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


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Gosselin, Pascal'
_publ_contact_author_email       gosselin@univ-lemans.fr

_publ_section_title              
;
Tandem Payne/Meinwald versus Meinwald Rearrangements
on the a-Hydroxy- or a-Silyloxy-Spiro Epoxide Skeleton
;
loop_
_publ_author_name
P.Gosselin
C.Gaulon-Nourry
J.Totobenazara
H.Haroun
J.Remond
;
K.Adil
;
J.LeBreton
F.Denes

# Attachment '- Structure_1b.cif'

data_rl26bisk
_database_code_depnum_ccdc_archive 'CCDC 835875'
#TrackingRef '- Structure_1b.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H32 O3 Si'
_chemical_formula_sum            'C16 H32 O3 Si'
_chemical_formula_weight         300.51

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           triclinic
_symmetry_space_group_name_H-M   ' P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5535(5)
_cell_length_b                   10.9957(10)
_cell_length_c                   14.1615(13)
_cell_angle_alpha                100.817(5)
_cell_angle_beta                 101.782(5)
_cell_angle_gamma                99.966(4)
_cell_volume                     957.23(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    339
_cell_measurement_theta_min      3
_cell_measurement_theta_max      16

_exptl_crystal_description       Fragment
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.656
_exptl_crystal_size_mid          0.431
_exptl_crystal_size_min          0.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.036
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6795
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS 2008/1, Bruker_AXS, Madison, WI.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 KAPPA APEX II'
_diffrn_measurement_method       '\w scans; 30 settings'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19706
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         29.25
_reflns_number_total             3981
_reflns_number_gt                2667
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997)
;
_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^)+(0.1041P)^2^+0.0858P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     shelxl
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3981
_refine_ls_number_parameters     272
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1825
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si 0.55834(10) 0.60991(5) 0.82094(4) 0.0349(2) Uani 1 1 d . A .
C1 C 0.5454(4) 0.77477(19) 0.88732(16) 0.0359(5) Uani 1 1 d . . .
C2 C 0.4345(5) 0.7645(2) 0.97298(18) 0.0512(7) Uani 1 1 d . . .
H2A H 0.4217 0.8490 1.0049 0.077 Uiso 1 1 calc R . .
H2B H 0.5198 0.7289 1.0217 0.077 Uiso 1 1 calc R . .
H2C H 0.2919 0.7089 0.9465 0.077 Uiso 1 1 calc R . .
C3 C 0.4168(5) 0.8387(2) 0.8141(2) 0.0623(8) Uani 1 1 d . . .
H3A H 0.4111 0.9234 0.8491 0.093 Uiso 1 1 calc R . .
H3B H 0.2714 0.7870 0.7871 0.093 Uiso 1 1 calc R . .
H3C H 0.4867 0.8462 0.7599 0.093 Uiso 1 1 calc R . .
C4 C 0.6807(5) 0.6136(3) 0.7127(2) 0.0698(9) Uani 1 1 d . . .
H4A H 0.6612 0.5268 0.6741 0.105 Uiso 1 1 calc R . .
H4B H 0.8337 0.6523 0.7368 0.105 Uiso 1 1 calc R . .
H4C H 0.6113 0.6635 0.6708 0.105 Uiso 1 1 calc R . .
C5 C 0.7172(4) 0.5314(2) 0.9080(2) 0.0534(7) Uani 1 1 d . . .
H5A H 0.6736 0.5434 0.9707 0.080 Uiso 1 1 calc R . .
H5B H 0.8697 0.5695 0.9205 0.080 Uiso 1 1 calc R . .
H5C H 0.6911 0.4405 0.8782 0.080 Uiso 1 1 calc R . .
C6 C 0.7748(5) 0.8580(2) 0.9305(2) 0.0538(7) Uani 1 1 d . . .
H6A H 0.8436 0.8679 0.8762 0.081 Uiso 1 1 calc R . .
H6B H 0.8581 0.8169 0.9756 0.081 Uiso 1 1 calc R . .
H6C H 0.7676 0.9416 0.9668 0.081 Uiso 1 1 calc R . .
O1 O 0.3050(3) 0.53136(14) 0.78251(12) 0.0472(5) Uani 1 1 d . . .
C7 C 0.2363(4) 0.40179(18) 0.72457(16) 0.0342(5) Uani 0.801(4) 1 d PU A 1
H7 H 0.3629 0.3623 0.7256 0.041 Uiso 0.801(4) 1 calc PR A 1
C8 C 0.0835(5) 0.3318(3) 0.7750(2) 0.0327(7) Uani 0.801(4) 1 d PU A 1
H8A H -0.0367 0.3749 0.7774 0.039 Uiso 0.801(4) 1 calc PR A 1
H8B H 0.1599 0.3375 0.8442 0.039 Uiso 0.801(4) 1 calc PR A 1
C9 C -0.0079(6) 0.1897(3) 0.7221(2) 0.0338(7) Uani 0.801(4) 1 d PU A 1
C10 C -0.0999(3) 0.17727(18) 0.61024(15) 0.0287(5) Uani 0.801(4) 1 d PU A 1
C11 C 0.0396(6) 0.2583(3) 0.5571(2) 0.0321(7) Uani 0.801(4) 1 d PU A 1
C12 C 0.1259(6) 0.3954(3) 0.6186(3) 0.0359(8) Uani 0.801(4) 1 d PU A 1
H12A H 0.2280 0.4408 0.5874 0.043 Uiso 0.801(4) 1 calc PR A 1
H12B H 0.0059 0.4392 0.6182 0.043 Uiso 0.801(4) 1 calc PR A 1
C13 C -0.3318(6) 0.1361(4) 0.5643(3) 0.0416(10) Uani 0.801(4) 1 d PU A 1
H13A H -0.4286 0.1215 0.6083 0.050 Uiso 0.801(4) 1 calc PR A 1
H13B H -0.3903 0.1706 0.5073 0.050 Uiso 0.801(4) 1 calc PR A 1
C14 C -0.1841(7) 0.1360(3) 0.7713(3) 0.0613(10) Uani 0.801(4) 1 d PU A 1
H14A H -0.2938 0.1865 0.7671 0.074 Uiso 0.801(4) 1 calc PR A 1
H14B H -0.1204 0.1403 0.8411 0.074 Uiso 0.801(4) 1 calc PR A 1
H14C H -0.2494 0.0476 0.7368 0.074 Uiso 0.801(4) 1 calc PR A 1
C15 C -0.0808(7) 0.2588(4) 0.4497(3) 0.0558(10) Uani 0.801(4) 1 d PU A 1
H15A H 0.0201 0.2997 0.4167 0.067 Uiso 0.801(4) 1 calc PR A 1
H15B H -0.1943 0.3058 0.4531 0.067 Uiso 0.801(4) 1 calc PR A 1
H15C H -0.1437 0.1713 0.4121 0.067 Uiso 0.801(4) 1 calc PR A 1
C16 C 0.1670(7) 0.1113(3) 0.7369(3) 0.0597(12) Uani 0.801(4) 1 d PU A 1
H16A H 0.1024 0.0210 0.7087 0.072 Uiso 0.801(4) 1 calc PR A 1
H16B H 0.2313 0.1244 0.8078 0.072 Uiso 0.801(4) 1 calc PR A 1
H16C H 0.2774 0.1389 0.7033 0.072 Uiso 0.801(4) 1 calc PR A 1
O2 O -0.1929(3) 0.04922(13) 0.54993(12) 0.0419(4) Uani 0.801(4) 1 d P A 1
O3 O 0.2278(3) 0.20763(19) 0.55088(16) 0.0461(7) Uani 0.801(4) 1 d P A 1
H17 H 0.1904 0.1314 0.5194 0.055 Uiso 0.801(4) 1 calc PR A 1
C7A C 0.2363(4) 0.40179(18) 0.72457(16) 0.0342(5) Uani 0.199(4) 1 d PU A 2
H7A H 0.3515 0.3830 0.6911 0.041 Uiso 0.199(4) 1 calc PR A 2
C8' C 0.167(2) 0.2893(13) 0.7686(9) 0.036(3) Uani 0.199(4) 1 d PU A 2
H8'1 H 0.2930 0.2825 0.8179 0.043 Uiso 0.199(4) 1 calc PR A 2
H8'2 H 0.0598 0.3104 0.8054 0.043 Uiso 0.199(4) 1 calc PR A 2
C9' C 0.074(2) 0.1585(12) 0.6996(10) 0.030(3) Uani 0.199(4) 1 d PU A 2
C10A C -0.0999(3) 0.17727(18) 0.61024(15) 0.0287(5) Uani 0.199(4) 1 d PU A 2
C11' C -0.069(3) 0.2818(13) 0.5614(9) 0.039(3) Uani 0.199(4) 1 d PU A 2
C12' C 0.036(2) 0.4048(12) 0.6413(11) 0.035(3) Uani 0.199(4) 1 d PU A 2
H12C H -0.0742 0.4303 0.6745 0.042 Uiso 0.199(4) 1 calc PR A 2
H12D H 0.0806 0.4722 0.6075 0.042 Uiso 0.199(4) 1 calc PR A 2
C13' C -0.328(3) 0.1050(16) 0.6057(13) 0.041(4) Uani 0.199(4) 1 d PU A 2
H13C H -0.3521 0.0727 0.6642 0.049 Uiso 0.199(4) 1 calc PR A 2
H13D H -0.4508 0.1325 0.5690 0.049 Uiso 0.199(4) 1 calc PR A 2
C14' C 0.008(3) 0.0565(13) 0.7536(10) 0.050(3) Uani 0.199(4) 1 d PU A 2
H14D H -0.0681 -0.0224 0.7050 0.060 Uiso 0.199(4) 1 calc PR A 2
H14E H -0.0865 0.0845 0.7947 0.060 Uiso 0.199(4) 1 calc PR A 2
H14F H 0.1352 0.0419 0.7958 0.060 Uiso 0.199(4) 1 calc PR A 2
C15' C -0.2746(17) 0.2961(7) 0.4962(9) 0.060(4) Uani 0.199(4) 1 d PU A 2
H15D H -0.3359 0.2184 0.4440 0.073 Uiso 0.199(4) 1 calc PR A 2
H15E H -0.2436 0.3682 0.4660 0.073 Uiso 0.199(4) 1 calc PR A 2
H15F H -0.3768 0.3108 0.5365 0.073 Uiso 0.199(4) 1 calc PR A 2
C16' C 0.2494(12) 0.1256(7) 0.6550(6) 0.017(2) Uani 0.199(4) 1 d PRU A 2
H16D H 0.2673 0.1744 0.6049 0.020 Uiso 0.199(4) 1 calc PR A 2
H16E H 0.2141 0.0347 0.6238 0.020 Uiso 0.199(4) 1 calc PR A 2
H16F H 0.3825 0.1458 0.7069 0.020 Uiso 0.199(4) 1 calc PR A 2
O2' O -0.1929(3) 0.04922(13) 0.54993(12) 0.0419(4) Uani 0.199(4) 1 d P A 2
O3' O 0.075(3) 0.2605(11) 0.4915(14) 0.101(6) Uani 0.199(4) 1 d P A 2
H17' H 0.0246 0.1898 0.4511 0.122 Uiso 0.199(4) 1 calc PR A 2

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
Si 0.0264(4) 0.0281(3) 0.0414(4) -0.0044(2) 0.0078(3) -0.0036(3)
C1 0.0362(13) 0.0237(11) 0.0372(11) 0.0025(9) -0.0038(10) -0.0015(10)
C2 0.0593(18) 0.0388(13) 0.0487(14) -0.0064(11) 0.0136(13) 0.0101(12)
C3 0.066(2) 0.0392(14) 0.0657(17) 0.0119(12) -0.0153(15) 0.0065(14)
C4 0.0531(19) 0.088(2) 0.0595(17) -0.0009(16) 0.0241(15) -0.0014(16)
C5 0.0444(16) 0.0387(14) 0.0756(18) 0.0086(12) 0.0147(14) 0.0106(12)
C6 0.0502(17) 0.0311(12) 0.0607(16) 0.0028(11) -0.0059(13) -0.0107(12)
O1 0.0296(9) 0.0297(8) 0.0648(11) -0.0213(7) 0.0121(8) -0.0052(7)
C7 0.0255(12) 0.0197(10) 0.0484(13) -0.0097(9) 0.0090(10) 0.0003(8)
C8 0.0291(18) 0.0276(17) 0.0329(15) -0.0040(12) 0.0017(13) 0.0024(12)
C9 0.0317(19) 0.0216(15) 0.0425(17) 0.0045(12) 0.0008(14) 0.0037(13)
C10 0.0210(11) 0.0186(10) 0.0374(11) -0.0073(8) 0.0008(8) 0.0026(8)
C11 0.0308(19) 0.0299(16) 0.0305(16) -0.0064(12) 0.0094(14) 0.0057(13)
C12 0.036(2) 0.0222(15) 0.0475(18) 0.0007(12) 0.0166(16) 0.0023(15)
C13 0.0248(16) 0.037(2) 0.053(3) -0.0072(17) 0.0045(17) 0.0064(15)
C14 0.063(3) 0.054(2) 0.059(2) 0.0167(16) 0.0151(18) -0.0117(18)
C15 0.057(3) 0.066(3) 0.0372(18) 0.0036(16) 0.0038(17) 0.013(2)
C16 0.062(3) 0.0296(17) 0.068(2) 0.0014(16) -0.021(2) 0.0162(18)
O2 0.0264(9) 0.0233(8) 0.0605(10) -0.0119(7) 0.0009(7) -0.0007(6)
O3 0.0280(12) 0.0310(11) 0.0681(15) -0.0175(10) 0.0167(10) 0.0029(9)
C7A 0.0255(12) 0.0197(10) 0.0484(13) -0.0097(9) 0.0090(10) 0.0003(8)
C8' 0.042(8) 0.035(6) 0.026(5) -0.005(4) 0.005(5) 0.012(5)
C9' 0.020(6) 0.017(5) 0.053(7) 0.000(5) 0.007(4) 0.008(5)
C10A 0.0210(11) 0.0186(10) 0.0374(11) -0.0073(8) 0.0008(8) 0.0026(8)
C11' 0.039(8) 0.041(7) 0.037(6) 0.005(4) 0.007(5) 0.012(6)
C12' 0.032(8) 0.014(5) 0.058(9) 0.009(5) 0.010(5) 0.005(5)
C13' 0.023(5) 0.039(9) 0.055(10) 0.001(7) 0.007(6) 0.006(5)
C14' 0.052(9) 0.050(7) 0.055(7) 0.018(6) 0.019(6) 0.013(6)
C15' 0.062(9) 0.056(8) 0.052(8) 0.021(6) -0.011(6) 0.006(7)
C16' 0.014(4) 0.011(4) 0.020(4) -0.005(3) 0.000(3) 0.003(3)
O2' 0.0264(9) 0.0233(8) 0.0605(10) -0.0119(7) 0.0009(7) -0.0007(6)
O3' 0.149(19) 0.036(7) 0.107(13) -0.008(7) 0.040(14) 0.007(8)

_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 O1 1.6605(17) . ?
Si C4 1.872(3) . ?
Si C5 1.880(3) . ?
Si C1 1.903(2) . ?
C1 C2 1.548(4) . ?
C1 C3 1.549(3) . ?
C1 C6 1.552(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O1 C7 1.447(2) . ?
C7 C12 1.509(4) . ?
C7 C8 1.528(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.555(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.547(4) . ?
C9 C16 1.553(5) . ?
C9 C14 1.554(5) . ?
C10 O2 1.457(2) . ?
C10 C13 1.478(4) . ?
C10 C11 1.564(4) . ?
C11 O3 1.451(5) . ?
C11 C12 1.537(4) . ?
C11 C15 1.565(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O2 1.445(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O3 H17 0.8400 . ?
C8' C9' 1.524(16) . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?
C9' C16' 1.486(16) . ?
C9' C14' 1.523(19) . ?
C11' O3' 1.52(2) . ?
C11' C15' 1.519(17) . ?
C11' C12' 1.540(18) . ?
C12' H12C 0.9900 . ?
C12' H12D 0.9900 . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 0.9800 . ?
O3' H17' 0.8400 . ?

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
O1 Si C4 110.24(12) . . ?
O1 Si C5 110.66(11) . . ?
C4 Si C5 108.38(15) . . ?
O1 Si C1 104.31(10) . . ?
C4 Si C1 112.30(14) . . ?
C5 Si C1 110.94(11) . . ?
C2 C1 C3 109.0(2) . . ?
C2 C1 C6 109.13(19) . . ?
C3 C1 C6 109.07(19) . . ?
C2 C1 Si 109.64(15) . . ?
C3 C1 Si 110.21(16) . . ?
C6 C1 Si 109.77(18) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si C4 H4A 109.5 . . ?
Si C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si C5 H5A 109.5 . . ?
Si C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 O1 Si 123.93(14) . . ?
O1 C7 C12 111.5(2) . . ?
O1 C7 C8 106.39(19) . . ?
C12 C7 C8 110.6(2) . . ?
O1 C7 H7 109.4 . . ?
C12 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C7 C8 C9 113.6(2) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C16 110.0(3) . . ?
C10 C9 C14 111.0(3) . . ?
C16 C9 C14 106.9(3) . . ?
C10 C9 C8 109.8(2) . . ?
C16 C9 C8 111.0(3) . . ?
C14 C9 C8 108.0(3) . . ?
O2 C10 C13 58.97(19) . . ?
O2 C10 C9 116.58(18) . . ?
C13 C10 C9 121.7(3) . . ?
O2 C10 C11 111.69(18) . . ?
C13 C10 C11 117.4(2) . . ?
C9 C10 C11 116.6(2) . . ?
O3 C11 C12 105.1(3) . . ?
O3 C11 C15 108.3(3) . . ?
C12 C11 C15 109.7(3) . . ?
O3 C11 C10 108.9(2) . . ?
C12 C11 C10 111.2(3) . . ?
C15 C11 C10 113.3(3) . . ?
C7 C12 C11 112.5(3) . . ?
C7 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C7 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O2 C13 C10 59.77(18) . . ?
O2 C13 H13A 117.8 . . ?
C10 C13 H13A 117.8 . . ?
O2 C13 H13B 117.8 . . ?
C10 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
C13 O2 C10 61.26(18) . . ?
C9' C8' H8'1 107.5 . . ?
C9' C8' H8'2 107.5 . . ?
H8'1 C8' H8'2 107.0 . . ?
C16' C9' C14' 107.9(11) . . ?
C16' C9' C8' 105.3(9) . . ?
C14' C9' C8' 113.2(11) . . ?
O3' C11' C15' 104.5(12) . . ?
O3' C11' C12' 108.9(12) . . ?
C15' C11' C12' 110.6(11) . . ?
C11' C12' H12C 107.9 . . ?
C11' C12' H12D 107.9 . . ?
H12C C12' H12D 107.2 . . ?
H13C C13' H13D 115.1 . . ?
C9' C14' H14D 109.5 . . ?
C9' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C9' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C11' C15' H15D 109.5 . . ?
C11' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C11' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C9' C16' H16D 109.5 . . ?
C9' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C9' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C11' O3' H17' 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.767
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.084

# Attachment '- Structure_8.cif'

data_hh171_0m
_database_code_depnum_ccdc_archive 'CCDC 835876'
#TrackingRef '- Structure_8.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H34 N2 O8 Si'
_chemical_formula_sum            'C23 H34 N2 O8 Si'
_chemical_formula_weight         494.61

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'
N N 0.0061 0.0033 '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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   39.763(9)
_cell_length_b                   7.0246(13)
_cell_length_c                   19.471(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.495(13)
_cell_angle_gamma                90.00
_cell_volume                     5240.9(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    339
_cell_measurement_theta_min      4
_cell_measurement_theta_max      15

_exptl_crystal_description       Fragment
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2112
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   'SADABS 2008/1, Bruker_AXS, Madison, WI.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 KAPPA APEX II'
_diffrn_measurement_method       '\w scans; 30 settings'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48881
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_sigmaI/netI    0.1014
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.06
_diffrn_reflns_theta_max         30.62
_reflns_number_total             7980
_reflns_number_gt                3744
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.1093P)^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    refall
_refine_ls_extinction_method     shelxl
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7980
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1646
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.2201
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.70594(2) 0.30551(10) 0.10682(4) 0.0357(2) Uani 1 1 d . . .
O1 O 0.69167(5) 0.2246(2) 0.17451(10) 0.0353(4) Uani 1 1 d . . .
O2 O 0.52121(5) 0.1760(3) 0.18648(10) 0.0404(5) Uani 1 1 d . . .
O3 O 0.41045(6) 0.8983(3) -0.00156(12) 0.0584(6) Uani 1 1 d . . .
O4 O 0.57973(5) 0.2454(2) 0.15394(9) 0.0353(4) Uani 1 1 d . . .
O5 O 0.53481(5) 0.4778(3) 0.22764(10) 0.0489(5) Uani 1 1 d . . .
O6 O 0.46722(6) 0.1131(3) -0.06872(11) 0.0553(6) Uani 1 1 d . . .
O7 O 0.42262(6) 0.2941(3) -0.11705(11) 0.0507(6) Uani 1 1 d . . .
O8 O 0.44468(6) 0.9596(3) 0.10356(11) 0.0489(5) Uani 1 1 d . . .
N1 N 0.43368(6) 0.8544(3) 0.05181(13) 0.0360(5) Uani 1 1 d . . .
N2 N 0.44787(7) 0.2506(3) -0.06794(13) 0.0375(6) Uani 1 1 d . . .
C1 C 0.62097(7) 0.0741(3) 0.24892(13) 0.0298(6) Uani 1 1 d . . .
C2 C 0.64129(7) 0.2457(3) 0.29569(14) 0.0321(6) Uani 1 1 d . . .
C3 C 0.65100(7) 0.3721(3) 0.23811(14) 0.0336(6) Uani 1 1 d . . .
H3A H 0.6327 0.4643 0.2194 0.040 Uiso 1 1 calc R . .
H3B H 0.6725 0.4404 0.2588 0.040 Uiso 1 1 calc R . .
C4 C 0.65550(7) 0.2386(3) 0.17734(14) 0.0299(6) Uani 1 1 d . . .
H4 H 0.6410 0.2847 0.1315 0.036 Uiso 1 1 calc R . .
C5 C 0.64217(7) 0.0424(3) 0.19385(14) 0.0307(6) Uani 1 1 d . . .
HA H 0.6617 -0.0424 0.2132 0.037 Uiso 1 1 calc R . .
H5B H 0.6275 -0.0142 0.1507 0.037 Uiso 1 1 calc R . .
C6 C 0.62056(8) 0.3547(4) 0.33924(15) 0.0397(7) Uani 1 1 d . . .
H6A H 0.6118 0.2667 0.3681 0.060 Uiso 1 1 calc R . .
H6B H 0.6013 0.4196 0.3075 0.060 Uiso 1 1 calc R . .
H6C H 0.6355 0.4458 0.3694 0.060 Uiso 1 1 calc R . .
C7 C 0.67513(8) 0.1716(4) 0.34783(16) 0.0457(7) Uani 1 1 d . . .
H7A H 0.6896 0.2774 0.3686 0.069 Uiso 1 1 calc R . .
H7B H 0.6875 0.0926 0.3225 0.069 Uiso 1 1 calc R . .
H7C H 0.6694 0.0985 0.3848 0.069 Uiso 1 1 calc R . .
C8 C 0.58434(7) 0.1487(3) 0.20801(13) 0.0309(6) Uani 1 1 d . . .
C9 C 0.55249(7) 0.1009(4) 0.23543(15) 0.0405(7) Uani 1 1 d . . .
H9A H 0.5505 -0.0360 0.2394 0.049 Uiso 1 1 calc R . .
H9B H 0.5554 0.1561 0.2823 0.049 Uiso 1 1 calc R . .
C10 C 0.51831(7) 0.3671(4) 0.18338(15) 0.0381(7) Uani 1 1 d . . .
C11 C 0.49052(7) 0.4277(4) 0.11701(13) 0.0324(6) Uani 1 1 d . . .
C12 C 0.47487(7) 0.6069(4) 0.11581(14) 0.0342(6) Uani 1 1 d . . .
H12 H 0.4810 0.6871 0.1552 0.041 Uiso 1 1 calc R . .
C13 C 0.44974(7) 0.6622(3) 0.05399(13) 0.0295(6) Uani 1 1 d . . .
C14 C 0.43979(7) 0.5490(3) -0.00658(13) 0.0286(6) Uani 1 1 d . . .
H14 H 0.4229 0.5881 -0.0471 0.034 Uiso 1 1 calc R . .
C15 C 0.45656(7) 0.3730(3) -0.00310(13) 0.0285(5) Uani 1 1 d . . .
C16 C 0.48165(7) 0.3098(3) 0.05686(13) 0.0312(6) Uani 1 1 d . . .
H16 H 0.4923 0.1919 0.0570 0.037 Uiso 1 1 calc R . .
C17 C 0.70307(8) 0.5752(4) 0.09902(15) 0.0401(7) Uani 1 1 d . . .
C18 C 0.66448(9) 0.6409(4) 0.07233(19) 0.0553(9) Uani 1 1 d . . .
H18A H 0.6524 0.6102 0.1074 0.083 Uiso 1 1 calc R . .
H18B H 0.6535 0.5772 0.0285 0.083 Uiso 1 1 calc R . .
H18C H 0.6637 0.7760 0.0646 0.083 Uiso 1 1 calc R . .
C19 C 0.72026(10) 0.6698(4) 0.17212(17) 0.0559(9) Uani 1 1 d . . .
H19A H 0.7213 0.8051 0.1660 0.084 Uiso 1 1 calc R . .
H19B H 0.7434 0.6206 0.1906 0.084 Uiso 1 1 calc R . .
H19C H 0.7066 0.6422 0.2049 0.084 Uiso 1 1 calc R . .
C20 C 0.72305(9) 0.6391(4) 0.04402(17) 0.0526(8) Uani 1 1 d . . .
H20A H 0.7124 0.5821 -0.0014 0.079 Uiso 1 1 calc R . .
H20B H 0.7470 0.5992 0.0601 0.079 Uiso 1 1 calc R . .
H20C H 0.7220 0.7752 0.0395 0.079 Uiso 1 1 calc R . .
C21 C 0.75251(8) 0.2232(4) 0.12689(18) 0.0499(8) Uani 1 1 d . . .
H21A H 0.7662 0.2895 0.1680 0.075 Uiso 1 1 calc R . .
H21B H 0.7615 0.2492 0.0868 0.075 Uiso 1 1 calc R . .
H21C H 0.7536 0.0888 0.1362 0.075 Uiso 1 1 calc R . .
C22 C 0.67977(9) 0.2012(4) 0.01902(16) 0.0534(9) Uani 1 1 d . . .
H22A H 0.6841 0.0668 0.0184 0.080 Uiso 1 1 calc R . .
H22B H 0.6866 0.2613 -0.0195 0.080 Uiso 1 1 calc R . .
H22C H 0.6554 0.2225 0.0137 0.080 Uiso 1 1 calc R . .
C23 C 0.61779(7) -0.1060(3) 0.29222(14) 0.0348(6) Uani 1 1 d . . .
H23A H 0.6032 -0.1976 0.2616 0.052 Uiso 1 1 calc R . .
H23B H 0.6077 -0.0728 0.3302 0.052 Uiso 1 1 calc R . .
H23C H 0.6405 -0.1597 0.3119 0.052 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 0.0359(5) 0.0376(4) 0.0378(4) 0.0029(3) 0.0173(4) -0.0001(3)
O1 0.0297(11) 0.0416(10) 0.0374(10) 0.0058(8) 0.0140(9) 0.0017(8)
O2 0.0256(11) 0.0550(12) 0.0379(11) 0.0166(9) 0.0033(9) 0.0031(9)
O3 0.0664(16) 0.0481(12) 0.0508(13) -0.0013(10) -0.0017(13) 0.0232(11)
O4 0.0357(11) 0.0402(9) 0.0301(10) 0.0094(8) 0.0087(9) 0.0035(8)
O5 0.0371(13) 0.0707(14) 0.0351(11) -0.0112(11) 0.0030(10) 0.0120(11)
O6 0.0568(15) 0.0433(11) 0.0592(14) -0.0161(10) 0.0040(12) 0.0055(10)
O7 0.0565(15) 0.0456(11) 0.0371(12) -0.0060(9) -0.0100(11) -0.0012(10)
O8 0.0581(14) 0.0440(11) 0.0461(12) -0.0144(10) 0.0166(11) -0.0031(10)
N1 0.0384(15) 0.0352(11) 0.0379(13) -0.0010(11) 0.0162(12) 0.0005(10)
N2 0.0424(16) 0.0296(11) 0.0388(14) -0.0037(10) 0.0078(13) -0.0062(10)
C1 0.0308(15) 0.0280(11) 0.0313(13) 0.0050(11) 0.0094(12) 0.0019(10)
C2 0.0314(16) 0.0345(12) 0.0296(13) 0.0012(11) 0.0067(12) -0.0006(11)
C3 0.0329(16) 0.0307(12) 0.0378(15) 0.0022(11) 0.0105(13) -0.0034(11)
C4 0.0268(15) 0.0330(12) 0.0311(14) 0.0027(11) 0.0100(12) -0.0007(11)
C5 0.0312(15) 0.0281(11) 0.0338(14) 0.0000(11) 0.0104(12) 0.0018(10)
C6 0.0428(18) 0.0418(14) 0.0344(15) -0.0049(12) 0.0099(14) -0.0007(13)
C7 0.0353(18) 0.0522(17) 0.0432(17) 0.0040(14) -0.0006(15) 0.0006(13)
C8 0.0319(16) 0.0328(12) 0.0265(13) 0.0020(11) 0.0055(12) -0.0009(11)
C9 0.0262(16) 0.0570(17) 0.0367(15) 0.0152(14) 0.0058(13) 0.0052(13)
C10 0.0276(16) 0.0562(17) 0.0335(15) -0.0001(14) 0.0134(13) 0.0040(13)
C11 0.0255(15) 0.0429(14) 0.0277(13) 0.0037(11) 0.0053(12) -0.0005(11)
C12 0.0278(15) 0.0482(15) 0.0275(13) -0.0015(12) 0.0089(12) -0.0030(12)
C13 0.0260(14) 0.0332(12) 0.0316(14) 0.0017(11) 0.0120(12) -0.0013(10)
C14 0.0254(14) 0.0313(12) 0.0282(13) 0.0034(10) 0.0055(12) -0.0024(10)
C15 0.0277(14) 0.0305(11) 0.0253(13) 0.0016(10) 0.0037(12) -0.0024(10)
C16 0.0264(15) 0.0334(12) 0.0348(14) 0.0050(11) 0.0099(12) -0.0016(11)
C17 0.0442(18) 0.0404(14) 0.0404(16) 0.0027(13) 0.0197(15) -0.0015(13)
C18 0.056(2) 0.0472(16) 0.070(2) 0.0172(16) 0.0305(19) 0.0118(15)
C19 0.069(2) 0.0501(17) 0.056(2) -0.0110(15) 0.0301(19) -0.0198(16)
C20 0.061(2) 0.0492(17) 0.0553(19) 0.0122(15) 0.0293(18) -0.0031(15)
C21 0.0430(19) 0.0536(17) 0.059(2) 0.0108(15) 0.0242(17) 0.0051(14)
C22 0.063(2) 0.0573(19) 0.0446(18) -0.0109(15) 0.0222(17) -0.0150(16)
C23 0.0341(16) 0.0326(13) 0.0380(15) 0.0120(11) 0.0102(13) 0.0032(11)

_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 O1 1.6679(19) . ?
Si1 C21 1.879(3) . ?
Si1 C22 1.895(3) . ?
Si1 C17 1.901(3) . ?
O1 C4 1.457(3) . ?
O2 C10 1.348(3) . ?
O2 C9 1.449(3) . ?
O3 N1 1.231(3) . ?
O4 C8 1.224(3) . ?
O5 C10 1.215(3) . ?
O6 N2 1.238(3) . ?
O7 N2 1.226(3) . ?
O8 N1 1.232(3) . ?
N1 C13 1.489(3) . ?
N2 C15 1.490(3) . ?
C1 C23 1.544(3) . ?
C1 C5 1.547(3) . ?
C1 C8 1.553(4) . ?
C1 C2 1.595(4) . ?
C2 C6 1.536(4) . ?
C2 C7 1.544(4) . ?
C2 C3 1.558(3) . ?
C3 C4 1.557(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.541(3) . ?
C4 H4 0.9800 . ?
C5 HA 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.537(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.520(4) . ?
C11 C16 1.400(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.398(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C14 C15 1.398(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.553(4) . ?
C17 C19 1.554(4) . ?
C17 C20 1.560(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
O1 Si1 C21 104.79(12) . . ?
O1 Si1 C22 111.11(12) . . ?
C21 Si1 C22 109.99(15) . . ?
O1 Si1 C17 112.13(11) . . ?
C21 Si1 C17 110.99(14) . . ?
C22 Si1 C17 107.84(14) . . ?
C4 O1 Si1 123.68(16) . . ?
C10 O2 C9 116.1(2) . . ?
O3 N1 O8 124.2(2) . . ?
O3 N1 C13 118.1(2) . . ?
O8 N1 C13 117.7(2) . . ?
O7 N2 O6 124.6(2) . . ?
O7 N2 C15 118.3(2) . . ?
O6 N2 C15 117.2(2) . . ?
C23 C1 C5 113.57(19) . . ?
C23 C1 C8 110.8(2) . . ?
C5 C1 C8 107.7(2) . . ?
C23 C1 C2 114.2(2) . . ?
C5 C1 C2 102.58(19) . . ?
C8 C1 C2 107.48(19) . . ?
C6 C2 C7 107.9(2) . . ?
C6 C2 C3 112.7(2) . . ?
C7 C2 C3 109.0(2) . . ?
C6 C2 C1 115.3(2) . . ?
C7 C2 C1 109.9(2) . . ?
C3 C2 C1 101.84(19) . . ?
C4 C3 C2 107.73(19) . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
O1 C4 C5 110.21(19) . . ?
O1 C4 C3 112.6(2) . . ?
C5 C4 C3 105.33(19) . . ?
O1 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
C4 C5 C1 107.30(18) . . ?
C4 C5 HA 110.3 . . ?
C1 C5 HA 110.3 . . ?
C4 C5 H5B 110.3 . . ?
C1 C5 H5B 110.3 . . ?
HA C5 H5B 108.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
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 . . ?
O4 C8 C9 118.2(2) . . ?
O4 C8 C1 122.2(2) . . ?
C9 C8 C1 119.7(2) . . ?
O2 C9 C8 109.5(2) . . ?
O2 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
O2 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
O5 C10 O2 125.6(3) . . ?
O5 C10 C11 123.8(3) . . ?
O2 C10 C11 110.6(2) . . ?
C16 C11 C12 120.4(2) . . ?
C16 C11 C10 120.6(2) . . ?
C12 C11 C10 119.0(2) . . ?
C13 C12 C11 118.4(2) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 C12 123.2(2) . . ?
C14 C13 N1 118.2(2) . . ?
C12 C13 N1 118.6(2) . . ?
C13 C14 C15 116.2(2) . . ?
C13 C14 H14 121.9 . . ?
C15 C14 H14 121.9 . . ?
C16 C15 C14 123.3(2) . . ?
C16 C15 N2 118.6(2) . . ?
C14 C15 N2 118.0(2) . . ?
C15 C16 C11 118.5(2) . . ?
C15 C16 H16 120.7 . . ?
C11 C16 H16 120.7 . . ?
C18 C17 C19 109.4(3) . . ?
C18 C17 C20 108.9(2) . . ?
C19 C17 C20 109.0(2) . . ?
C18 C17 Si1 110.9(2) . . ?
C19 C17 Si1 110.5(2) . . ?
C20 C17 Si1 108.10(19) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 C23 H23A 109.5 . . ?
C1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        30.62
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.168