -0.0002(16)
C2 0.0527(16) 0.0406(16) 0.062(2) -0.0032(15) -0.0051(15) -0.0067(14)
C3 0.0596(18) 0.0517(18) 0.0543(18) -0.0166(15) -0.0060(15) 0.0021(15)
C4 0.0497(16) 0.0558(18) 0.0322(14) -0.0006(13) -0.0013(12) -0.0005(14)
C5 0.0599(19) 0.0557(19) 0.0503(19) 0.0113(15) -0.0091(16) -0.0103(16)
C6 0.0591(19) 0.0437(17) 0.0577(19) 0.0008(15) -0.0143(16) 0.0059(15)
C7 0.086(3) 0.053(2) 0.123(4) -0.029(2) 0.007(3) 0.008(2)
C8 0.0530(18) 0.079(2) 0.074(2) -0.0089(19) 0.0080(17) 0.0096(17)
C9 0.064(2) 0.070(2) 0.091(3) 0.016(2) -0.006(2) -0.0165(18)
C10 0.067(2) 0.0575(18) 0.0447(16) -0.0044(14) -0.0150(14) 0.0122(17)
C11 0.104(3) 0.091(3) 0.073(3) -0.036(2) -0.010(3) 0.023(3)
C12 0.114(4) 0.087(3) 0.0493(19) 0.012(2) -0.003(2) 0.005(2)
C13 0.080(3) 0.142(4) 0.085(3) -0.018(3) -0.044(2) 0.017(3)
I1 0.05116(13) 0.1037(2) 0.08119(19) -0.00789(16) 0.00454(12) 0.00260(13)
O2 0.0422(9) 0.0546(11) 0.0338(9) 0.0015(9) -0.0029(8) 0.0011(8)
O1 0.0744(17) 0.0732(16) 0.0742(17) 0.0310(14) 0.0030(14) 0.0007(12)
Si1 0.0415(4) 0.0494(4) 0.0457(4) 0.0015(3) -0.0033(3) -0.0001(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
C1 C6 1.311(5) . ?
C1 C2 1.491(4) . ?
C1 I1 2.108(3) . ?
C2 O1 1.420(4) . ?
C2 C3 1.528(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.512(4) . ?
C3 C7 1.532(5) . ?
C3 H3 0.9800 . ?
C4 O2 1.440(3) . ?
C4 C5 1.511(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.488(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 Si1 1.853(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 Si1 1.858(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.516(5) . ?
C10 C12 1.522(5) . ?
C10 C13 1.535(5) . ?
C10 Si1 1.878(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O2 Si1 1.654(2) . ?
O1 H1 0.8200 . ?

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
C6 C1 C2 124.7(3) . . ?
C6 C1 I1 120.3(2) . . ?
C2 C1 I1 114.9(2) . . ?
O1 C2 C1 110.5(3) . . ?
O1 C2 C3 113.0(3) . . ?
C1 C2 C3 109.9(3) . . ?
O1 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C4 C3 C2 111.4(2) . . ?
C4 C3 C7 113.2(3) . . ?
C2 C3 C7 111.5(3) . . ?
C4 C3 H3 106.8 . . ?
C2 C3 H3 106.8 . . ?
C7 C3 H3 106.8 . . ?
O2 C4 C5 109.9(2) . . ?
O2 C4 C3 108.7(2) . . ?
C5 C4 C3 110.7(3) . . ?
O2 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C6 C5 C4 113.3(3) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C1 C6 C5 122.9(3) . . ?
C1 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C12 109.3(3) . . ?
C11 C10 C13 108.5(4) . . ?
C12 C10 C13 110.4(4) . . ?
C11 C10 Si1 110.0(3) . . ?
C12 C10 Si1 109.5(2) . . ?
C13 C10 Si1 109.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 O2 Si1 123.00(18) . . ?
C2 O1 H1 109.5 . . ?
O2 Si1 C8 109.43(15) . . ?
O2 Si1 C9 110.26(15) . . ?
C8 Si1 C9 108.64(19) . . ?
O2 Si1 C10 104.09(14) . . ?
C8 Si1 C10 111.80(17) . . ?
C9 Si1 C10 112.54(18) . . ?

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
C6 C1 C2 O1 106.6(4) . . . . ?
I1 C1 C2 O1 -70.5(3) . . . . ?
C6 C1 C2 C3 -18.7(4) . . . . ?
I1 C1 C2 C3 164.20(19) . . . . ?
O1 C2 C3 C4 -76.2(3) . . . . ?
C1 C2 C3 C4 47.7(3) . . . . ?
O1 C2 C3 C7 51.3(4) . . . . ?
C1 C2 C3 C7 175.2(3) . . . . ?
C2 C3 C4 O2 60.4(3) . . . . ?
C7 C3 C4 O2 -66.2(4) . . . . ?
C2 C3 C4 C5 -60.4(3) . . . . ?
C7 C3 C4 C5 173.0(3) . . . . ?
O2 C4 C5 C6 -79.1(3) . . . . ?
C3 C4 C5 C6 41.0(4) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
I1 C1 C6 C5 177.7(2) . . . . ?
C4 C5 C6 C1 -12.0(5) . . . . ?
C5 C4 O2 Si1 -105.8(3) . . . . ?
C3 C4 O2 Si1 132.8(2) . . . . ?
C4 O2 Si1 C8 -65.7(2) . . . . ?
C4 O2 Si1 C9 53.8(3) . . . . ?
C4 O2 Si1 C10 174.7(2) . . . . ?
C11 C10 Si1 O2 -62.6(3) . . . . ?
C12 C10 Si1 O2 57.5(3) . . . . ?
C13 C10 Si1 O2 178.4(3) . . . . ?
C11 C10 Si1 C8 179.4(3) . . . . ?
C12 C10 Si1 C8 -60.6(3) . . . . ?
C13 C10 Si1 C8 60.4(3) . . . . ?
C11 C10 Si1 C9 56.8(3) . . . . ?
C12 C10 Si1 C9 176.8(3) . . . . ?
C13 C10 Si1 C9 -62.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.053