3-(Tri­methyl­silyl­ethynyl)­carbazole

Khan, M.S.; Male, L.; Raithby, P.R.; Teat, S.J.; Bond, A.D.

doi:10.1107/S1600536803017963

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3-(Trimethylsilylethynyl)carbazole

M. S. Khan, L. Male, P. R. Raithby, S. J. Teat and A. D. Bond

The title compound, [Si(CH₃)₃(C₁₄H₈N)] is a TMS-protected mono-alkyne. It is used as a model species for platinum σ-acetylide compounds of which it is a precursor. Such compounds are of interest due to the extended π-conjugation through the hetero-aromatic linker unit in the backbone.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017963/ww6110sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017963/ww6110Isup2.hkl Contains datablock I

CCDC reference: 222888

checkCIF report

Key indicators

Single-crystal synchrotron study
T = 150 K
Mean (C-C) = 0.005 Å
R factor = 0.081
wR factor = 0.187
Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.98 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.55 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       Si21
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5     -   C6       =       1.46 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C105   -   C106     =       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C205   -   C206     =       1.45 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N101   -   H101   ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N201   -   H201   ...          ?
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            SI1 -C4  -C5  -C6      0.00 26.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            C4  -C5  -C6  -C11   152.00 21.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            C4  -C5  -C6  -C7    -27.00 21.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            SI11-C104-C105-C106   65.00 16.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            C104-C105-C106-C111  140.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         34
            C104-C105-C106-C107  -39.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         63
            SI21-C204-C205-C206   89.00 22.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         64
            C204-C205-C206-C211  141.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         65
            C204-C205-C206-C207  -37.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         94
            C5  -C4  -SI1 -C1     -2.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         95
            C5  -C4  -SI1 -C3    117.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         96
            C5  -C4  -SI1 -C2   -123.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         97
            C105-C104-SI11-C102    7.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         98
            C105-C104-SI11-C101  128.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         99
            C105-C104-SI11-C103 -110.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        100
            C205-C204-SI21-C203  105.00 21.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        101
            C205-C204-SI21-C202  -16.00 21.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        102
            C205-C204-SI21-C201 -135.00 21.00   1.555   1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C17 H17 N Si

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  32 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  19 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

In this paper, we report the structural characterization of the title compound, (I), which is a TMS-protected mono-alkyne and a precursor of the mononuclear platinum(II) di-yne species, trans-[Pt(PⁿBu₃)₂(—C≡ CR)₂] (R = carbazol-3-yl). Such platinum-containing species form the building blocks for rigid-rod orgnaometallic poly-ynes of general formula trans-[Pt(PⁿBu₃)₂—C≡C—R—C≡C—]_∞ (R = aromatic or heteroaromatic linker unit). Platinum poly-ynes are of immense current interest due to π-electron conjugation along the backbone, novel donor-acceptor interactions between the metal centres and the conjugated ligands and the unique photophysical properties arising from the large spin-orbit coupling (Wittmann et al., 1994; Beljonne et al., 1996; Younus et al., 1998; Chawdhury et al., 1998, 1999; Wilson et al., 2000, 2001; Khan, Al-Mandhary, Al-Suti, Feeder et al., 2002; Khan, Al-Mandhary, Al-Suti, Hisahm et al., 2002; Khan, Al-Mandhary, Al-Suti, Ahrens et al., 2003; Khan, Al-Mandhary, Al-Suti, Corcoran et al., 2003; Khan, Al-Suti et al., 2003). Precursors to these species, such as the title compound, are studied as models of the molecular and electronic properties and structurep-property relationships in the metal poly-ynes.

Experimental top

3-Trimethylsilylethynylcarbazole was synthesized by the following procedure. To a stirred solution of 3-bromocarbazole (2.0 g, 6.13 mmol) in ⁱPr₂NH/THF (70 ml, 1:1 v/v) under nitrogen was added a catalyst mixture of CuI (15 mg), Pd(OAc)₂ (15 mg) and PPh₃ (50 mg). The solution was stirred for 20 min. at 323 K and then trimethylsilylethyne (1.5 g, 15.3 mmol) was added and the mixture stirred for another 20 min. The reaction temperature was then raised to 348 K and left with stirring for 20 h. The completion of the reaction was determined by silica TLC and IR spectroscopy. The solution was allowed to cool down to room temperature. The crude product was filtered to eliminate the ammonium salt and the solvent was removed under vacuum. The residue was subjected to silica column chromatography using hexane/CH₂Cl₂ (1:1) as eluant to afford the target compound as a colorless solid in 77% yield.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of 3-trimethylsilylethynylcarbazole, showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(I) top

Crystal data top

[Si(CH₃)₃(C₁₄H₈N)]	F(000) = 1680
M_r = 263.41	D_x = 1.196 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.688 Å
Hall symbol: -P 2ybc	Cell parameters from 13603 reflections
a = 33.402 (3) Å	θ = 2.3–29.1°
b = 5.8135 (4) Å	µ = 0.15 mm⁻¹
c = 22.8511 (17) Å	T = 150 K
β = 98.394 (2)°	Plate, white
V = 4389.7 (6) Å³	0.2 × 0.2 × 0.04 mm
Z = 12

Data collection top

Bruker AXS SMART 1K CCD diffractometer	5999 reflections with I > 2σ(I)
ω rotation with narrow frames scans	R_int = 0.047
Absorption correction: multi-scan (SADABS; Siemens, 1996)	θ_max = 24.5°, θ_min = 3.4°
T_min = 0.971, T_max = 0.994	h = −39→40
21435 measured reflections	k = −7→6
7939 independent reflections	l = −20→27

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.081	w = 1/[σ²(F_o²) + (0.0602P)² + 9.4726P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.187	(Δ/σ)_max = 0.001
S = 1.14	Δρ_max = 0.37 e Å⁻³
7939 reflections	Δρ_min = −0.42 e Å⁻³
514 parameters

Crystal data top

[Si(CH₃)₃(C₁₄H₈N)]	V = 4389.7 (6) Å³
M_r = 263.41	Z = 12
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.688 Å
a = 33.402 (3) Å	µ = 0.15 mm⁻¹
b = 5.8135 (4) Å	T = 150 K
c = 22.8511 (17) Å	0.2 × 0.2 × 0.04 mm
β = 98.394 (2)°

Data collection top

Bruker AXS SMART 1K CCD diffractometer	7939 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	5999 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.994	R_int = 0.047
21435 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 1.14	Δρ_max = 0.37 e Å⁻³
7939 reflections	Δρ_min = −0.42 e Å⁻³
514 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.94927 (13)	−0.0968 (8)	0.6145 (2)	0.0374 (11)
H1A	0.924	−0.0131	0.6019	0.056*
H1B	0.9469	−0.1848	0.6504	0.056*
H1C	0.9545	−0.2022	0.5831	0.056*
C2	0.99822 (15)	0.2811 (8)	0.5628 (2)	0.0418 (12)
H2A	0.9737	0.3709	0.5502	0.063*
H2B	1.003	0.1761	0.531	0.063*
H2C	1.0213	0.3853	0.5719	0.063*
C3	0.98149 (13)	0.3125 (8)	0.6897 (2)	0.0340 (10)
H3A	0.9567	0.3998	0.6763	0.051*
H3B	1.0043	0.419	0.699	0.051*
H3C	0.978	0.2243	0.7252	0.051*
C4	1.03774 (11)	−0.0556 (7)	0.65314 (18)	0.0272 (9)
C5	1.06694 (11)	−0.1755 (7)	0.66811 (18)	0.0239 (8)
C6	1.10161 (11)	−0.3241 (7)	0.68605 (17)	0.0227 (8)
C7	1.09550 (12)	−0.5361 (7)	0.71416 (17)	0.0240 (8)
H7	1.0691	−0.5754	0.7216	0.029*
C8	1.12717 (12)	−0.6873 (7)	0.73096 (18)	0.0258 (9)
H8	1.1229	−0.8288	0.7499	0.031*
C9	1.16529 (11)	−0.6252 (6)	0.71922 (17)	0.0212 (8)
C10	1.17245 (11)	−0.4130 (6)	0.69193 (16)	0.0187 (8)
C11	1.13991 (11)	−0.2628 (6)	0.67515 (17)	0.0200 (8)
H11	1.1441	−0.1205	0.6565	0.024*
C12	1.23184 (12)	−0.6156 (6)	0.71115 (17)	0.0245 (8)
C13	1.27288 (12)	−0.6655 (7)	0.71316 (17)	0.0262 (9)
H13	1.2841	−0.8048	0.7301	0.031*
C14	1.29661 (12)	−0.5056 (8)	0.68979 (19)	0.0320 (10)
H14	1.3245	−0.537	0.69	0.038*
C15	1.28047 (12)	−0.2972 (7)	0.66559 (19)	0.0298 (9)
H15	1.2977	−0.1894	0.6504	0.036*
C16	1.23991 (11)	−0.2479 (7)	0.66376 (17)	0.0238 (8)
H16	1.229	−0.1082	0.6467	0.029*
C17	1.21512 (11)	−0.4058 (6)	0.68726 (16)	0.0208 (8)
C101	0.58960 (14)	0.7704 (8)	0.2666 (2)	0.0417 (12)
H10A	0.5669	0.8638	0.2758	0.062*
H10B	0.6101	0.8708	0.2535	0.062*
H10C	0.6015	0.6862	0.3021	0.062*
C102	0.53326 (13)	0.3609 (8)	0.2296 (2)	0.0386 (11)
H10D	0.5098	0.4479	0.2387	0.058*
H10E	0.5453	0.2758	0.2648	0.058*
H10F	0.5246	0.2526	0.1974	0.058*
C103	0.54720 (15)	0.7168 (10)	0.1393 (3)	0.0539 (14)
H10G	0.5243	0.8079	0.1487	0.081*
H10H	0.5376	0.6048	0.1084	0.081*
H10I	0.5671	0.819	0.1252	0.081*
C104	0.61408 (12)	0.3909 (7)	0.19062 (19)	0.0289 (9)
C105	0.64175 (12)	0.2721 (7)	0.18010 (19)	0.0273 (9)
C106	0.67299 (11)	0.1251 (6)	0.16391 (17)	0.0222 (8)
C107	0.66163 (11)	−0.0945 (7)	0.13963 (18)	0.0248 (9)
H107	0.6341	−0.1411	0.1366	0.03*
C108	0.68905 (11)	−0.2407 (7)	0.12054 (18)	0.0245 (9)
H108	0.6809	−0.3861	0.104	0.029*
C109	0.72895 (11)	−0.1712 (6)	0.12597 (16)	0.0195 (8)
C110	0.74177 (11)	0.0455 (6)	0.15089 (16)	0.0186 (8)
C111	0.71361 (11)	0.1916 (6)	0.17104 (16)	0.0196 (8)
H111	0.7219	0.334	0.1893	0.024*
C112	0.79577 (11)	−0.1404 (6)	0.11935 (16)	0.0191 (8)
C113	0.83489 (11)	−0.1776 (7)	0.10763 (17)	0.0233 (8)
H113	0.8421	−0.3151	0.0893	0.028*
C114	0.86314 (11)	−0.0036 (7)	0.12399 (17)	0.0248 (9)
H114	0.8901	−0.0222	0.116	0.03*
C115	0.85278 (11)	0.1970 (7)	0.15186 (18)	0.0246 (9)
H115	0.8729	0.3102	0.1633	0.03*
C116	0.81385 (11)	0.2334 (6)	0.16300 (17)	0.0215 (8)
H116	0.807	0.3715	0.1814	0.026*
C117	0.78442 (10)	0.0637 (6)	0.14678 (16)	0.0180 (8)
C201	0.58367 (16)	0.2827 (10)	0.5181 (2)	0.0547 (14)
H20A	0.5587	0.192	0.5131	0.082*
H20B	0.5829	0.3963	0.5496	0.082*
H20C	0.6069	0.1804	0.5287	0.082*
C202	0.54518 (15)	0.6333 (9)	0.4287 (3)	0.0684 (19)
H20D	0.5198	0.5459	0.4243	0.103*
H20E	0.5476	0.7125	0.3915	0.103*
H20F	0.5452	0.7468	0.4604	0.103*
C203	0.59114 (18)	0.2198 (9)	0.3883 (2)	0.0533 (14)
H20G	0.5665	0.1257	0.3833	0.08*
H20H	0.6148	0.1209	0.3991	0.08*
H20I	0.5934	0.2994	0.3511	0.08*
C204	0.63507 (13)	0.6057 (8)	0.4551 (2)	0.0368 (11)
C205	0.66520 (12)	0.7223 (7)	0.45955 (19)	0.0293 (9)
C206	0.70077 (12)	0.8676 (7)	0.46843 (18)	0.0260 (9)
C207	0.69732 (12)	1.0870 (7)	0.49484 (17)	0.0257 (9)
H207	0.6717	1.1359	0.5037	0.031*
C208	0.73045 (12)	1.2305 (7)	0.50781 (18)	0.0250 (9)
H208	0.7281	1.3763	0.5258	0.03*
C209	0.76714 (11)	1.1539 (6)	0.49368 (16)	0.0216 (8)
C210	0.77150 (11)	0.9360 (6)	0.46671 (17)	0.0226 (8)
C211	0.73748 (12)	0.7961 (7)	0.45339 (17)	0.0240 (8)
H211	0.7395	0.6526	0.4341	0.029*
C212	0.83313 (12)	1.1194 (6)	0.48325 (17)	0.0233 (8)
C213	0.87428 (12)	1.1524 (7)	0.48430 (18)	0.0292 (9)
H213	0.8872	1.2883	0.5007	0.035*
C214	0.89606 (12)	0.9817 (7)	0.46078 (18)	0.0298 (9)
H214	0.9243	1.0015	0.4608	0.036*
C215	0.87720 (13)	0.7799 (7)	0.43692 (18)	0.0294 (9)
H215	0.8929	0.6649	0.4213	0.035*
C216	0.83621 (12)	0.7464 (7)	0.43579 (17)	0.0253 (9)
H216	0.8235	0.6102	0.4192	0.03*
C217	0.81374 (11)	0.9154 (6)	0.45937 (16)	0.0221 (8)
Si1	0.99182 (3)	0.11166 (19)	0.63010 (5)	0.0244 (3)
Si11	0.57117 (3)	0.56253 (19)	0.20686 (6)	0.0286 (3)
Si21	0.58857 (4)	0.4339 (2)	0.44733 (6)	0.0364 (3)
N1	1.20135 (10)	−0.7431 (5)	0.73063 (15)	0.0254 (7)
H1	1.2045	−0.8789	0.7477	0.03*
N101	0.76177 (9)	−0.2807 (5)	0.10800 (14)	0.0225 (7)
H101	0.7613	−0.4182	0.0918	0.027*
N201	0.80458 (10)	1.2608 (5)	0.50257 (15)	0.0250 (7)
H201	0.8094	1.3982	0.5182	0.03*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.034 (2)	0.028 (2)	0.049 (3)	−0.0016 (19)	−0.001 (2)	0.001 (2)
C2	0.053 (3)	0.035 (3)	0.040 (3)	0.007 (2)	0.013 (2)	0.014 (2)
C3	0.031 (2)	0.027 (2)	0.044 (3)	0.0061 (18)	0.0067 (19)	−0.002 (2)
C4	0.025 (2)	0.027 (2)	0.032 (2)	0.0007 (17)	0.0085 (17)	−0.0009 (18)
C5	0.025 (2)	0.020 (2)	0.027 (2)	−0.0015 (16)	0.0061 (16)	−0.0011 (17)
C6	0.026 (2)	0.0167 (19)	0.026 (2)	0.0021 (15)	0.0026 (16)	−0.0049 (16)
C7	0.027 (2)	0.020 (2)	0.025 (2)	−0.0040 (16)	0.0037 (16)	−0.0009 (17)
C8	0.039 (2)	0.0130 (19)	0.026 (2)	−0.0009 (16)	0.0064 (17)	0.0023 (17)
C9	0.028 (2)	0.0133 (19)	0.022 (2)	−0.0003 (15)	0.0010 (15)	−0.0017 (16)
C10	0.0260 (19)	0.0124 (18)	0.0167 (18)	−0.0008 (15)	−0.0001 (14)	−0.0008 (15)
C11	0.029 (2)	0.0094 (18)	0.022 (2)	0.0009 (15)	0.0022 (15)	0.0010 (15)
C12	0.036 (2)	0.0141 (19)	0.022 (2)	0.0001 (16)	−0.0010 (16)	0.0000 (16)
C13	0.030 (2)	0.020 (2)	0.025 (2)	0.0070 (16)	−0.0064 (16)	−0.0008 (17)
C14	0.028 (2)	0.033 (2)	0.033 (2)	0.0041 (18)	−0.0022 (17)	−0.004 (2)
C15	0.033 (2)	0.028 (2)	0.029 (2)	−0.0033 (18)	0.0073 (18)	−0.0013 (19)
C16	0.028 (2)	0.018 (2)	0.024 (2)	−0.0002 (16)	−0.0012 (16)	0.0001 (16)
C17	0.0273 (19)	0.0138 (18)	0.0203 (19)	0.0019 (15)	0.0000 (15)	0.0003 (15)
C101	0.045 (3)	0.025 (2)	0.057 (3)	0.004 (2)	0.016 (2)	−0.008 (2)
C102	0.032 (2)	0.025 (2)	0.059 (3)	0.0000 (19)	0.011 (2)	−0.001 (2)
C103	0.036 (3)	0.059 (4)	0.065 (4)	0.010 (2)	0.003 (2)	0.019 (3)
C104	0.028 (2)	0.021 (2)	0.038 (2)	0.0022 (17)	0.0058 (17)	0.0019 (19)
C105	0.030 (2)	0.022 (2)	0.031 (2)	−0.0023 (17)	0.0060 (17)	0.0021 (18)
C106	0.0256 (19)	0.0131 (18)	0.029 (2)	0.0041 (15)	0.0083 (16)	0.0035 (16)
C107	0.025 (2)	0.019 (2)	0.030 (2)	−0.0029 (16)	0.0051 (16)	0.0034 (17)
C108	0.029 (2)	0.0158 (19)	0.028 (2)	−0.0017 (16)	−0.0001 (16)	0.0006 (16)
C109	0.0235 (19)	0.0141 (18)	0.0205 (19)	0.0028 (14)	0.0016 (15)	0.0027 (15)
C110	0.0275 (19)	0.0114 (18)	0.0169 (18)	0.0019 (14)	0.0034 (15)	0.0033 (15)
C111	0.0264 (19)	0.0115 (18)	0.0211 (19)	0.0023 (14)	0.0042 (15)	0.0009 (15)
C112	0.0244 (19)	0.0162 (19)	0.0161 (18)	0.0006 (15)	0.0006 (14)	0.0034 (15)
C113	0.030 (2)	0.020 (2)	0.020 (2)	0.0081 (16)	0.0021 (16)	0.0029 (16)
C114	0.0209 (19)	0.026 (2)	0.027 (2)	0.0050 (16)	0.0018 (16)	0.0059 (17)
C115	0.025 (2)	0.019 (2)	0.029 (2)	−0.0012 (16)	−0.0009 (16)	0.0039 (17)
C116	0.028 (2)	0.0103 (18)	0.025 (2)	0.0003 (15)	−0.0013 (16)	−0.0009 (16)
C117	0.0230 (18)	0.0121 (18)	0.0186 (18)	0.0017 (14)	0.0015 (14)	0.0014 (15)
C201	0.050 (3)	0.064 (4)	0.050 (3)	−0.018 (3)	0.007 (2)	−0.001 (3)
C202	0.034 (3)	0.036 (3)	0.129 (6)	−0.006 (2)	−0.009 (3)	0.001 (3)
C203	0.077 (4)	0.032 (3)	0.046 (3)	−0.012 (3)	−0.008 (3)	−0.004 (2)
C204	0.035 (2)	0.026 (2)	0.048 (3)	−0.0018 (19)	0.002 (2)	0.001 (2)
C205	0.029 (2)	0.024 (2)	0.034 (2)	0.0012 (17)	−0.0010 (17)	−0.0020 (19)
C206	0.029 (2)	0.018 (2)	0.029 (2)	−0.0042 (16)	−0.0015 (16)	0.0019 (17)
C207	0.032 (2)	0.019 (2)	0.026 (2)	0.0050 (16)	0.0034 (16)	0.0049 (17)
C208	0.034 (2)	0.0133 (19)	0.027 (2)	0.0011 (16)	0.0033 (17)	−0.0001 (16)
C209	0.032 (2)	0.0139 (19)	0.0184 (19)	−0.0018 (15)	0.0017 (15)	0.0044 (15)
C210	0.031 (2)	0.0143 (19)	0.022 (2)	0.0000 (15)	0.0008 (16)	0.0034 (16)
C211	0.031 (2)	0.0159 (19)	0.024 (2)	−0.0032 (16)	0.0009 (16)	0.0011 (16)
C212	0.034 (2)	0.0147 (19)	0.022 (2)	−0.0016 (16)	0.0050 (16)	0.0026 (16)
C213	0.033 (2)	0.027 (2)	0.026 (2)	−0.0053 (18)	0.0009 (17)	−0.0016 (18)
C214	0.031 (2)	0.033 (2)	0.026 (2)	−0.0004 (18)	0.0048 (17)	0.0043 (19)
C215	0.037 (2)	0.027 (2)	0.025 (2)	0.0062 (18)	0.0051 (17)	0.0002 (18)
C216	0.042 (2)	0.015 (2)	0.017 (2)	0.0011 (17)	0.0025 (17)	0.0003 (16)
C217	0.033 (2)	0.0145 (19)	0.0191 (19)	−0.0046 (16)	0.0044 (15)	0.0019 (16)
Si1	0.0243 (5)	0.0179 (6)	0.0309 (6)	0.0011 (4)	0.0033 (4)	0.0016 (5)
Si11	0.0237 (6)	0.0197 (6)	0.0434 (7)	0.0044 (4)	0.0082 (5)	0.0030 (5)
Si21	0.0343 (7)	0.0235 (6)	0.0483 (8)	−0.0081 (5)	−0.0044 (5)	−0.0024 (6)
N1	0.0315 (18)	0.0135 (16)	0.0304 (19)	0.0026 (13)	0.0016 (14)	0.0053 (14)
N101	0.0281 (17)	0.0116 (16)	0.0280 (18)	0.0016 (13)	0.0052 (14)	−0.0023 (14)
N201	0.0326 (18)	0.0132 (16)	0.0293 (19)	−0.0041 (13)	0.0051 (14)	−0.0060 (14)

Geometric parameters (Å, º) top

C1—Si1	1.862 (4)	C108—H108	0.95
C1—H1A	0.98	C109—N101	1.381 (5)
C1—H1B	0.98	C109—C110	1.423 (5)
C1—H1C	0.98	C110—C111	1.394 (5)
C2—Si1	1.864 (5)	C110—C117	1.445 (5)
C2—H2A	0.98	C111—H111	0.95
C2—H2B	0.98	C112—C113	1.389 (5)
C2—H2C	0.98	C112—N101	1.391 (5)
C3—Si1	1.864 (4)	C112—C117	1.419 (5)
C3—H3A	0.98	C113—C114	1.396 (6)
C3—H3B	0.98	C113—H113	0.95
C3—H3C	0.98	C114—C115	1.396 (6)
C4—C5	1.207 (5)	C114—H114	0.95
C4—Si1	1.827 (4)	C115—C116	1.377 (5)
C5—C6	1.455 (5)	C115—H115	0.95
C6—C11	1.385 (5)	C116—C117	1.404 (5)
C6—C7	1.418 (5)	C116—H116	0.95
C7—C8	1.386 (5)	C201—Si21	1.869 (6)
C7—H7	0.95	C201—H20A	0.98
C8—C9	1.387 (5)	C201—H20B	0.98
C8—H8	0.95	C201—H20C	0.98
C9—N1	1.377 (5)	C202—Si21	1.856 (5)
C9—C10	1.418 (5)	C202—H20D	0.98
C10—C11	1.403 (5)	C202—H20E	0.98
C10—C17	1.445 (5)	C202—H20F	0.98
C11—H11	0.95	C203—Si21	1.847 (5)
C12—N1	1.385 (5)	C203—H20G	0.98
C12—C13	1.395 (5)	C203—H20H	0.98
C12—C17	1.417 (5)	C203—H20I	0.98
C13—C14	1.379 (6)	C204—C205	1.205 (6)
C13—H13	0.95	C204—Si21	1.833 (4)
C14—C15	1.406 (6)	C205—C206	1.448 (5)
C14—H14	0.95	C206—C211	1.385 (6)
C15—C16	1.379 (6)	C206—C207	1.423 (6)
C15—H15	0.95	C207—C208	1.383 (5)
C16—C17	1.395 (5)	C207—H207	0.95
C16—H16	0.95	C208—C209	1.386 (5)
C101—Si11	1.860 (5)	C208—H208	0.95
C101—H10A	0.98	C209—N201	1.385 (5)
C101—H10B	0.98	C209—C210	1.426 (5)
C101—H10C	0.98	C210—C211	1.394 (5)
C102—Si11	1.855 (4)	C210—C217	1.450 (5)
C102—H10D	0.98	C211—H211	0.95
C102—H10E	0.98	C212—N201	1.379 (5)
C102—H10F	0.98	C212—C213	1.385 (5)
C103—Si11	1.862 (5)	C212—C217	1.422 (5)
C103—H10G	0.98	C213—C214	1.385 (6)
C103—H10H	0.98	C213—H213	0.95
C103—H10I	0.98	C214—C215	1.403 (6)
C104—C105	1.206 (6)	C214—H214	0.95
C104—Si11	1.828 (4)	C215—C216	1.380 (6)
C105—C106	1.438 (5)	C215—H215	0.95
C106—C111	1.397 (5)	C216—C217	1.392 (5)
C106—C107	1.421 (5)	C216—H216	0.95
C107—C108	1.367 (5)	N1—H1	0.88
C107—H107	0.95	N101—H101	0.88
C108—C109	1.381 (5)	N201—H201	0.88

Si1—C1—H1A	109.5	C112—C113—H113	121.5
Si1—C1—H1B	109.5	C114—C113—H113	121.5
H1A—C1—H1B	109.5	C115—C114—C113	121.6 (4)
Si1—C1—H1C	109.5	C115—C114—H114	119.2
H1A—C1—H1C	109.5	C113—C114—H114	119.2
H1B—C1—H1C	109.5	C116—C115—C114	121.1 (4)
Si1—C2—H2A	109.5	C116—C115—H115	119.5
Si1—C2—H2B	109.5	C114—C115—H115	119.5
H2A—C2—H2B	109.5	C115—C116—C117	119.1 (3)
Si1—C2—H2C	109.5	C115—C116—H116	120.4
H2A—C2—H2C	109.5	C117—C116—H116	120.4
H2B—C2—H2C	109.5	C116—C117—C112	118.8 (3)
Si1—C3—H3A	109.5	C116—C117—C110	133.9 (3)
Si1—C3—H3B	109.5	C112—C117—C110	107.3 (3)
H3A—C3—H3B	109.5	Si21—C201—H20A	109.5
Si1—C3—H3C	109.5	Si21—C201—H20B	109.5
H3A—C3—H3C	109.5	H20A—C201—H20B	109.5
H3B—C3—H3C	109.5	Si21—C201—H20C	109.5
C5—C4—Si1	176.8 (4)	H20A—C201—H20C	109.5
C4—C5—C6	178.9 (4)	H20B—C201—H20C	109.5
C11—C6—C7	120.2 (3)	Si21—C202—H20D	109.5
C11—C6—C5	121.0 (4)	Si21—C202—H20E	109.5
C7—C6—C5	118.8 (3)	H20D—C202—H20E	109.5
C8—C7—C6	121.5 (4)	Si21—C202—H20F	109.5
C8—C7—H7	119.3	H20D—C202—H20F	109.5
C6—C7—H7	119.3	H20E—C202—H20F	109.5
C7—C8—C9	117.8 (4)	Si21—C203—H20G	109.5
C7—C8—H8	121.1	Si21—C203—H20H	109.5
C9—C8—H8	121.1	H20G—C203—H20H	109.5
N1—C9—C8	129.5 (4)	Si21—C203—H20I	109.5
N1—C9—C10	108.5 (3)	H20G—C203—H20I	109.5
C8—C9—C10	122.0 (3)	H20H—C203—H20I	109.5
C11—C10—C9	119.2 (3)	C205—C204—Si21	178.7 (4)
C11—C10—C17	134.0 (3)	C204—C205—C206	176.4 (5)
C9—C10—C17	106.8 (3)	C211—C206—C207	120.3 (4)
C6—C11—C10	119.3 (3)	C211—C206—C205	121.9 (4)
C6—C11—H11	120.3	C207—C206—C205	117.8 (4)
C10—C11—H11	120.3	C208—C207—C206	121.3 (4)
N1—C12—C13	130.1 (4)	C208—C207—H207	119.3
N1—C12—C17	108.5 (3)	C206—C207—H207	119.3
C13—C12—C17	121.4 (4)	C207—C208—C209	117.6 (4)
C14—C13—C12	117.7 (4)	C207—C208—H208	121.2
C14—C13—H13	121.2	C209—C208—H208	121.2
C12—C13—H13	121.2	N201—C209—C208	129.2 (4)
C13—C14—C15	121.6 (4)	N201—C209—C210	108.4 (3)
C13—C14—H14	119.2	C208—C209—C210	122.4 (3)
C15—C14—H14	119.2	C211—C210—C209	118.8 (4)
C16—C15—C14	120.6 (4)	C211—C210—C217	134.6 (4)
C16—C15—H15	119.7	C209—C210—C217	106.6 (3)
C14—C15—H15	119.7	C206—C211—C210	119.6 (4)
C15—C16—C17	119.1 (4)	C206—C211—H211	120.2
C15—C16—H16	120.4	C210—C211—H211	120.2
C17—C16—H16	120.4	N201—C212—C213	130.0 (4)
C16—C17—C12	119.5 (3)	N201—C212—C217	108.8 (3)
C16—C17—C10	134.0 (3)	C213—C212—C217	121.2 (4)
C12—C17—C10	106.5 (3)	C212—C213—C214	118.0 (4)
Si11—C101—H10A	109.5	C212—C213—H213	121
Si11—C101—H10B	109.5	C214—C213—H213	121
H10A—C101—H10B	109.5	C213—C214—C215	121.2 (4)
Si11—C101—H10C	109.5	C213—C214—H214	119.4
H10A—C101—H10C	109.5	C215—C214—H214	119.4
H10B—C101—H10C	109.5	C216—C215—C214	120.9 (4)
Si11—C102—H10D	109.5	C216—C215—H215	119.6
Si11—C102—H10E	109.5	C214—C215—H215	119.6
H10D—C102—H10E	109.5	C215—C216—C217	118.9 (4)
Si11—C102—H10F	109.5	C215—C216—H216	120.6
H10D—C102—H10F	109.5	C217—C216—H216	120.6
H10E—C102—H10F	109.5	C216—C217—C212	119.8 (4)
Si11—C103—H10G	109.5	C216—C217—C210	133.8 (4)
Si11—C103—H10H	109.5	C212—C217—C210	106.4 (3)
H10G—C103—H10H	109.5	C4—Si1—C1	107.1 (2)
Si11—C103—H10I	109.5	C4—Si1—C3	111.1 (2)
H10G—C103—H10I	109.5	C1—Si1—C3	109.2 (2)
H10H—C103—H10I	109.5	C4—Si1—C2	109.0 (2)
C105—C104—Si11	178.1 (4)	C1—Si1—C2	111.3 (2)
C104—C105—C106	176.0 (5)	C3—Si1—C2	109.1 (2)
C111—C106—C107	119.6 (3)	C104—Si11—C102	107.44 (19)
C111—C106—C105	122.3 (3)	C104—Si11—C101	108.6 (2)
C107—C106—C105	118.2 (3)	C102—Si11—C101	111.8 (2)
C108—C107—C106	122.0 (4)	C104—Si11—C103	110.5 (2)
C108—C107—H107	119	C102—Si11—C103	108.0 (2)
C106—C107—H107	119	C101—Si11—C103	110.6 (3)
C107—C108—C109	118.2 (4)	C204—Si21—C203	108.0 (2)
C107—C108—H108	120.9	C204—Si21—C202	107.7 (2)
C109—C108—H108	120.9	C203—Si21—C202	111.8 (3)
N101—C109—C108	129.5 (4)	C204—Si21—C201	110.7 (2)
N101—C109—C110	108.8 (3)	C203—Si21—C201	109.6 (3)
C108—C109—C110	121.7 (3)	C202—Si21—C201	109.2 (3)
C111—C110—C109	119.6 (3)	C9—N1—C12	109.7 (3)
C111—C110—C117	134.1 (3)	C9—N1—H1	125.2
C109—C110—C117	106.3 (3)	C12—N1—H1	125.2
C110—C111—C106	118.9 (3)	C109—N101—C112	109.6 (3)
C110—C111—H111	120.5	C109—N101—H101	125.2
C106—C111—H111	120.5	C112—N101—H101	125.2
C113—C112—N101	129.7 (3)	C212—N201—C209	109.7 (3)
C113—C112—C117	122.3 (3)	C212—N201—H201	125.2
N101—C112—C117	108.0 (3)	C209—N201—H201	125.2
C112—C113—C114	117.0 (4)

Si1—C4—C5—C6	0 (26)	N101—C112—C117—C110	−1.1 (4)
C4—C5—C6—C11	152 (21)	C111—C110—C117—C116	2.0 (7)
C4—C5—C6—C7	−27 (21)	C109—C110—C117—C116	179.5 (4)
C11—C6—C7—C8	−0.5 (6)	C111—C110—C117—C112	−177.2 (4)
C5—C6—C7—C8	178.4 (4)	C109—C110—C117—C112	0.4 (4)
C6—C7—C8—C9	−0.2 (6)	Si21—C204—C205—C206	89 (22)
C7—C8—C9—N1	−179.3 (4)	C204—C205—C206—C211	141 (7)
C7—C8—C9—C10	1.1 (6)	C204—C205—C206—C207	−37 (8)
N1—C9—C10—C11	179.1 (3)	C211—C206—C207—C208	−2.1 (6)
C8—C9—C10—C11	−1.3 (5)	C205—C206—C207—C208	176.3 (4)
N1—C9—C10—C17	−0.2 (4)	C206—C207—C208—C209	0.6 (6)
C8—C9—C10—C17	179.4 (3)	C207—C208—C209—N201	−179.0 (4)
C7—C6—C11—C10	0.3 (6)	C207—C208—C209—C210	0.0 (6)
C5—C6—C11—C10	−178.6 (3)	N201—C209—C210—C211	−179.9 (3)
C9—C10—C11—C6	0.5 (5)	C208—C209—C210—C211	0.8 (6)
C17—C10—C11—C6	179.6 (4)	N201—C209—C210—C217	−0.2 (4)
N1—C12—C13—C14	179.6 (4)	C208—C209—C210—C217	−179.4 (3)
C17—C12—C13—C14	−1.5 (6)	C207—C206—C211—C210	2.9 (6)
C12—C13—C14—C15	1.1 (6)	C205—C206—C211—C210	−175.4 (4)
C13—C14—C15—C16	−1.0 (6)	C209—C210—C211—C206	−2.3 (6)
C14—C15—C16—C17	1.2 (6)	C217—C210—C211—C206	178.0 (4)
C15—C16—C17—C12	−1.6 (6)	N201—C212—C213—C214	−178.9 (4)
C15—C16—C17—C10	−178.7 (4)	C217—C212—C213—C214	0.7 (6)
N1—C12—C17—C16	−179.1 (3)	C212—C213—C214—C215	−0.5 (6)
C13—C12—C17—C16	1.8 (6)	C213—C214—C215—C216	0.5 (6)
N1—C12—C17—C10	−1.2 (4)	C214—C215—C216—C217	−0.7 (6)
C13—C12—C17—C10	179.6 (3)	C215—C216—C217—C212	0.9 (6)
C11—C10—C17—C16	−0.8 (7)	C215—C216—C217—C210	−178.5 (4)
C9—C10—C17—C16	178.3 (4)	N201—C212—C217—C216	178.8 (3)
C11—C10—C17—C12	−178.3 (4)	C213—C212—C217—C216	−0.9 (6)
C9—C10—C17—C12	0.9 (4)	N201—C212—C217—C210	−1.7 (4)
Si11—C104—C105—C106	65 (16)	C213—C212—C217—C210	178.6 (4)
C104—C105—C106—C111	140 (6)	C211—C210—C217—C216	0.3 (8)
C104—C105—C106—C107	−39 (6)	C209—C210—C217—C216	−179.5 (4)
C111—C106—C107—C108	−2.8 (6)	C211—C210—C217—C212	−179.2 (4)
C105—C106—C107—C108	176.9 (4)	C209—C210—C217—C212	1.1 (4)
C106—C107—C108—C109	0.8 (6)	C5—C4—Si1—C1	−2 (7)
C107—C108—C109—N101	−176.9 (4)	C5—C4—Si1—C3	117 (7)
C107—C108—C109—C110	0.3 (6)	C5—C4—Si1—C2	−123 (7)
N101—C109—C110—C111	178.4 (3)	C105—C104—Si11—C102	7 (13)
C108—C109—C110—C111	0.7 (5)	C105—C104—Si11—C101	128 (13)
N101—C109—C110—C117	0.4 (4)	C105—C104—Si11—C103	−110 (13)
C108—C109—C110—C117	−177.3 (3)	C205—C204—Si21—C203	105 (21)
C109—C110—C111—C106	−2.7 (5)	C205—C204—Si21—C202	−16 (21)
C117—C110—C111—C106	174.6 (4)	C205—C204—Si21—C201	−135 (21)
C107—C106—C111—C110	3.7 (5)	C8—C9—N1—C12	179.9 (4)
C105—C106—C111—C110	−176.0 (4)	C10—C9—N1—C12	−0.6 (4)
N101—C112—C113—C114	179.8 (4)	C13—C12—N1—C9	−179.8 (4)
C117—C112—C113—C114	−0.1 (5)	C17—C12—N1—C9	1.1 (4)
C112—C113—C114—C115	1.1 (5)	C108—C109—N101—C112	176.4 (4)
C113—C114—C115—C116	−1.6 (6)	C110—C109—N101—C112	−1.1 (4)
C114—C115—C116—C117	1.0 (6)	C113—C112—N101—C109	−178.6 (4)
C115—C116—C117—C112	0.0 (5)	C117—C112—N101—C109	1.3 (4)
C115—C116—C117—C110	−179.1 (4)	C213—C212—N201—C209	−178.7 (4)
C113—C112—C117—C116	−0.4 (5)	C217—C212—N201—C209	1.6 (4)
N101—C112—C117—C116	179.6 (3)	C208—C209—N201—C212	178.3 (4)
C113—C112—C117—C110	178.9 (3)	C210—C209—N201—C212	−0.9 (4)

Experimental details

Crystal data
Chemical formula	[Si(CH₃)₃(C₁₄H₈N)]
M_r	263.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	33.402 (3), 5.8135 (4), 22.8511 (17)
β (°)	98.394 (2)
V (Å³)	4389.7 (6)
Z	12
Radiation type	Synchrotron, λ = 0.688 Å
µ (mm⁻¹)	0.15
Crystal size (mm)	0.2 × 0.2 × 0.04

Data collection
Diffractometer	Bruker AXS SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.971, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	21435, 7939, 5999
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.187, 1.14
No. of reflections	7939
No. of parameters	514
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.42

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Selected geometric parameters (Å, º) top

C1—Si1	1.862 (4)	C109—N101	1.381 (5)
C2—Si1	1.864 (5)	C109—C110	1.423 (5)
C3—Si1	1.864 (4)	C110—C117	1.445 (5)
C4—C5	1.207 (5)	C112—N101	1.391 (5)
C4—Si1	1.827 (4)	C112—C117	1.419 (5)
C5—C6	1.455 (5)	C201—Si21	1.869 (6)
C9—N1	1.377 (5)	C202—Si21	1.856 (5)
C9—C10	1.418 (5)	C203—Si21	1.847 (5)
C10—C17	1.445 (5)	C204—C205	1.205 (6)
C12—N1	1.385 (5)	C204—Si21	1.833 (4)
C12—C17	1.417 (5)	C205—C206	1.448 (5)
C101—Si11	1.860 (5)	C209—N201	1.385 (5)
C102—Si11	1.855 (4)	C209—C210	1.426 (5)
C103—Si11	1.862 (5)	C210—C217	1.450 (5)
C104—C105	1.206 (6)	C212—N201	1.379 (5)
C104—Si11	1.828 (4)	C212—C217	1.422 (5)
C105—C106	1.438 (5)

C5—C4—Si1	176.8 (4)	C1—Si1—C3	109.2 (2)
C4—C5—C6	178.9 (4)	C4—Si1—C2	109.0 (2)
N1—C9—C10	108.5 (3)	C1—Si1—C2	111.3 (2)
C9—C10—C17	106.8 (3)	C3—Si1—C2	109.1 (2)
N1—C12—C17	108.5 (3)	C104—Si11—C102	107.44 (19)
C12—C17—C10	106.5 (3)	C104—Si11—C101	108.6 (2)
C105—C104—Si11	178.1 (4)	C102—Si11—C101	111.8 (2)
C104—C105—C106	176.0 (5)	C104—Si11—C103	110.5 (2)
N101—C109—C110	108.8 (3)	C102—Si11—C103	108.0 (2)
C109—C110—C117	106.3 (3)	C101—Si11—C103	110.6 (3)
N101—C112—C117	108.0 (3)	C204—Si21—C203	108.0 (2)
C112—C117—C110	107.3 (3)	C204—Si21—C202	107.7 (2)
C205—C204—Si21	178.7 (4)	C203—Si21—C202	111.8 (3)
C204—C205—C206	176.4 (5)	C204—Si21—C201	110.7 (2)
N201—C209—C210	108.4 (3)	C203—Si21—C201	109.6 (3)
C209—C210—C217	106.6 (3)	C202—Si21—C201	109.2 (3)
N201—C212—C217	108.8 (3)	C9—N1—C12	109.7 (3)
C212—C217—C210	106.4 (3)	C109—N101—C112	109.6 (3)
C4—Si1—C1	107.1 (2)	C212—N201—C209	109.7 (3)
C4—Si1—C3	111.1 (2)

C5—C6—C7—C8	178.4 (4)	C5—C4—Si1—C2	−123 (7)
N1—C9—C10—C17	−0.2 (4)	C105—C104—Si11—C102	7 (13)
N1—C12—C17—C10	−1.2 (4)	C105—C104—Si11—C101	128 (13)
C9—C10—C17—C12	0.9 (4)	C105—C104—Si11—C103	−110 (13)
C105—C106—C107—C108	176.9 (4)	C205—C204—Si21—C203	105 (21)
N101—C109—C110—C117	0.4 (4)	C205—C204—Si21—C202	−16 (21)
N101—C112—C117—C110	−1.1 (4)	C205—C204—Si21—C201	−135 (21)
C109—C110—C117—C112	0.4 (4)	C10—C9—N1—C12	−0.6 (4)
C205—C206—C207—C208	176.3 (4)	C17—C12—N1—C9	1.1 (4)
N201—C209—C210—C217	−0.2 (4)	C110—C109—N101—C112	−1.1 (4)
N201—C212—C217—C210	−1.7 (4)	C117—C112—N101—C109	1.3 (4)
C209—C210—C217—C212	1.1 (4)	C217—C212—N201—C209	1.6 (4)
C5—C4—Si1—C1	−2 (7)	C210—C209—N201—C212	−0.9 (4)
C5—C4—Si1—C3	117 (7)

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