# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Zhenfeng Xi'
_publ_contact_author_email       zfxi@pku.edu.cn
_publ_author_name                'Zhenfeng Xi'

data_a
_database_code_depnum_ccdc_archive 'CCDC 823538'
#TrackingRef '- 6e.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N Si'
_chemical_formula_weight         353.52

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'
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

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

_cell_length_a                   9.3619(19)
_cell_length_b                   10.083(2)
_cell_length_c                   10.655(2)
_cell_angle_alpha                87.11(3)
_cell_angle_beta                 82.02(3)
_cell_angle_gamma                88.24(3)
_cell_volume                     994.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.48

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_process_details   
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;

_diffrn_ambient_temperature      298(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  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       \W
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6104
_diffrn_reflns_av_R_equivalents  0.1614
_diffrn_reflns_av_sigmaI/netI    0.2513
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4195
_reflns_number_gt                1316
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_cell_refinement       Rapid-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,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^)+(0.0300P)^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    none
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.043(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4195
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1855
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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 0.5881(4) 0.7284(4) 0.6697(4) 0.0710(13) Uani 1 1 d . . .
H1A H 0.5435 0.6903 0.7494 0.107 Uiso 1 1 calc R . .
H1B H 0.6658 0.6710 0.6350 0.107 Uiso 1 1 calc R . .
H1C H 0.5180 0.7386 0.6119 0.107 Uiso 1 1 calc R . .
C2 C 0.7986(4) 0.8822(4) 0.8099(4) 0.0773(14) Uani 1 1 d . . .
H2A H 0.8459 0.9656 0.8079 0.116 Uiso 1 1 calc R . .
H2B H 0.8688 0.8134 0.7857 0.116 Uiso 1 1 calc R . .
H2C H 0.7511 0.8619 0.8941 0.116 Uiso 1 1 calc R . .
C3 C 0.7278(3) 0.9766(4) 0.5397(3) 0.0530(11) Uani 1 1 d . . .
H3A H 0.8184 0.9341 0.5060 0.064 Uiso 1 1 calc R . .
H3B H 0.6595 0.9646 0.4808 0.064 Uiso 1 1 calc R . .
C4 C 0.7507(4) 1.1223(4) 0.5476(3) 0.0497(11) Uani 1 1 d . . .
C5 C 0.8744(4) 1.1827(5) 0.4841(4) 0.0676(13) Uani 1 1 d . . .
H5 H 0.9453 1.1302 0.4391 0.081 Uiso 1 1 calc R . .
C6 C 0.8951(5) 1.3177(5) 0.4857(4) 0.0765(14) Uani 1 1 d . . .
H6 H 0.9792 1.3541 0.4427 0.092 Uiso 1 1 calc R . .
C7 C 0.7931(4) 1.3984(5) 0.5499(4) 0.0791(15) Uani 1 1 d . . .
H7 H 0.8058 1.4895 0.5502 0.095 Uiso 1 1 calc R . .
C8 C 0.6702(4) 1.3404(4) 0.6146(4) 0.0611(12) Uani 1 1 d . . .
H8 H 0.6013 1.3944 0.6600 0.073 Uiso 1 1 calc R . .
C9 C 0.6455(4) 1.2058(4) 0.6145(3) 0.0462(10) Uani 1 1 d . . .
C10 C 0.5172(3) 1.1449(4) 0.6891(3) 0.0426(10) Uani 1 1 d . . .
C11 C 0.5141(3) 1.0167(4) 0.7399(3) 0.0431(10) Uani 1 1 d . . .
C12 C 0.3752(4) 1.2067(4) 0.7226(3) 0.0444(10) Uani 1 1 d . . .
C13 C 0.3096(4) 1.3285(4) 0.6922(4) 0.0643(12) Uani 1 1 d . . .
H13 H 0.3624 1.3952 0.6452 0.077 Uiso 1 1 calc R . .
C14 C 0.1640(4) 1.3473(4) 0.7338(4) 0.0761(14) Uani 1 1 d . . .
H14 H 0.1188 1.4272 0.7131 0.091 Uiso 1 1 calc R . .
C15 C 0.0830(4) 1.2491(5) 0.8064(4) 0.0774(14) Uani 1 1 d . . .
H15 H -0.0147 1.2649 0.8327 0.093 Uiso 1 1 calc R . .
C16 C 0.1463(4) 1.1287(4) 0.8395(4) 0.0616(12) Uani 1 1 d . . .
H16 H 0.0930 1.0637 0.8886 0.074 Uiso 1 1 calc R . .
C17 C 0.2927(4) 1.1082(4) 0.7969(3) 0.0478(10) Uani 1 1 d . . .
C18 C 0.3362(4) 0.8732(4) 0.8759(4) 0.0461(10) Uani 1 1 d . . .
C19 C 0.4127(4) 0.8201(4) 0.9693(4) 0.0522(11) Uani 1 1 d . . .
H19 H 0.4887 0.8665 0.9922 0.063 Uiso 1 1 calc R . .
C20 C 0.3769(4) 0.6985(4) 1.0286(4) 0.0559(11) Uani 1 1 d . . .
H20 H 0.4274 0.6641 1.0927 0.067 Uiso 1 1 calc R . .
C21 C 0.2662(4) 0.6278(4) 0.9930(4) 0.0554(11) Uani 1 1 d . . .
C22 C 0.1886(4) 0.6826(4) 0.9022(4) 0.0702(13) Uani 1 1 d . . .
H22 H 0.1113 0.6365 0.8814 0.084 Uiso 1 1 calc R . .
C23 C 0.2215(4) 0.8037(4) 0.8410(4) 0.0661(13) Uani 1 1 d . . .
H23 H 0.1691 0.8384 0.7783 0.079 Uiso 1 1 calc R . .
C24 C 0.2293(4) 0.4904(4) 1.0572(4) 0.0858(15) Uani 1 1 d . . .
H24A H 0.1319 0.4700 1.0482 0.129 Uiso 1 1 calc R . .
H24B H 0.2392 0.4914 1.1456 0.129 Uiso 1 1 calc R . .
H24C H 0.2940 0.4242 1.0177 0.129 Uiso 1 1 calc R . .
N1 N 0.3775(3) 0.9955(3) 0.8079(3) 0.0449(8) Uani 1 1 d . . .
Si1 Si 0.65972(10) 0.89348(11) 0.69437(11) 0.0504(4) 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 0.079(3) 0.062(3) 0.069(3) -0.005(3) 0.000(2) 0.009(2)
C2 0.050(2) 0.108(4) 0.074(3) -0.002(3) -0.016(2) 0.012(2)
C3 0.0332(19) 0.077(3) 0.048(3) -0.006(2) -0.0051(17) 0.015(2)
C4 0.043(2) 0.066(3) 0.040(3) 0.004(2) -0.0078(18) -0.008(2)
C5 0.054(3) 0.092(4) 0.052(3) 0.010(3) 0.005(2) 0.002(3)
C6 0.062(3) 0.082(4) 0.081(4) 0.018(3) 0.003(3) -0.019(3)
C7 0.076(3) 0.079(4) 0.081(4) 0.010(3) -0.004(3) -0.027(3)
C8 0.064(3) 0.053(3) 0.063(3) 0.010(2) -0.001(2) -0.014(2)
C9 0.047(2) 0.055(3) 0.037(2) 0.001(2) -0.0057(18) -0.001(2)
C10 0.041(2) 0.041(2) 0.045(2) -0.004(2) -0.0040(17) -0.0019(18)
C11 0.0349(19) 0.053(3) 0.042(2) -0.012(2) -0.0011(17) -0.0088(18)
C12 0.054(2) 0.037(2) 0.040(2) 0.001(2) -0.0018(18) 0.003(2)
C13 0.063(3) 0.063(3) 0.064(3) -0.005(3) 0.000(2) 0.008(2)
C14 0.066(3) 0.071(3) 0.084(4) -0.002(3) 0.005(3) 0.028(2)
C15 0.045(3) 0.104(4) 0.076(4) 0.005(3) 0.009(2) 0.020(3)
C16 0.044(2) 0.079(3) 0.058(3) 0.003(2) 0.003(2) 0.012(2)
C17 0.047(2) 0.054(3) 0.041(2) 0.000(2) -0.0019(18) 0.001(2)
C18 0.037(2) 0.052(3) 0.048(3) 0.006(2) -0.0019(18) -0.003(2)
C19 0.047(2) 0.054(3) 0.057(3) 0.000(2) -0.014(2) -0.011(2)
C20 0.069(3) 0.049(3) 0.051(3) 0.003(2) -0.014(2) -0.005(2)
C21 0.056(3) 0.058(3) 0.050(3) 0.020(2) -0.004(2) -0.010(2)
C22 0.053(3) 0.076(3) 0.084(4) 0.010(3) -0.016(2) -0.028(3)
C23 0.046(2) 0.086(3) 0.070(3) 0.010(3) -0.020(2) -0.018(2)
C24 0.080(3) 0.074(3) 0.101(4) 0.021(3) -0.007(3) -0.020(3)
N1 0.0391(18) 0.041(2) 0.053(2) 0.0008(17) -0.0035(15) 0.0015(16)
Si1 0.0419(6) 0.0587(8) 0.0505(7) -0.0015(6) -0.0080(5) 0.0057(5)

_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 Si1 1.858(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 Si1 1.908(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.500(5) . ?
C3 Si1 1.851(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.398(4) . ?
C4 C9 1.415(5) . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.477(4) . ?
C10 C11 1.376(5) . ?
C10 C12 1.456(5) . ?
C11 N1 1.396(4) . ?
C11 Si1 1.847(4) . ?
C12 C13 1.400(5) . ?
C12 C17 1.417(4) . ?
C13 C14 1.384(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.395(4) . ?
C16 H16 0.9300 . ?
C17 N1 1.376(4) . ?
C18 C19 1.382(5) . ?
C18 C23 1.402(4) . ?
C18 N1 1.435(4) . ?
C19 C20 1.380(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(6) . ?
C21 C24 1.541(5) . ?
C22 C23 1.378(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 Si1 113.4(3) . . ?
C4 C3 H3A 108.9 . . ?
Si1 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
Si1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C9 117.0(4) . . ?
C5 C4 C3 121.3(3) . . ?
C9 C4 C3 121.6(3) . . ?
C6 C5 C4 122.3(4) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 118.0(4) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
C9 C8 C7 122.9(4) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C8 C9 C4 119.1(3) . . ?
C8 C9 C10 122.1(3) . . ?
C4 C9 C10 118.7(3) . . ?
C11 C10 C12 108.3(3) . . ?
C11 C10 C9 124.3(3) . . ?
C12 C10 C9 127.4(3) . . ?
C10 C11 N1 108.3(3) . . ?
C10 C11 Si1 122.2(3) . . ?
N1 C11 Si1 128.5(3) . . ?
C13 C12 C17 119.6(3) . . ?
C13 C12 C10 135.1(3) . . ?
C17 C12 C10 105.2(3) . . ?
C14 C13 C12 118.3(4) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 121.7(4) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 117.8(4) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
N1 C17 C16 129.2(4) . . ?
N1 C17 C12 109.0(3) . . ?
C16 C17 C12 121.6(4) . . ?
C19 C18 C23 120.1(4) . . ?
C19 C18 N1 121.0(3) . . ?
C23 C18 N1 118.8(4) . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 119.2(4) . . ?
C22 C21 C24 120.9(4) . . ?
C20 C21 C24 119.8(4) . . ?
C21 C22 C23 122.2(3) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C22 C23 C18 118.0(4) . . ?
C22 C23 H23 121.0 . . ?
C18 C23 H23 121.0 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C17 N1 C11 109.2(3) . . ?
C17 N1 C18 127.0(3) . . ?
C11 N1 C18 123.8(3) . . ?
C11 Si1 C3 96.15(17) . . ?
C11 Si1 C1 112.07(16) . . ?
C3 Si1 C1 110.07(19) . . ?
C11 Si1 C2 112.27(17) . . ?
C3 Si1 C2 113.19(16) . . ?
C1 Si1 C2 112.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.920
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.920
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.078

# Attachment '- 8a.cif'

data_ly
_database_code_depnum_ccdc_archive 'CCDC 824123'
#TrackingRef '- 8a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N Si'
_chemical_formula_weight         339.50

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'
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   P2(1)/n

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

_cell_length_a                   13.268(3)
_cell_length_b                   10.072(2)
_cell_length_c                   13.822(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.60(3)
_cell_angle_gamma                90.00
_cell_volume                     1846.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      27.48

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_process_details   
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       \W
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7929
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.1296
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4229
_reflns_number_gt                1897
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_cell_refinement       Rapid-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,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^)+(0.0120P)^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    none
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0276(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4229
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
C1 C 0.35103(15) 0.1955(2) 0.44656(16) 0.0331(6) Uani 1 1 d . . .
C2 C 0.28054(16) 0.2556(2) 0.50479(17) 0.0394(6) Uani 1 1 d . . .
H2 H 0.2118 0.2424 0.4940 0.047 Uiso 1 1 calc R . .
C3 C 0.31626(17) 0.3352(2) 0.57889(19) 0.0478(7) Uani 1 1 d . . .
H3 H 0.2706 0.3785 0.6178 0.057 Uiso 1 1 calc R . .
C4 C 0.41927(17) 0.3525(2) 0.59706(18) 0.0503(7) Uani 1 1 d . . .
H4 H 0.4413 0.4046 0.6491 0.060 Uiso 1 1 calc R . .
C5 C 0.48872(17) 0.2934(2) 0.53895(18) 0.0446(7) Uani 1 1 d . . .
H5 H 0.5573 0.3059 0.5514 0.054 Uiso 1 1 calc R . .
C6 C 0.45606(15) 0.2150(2) 0.46152(16) 0.0331(6) Uani 1 1 d . . .
C7 C 0.50535(16) 0.1468(2) 0.38487(17) 0.0338(6) Uani 1 1 d . . .
C8 C 0.43276(16) 0.0878(2) 0.32580(17) 0.0345(6) Uani 1 1 d . . .
C9 C 0.24575(15) 0.0540(2) 0.33220(18) 0.0345(6) Uani 1 1 d . . .
C10 C 0.17964(16) 0.0065(2) 0.40015(18) 0.0417(6) Uani 1 1 d . . .
H10 H 0.1952 0.0156 0.4658 0.050 Uiso 1 1 calc R . .
C11 C 0.09053(16) -0.0545(2) 0.3703(2) 0.0481(7) Uani 1 1 d . . .
H11 H 0.0451 -0.0835 0.4158 0.058 Uiso 1 1 calc R . .
C12 C 0.06950(17) -0.0719(2) 0.2733(2) 0.0479(7) Uani 1 1 d . . .
H12 H 0.0098 -0.1128 0.2529 0.058 Uiso 1 1 calc R . .
C13 C 0.13749(15) -0.0282(2) 0.20593(19) 0.0427(6) Uani 1 1 d . . .
H13 H 0.1231 -0.0422 0.1405 0.051 Uiso 1 1 calc R . .
C14 C 0.22667(15) 0.0360(2) 0.23333(17) 0.0345(6) Uani 1 1 d . . .
C15 C 0.30173(16) 0.0795(2) 0.16104(17) 0.0446(7) Uani 1 1 d . . .
H15A H 0.3015 0.1755 0.1561 0.054 Uiso 1 1 calc R . .
H15B H 0.2837 0.0432 0.0979 0.054 Uiso 1 1 calc R . .
C16 C 0.61527(15) 0.1390(2) 0.37157(17) 0.0364(6) Uani 1 1 d . . .
C17 C 0.67663(17) 0.2505(2) 0.38519(18) 0.0478(7) Uani 1 1 d . . .
H17 H 0.6481 0.3312 0.4024 0.057 Uiso 1 1 calc R . .
C18 C 0.78081(18) 0.2414(3) 0.37302(19) 0.0572(8) Uani 1 1 d . . .
H18 H 0.8214 0.3156 0.3835 0.069 Uiso 1 1 calc R . .
C19 C 0.82329(18) 0.1233(3) 0.34559(19) 0.0551(8) Uani 1 1 d . . .
H19 H 0.8924 0.1182 0.3366 0.066 Uiso 1 1 calc R . .
C20 C 0.76407(17) 0.0129(3) 0.33143(17) 0.0491(7) Uani 1 1 d . . .
H20 H 0.7929 -0.0669 0.3128 0.059 Uiso 1 1 calc R . .
C21 C 0.66087(16) 0.0209(2) 0.34507(16) 0.0411(6) Uani 1 1 d . . .
H21 H 0.6214 -0.0547 0.3362 0.049 Uiso 1 1 calc R . .
C22 C 0.43652(17) -0.1633(2) 0.1967(2) 0.0574(8) Uani 1 1 d . . .
H22A H 0.4962 -0.1928 0.2312 0.086 Uiso 1 1 calc R . .
H22B H 0.4384 -0.1929 0.1308 0.086 Uiso 1 1 calc R . .
H22C H 0.3781 -0.1995 0.2266 0.086 Uiso 1 1 calc R . .
C23 C 0.53163(16) 0.0956(2) 0.12660(18) 0.0545(8) Uani 1 1 d . . .
H23A H 0.5351 0.1893 0.1392 0.082 Uiso 1 1 calc R . .
H23B H 0.5167 0.0811 0.0591 0.082 Uiso 1 1 calc R . .
H23C H 0.5951 0.0552 0.1439 0.082 Uiso 1 1 calc R . .
N1 N 0.33791(12) 0.11685(17) 0.36515(14) 0.0357(5) Uani 1 1 d . . .
Si1 Si 0.43040(5) 0.02037(7) 0.19975(5) 0.0418(2) 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 0.0347(14) 0.0351(15) 0.0296(15) -0.0029(12) 0.0023(12) -0.0013(11)
C2 0.0348(13) 0.0419(16) 0.0416(17) -0.0057(13) 0.0008(12) 0.0004(12)
C3 0.0447(16) 0.0567(18) 0.0425(17) -0.0109(15) 0.0094(13) 0.0051(14)
C4 0.0511(16) 0.0586(18) 0.0411(18) -0.0167(14) -0.0015(14) -0.0067(14)
C5 0.0384(14) 0.0519(17) 0.0436(17) -0.0052(14) 0.0031(13) -0.0057(13)
C6 0.0333(13) 0.0372(15) 0.0288(15) -0.0033(12) -0.0007(11) -0.0028(11)
C7 0.0321(13) 0.0361(15) 0.0333(15) 0.0002(12) 0.0008(11) -0.0005(11)
C8 0.0313(13) 0.0381(15) 0.0342(15) -0.0030(12) 0.0042(11) -0.0031(11)
C9 0.0293(12) 0.0328(15) 0.0413(17) -0.0020(13) -0.0009(12) 0.0011(11)
C10 0.0401(13) 0.0448(16) 0.0401(15) -0.0017(14) 0.0011(12) -0.0015(13)
C11 0.0360(14) 0.0472(17) 0.061(2) 0.0001(15) 0.0060(14) -0.0099(12)
C12 0.0342(14) 0.0421(16) 0.067(2) -0.0032(15) -0.0062(15) -0.0014(12)
C13 0.0395(14) 0.0381(15) 0.0500(17) -0.0067(14) -0.0096(13) 0.0054(12)
C14 0.0317(13) 0.0373(15) 0.0343(16) -0.0013(13) -0.0020(11) 0.0052(11)
C15 0.0505(15) 0.0482(16) 0.0349(16) -0.0067(13) -0.0027(13) 0.0008(12)
C16 0.0334(13) 0.0437(16) 0.0322(15) 0.0016(13) 0.0036(11) -0.0016(13)
C17 0.0406(15) 0.0490(17) 0.0541(19) 0.0005(14) 0.0041(13) -0.0058(13)
C18 0.0402(16) 0.064(2) 0.068(2) 0.0020(17) 0.0094(15) -0.0177(15)
C19 0.0354(15) 0.084(2) 0.0467(19) 0.0100(17) 0.0107(13) 0.0030(16)
C20 0.0403(15) 0.0639(19) 0.0434(17) 0.0010(16) 0.0086(13) 0.0054(15)
C21 0.0386(14) 0.0467(16) 0.0379(15) 0.0019(14) 0.0000(11) 0.0021(13)
C22 0.0526(16) 0.0511(18) 0.068(2) -0.0175(16) -0.0062(14) 0.0005(14)
C23 0.0540(16) 0.063(2) 0.0470(18) -0.0053(15) 0.0131(14) -0.0037(14)
N1 0.0291(11) 0.0449(13) 0.0334(13) -0.0061(10) 0.0025(9) -0.0004(9)
Si1 0.0396(4) 0.0474(5) 0.0386(5) -0.0065(4) 0.0037(3) -0.0001(4)

_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 N1 1.383(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.417(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.435(3) . ?
C7 C8 1.380(3) . ?
C7 C16 1.477(3) . ?
C8 N1 1.415(2) . ?
C8 Si1 1.869(2) . ?
C9 C10 1.388(3) . ?
C9 C14 1.395(3) . ?
C9 N1 1.439(2) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.496(3) . ?
C15 Si1 1.872(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.389(3) . ?
C16 C17 1.396(3) . ?
C17 C18 1.400(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 Si1 1.852(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 Si1 1.865(2) . ?
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
N1 C1 C2 130.5(2) . . ?
N1 C1 C6 107.41(19) . . ?
C2 C1 C6 122.0(2) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 134.6(2) . . ?
C1 C6 C7 107.0(2) . . ?
C8 C7 C6 108.55(19) . . ?
C8 C7 C16 125.4(2) . . ?
C6 C7 C16 126.1(2) . . ?
C7 C8 N1 107.26(19) . . ?
C7 C8 Si1 134.53(18) . . ?
N1 C8 Si1 116.19(15) . . ?
C10 C9 C14 121.1(2) . . ?
C10 C9 N1 119.0(2) . . ?
C14 C9 N1 119.8(2) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 121.9(2) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C9 117.2(2) . . ?
C13 C14 C15 122.1(2) . . ?
C9 C14 C15 120.7(2) . . ?
C14 C15 Si1 109.57(16) . . ?
C14 C15 H15A 109.8 . . ?
Si1 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
Si1 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C21 C16 C17 117.9(2) . . ?
C21 C16 C7 121.1(2) . . ?
C17 C16 C7 121.0(2) . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.7(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 121.6(2) . . ?
C16 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
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 . . ?
Si1 C23 H23A 109.5 . . ?
Si1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Si1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C8 109.76(17) . . ?
C1 N1 C9 126.56(19) . . ?
C8 N1 C9 122.95(19) . . ?
C22 Si1 C23 111.17(11) . . ?
C22 Si1 C8 112.59(12) . . ?
C23 Si1 C8 111.36(11) . . ?
C22 Si1 C15 110.57(11) . . ?
C23 Si1 C15 112.38(11) . . ?
C8 Si1 C15 98.19(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.055