Bromo­triphenyl­silane

Steinert, H.; Lerner, H.-W.; Bolte, M.

doi:10.1107/S1600536808010520

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o880

doi:10.1107/S1600536808010520

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Bromotriphenylsilane

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

^aInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 9 April 2008; accepted 16 April 2008; online 23 April 2008)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.094
wR(F²) = 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).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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).

Figures top

	Fig. 1. Perspective view of the title compound with the atom numbering scheme; displacement ellipsoids are at the 50% probability level; H atoms are drawn as small spheres of arbitrary radii.
	Fig. 2. Reaction scheme.

Bromotriphenylsilane top

Crystal data top

C₁₈H₁₅BrSi	F(000) = 1376
M_r = 339.30	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 32075 reflections
a = 18.6306 (13) Å	θ = 2.4–26.3°
b = 9.6160 (4) Å	µ = 2.68 mm⁻¹
c = 18.3618 (13) Å	T = 173 K
β = 107.174 (5)°	Block, colourless
V = 3142.9 (3) Å³	0.31 × 0.25 × 0.19 mm
Z = 8

Data collection top

Stoe IPDSII two-circle diffractometer	6141 independent reflections
Radiation source: fine-focus sealed tube	4739 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ω scans	θ_max = 26.1°, θ_min = 2.3°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −22→21
T_min = 0.491, T_max = 0.630	k = 0→11
47324 measured reflections	l = 0→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.094	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.288	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
6141 reflections	(Δ/σ)_max < 0.001
362 parameters	Δρ_max = 2.34 e Å⁻³
0 restraints	Δρ_min = −2.22 e Å⁻³

Crystal data top

C₁₈H₁₅BrSi	V = 3142.9 (3) Å³
M_r = 339.30	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.6306 (13) Å	µ = 2.68 mm⁻¹
b = 9.6160 (4) Å	T = 173 K
c = 18.3618 (13) Å	0.31 × 0.25 × 0.19 mm
β = 107.174 (5)°

Data collection top

Stoe IPDSII two-circle diffractometer	6141 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	4739 reflections with I > 2σ(I)
T_min = 0.491, T_max = 0.630	R_int = 0.073
47324 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.094	0 restraints
wR(F²) = 0.288	H-atom parameters constrained
S = 1.16	Δρ_max = 2.34 e Å⁻³
6141 reflections	Δρ_min = −2.22 e Å⁻³
362 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Br1	0.40043 (4)	0.50324 (9)	0.36669 (5)	0.0513 (3)
Si1	0.44440 (9)	0.32247 (18)	0.31491 (10)	0.0287 (4)
C1	0.4064 (3)	0.3378 (6)	0.2089 (4)	0.0297 (12)
C2	0.3696 (4)	0.4572 (7)	0.1712 (4)	0.0384 (15)
H2	0.3634	0.5354	0.2003	0.046*
C3	0.3425 (4)	0.4625 (9)	0.0928 (5)	0.0472 (18)
H3	0.3173	0.5436	0.0685	0.057*
C4	0.3518 (5)	0.3503 (9)	0.0492 (4)	0.051 (2)
H4	0.3332	0.3542	−0.0048	0.061*
C5	0.3888 (5)	0.2303 (9)	0.0855 (4)	0.053 (2)
H5	0.3963	0.1534	0.0560	0.064*
C6	0.4143 (4)	0.2251 (8)	0.1642 (4)	0.0425 (16)
H6	0.4378	0.1427	0.1884	0.051*
C7	0.5489 (3)	0.3357 (6)	0.3495 (4)	0.0304 (13)
C8	0.5925 (3)	0.3310 (7)	0.2984 (4)	0.0314 (13)
H8	0.5689	0.3217	0.2452	0.038*
C9	0.6711 (4)	0.3402 (8)	0.3269 (4)	0.0421 (16)
H9	0.7004	0.3367	0.2924	0.051*
C10	0.7064 (4)	0.3543 (8)	0.4039 (4)	0.0426 (16)
H10	0.7596	0.3606	0.4225	0.051*
C11	0.6628 (4)	0.3593 (8)	0.4542 (4)	0.0402 (15)
H11	0.6867	0.3695	0.5073	0.048*
C12	0.5858 (4)	0.3494 (8)	0.4276 (4)	0.0370 (15)
H12	0.5573	0.3519	0.4627	0.044*
C13	0.4096 (3)	0.1588 (7)	0.3471 (4)	0.0312 (13)
C14	0.3318 (3)	0.1342 (7)	0.3281 (4)	0.0327 (13)
H14	0.2977	0.2032	0.3012	0.039*
C15	0.3040 (4)	0.0106 (9)	0.3482 (4)	0.0431 (17)
H15	0.2513	−0.0048	0.3347	0.052*
C16	0.3533 (4)	−0.0902 (7)	0.3881 (4)	0.0382 (15)
H16	0.3354	−0.1754	0.4024	0.046*
C17	0.4277 (5)	−0.0635 (8)	0.4059 (4)	0.0456 (18)
H17	0.4614	−0.1331	0.4327	0.055*
C18	0.4574 (4)	0.0556 (7)	0.3882 (4)	0.0355 (14)
H18	0.5103	0.0689	0.4036	0.043*
Br2	0.09145 (4)	−0.23720 (9)	0.11290 (5)	0.0511 (3)
Si2	0.05044 (9)	−0.06392 (18)	0.17217 (10)	0.0290 (4)
C19	−0.0543 (3)	−0.0792 (6)	0.1436 (4)	0.0301 (12)
C20	−0.0925 (3)	−0.0806 (7)	0.1995 (3)	0.0310 (13)
H20	−0.0650	−0.0729	0.2519	0.037*
C21	−0.1708 (4)	−0.0932 (8)	0.1780 (4)	0.0419 (16)
H21	−0.1963	−0.0921	0.2158	0.050*
C22	−0.2112 (4)	−0.1073 (7)	0.1022 (4)	0.0375 (14)
H22	−0.2643	−0.1169	0.0879	0.045*
C23	−0.1737 (4)	−0.1074 (8)	0.0466 (4)	0.0404 (15)
H23	−0.2014	−0.1183	−0.0056	0.048*
C24	−0.0975 (4)	−0.0918 (8)	0.0668 (4)	0.0377 (15)
H24	−0.0731	−0.0894	0.0281	0.045*
C25	0.0929 (3)	−0.0861 (6)	0.2773 (4)	0.0291 (12)
C26	0.0895 (4)	0.0262 (7)	0.3249 (4)	0.0371 (14)
H26	0.0662	0.1106	0.3032	0.044*
C27	0.1195 (5)	0.0154 (9)	0.4025 (4)	0.0481 (18)
H27	0.1169	0.0924	0.4341	0.058*
C28	0.1542 (4)	−0.1087 (9)	0.4358 (4)	0.0438 (17)
H28	0.1747	−0.1163	0.4896	0.053*
C29	0.1577 (4)	−0.2189 (8)	0.3892 (4)	0.0414 (16)
H29	0.1812	−0.3028	0.4113	0.050*
C30	0.1278 (4)	−0.2103 (7)	0.3101 (4)	0.0373 (14)
H30	0.1309	−0.2873	0.2788	0.045*
C31	0.0848 (3)	0.1019 (7)	0.1422 (3)	0.0315 (13)
C32	0.1619 (4)	0.1250 (8)	0.1564 (4)	0.0355 (14)
H32	0.1962	0.0530	0.1791	0.043*
C33	0.1895 (4)	0.2494 (9)	0.1384 (4)	0.0460 (17)
H33	0.2421	0.2612	0.1482	0.055*
C34	0.1420 (4)	0.3557 (8)	0.1065 (4)	0.0428 (16)
H34	0.1617	0.4414	0.0952	0.051*
C35	0.0630 (4)	0.3379 (8)	0.0904 (4)	0.0444 (17)
H35	0.0291	0.4106	0.0680	0.053*
C36	0.0370 (4)	0.2111 (7)	0.1083 (4)	0.0360 (14)
H36	−0.0156	0.1978	0.0969	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0467 (5)	0.0495 (5)	0.0644 (5)	−0.0007 (3)	0.0268 (4)	−0.0178 (4)
Si1	0.0234 (8)	0.0314 (9)	0.0324 (8)	−0.0019 (6)	0.0098 (6)	−0.0012 (7)
C1	0.020 (3)	0.028 (3)	0.041 (3)	−0.003 (2)	0.009 (2)	0.001 (3)
C2	0.028 (3)	0.035 (3)	0.051 (4)	0.000 (3)	0.010 (3)	0.009 (3)
C3	0.034 (4)	0.049 (4)	0.052 (4)	−0.006 (3)	0.004 (3)	0.017 (3)
C4	0.054 (4)	0.061 (5)	0.029 (3)	−0.020 (4)	−0.001 (3)	0.014 (3)
C5	0.073 (6)	0.051 (5)	0.034 (4)	−0.015 (4)	0.013 (4)	−0.009 (3)
C6	0.051 (4)	0.035 (4)	0.041 (4)	0.001 (3)	0.013 (3)	0.004 (3)
C7	0.022 (3)	0.032 (3)	0.036 (3)	−0.002 (2)	0.007 (2)	0.002 (2)
C8	0.027 (3)	0.034 (3)	0.035 (3)	−0.004 (2)	0.012 (2)	0.002 (3)
C9	0.033 (3)	0.050 (4)	0.051 (4)	0.000 (3)	0.023 (3)	0.008 (3)
C10	0.029 (3)	0.049 (4)	0.049 (4)	−0.006 (3)	0.010 (3)	0.001 (3)
C11	0.033 (3)	0.044 (4)	0.038 (3)	−0.003 (3)	0.002 (3)	0.002 (3)
C12	0.030 (3)	0.049 (4)	0.033 (3)	−0.008 (3)	0.011 (3)	−0.004 (3)
C13	0.029 (3)	0.032 (3)	0.033 (3)	−0.004 (2)	0.010 (2)	0.004 (2)
C14	0.026 (3)	0.039 (3)	0.033 (3)	−0.002 (3)	0.008 (2)	0.004 (3)
C15	0.030 (3)	0.061 (5)	0.040 (4)	−0.011 (3)	0.012 (3)	0.004 (3)
C16	0.047 (4)	0.029 (3)	0.045 (4)	−0.005 (3)	0.024 (3)	0.005 (3)
C17	0.053 (4)	0.050 (4)	0.046 (4)	−0.024 (4)	0.033 (3)	−0.018 (3)
C18	0.026 (3)	0.041 (4)	0.041 (3)	0.003 (3)	0.013 (3)	0.003 (3)
Br2	0.0459 (5)	0.0498 (5)	0.0634 (5)	0.0038 (3)	0.0250 (4)	−0.0172 (4)
Si2	0.0226 (8)	0.0325 (9)	0.0340 (8)	0.0000 (6)	0.0120 (6)	−0.0026 (7)
C19	0.027 (3)	0.031 (3)	0.034 (3)	−0.001 (2)	0.013 (2)	0.000 (2)
C20	0.027 (3)	0.039 (3)	0.027 (3)	−0.001 (2)	0.009 (2)	0.003 (2)
C21	0.032 (3)	0.057 (4)	0.041 (4)	−0.002 (3)	0.017 (3)	0.007 (3)
C22	0.029 (3)	0.037 (4)	0.047 (4)	−0.002 (3)	0.012 (3)	0.000 (3)
C23	0.037 (3)	0.051 (4)	0.032 (3)	0.002 (3)	0.008 (3)	−0.005 (3)
C24	0.038 (3)	0.045 (4)	0.034 (3)	0.003 (3)	0.017 (3)	−0.006 (3)
C25	0.019 (3)	0.026 (3)	0.043 (3)	0.000 (2)	0.010 (2)	0.005 (2)
C26	0.043 (4)	0.031 (3)	0.037 (3)	0.005 (3)	0.011 (3)	0.006 (3)
C27	0.055 (5)	0.050 (4)	0.039 (4)	−0.013 (4)	0.014 (3)	0.002 (3)
C28	0.037 (4)	0.056 (4)	0.034 (3)	−0.011 (3)	0.003 (3)	0.012 (3)
C29	0.033 (3)	0.040 (4)	0.046 (4)	−0.004 (3)	0.005 (3)	0.013 (3)
C30	0.031 (3)	0.033 (3)	0.047 (4)	0.000 (3)	0.010 (3)	0.004 (3)
C31	0.025 (3)	0.040 (3)	0.031 (3)	−0.003 (3)	0.011 (2)	−0.002 (3)
C32	0.030 (3)	0.047 (4)	0.033 (3)	−0.005 (3)	0.013 (2)	−0.001 (3)
C33	0.042 (4)	0.059 (5)	0.038 (4)	−0.015 (3)	0.014 (3)	0.005 (3)
C34	0.051 (4)	0.043 (4)	0.041 (4)	−0.007 (3)	0.023 (3)	0.005 (3)
C35	0.050 (4)	0.039 (4)	0.048 (4)	0.014 (3)	0.020 (3)	0.014 (3)
C36	0.036 (3)	0.037 (3)	0.039 (3)	0.001 (3)	0.019 (3)	0.001 (3)

Geometric parameters (Å, º) top

Br1—Si1	2.2486 (18)	Br2—Si2	2.2440 (18)
Si1—C13	1.863 (6)	Si2—C31	1.861 (7)
Si1—C7	1.865 (6)	Si2—C25	1.870 (7)
Si1—C1	1.870 (7)	Si2—C19	1.870 (6)
C1—C6	1.393 (10)	C19—C24	1.407 (9)
C1—C2	1.409 (9)	C19—C20	1.412 (8)
C2—C3	1.379 (11)	C20—C21	1.399 (9)
C2—H2	0.9500	C20—H20	0.9500
C3—C4	1.384 (13)	C21—C22	1.379 (10)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.406 (12)	C22—C23	1.398 (10)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.383 (11)	C23—C24	1.365 (10)
C5—H5	0.9500	C23—H23	0.9500
C6—H6	0.9500	C24—H24	0.9500
C7—C12	1.403 (9)	C25—C26	1.401 (9)
C7—C8	1.412 (9)	C25—C30	1.408 (9)
C8—C9	1.404 (9)	C26—C27	1.373 (10)
C8—H8	0.9500	C26—H26	0.9500
C9—C10	1.379 (11)	C27—C28	1.408 (11)
C9—H9	0.9500	C27—H27	0.9500
C10—C11	1.400 (10)	C28—C29	1.376 (12)
C10—H10	0.9500	C28—H28	0.9500
C11—C12	1.376 (9)	C29—C30	1.395 (10)
C11—H11	0.9500	C29—H29	0.9500
C12—H12	0.9500	C30—H30	0.9500
C13—C18	1.397 (9)	C31—C36	1.398 (9)
C13—C14	1.407 (8)	C31—C32	1.401 (9)
C14—C15	1.389 (10)	C32—C33	1.380 (10)
C14—H14	0.9500	C32—H32	0.9500
C15—C16	1.387 (10)	C33—C34	1.365 (11)
C15—H15	0.9500	C33—H33	0.9500
C16—C17	1.351 (10)	C34—C35	1.424 (11)
C16—H16	0.9500	C34—H34	0.9500
C17—C18	1.353 (10)	C35—C36	1.387 (10)
C17—H17	0.9500	C35—H35	0.9500
C18—H18	0.9500	C36—H36	0.9500

C13—Si1—C7	112.1 (3)	C31—Si2—C25	109.0 (3)
C13—Si1—C1	109.7 (3)	C31—Si2—C19	113.9 (3)
C7—Si1—C1	112.6 (3)	C25—Si2—C19	111.6 (3)
C13—Si1—Br1	108.3 (2)	C31—Si2—Br2	107.3 (2)
C7—Si1—Br1	106.1 (2)	C25—Si2—Br2	108.4 (2)
C1—Si1—Br1	107.8 (2)	C19—Si2—Br2	106.3 (2)
C6—C1—C2	117.7 (6)	C24—C19—C20	117.7 (6)
C6—C1—Si1	118.6 (5)	C24—C19—Si2	122.0 (5)
C2—C1—Si1	123.7 (5)	C20—C19—Si2	120.3 (5)
C3—C2—C1	121.2 (7)	C21—C20—C19	120.2 (6)
C3—C2—H2	119.4	C21—C20—H20	119.9
C1—C2—H2	119.4	C19—C20—H20	119.9
C2—C3—C4	120.3 (7)	C22—C21—C20	120.4 (6)
C2—C3—H3	119.8	C22—C21—H21	119.8
C4—C3—H3	119.8	C20—C21—H21	119.8
C3—C4—C5	119.6 (7)	C21—C22—C23	119.7 (6)
C3—C4—H4	120.2	C21—C22—H22	120.2
C5—C4—H4	120.2	C23—C22—H22	120.2
C6—C5—C4	119.6 (8)	C24—C23—C22	120.4 (6)
C6—C5—H5	120.2	C24—C23—H23	119.8
C4—C5—H5	120.2	C22—C23—H23	119.8
C5—C6—C1	121.6 (7)	C23—C24—C19	121.6 (6)
C5—C6—H6	119.2	C23—C24—H24	119.2
C1—C6—H6	119.2	C19—C24—H24	119.2
C12—C7—C8	118.5 (5)	C26—C25—C30	119.1 (6)
C12—C7—Si1	120.2 (5)	C26—C25—Si2	118.2 (5)
C8—C7—Si1	121.4 (5)	C30—C25—Si2	122.6 (5)
C7—C8—C9	119.5 (6)	C27—C26—C25	120.6 (7)
C7—C8—H8	120.2	C27—C26—H26	119.7
C9—C8—H8	120.2	C25—C26—H26	119.7
C10—C9—C8	121.2 (6)	C26—C27—C28	120.6 (7)
C10—C9—H9	119.4	C26—C27—H27	119.7
C8—C9—H9	119.4	C28—C27—H27	119.7
C9—C10—C11	119.1 (6)	C29—C28—C27	118.8 (7)
C9—C10—H10	120.5	C29—C28—H28	120.6
C11—C10—H10	120.5	C27—C28—H28	120.6
C12—C11—C10	120.8 (6)	C28—C29—C30	121.6 (7)
C12—C11—H11	119.6	C28—C29—H29	119.2
C10—C11—H11	119.6	C30—C29—H29	119.2
C11—C12—C7	121.0 (6)	C29—C30—C25	119.2 (7)
C11—C12—H12	119.5	C29—C30—H30	120.4
C7—C12—H12	119.5	C25—C30—H30	120.4
C18—C13—C14	117.4 (6)	C36—C31—C32	116.5 (6)
C18—C13—Si1	123.0 (5)	C36—C31—Si2	123.1 (5)
C14—C13—Si1	119.5 (5)	C32—C31—Si2	120.3 (5)
C15—C14—C13	121.1 (6)	C33—C32—C31	121.8 (7)
C15—C14—H14	119.5	C33—C32—H32	119.1
C13—C14—H14	119.5	C31—C32—H32	119.1
C14—C15—C16	119.8 (6)	C34—C33—C32	120.8 (7)
C14—C15—H15	120.1	C34—C33—H33	119.6
C16—C15—H15	120.1	C32—C33—H33	119.6
C17—C16—C15	117.9 (7)	C33—C34—C35	119.9 (7)
C17—C16—H16	121.1	C33—C34—H34	120.0
C15—C16—H16	121.1	C35—C34—H34	120.0
C16—C17—C18	124.5 (8)	C36—C35—C34	117.9 (6)
C16—C17—H17	117.7	C36—C35—H35	121.1
C18—C17—H17	117.7	C34—C35—H35	121.1
C17—C18—C13	119.3 (7)	C35—C36—C31	123.1 (6)
C17—C18—H18	120.3	C35—C36—H36	118.5
C13—C18—H18	120.3	C31—C36—H36	118.5

C13—Si1—C1—C6	−50.7 (6)	C31—Si2—C19—C24	67.8 (6)
C7—Si1—C1—C6	74.9 (6)	C25—Si2—C19—C24	−168.1 (5)
Br1—Si1—C1—C6	−168.4 (5)	Br2—Si2—C19—C24	−50.1 (6)
C13—Si1—C1—C2	129.0 (5)	C31—Si2—C19—C20	−113.1 (5)
C7—Si1—C1—C2	−105.5 (5)	C25—Si2—C19—C20	10.9 (6)
Br1—Si1—C1—C2	11.2 (6)	Br2—Si2—C19—C20	129.0 (5)
C6—C1—C2—C3	−0.1 (10)	C24—C19—C20—C21	−0.4 (10)
Si1—C1—C2—C3	−179.8 (5)	Si2—C19—C20—C21	−179.5 (5)
C1—C2—C3—C4	−0.8 (11)	C19—C20—C21—C22	1.3 (11)
C2—C3—C4—C5	0.2 (12)	C20—C21—C22—C23	−0.7 (11)
C3—C4—C5—C6	1.2 (13)	C21—C22—C23—C24	−0.9 (11)
C4—C5—C6—C1	−2.1 (13)	C22—C23—C24—C19	1.8 (12)
C2—C1—C6—C5	1.6 (11)	C20—C19—C24—C23	−1.2 (10)
Si1—C1—C6—C5	−178.8 (7)	Si2—C19—C24—C23	177.9 (6)
C13—Si1—C7—C12	−66.3 (6)	C31—Si2—C25—C26	49.0 (6)
C1—Si1—C7—C12	169.5 (5)	C19—Si2—C25—C26	−77.8 (5)
Br1—Si1—C7—C12	51.8 (6)	Br2—Si2—C25—C26	165.4 (4)
C13—Si1—C7—C8	113.1 (5)	C31—Si2—C25—C30	−131.0 (5)
C1—Si1—C7—C8	−11.1 (6)	C19—Si2—C25—C30	102.3 (5)
Br1—Si1—C7—C8	−128.9 (5)	Br2—Si2—C25—C30	−14.5 (6)
C12—C7—C8—C9	−0.1 (10)	C30—C25—C26—C27	−0.3 (10)
Si1—C7—C8—C9	−179.5 (5)	Si2—C25—C26—C27	179.8 (6)
C7—C8—C9—C10	−0.2 (11)	C25—C26—C27—C28	−0.1 (11)
C8—C9—C10—C11	0.1 (12)	C26—C27—C28—C29	0.3 (11)
C9—C10—C11—C12	0.4 (12)	C27—C28—C29—C30	−0.2 (11)
C10—C11—C12—C7	−0.7 (12)	C28—C29—C30—C25	−0.2 (10)
C8—C7—C12—C11	0.6 (10)	C26—C25—C30—C29	0.4 (9)
Si1—C7—C12—C11	180.0 (6)	Si2—C25—C30—C29	−179.6 (5)
C7—Si1—C13—C18	−3.8 (7)	C25—Si2—C31—C36	−119.2 (5)
C1—Si1—C13—C18	122.1 (6)	C19—Si2—C31—C36	6.2 (7)
Br1—Si1—C13—C18	−120.5 (5)	Br2—Si2—C31—C36	123.6 (5)
C7—Si1—C13—C14	177.9 (5)	C25—Si2—C31—C32	57.7 (6)
C1—Si1—C13—C14	−56.2 (6)	C19—Si2—C31—C32	−176.9 (5)
Br1—Si1—C13—C14	61.2 (5)	Br2—Si2—C31—C32	−59.4 (5)
C18—C13—C14—C15	−1.3 (10)	C36—C31—C32—C33	0.5 (10)
Si1—C13—C14—C15	177.1 (5)	Si2—C31—C32—C33	−176.7 (5)
C13—C14—C15—C16	0.5 (10)	C31—C32—C33—C34	0.7 (11)
C14—C15—C16—C17	−0.1 (10)	C32—C33—C34—C35	−1.1 (11)
C15—C16—C17—C18	0.7 (11)	C33—C34—C35—C36	0.2 (11)
C16—C17—C18—C13	−1.6 (11)	C34—C35—C36—C31	1.0 (11)
C14—C13—C18—C17	1.9 (10)	C32—C31—C36—C35	−1.3 (10)
Si1—C13—C18—C17	−176.5 (5)	Si2—C31—C36—C35	175.8 (6)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅BrSi
M_r	339.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	18.6306 (13), 9.6160 (4), 18.3618 (13)
β (°)	107.174 (5)
V (Å³)	3142.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.68
Crystal size (mm)	0.31 × 0.25 × 0.19

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.491, 0.630
No. of measured, independent and observed [I > 2σ(I)] reflections	47324, 6141, 4739
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.094, 0.288, 1.16
No. of reflections	6141
No. of parameters	362
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.34, −2.22

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008), PLATON (Spek, 2003).

References

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Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar