# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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 
#  to carry out CIF format checking respectively.
#
data_sihph2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H34 N P Si'
_chemical_formula_sum            'C34 H34 N P Si'
_chemical_formula_weight         515.68

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'
P P 0.1023 0.0942 '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 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'

_cell_length_a                   17.002(9)
_cell_length_b                   8.839(5)
_cell_length_c                   20.361(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.6137(19)
_cell_angle_gamma                90.00
_cell_volume                     2825(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4684
_cell_measurement_theta_min      3.0402
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9527
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_process_details   
;
Jacobson R (1988) Private communication
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK(J\(Ba
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           40.0000
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury CCD (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_number            8803
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.1234
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4518
_reflns_number_gt                3520
_reflns_threshold_expression     >2sigma(I)
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details      
;
scan:
Number of images: 600
Slice: -70.0000 - 110.0000
Image width: 0.3000
Exp time: 21.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 0.0000
XTD: 45.0843
2theta: 19.6674
scan:
Number of images: 600
Slice: -70.0000 - 110.0000
Image width: 0.3000
Exp time: 21.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 90.0000
XTD: 45.0843
2theta: 19.6674

;
_diffrn_measurement_device_details 
;
AFC8: Eulerian 3-circle
;
_diffrn_orient_matrix_UB_11      0.0599
_diffrn_orient_matrix_UB_12      0.0094
_diffrn_orient_matrix_UB_13      -0.0196
_diffrn_orient_matrix_UB_21      -0.0234
_diffrn_orient_matrix_UB_22      0.1090
_diffrn_orient_matrix_UB_23      -0.0191
_diffrn_orient_matrix_UB_31      0.0326
_diffrn_orient_matrix_UB_32      0.0140
_diffrn_orient_matrix_UB_33      0.0397
_diffrn_orient_matrix_type       d*Trek


_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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/[(J\(Bs^2^(Fo^2^)+(0.0000P)^2^+(-0.9400P)] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_number_reflns         4518
_refine_ls_number_parameters     340
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0390
_refine_ls_wR_factor_gt          0.0354
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_restrained_S_all      0.790
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 0.62836(4) 0.61507(9) 0.21508(4) 0.02069(19) Uani 1 1 d . . .
H1 H 0.5790(14) 0.659(2) 0.2550(13) 0.025 Uiso 1 1 d . . .
C1 C 0.72422(16) 0.4919(3) 0.26560(15) 0.0183(7) Uani 1 1 d . . .
C2 C 0.73072(16) 0.3557(3) 0.23427(15) 0.0234(7) Uani 1 1 d . . .
H2 H 0.6854 0.3266 0.1915 0.028 Uiso 1 1 calc R . .
C3 C 0.80066(17) 0.2599(3) 0.26273(16) 0.0244(7) Uani 1 1 d . . .
H3 H 0.8027 0.1683 0.2390 0.029 Uiso 1 1 calc R . .
C4 C 0.86641(17) 0.2975(3) 0.32471(16) 0.0291(8) Uani 1 1 d . . .
H4 H 0.9141 0.2321 0.3448 0.035 Uiso 1 1 calc R . .
C5 C 0.86237(16) 0.4331(3) 0.35788(16) 0.0251(7) Uani 1 1 d . . .
H5 H 0.9076 0.4599 0.4011 0.030 Uiso 1 1 calc R . .
C6 C 0.79305(17) 0.5304(3) 0.32879(15) 0.0202(7) Uani 1 1 d . . .
P1 P 0.79569(5) 0.70490(8) 0.37668(4) 0.01887(17) Uani 1 1 d . . .
N1 N 0.71198(13) 0.7926(2) 0.33351(12) 0.0195(6) Uani 1 1 d . . .
C7 C 0.81499(16) 0.6493(3) 0.46830(15) 0.0210(7) Uani 1 1 d . . .
C8 C 0.77398(17) 0.5211(3) 0.47864(16) 0.0253(7) Uani 1 1 d . . .
H6 H 0.7434 0.4579 0.4393 0.030 Uiso 1 1 calc R . .
C9 C 0.77729(17) 0.4845(3) 0.54602(18) 0.0298(8) Uani 1 1 d . . .
H7 H 0.7489 0.3970 0.5529 0.036 Uiso 1 1 calc R . .
C10 C 0.82283(18) 0.5779(4) 0.60370(17) 0.0343(9) Uani 1 1 d . . .
H8 H 0.8251 0.5540 0.6499 0.041 Uiso 1 1 calc R . .
C11 C 0.86419(18) 0.7040(3) 0.59373(17) 0.0311(8) Uani 1 1 d . . .
H9 H 0.8954 0.7665 0.6331 0.037 Uiso 1 1 calc R . .
C12 C 0.86042(16) 0.7404(3) 0.52585(16) 0.0241(7) Uani 1 1 d . . .
H10 H 0.8890 0.8277 0.5191 0.029 Uiso 1 1 calc R . .
C13 C 0.89560(16) 0.7903(3) 0.38153(15) 0.0179(7) Uani 1 1 d . . .
C14 C 0.97675(16) 0.7450(3) 0.42871(15) 0.0223(7) Uani 1 1 d . . .
H11 H 0.9822 0.6746 0.4655 0.027 Uiso 1 1 calc R . .
C15 C 1.04879(17) 0.8024(3) 0.42181(16) 0.0260(8) Uani 1 1 d . . .
H12 H 1.1036 0.7726 0.4545 0.031 Uiso 1 1 calc R . .
C16 C 1.04169(17) 0.9036(3) 0.36731(17) 0.0292(8) Uani 1 1 d . . .
H13 H 1.0913 0.9401 0.3617 0.035 Uiso 1 1 calc R . .
C17 C 0.96247(16) 0.9501(3) 0.32187(15) 0.0243(7) Uani 1 1 d . . .
H14 H 0.9573 1.0212 0.2854 0.029 Uiso 1 1 calc R . .
C18 C 0.89005(16) 0.8940(3) 0.32878(14) 0.0207(7) Uani 1 1 d . . .
H15 H 0.8356 0.9270 0.2968 0.025 Uiso 1 1 calc R . .
C19 C 0.67191(18) 0.9157(3) 0.35777(17) 0.0260(8) Uani 1 1 d . . .
C20 C 0.73683(16) 1.0321(3) 0.40526(16) 0.0295(8) Uani 1 1 d . . .
H16 H 0.7714 1.0709 0.3800 0.044 Uiso 1 1 calc R . .
H17 H 0.7739 0.9831 0.4495 0.044 Uiso 1 1 calc R . .
H18 H 0.7063 1.1159 0.4163 0.044 Uiso 1 1 calc R . .
C21 C 0.61009(17) 1.0001(3) 0.29162(16) 0.0352(9) Uani 1 1 d . . .
H19 H 0.5631 0.9327 0.2644 0.053 Uiso 1 1 calc R . .
H20 H 0.6406 1.0316 0.2617 0.053 Uiso 1 1 calc R . .
H21 H 0.5874 1.0895 0.3068 0.053 Uiso 1 1 calc R . .
C22 C 0.62058(16) 0.8515(3) 0.39900(15) 0.0348(9) Uani 1 1 d . . .
H22 H 0.6594 0.8031 0.4428 0.052 Uiso 1 1 calc R . .
H23 H 0.5797 0.7767 0.3695 0.052 Uiso 1 1 calc R . .
H24 H 0.5899 0.9338 0.4111 0.052 Uiso 1 1 calc R . .
C23 C 0.55630(17) 0.4866(3) 0.14137(16) 0.0215(7) Uani 1 1 d . . .
C24 C 0.54921(18) 0.4936(3) 0.07124(16) 0.0281(8) Uani 1 1 d . . .
H25 H 0.5829 0.5650 0.0587 0.034 Uiso 1 1 calc R . .
C25 C 0.49429(18) 0.3994(3) 0.01850(17) 0.0361(8) Uani 1 1 d . . .
H26 H 0.4904 0.4082 -0.0292 0.043 Uiso 1 1 calc R . .
C26 C 0.44569(19) 0.2935(4) 0.03572(18) 0.0342(8) Uani 1 1 d . . .
H27 H 0.4076 0.2300 -0.0001 0.041 Uiso 1 1 calc R . .
C27 C 0.45283(19) 0.2806(4) 0.1055(2) 0.0390(10) Uani 1 1 d . . .
H28 H 0.4205 0.2063 0.1178 0.047 Uiso 1 1 calc R . .
C28 C 0.50748(16) 0.3764(3) 0.15798(17) 0.0336(8) Uani 1 1 d . . .
H29 H 0.5116 0.3666 0.2056 0.040 Uiso 1 1 calc R . .
C29 C 0.65656(16) 0.7745(3) 0.16708(15) 0.0180(7) Uani 1 1 d . . .
C30 C 0.73856(16) 0.7895(3) 0.16714(15) 0.0211(7) Uani 1 1 d . . .
H30 H 0.7812 0.7184 0.1928 0.025 Uiso 1 1 calc R . .
C31 C 0.75909(18) 0.9057(3) 0.13064(16) 0.0279(8) Uani 1 1 d . . .
H31 H 0.8154 0.9144 0.1321 0.033 Uiso 1 1 calc R . .
C32 C 0.69745(18) 1.0085(3) 0.09222(16) 0.0267(8) Uani 1 1 d . . .
H32 H 0.7112 1.0878 0.0670 0.032 Uiso 1 1 calc R . .
C33 C 0.61559(17) 0.9955(3) 0.09059(16) 0.0303(8) Uani 1 1 d . . .
H33 H 0.5730 1.0664 0.0647 0.036 Uiso 1 1 calc R . .
C34 C 0.59627(18) 0.8778(3) 0.12714(17) 0.0269(7) Uani 1 1 d . . .
H34 H 0.5395 0.8681 0.1245 0.032 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 0.0200(4) 0.0206(5) 0.0183(5) 0.0000(4) 0.0039(4) -0.0007(4)
C1 0.0222(16) 0.0160(16) 0.0158(16) 0.0009(12) 0.0063(13) -0.0037(13)
C2 0.0238(16) 0.0260(17) 0.0169(16) 0.0005(14) 0.0042(13) -0.0002(14)
C3 0.0333(18) 0.0183(17) 0.0227(17) -0.0022(14) 0.0119(15) 0.0005(14)
C4 0.0247(17) 0.0206(18) 0.036(2) 0.0075(15) 0.0049(15) 0.0090(15)
C5 0.0238(16) 0.0192(17) 0.0268(19) -0.0003(14) 0.0037(14) 0.0017(14)
C6 0.0227(16) 0.0168(16) 0.0197(17) 0.0027(13) 0.0066(14) -0.0013(13)
P1 0.0192(4) 0.0185(4) 0.0166(4) 0.0003(4) 0.0043(3) 0.0004(4)
N1 0.0190(13) 0.0179(14) 0.0206(14) -0.0010(11) 0.0064(11) 0.0019(11)
C7 0.0194(16) 0.0238(17) 0.0212(18) 0.0084(14) 0.0095(14) 0.0075(13)
C8 0.0200(16) 0.0286(19) 0.0257(19) 0.0060(15) 0.0070(14) 0.0046(14)
C9 0.0276(19) 0.032(2) 0.037(2) 0.0153(16) 0.0202(17) 0.0038(15)
C10 0.036(2) 0.048(2) 0.0237(19) 0.0150(17) 0.0170(16) 0.0168(17)
C11 0.0317(18) 0.039(2) 0.0220(19) -0.0014(16) 0.0101(15) 0.0086(16)
C12 0.0237(17) 0.0303(18) 0.0197(17) 0.0010(14) 0.0099(14) 0.0059(14)
C13 0.0209(16) 0.0157(16) 0.0155(16) -0.0026(13) 0.0050(13) -0.0022(13)
C14 0.0234(16) 0.0247(17) 0.0174(16) -0.0033(14) 0.0062(13) 0.0041(14)
C15 0.0190(17) 0.0303(19) 0.0271(19) -0.0068(15) 0.0071(15) -0.0017(14)
C16 0.0249(18) 0.0301(19) 0.039(2) -0.0096(16) 0.0192(17) -0.0068(14)
C17 0.0333(18) 0.0187(17) 0.0281(19) -0.0029(14) 0.0200(16) 0.0006(14)
C18 0.0234(17) 0.0147(16) 0.0214(17) 0.0000(13) 0.0057(14) -0.0009(13)
C19 0.0245(17) 0.0287(19) 0.026(2) -0.0018(15) 0.0108(15) 0.0051(15)
C20 0.0268(18) 0.030(2) 0.031(2) -0.0030(16) 0.0102(15) 0.0010(15)
C21 0.038(2) 0.029(2) 0.031(2) -0.0029(16) 0.0045(17) 0.0137(16)
C22 0.0316(18) 0.037(2) 0.039(2) -0.0042(17) 0.0168(17) 0.0027(16)
C23 0.0163(16) 0.0204(17) 0.0281(18) -0.0005(14) 0.0089(14) 0.0038(13)
C24 0.0310(18) 0.0226(18) 0.0243(19) 0.0056(14) 0.0035(15) -0.0015(14)
C25 0.047(2) 0.031(2) 0.0195(18) 0.0008(16) 0.0004(17) 0.0038(17)
C26 0.0233(18) 0.0299(19) 0.039(2) -0.0153(17) 0.0005(16) -0.0035(15)
C27 0.0326(19) 0.035(2) 0.058(3) -0.0226(19) 0.0273(19) -0.0145(16)
C28 0.0290(18) 0.043(2) 0.031(2) -0.0124(17) 0.0146(16) -0.0118(17)
C29 0.0191(16) 0.0207(17) 0.0142(16) -0.0036(13) 0.0062(12) -0.0002(13)
C30 0.0209(16) 0.0207(17) 0.0198(17) 0.0012(14) 0.0056(13) 0.0036(13)
C31 0.0276(17) 0.0320(19) 0.0265(19) 0.0024(15) 0.0132(15) -0.0022(15)
C32 0.0350(18) 0.0218(18) 0.0246(18) 0.0044(14) 0.0130(15) -0.0076(14)
C33 0.0306(18) 0.029(2) 0.026(2) 0.0072(15) 0.0049(16) 0.0060(15)
C34 0.0228(16) 0.0285(19) 0.0266(18) 0.0028(16) 0.0063(14) -0.0014(15)

_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 C29 1.880(3) . ?
Si1 C1 1.900(3) . ?
Si1 C23 1.905(3) . ?
Si1 H1 1.43(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 P1 1.816(3) . ?
P1 N1 1.561(2) . ?
P1 C13 1.827(3) . ?
P1 C7 1.833(3) . ?
N1 C19 1.466(3) . ?
C7 C12 1.386(4) . ?
C7 C8 1.388(3) . ?
C8 C9 1.389(4) . ?
C8 H6 0.9500 . ?
C9 C10 1.400(4) . ?
C9 H7 0.9500 . ?
C10 C11 1.374(4) . ?
C10 H8 0.9500 . ?
C11 C12 1.396(4) . ?
C11 H9 0.9500 . ?
C12 H10 0.9500 . ?
C13 C18 1.387(4) . ?
C13 C14 1.403(3) . ?
C14 C15 1.382(4) . ?
C14 H11 0.9500 . ?
C15 C16 1.394(4) . ?
C15 H12 0.9500 . ?
C16 C17 1.371(4) . ?
C16 H13 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H14 0.9500 . ?
C18 H15 0.9500 . ?
C19 C22 1.533(4) . ?
C19 C21 1.545(4) . ?
C19 C20 1.546(4) . ?
C20 H16 0.9800 . ?
C20 H17 0.9800 . ?
C20 H18 0.9800 . ?
C21 H19 0.9800 . ?
C21 H20 0.9800 . ?
C21 H21 0.9800 . ?
C22 H22 0.9800 . ?
C22 H23 0.9800 . ?
C22 H24 0.9800 . ?
C23 C24 1.387(4) . ?
C23 C28 1.403(4) . ?
C24 C25 1.395(4) . ?
C24 H25 0.9500 . ?
C25 C26 1.380(4) . ?
C25 H26 0.9500 . ?
C26 C27 1.383(5) . ?
C26 H27 0.9500 . ?
C27 C28 1.400(4) . ?
C27 H28 0.9500 . ?
C28 H29 0.9500 . ?
C29 C34 1.380(4) . ?
C29 C30 1.400(3) . ?
C30 C31 1.389(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.380(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.384(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

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
C29 Si1 C1 111.97(12) . . ?
C29 Si1 C23 104.65(13) . . ?
C1 Si1 C23 104.05(12) . . ?
C29 Si1 H1 114.7(9) . . ?
C1 Si1 H1 114.6(9) . . ?
C23 Si1 H1 105.6(9) . . ?
C2 C1 C6 116.4(2) . . ?
C2 C1 Si1 116.9(2) . . ?
C6 C1 Si1 126.5(2) . . ?
C1 C2 C3 122.9(3) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 P1 117.0(2) . . ?
C1 C6 P1 122.4(2) . . ?
N1 P1 C6 106.89(13) . . ?
N1 P1 C13 116.92(13) . . ?
C6 P1 C13 102.16(12) . . ?
N1 P1 C7 118.28(13) . . ?
C6 P1 C7 106.06(14) . . ?
C13 P1 C7 104.89(13) . . ?
C19 N1 P1 128.3(2) . . ?
C12 C7 C8 119.7(3) . . ?
C12 C7 P1 121.9(2) . . ?
C8 C7 P1 118.0(2) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H6 119.7 . . ?
C9 C8 H6 119.7 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H7 120.3 . . ?
C10 C9 H7 120.3 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H8 119.9 . . ?
C9 C10 H8 119.9 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H9 119.9 . . ?
C12 C11 H9 119.9 . . ?
C7 C12 C11 120.1(3) . . ?
C7 C12 H10 120.0 . . ?
C11 C12 H10 120.0 . . ?
C18 C13 C14 118.4(2) . . ?
C18 C13 P1 116.5(2) . . ?
C14 C13 P1 124.6(2) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H11 119.9 . . ?
C13 C14 H11 119.9 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H12 119.7 . . ?
C16 C15 H12 119.7 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H13 120.3 . . ?
C15 C16 H13 120.3 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H14 119.8 . . ?
C18 C17 H14 119.8 . . ?
C17 C18 C13 121.1(3) . . ?
C17 C18 H15 119.4 . . ?
C13 C18 H15 119.4 . . ?
N1 C19 C22 110.2(2) . . ?
N1 C19 C21 108.2(2) . . ?
C22 C19 C21 108.4(2) . . ?
N1 C19 C20 113.1(2) . . ?
C22 C19 C20 108.9(3) . . ?
C21 C19 C20 107.9(2) . . ?
C19 C20 H16 109.5 . . ?
C19 C20 H17 109.5 . . ?
H16 C20 H17 109.5 . . ?
C19 C20 H18 109.5 . . ?
H16 C20 H18 109.5 . . ?
H17 C20 H18 109.5 . . ?
C19 C21 H19 109.5 . . ?
C19 C21 H20 109.5 . . ?
H19 C21 H20 109.5 . . ?
C19 C21 H21 109.5 . . ?
H19 C21 H21 109.5 . . ?
H20 C21 H21 109.5 . . ?
C19 C22 H22 109.5 . . ?
C19 C22 H23 109.5 . . ?
H22 C22 H23 109.5 . . ?
C19 C22 H24 109.5 . . ?
H22 C22 H24 109.5 . . ?
H23 C22 H24 109.5 . . ?
C24 C23 C28 117.0(3) . . ?
C24 C23 Si1 124.0(2) . . ?
C28 C23 Si1 119.0(2) . . ?
C23 C24 C25 122.2(3) . . ?
C23 C24 H25 118.9 . . ?
C25 C24 H25 118.9 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H26 120.1 . . ?
C24 C25 H26 120.1 . . ?
C25 C26 C27 119.5(3) . . ?
C25 C26 H27 120.3 . . ?
C27 C26 H27 120.3 . . ?
C26 C27 C28 120.3(3) . . ?
C26 C27 H28 119.8 . . ?
C28 C27 H28 119.8 . . ?
C27 C28 C23 121.1(3) . . ?
C27 C28 H29 119.5 . . ?
C23 C28 H29 119.5 . . ?
C34 C29 C30 116.9(3) . . ?
C34 C29 Si1 121.5(2) . . ?
C30 C29 Si1 121.6(2) . . ?
C31 C30 C29 121.6(3) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C32 C31 C30 119.9(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 119.7(3) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C32 C33 C34 119.5(3) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C29 C34 C33 122.4(3) . . ?
C29 C34 H34 118.8 . . ?
C33 C34 H34 118.8 . . ?

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
C29 Si1 C1 C2 -101.2(2) . . . . ?
C23 Si1 C1 C2 11.2(3) . . . . ?
C29 Si1 C1 C6 73.1(3) . . . . ?
C23 Si1 C1 C6 -174.5(3) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
Si1 C1 C2 C3 175.1(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C5 C6 P1 -179.4(2) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
Si1 C1 C6 C5 -175.6(2) . . . . ?
C2 C1 C6 P1 179.6(2) . . . . ?
Si1 C1 C6 P1 5.3(4) . . . . ?
C5 C6 P1 N1 179.9(2) . . . . ?
C1 C6 P1 N1 -1.0(3) . . . . ?
C5 C6 P1 C13 56.5(2) . . . . ?
C1 C6 P1 C13 -124.3(2) . . . . ?
C5 C6 P1 C7 -53.1(2) . . . . ?
C1 C6 P1 C7 126.1(2) . . . . ?
C6 P1 N1 C19 161.5(2) . . . . ?
C13 P1 N1 C19 -84.9(3) . . . . ?
C7 P1 N1 C19 42.0(3) . . . . ?
N1 P1 C7 C12 -92.2(3) . . . . ?
C6 P1 C7 C12 148.0(2) . . . . ?
C13 P1 C7 C12 40.3(3) . . . . ?
N1 P1 C7 C8 80.1(2) . . . . ?
C6 P1 C7 C8 -39.8(2) . . . . ?
C13 P1 C7 C8 -147.5(2) . . . . ?
C12 C7 C8 C9 0.8(4) . . . . ?
P1 C7 C8 C9 -171.6(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C8 C7 C12 C11 -0.6(4) . . . . ?
P1 C7 C12 C11 171.5(2) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
N1 P1 C13 C18 -21.6(3) . . . . ?
C6 P1 C13 C18 94.7(2) . . . . ?
C7 P1 C13 C18 -154.8(2) . . . . ?
N1 P1 C13 C14 166.6(2) . . . . ?
C6 P1 C13 C14 -77.1(3) . . . . ?
C7 P1 C13 C14 33.4(3) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
P1 C13 C14 C15 171.1(2) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C17 2.2(5) . . . . ?
C15 C16 C17 C18 -1.7(4) . . . . ?
C16 C17 C18 C13 0.1(4) . . . . ?
C14 C13 C18 C17 1.0(4) . . . . ?
P1 C13 C18 C17 -171.3(2) . . . . ?
P1 N1 C19 C22 -80.7(3) . . . . ?
P1 N1 C19 C21 160.8(2) . . . . ?
P1 N1 C19 C20 41.4(4) . . . . ?
C29 Si1 C23 C24 15.9(3) . . . . ?
C1 Si1 C23 C24 -101.8(3) . . . . ?
C29 Si1 C23 C28 -164.8(2) . . . . ?
C1 Si1 C23 C28 77.6(2) . . . . ?
C28 C23 C24 C25 2.0(5) . . . . ?
Si1 C23 C24 C25 -178.6(2) . . . . ?
C23 C24 C25 C26 -0.9(5) . . . . ?
C24 C25 C26 C27 -0.8(5) . . . . ?
C25 C26 C27 C28 1.4(5) . . . . ?
C26 C27 C28 C23 -0.3(5) . . . . ?
C24 C23 C28 C27 -1.4(4) . . . . ?
Si1 C23 C28 C27 179.2(2) . . . . ?
C1 Si1 C29 C34 -179.9(2) . . . . ?
C23 Si1 C29 C34 68.0(3) . . . . ?
C1 Si1 C29 C30 3.5(3) . . . . ?
C23 Si1 C29 C30 -108.6(2) . . . . ?
C34 C29 C30 C31 2.0(4) . . . . ?
Si1 C29 C30 C31 178.8(2) . . . . ?
C29 C30 C31 C32 -1.0(5) . . . . ?
C30 C31 C32 C33 0.3(5) . . . . ?
C31 C32 C33 C34 -0.7(5) . . . . ?
C30 C29 C34 C33 -2.5(4) . . . . ?
Si1 C29 C34 C33 -179.2(2) . . . . ?
C32 C33 C34 C29 1.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045


_database_code_depnum_ccdc_archive 'CCDC 867750'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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 
#  to carry out CIF format checking respectively.
#
data_me3si2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H32 N P Si'
_chemical_formula_sum            'C25 H32 N P Si'
_chemical_formula_weight         405.58

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'
P P 0.1023 0.0942 '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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.745(2)
_cell_length_b                   16.531(4)
_cell_length_c                   16.017(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.8059(11)
_cell_angle_gamma                90.00
_cell_volume                     2294.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7415
_cell_measurement_theta_min      3.0863
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8984
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_process_details   
;
Jacobson, R (1998), Private communication
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK(J\(Ba
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           40.0000
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury CCD (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measurement_method       dtintegrate.ref
_diffrn_reflns_number            17061
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5207
_reflns_number_gt                4740
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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/[(J\(Bs^2^(Fo^2^)+(0.0472P)^2^+0.7643P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5207
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
Si1 Si 0.71353(4) -0.006218(19) 0.39963(2) 0.01675(9) Uani 1 1 d . . .
C1 C 0.87969(13) -0.02135(7) 0.33570(7) 0.0158(2) Uani 1 1 d . . .
C2 C 0.97414(14) -0.08802(7) 0.36129(8) 0.0199(2) Uani 1 1 d . . .
H1 H 0.9506 -0.1194 0.4076 0.024 Uiso 1 1 calc R . .
C3 C 1.10025(14) -0.11042(7) 0.32237(8) 0.0218(3) Uani 1 1 d . . .
H2 H 1.1595 -0.1567 0.3412 0.026 Uiso 1 1 calc R . .
C4 C 1.13868(13) -0.06487(7) 0.25617(8) 0.0211(2) Uani 1 1 d . . .
H3 H 1.2252 -0.0792 0.2292 0.025 Uiso 1 1 calc R . .
C5 C 1.04956(13) 0.00222(7) 0.22924(8) 0.0180(2) Uani 1 1 d . . .
H4 H 1.0773 0.0341 0.1843 0.022 Uiso 1 1 calc R . .
C6 C 0.91999(12) 0.02398(6) 0.26669(7) 0.0147(2) Uani 1 1 d . . .
P1 P 0.80918(3) 0.111283(16) 0.222275(18) 0.01344(8) Uani 1 1 d . . .
C7 C 0.88343(13) 0.19659(7) 0.28848(7) 0.0166(2) Uani 1 1 d . . .
C8 C 1.03253(14) 0.19553(8) 0.33257(8) 0.0236(3) Uani 1 1 d . . .
H5 H 1.0945 0.1484 0.3314 0.028 Uiso 1 1 calc R . .
C9 C 1.09095(16) 0.26291(8) 0.37812(9) 0.0306(3) Uani 1 1 d . . .
H6 H 1.1923 0.2616 0.4082 0.037 Uiso 1 1 calc R . .
C10 C 1.00195(18) 0.33198(8) 0.37985(8) 0.0297(3) Uani 1 1 d . . .
H7 H 1.0428 0.3781 0.4105 0.036 Uiso 1 1 calc R . .
C11 C 0.85342(17) 0.33392(8) 0.33695(9) 0.0283(3) Uani 1 1 d . . .
H8 H 0.7922 0.3812 0.3383 0.034 Uiso 1 1 calc R . .
C12 C 0.79415(15) 0.26634(8) 0.29190(8) 0.0230(3) Uani 1 1 d . . .
H9 H 0.6918 0.2676 0.2631 0.028 Uiso 1 1 calc R . .
C13 C 0.88533(12) 0.13319(7) 0.12363(7) 0.0160(2) Uani 1 1 d . . .
C14 C 0.97572(14) 0.20059(7) 0.11142(8) 0.0216(2) Uani 1 1 d . . .
H10 H 1.0026 0.2378 0.1562 0.026 Uiso 1 1 calc R . .
C15 C 1.02681(16) 0.21366(8) 0.03388(9) 0.0286(3) Uani 1 1 d . . .
H11 H 1.0880 0.2598 0.0260 0.034 Uiso 1 1 calc R . .
C16 C 0.98895(16) 0.15975(9) -0.03181(9) 0.0289(3) Uani 1 1 d . . .
H12 H 1.0246 0.1687 -0.0845 0.035 Uiso 1 1 calc R . .
C17 C 0.89860(15) 0.09239(8) -0.02047(8) 0.0257(3) Uani 1 1 d . . .
H13 H 0.8723 0.0553 -0.0654 0.031 Uiso 1 1 calc R . .
C18 C 0.84697(14) 0.07945(7) 0.05650(8) 0.0206(2) Uani 1 1 d . . .
H14 H 0.7848 0.0335 0.0638 0.025 Uiso 1 1 calc R . .
N1 N 0.63588(11) 0.08892(6) 0.21377(6) 0.0171(2) Uani 1 1 d . . .
C19 C 0.49504(13) 0.12476(7) 0.16871(8) 0.0177(2) Uani 1 1 d . . .
C20 C 0.52235(14) 0.19252(7) 0.10674(8) 0.0220(2) Uani 1 1 d . . .
H15 H 0.5809 0.2364 0.1373 0.033 Uiso 1 1 calc R . .
H16 H 0.4228 0.2133 0.0798 0.033 Uiso 1 1 calc R . .
H17 H 0.5807 0.1711 0.0636 0.033 Uiso 1 1 calc R . .
C21 C 0.40602(14) 0.05701(8) 0.11743(9) 0.0256(3) Uani 1 1 d . . .
H18 H 0.4678 0.0365 0.0753 0.038 Uiso 1 1 calc R . .
H19 H 0.3081 0.0784 0.0890 0.038 Uiso 1 1 calc R . .
H20 H 0.3855 0.0129 0.1553 0.038 Uiso 1 1 calc R . .
C22 C 0.39541(14) 0.15704(8) 0.23321(8) 0.0251(3) Uani 1 1 d . . .
H21 H 0.3771 0.1137 0.2724 0.038 Uiso 1 1 calc R . .
H22 H 0.2964 0.1761 0.2038 0.038 Uiso 1 1 calc R . .
H23 H 0.4491 0.2019 0.2647 0.038 Uiso 1 1 calc R . .
C23 C 0.76367(16) -0.06332(8) 0.50114(8) 0.0268(3) Uani 1 1 d . . .
H24 H 0.6868 -0.0517 0.5387 0.040 Uiso 1 1 calc R . .
H25 H 0.8660 -0.0466 0.5283 0.040 Uiso 1 1 calc R . .
H26 H 0.7644 -0.1215 0.4894 0.040 Uiso 1 1 calc R . .
C24 C 0.53410(14) -0.05306(8) 0.34447(8) 0.0233(3) Uani 1 1 d . . .
H27 H 0.4493 -0.0444 0.3777 0.035 Uiso 1 1 calc R . .
H28 H 0.5504 -0.1112 0.3379 0.035 Uiso 1 1 calc R . .
H29 H 0.5081 -0.0282 0.2888 0.035 Uiso 1 1 calc R . .
C25 C 0.68555(15) 0.10110(8) 0.43107(8) 0.0237(3) Uani 1 1 d . . .
H30 H 0.6425 0.1325 0.3815 0.036 Uiso 1 1 calc R . .
H31 H 0.7851 0.1242 0.4550 0.036 Uiso 1 1 calc R . .
H32 H 0.6143 0.1029 0.4733 0.036 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 0.01809(16) 0.01673(16) 0.01624(17) 0.00020(11) 0.00526(12) 0.00002(11)
C1 0.0159(5) 0.0144(5) 0.0170(5) -0.0018(4) 0.0015(4) -0.0017(4)
C2 0.0210(5) 0.0165(5) 0.0225(6) 0.0027(4) 0.0041(5) -0.0002(4)
C3 0.0199(5) 0.0166(5) 0.0285(7) 0.0018(5) 0.0025(5) 0.0044(4)
C4 0.0152(5) 0.0218(6) 0.0267(6) -0.0011(5) 0.0048(4) 0.0023(4)
C5 0.0161(5) 0.0198(5) 0.0184(6) 0.0016(4) 0.0035(4) -0.0004(4)
C6 0.0142(5) 0.0130(5) 0.0166(5) -0.0012(4) 0.0007(4) -0.0001(4)
P1 0.01371(14) 0.01249(14) 0.01440(15) -0.00004(10) 0.00295(10) -0.00024(9)
C7 0.0206(5) 0.0149(5) 0.0146(5) -0.0006(4) 0.0037(4) -0.0028(4)
C8 0.0248(6) 0.0207(6) 0.0240(6) -0.0003(5) -0.0008(5) -0.0011(5)
C9 0.0329(7) 0.0278(7) 0.0278(7) -0.0018(5) -0.0072(5) -0.0081(5)
C10 0.0470(8) 0.0197(6) 0.0210(6) -0.0027(5) 0.0001(6) -0.0102(5)
C11 0.0424(8) 0.0174(6) 0.0256(7) -0.0028(5) 0.0063(6) 0.0016(5)
C12 0.0253(6) 0.0196(6) 0.0239(6) -0.0026(5) 0.0030(5) 0.0012(5)
C13 0.0148(5) 0.0169(5) 0.0167(5) 0.0021(4) 0.0033(4) 0.0022(4)
C14 0.0218(6) 0.0196(6) 0.0238(6) 0.0042(5) 0.0042(5) -0.0014(4)
C15 0.0275(6) 0.0294(7) 0.0302(7) 0.0119(6) 0.0090(5) -0.0022(5)
C16 0.0284(6) 0.0393(8) 0.0209(6) 0.0106(6) 0.0098(5) 0.0071(6)
C17 0.0272(6) 0.0322(7) 0.0181(6) -0.0008(5) 0.0044(5) 0.0071(5)
C18 0.0218(5) 0.0208(6) 0.0198(6) -0.0009(5) 0.0049(4) 0.0010(4)
N1 0.0139(4) 0.0184(5) 0.0190(5) 0.0032(4) 0.0025(4) 0.0003(3)
C19 0.0146(5) 0.0179(5) 0.0203(6) 0.0007(4) 0.0020(4) 0.0017(4)
C20 0.0224(6) 0.0204(6) 0.0229(6) 0.0037(5) 0.0012(5) 0.0028(4)
C21 0.0226(6) 0.0239(6) 0.0283(7) -0.0006(5) -0.0033(5) -0.0029(5)
C22 0.0194(6) 0.0297(6) 0.0269(7) 0.0010(5) 0.0063(5) 0.0061(5)
C23 0.0306(6) 0.0295(7) 0.0212(6) 0.0047(5) 0.0069(5) 0.0018(5)
C24 0.0200(5) 0.0252(6) 0.0254(6) 0.0001(5) 0.0060(5) -0.0040(5)
C25 0.0295(6) 0.0220(6) 0.0211(6) -0.0032(5) 0.0091(5) 0.0008(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
Si1 C24 1.8617(13) . ?
Si1 C25 1.8693(13) . ?
Si1 C23 1.8796(14) . ?
Si1 C1 1.9043(12) . ?
C1 C2 1.4046(16) . ?
C1 C6 1.4190(16) . ?
C2 C3 1.3888(17) . ?
C2 H1 0.9500 . ?
C3 C4 1.3787(18) . ?
C3 H2 0.9500 . ?
C4 C5 1.3900(16) . ?
C4 H3 0.9500 . ?
C5 C6 1.3991(16) . ?
C5 H4 0.9500 . ?
C6 P1 1.8277(12) . ?
P1 N1 1.5479(10) . ?
P1 C7 1.8297(12) . ?
P1 C13 1.8322(12) . ?
C7 C8 1.3960(17) . ?
C7 C12 1.3977(17) . ?
C8 C9 1.3902(18) . ?
C8 H5 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H6 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H7 0.9500 . ?
C11 C12 1.3913(18) . ?
C11 H8 0.9500 . ?
C12 H9 0.9500 . ?
C13 C14 1.3952(16) . ?
C13 C18 1.3999(17) . ?
C14 C15 1.3927(19) . ?
C14 H10 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H11 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H12 0.9500 . ?
C17 C18 1.3859(18) . ?
C17 H13 0.9500 . ?
C18 H14 0.9500 . ?
N1 C19 1.4654(14) . ?
C19 C22 1.5349(17) . ?
C19 C21 1.5366(16) . ?
C19 C20 1.5366(17) . ?
C20 H15 0.9800 . ?
C20 H16 0.9800 . ?
C20 H17 0.9800 . ?
C21 H18 0.9800 . ?
C21 H19 0.9800 . ?
C21 H20 0.9800 . ?
C22 H21 0.9800 . ?
C22 H22 0.9800 . ?
C22 H23 0.9800 . ?
C23 H24 0.9800 . ?
C23 H25 0.9800 . ?
C23 H26 0.9800 . ?
C24 H27 0.9800 . ?
C24 H28 0.9800 . ?
C24 H29 0.9800 . ?
C25 H30 0.9800 . ?
C25 H31 0.9800 . ?
C25 H32 0.9800 . ?

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
C24 Si1 C25 112.94(6) . . ?
C24 Si1 C23 106.51(6) . . ?
C25 Si1 C23 105.50(6) . . ?
C24 Si1 C1 110.22(6) . . ?
C25 Si1 C1 114.01(5) . . ?
C23 Si1 C1 107.08(6) . . ?
C2 C1 C6 116.31(10) . . ?
C2 C1 Si1 114.05(9) . . ?
C6 C1 Si1 129.64(8) . . ?
C3 C2 C1 123.34(11) . . ?
C3 C2 H1 118.3 . . ?
C1 C2 H1 118.3 . . ?
C4 C3 C2 119.41(11) . . ?
C4 C3 H2 120.3 . . ?
C2 C3 H2 120.3 . . ?
C3 C4 C5 119.30(11) . . ?
C3 C4 H3 120.4 . . ?
C5 C4 H3 120.4 . . ?
C4 C5 C6 121.65(11) . . ?
C4 C5 H4 119.2 . . ?
C6 C5 H4 119.2 . . ?
C5 C6 C1 119.97(10) . . ?
C5 C6 P1 116.97(9) . . ?
C1 C6 P1 123.06(8) . . ?
N1 P1 C6 107.86(5) . . ?
N1 P1 C7 120.08(5) . . ?
C6 P1 C7 104.79(5) . . ?
N1 P1 C13 115.94(5) . . ?
C6 P1 C13 104.84(5) . . ?
C7 P1 C13 101.86(5) . . ?
C8 C7 C12 118.61(11) . . ?
C8 C7 P1 121.14(9) . . ?
C12 C7 P1 120.15(9) . . ?
C9 C8 C7 120.45(12) . . ?
C9 C8 H5 119.8 . . ?
C7 C8 H5 119.8 . . ?
C10 C9 C8 120.25(12) . . ?
C10 C9 H6 119.9 . . ?
C8 C9 H6 119.9 . . ?
C9 C10 C11 120.08(12) . . ?
C9 C10 H7 120.0 . . ?
C11 C10 H7 120.0 . . ?
C10 C11 C12 119.80(12) . . ?
C10 C11 H8 120.1 . . ?
C12 C11 H8 120.1 . . ?
C11 C12 C7 120.79(12) . . ?
C11 C12 H9 119.6 . . ?
C7 C12 H9 119.6 . . ?
C14 C13 C18 118.71(11) . . ?
C14 C13 P1 123.91(9) . . ?
C18 C13 P1 117.37(9) . . ?
C15 C14 C13 120.35(12) . . ?
C15 C14 H10 119.8 . . ?
C13 C14 H10 119.8 . . ?
C16 C15 C14 120.36(12) . . ?
C16 C15 H11 119.8 . . ?
C14 C15 H11 119.8 . . ?
C15 C16 C17 119.83(12) . . ?
C15 C16 H12 120.1 . . ?
C17 C16 H12 120.1 . . ?
C18 C17 C16 119.93(13) . . ?
C18 C17 H13 120.0 . . ?
C16 C17 H13 120.0 . . ?
C17 C18 C13 120.82(12) . . ?
C17 C18 H14 119.6 . . ?
C13 C18 H14 119.6 . . ?
C19 N1 P1 133.96(8) . . ?
N1 C19 C22 108.96(10) . . ?
N1 C19 C21 107.43(9) . . ?
C22 C19 C21 108.69(10) . . ?
N1 C19 C20 114.77(9) . . ?
C22 C19 C20 109.49(10) . . ?
C21 C19 C20 107.33(10) . . ?
C19 C20 H15 109.5 . . ?
C19 C20 H16 109.5 . . ?
H15 C20 H16 109.5 . . ?
C19 C20 H17 109.5 . . ?
H15 C20 H17 109.5 . . ?
H16 C20 H17 109.5 . . ?
C19 C21 H18 109.5 . . ?
C19 C21 H19 109.5 . . ?
H18 C21 H19 109.5 . . ?
C19 C21 H20 109.5 . . ?
H18 C21 H20 109.5 . . ?
H19 C21 H20 109.5 . . ?
C19 C22 H21 109.5 . . ?
C19 C22 H22 109.5 . . ?
H21 C22 H22 109.5 . . ?
C19 C22 H23 109.5 . . ?
H21 C22 H23 109.5 . . ?
H22 C22 H23 109.5 . . ?
Si1 C23 H24 109.5 . . ?
Si1 C23 H25 109.5 . . ?
H24 C23 H25 109.5 . . ?
Si1 C23 H26 109.5 . . ?
H24 C23 H26 109.5 . . ?
H25 C23 H26 109.5 . . ?
Si1 C24 H27 109.5 . . ?
Si1 C24 H28 109.5 . . ?
H27 C24 H28 109.5 . . ?
Si1 C24 H29 109.5 . . ?
H27 C24 H29 109.5 . . ?
H28 C24 H29 109.5 . . ?
Si1 C25 H30 109.5 . . ?
Si1 C25 H31 109.5 . . ?
H30 C25 H31 109.5 . . ?
Si1 C25 H32 109.5 . . ?
H30 C25 H32 109.5 . . ?
H31 C25 H32 109.5 . . ?

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
C24 Si1 C1 C2 -96.41(9) . . . . ?
C25 Si1 C1 C2 135.36(9) . . . . ?
C23 Si1 C1 C2 19.06(10) . . . . ?
C24 Si1 C1 C6 83.00(11) . . . . ?
C25 Si1 C1 C6 -45.24(12) . . . . ?
C23 Si1 C1 C6 -161.53(10) . . . . ?
C6 C1 C2 C3 -0.40(17) . . . . ?
Si1 C1 C2 C3 179.08(10) . . . . ?
C1 C2 C3 C4 1.32(19) . . . . ?
C2 C3 C4 C5 -0.54(18) . . . . ?
C3 C4 C5 C6 -1.13(18) . . . . ?
C4 C5 C6 C1 2.06(17) . . . . ?
C4 C5 C6 P1 -177.69(9) . . . . ?
C2 C1 C6 C5 -1.26(16) . . . . ?
Si1 C1 C6 C5 179.35(9) . . . . ?
C2 C1 C6 P1 178.48(8) . . . . ?
Si1 C1 C6 P1 -0.91(15) . . . . ?
C5 C6 P1 N1 135.21(9) . . . . ?
C1 C6 P1 N1 -44.53(11) . . . . ?
C5 C6 P1 C7 -95.76(10) . . . . ?
C1 C6 P1 C7 84.50(10) . . . . ?
C5 C6 P1 C13 11.10(10) . . . . ?
C1 C6 P1 C13 -168.65(9) . . . . ?
N1 P1 C7 C8 146.61(10) . . . . ?
C6 P1 C7 C8 25.31(11) . . . . ?
C13 P1 C7 C8 -83.73(11) . . . . ?
N1 P1 C7 C12 -37.10(12) . . . . ?
C6 P1 C7 C12 -158.40(10) . . . . ?
C13 P1 C7 C12 92.57(10) . . . . ?
C12 C7 C8 C9 -0.64(19) . . . . ?
P1 C7 C8 C9 175.71(10) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 C7 -0.8(2) . . . . ?
C8 C7 C12 C11 1.20(19) . . . . ?
P1 C7 C12 C11 -175.19(10) . . . . ?
N1 P1 C13 C14 132.16(10) . . . . ?
C6 P1 C13 C14 -109.04(10) . . . . ?
C7 P1 C13 C14 -0.04(11) . . . . ?
N1 P1 C13 C18 -46.48(11) . . . . ?
C6 P1 C13 C18 72.31(10) . . . . ?
C7 P1 C13 C18 -178.69(9) . . . . ?
C18 C13 C14 C15 -0.20(18) . . . . ?
P1 C13 C14 C15 -178.83(10) . . . . ?
C13 C14 C15 C16 -0.24(19) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 -0.06(19) . . . . ?
C16 C17 C18 C13 -0.39(19) . . . . ?
C14 C13 C18 C17 0.52(17) . . . . ?
P1 C13 C18 C17 179.24(9) . . . . ?
C6 P1 N1 C19 -165.65(11) . . . . ?
C7 P1 N1 C19 74.57(13) . . . . ?
C13 P1 N1 C19 -48.52(13) . . . . ?
P1 N1 C19 C22 -113.43(12) . . . . ?
P1 N1 C19 C21 128.99(11) . . . . ?
P1 N1 C19 C20 9.73(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.047


_database_code_depnum_ccdc_archive 'CCDC 867751'