Bromo­triphenyl­silane

Hannah Steinert; Hans-Wolfram Lerner; Michael Bolte

doi:10.1107/S1600536808010520

. 2008 Apr 23;64(Pt 5):o880. doi: 10.1107/S1600536808010520

Bromotriphenylsilane

Hannah Steinert ^a, Hans-Wolfram Lerner ^a, Michael Bolte ^a,^*

PMCID: PMC2961209 PMID: 21202364

Abstract

The title compound, C₁₈H₁₅BrSi, crystallizes with two almost identical molecules (r.m.s. deviation for all non-H atoms = 0.074 Å) in the asymmetric unit. It is isomorphous with chlorotriphenylsilane.

Related literature

For related literature, see: Lerner et al. (2001 ▶, 2005 ▶, 2006 ▶); Lobkovskii et al. (1981 ▶).

Experimental

Crystal data

C₁₈H₁₅BrSi
M _r = 339.30
Monoclinic,
a = 18.6306 (13) Å
b = 9.6160 (4) Å
c = 18.3618 (13) Å
β = 107.174 (5)°
V = 3142.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 2.68 mm⁻¹
T = 173 (2) K
0.31 × 0.25 × 0.19 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T _min = 0.490, T _max = 0.630
47324 measured reflections
6141 independent reflections
4739 reflections with I > 2σ(I)
R _int = 0.073

Refinement

R[F ² > 2σ(F ²)] = 0.094
wR(F ²) = 0.288
S = 1.16
6141 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 2.34 e Å⁻³
Δρ_min = −2.22 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010520/pv2078sup1.cif

e-64-0o880-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010520/pv2078Isup2.hkl

e-64-0o880-Isup2.hkl^{(300.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

We report here the X-ray crystal structure analysis of Ph₃SiBr. Recently we have synthesized the silanimines Me₂Si=N-SitBu₃ and tBu₂Si=N-SiXtBu₂ (X = tBu, Cl) as donor adducts (Lerner et al., 2006) (Fig. 2) and the donor-free silanimines tBu₂Si=N-SiXtBu₂ (X = tBu, Cl, Ph) (Lerner et al., 2001) by salt elimination reactions of Me₂SiCl-NLi-SitBu₃ and tBu₂SiCl-NM-SiXtBu₂ (X = tBu, Cl, Ph; M = Li, Na). However, at room temperature we observed a partial degradation of the donor-free silanimines tBu₂Si=N-SiXtBu₂ (X = tBu, Cl, Ph) with the formation of isobutene (Lerner et al., 2005). Now we are interested in preparing the phenyl substituted silanimine tBu₂Si=N-SiPh₃. In an attempt to synthesize the bromosilylated amine tBu₂SiBr-NH-SiPh₃ from tBu₂SiH-NH-SiPh₃ and N-bromosuccinimide we obtained Ph₃SiBr as a by-product. X-ray quality crystals of this by-product were grown from a filtrated hexane solution at room temperature.

The title compound, C₁₈H₁₅BrSi, crystallizes with two almost identical molecules (r.m.s. deviation for all non-H atoms 0.074 Å) in the asymmetric unit. Geometric parameters are in the usual ranges (Bruno et al., 2004). It is isomorphous with chlorotriphenylsilane (Lobkovskii et al., 1981).

Experimental

A mixture of tBu₂SiH-NH-SiPh₃ (0.374 g, 0.90 mmol) and N-bromosuccinimide (0.262 g, 1.47 mmol) in 5 ml benzene was stirred for 24 h at room temperature. First the solvent was removed in vacuo and then the residue was extracted in hexane. X-ray quality crystals of this by-product were grown from a filtrated hexane solution at room temperature.