organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Bromo­tri­phenyl­silane

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[Lerner, H.-W., Scholz, S. & Bolte, M. (2001). Z. Anorg. Allg. Chem. 627, 1638-1642.], 2005[Lerner, H.-W., Wiberg, N. & Bats, J. W. (2005). J. Organomet. Chem. 690, 3898-3907.], 2006[Lerner, H.-W., Bolte, M., Schurz, K., Wiberg, N., Baum, G., Fenske, D., Bats, J. W. & Wagner, M. (2006). Eur. J. Inorg. Chem. pp. 4998-5005.]); Lobkovskii et al. (1981[Lobkovskii, E. B., Fokin, V. N. & Semenenko, K. N. (1981). Zh. Strukt. Khim. 22, 152-155.]).

[Scheme 1]

Experimental

Crystal data
  • C18H15BrSi

  • Mr = 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[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.490, Tmax = 0.630

  • 47324 measured reflections

  • 6141 independent reflections

  • 4739 reflections with I > 2σ(I)

  • Rint = 0.073

Refinement
  • R[F2 > 2σ(F2)] = 0.094

  • wR(F2) = 0.288

  • S = 1.16

  • 6141 reflections

  • 362 parameters

  • H-atom parameters constrained

  • Δρmax = 2.34 e Å−3

  • Δρmin = −2.22 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


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.

Refinement top

H atoms were geometrically positioned and refined using a riding model with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] and with C—H = 0.95 Å. The final difference map had residual electron density which was located in the center of the phenyl ring C31-C36 and was meaningless.

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
[Figure 1] 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.
[Figure 2] Fig. 2. Reaction scheme.
Bromotriphenylsilane top
Crystal data top
C18H15BrSiF(000) = 1376
Mr = 339.30Dx = 1.434 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 32075 reflections
a = 18.6306 (13) Åθ = 2.4–26.3°
b = 9.6160 (4) ŵ = 2.68 mm1
c = 18.3618 (13) ÅT = 173 K
β = 107.174 (5)°Block, colourless
V = 3142.9 (3) Å30.31 × 0.25 × 0.19 mm
Z = 8
Data collection top
Stoe IPDSII two-circle
diffractometer
6141 independent reflections
Radiation source: fine-focus sealed tube4739 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
ω scansθmax = 26.1°, θmin = 2.3°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 2221
Tmin = 0.491, Tmax = 0.630k = 011
47324 measured reflectionsl = 022
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.094Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.288H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
6141 reflections(Δ/σ)max < 0.001
362 parametersΔρmax = 2.34 e Å3
0 restraintsΔρmin = 2.22 e Å3
Crystal data top
C18H15BrSiV = 3142.9 (3) Å3
Mr = 339.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 18.6306 (13) ŵ = 2.68 mm1
b = 9.6160 (4) ÅT = 173 K
c = 18.3618 (13) Å0.31 × 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)
Tmin = 0.491, Tmax = 0.630Rint = 0.073
47324 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0940 restraints
wR(F2) = 0.288H-atom parameters constrained
S = 1.16Δρmax = 2.34 e Å3
6141 reflectionsΔρmin = 2.22 e Å3
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
xyzUiso*/Ueq
Br10.40043 (4)0.50324 (9)0.36669 (5)0.0513 (3)
Si10.44440 (9)0.32247 (18)0.31491 (10)0.0287 (4)
C10.4064 (3)0.3378 (6)0.2089 (4)0.0297 (12)
C20.3696 (4)0.4572 (7)0.1712 (4)0.0384 (15)
H20.36340.53540.20030.046*
C30.3425 (4)0.4625 (9)0.0928 (5)0.0472 (18)
H30.31730.54360.06850.057*
C40.3518 (5)0.3503 (9)0.0492 (4)0.051 (2)
H40.33320.35420.00480.061*
C50.3888 (5)0.2303 (9)0.0855 (4)0.053 (2)
H50.39630.15340.05600.064*
C60.4143 (4)0.2251 (8)0.1642 (4)0.0425 (16)
H60.43780.14270.18840.051*
C70.5489 (3)0.3357 (6)0.3495 (4)0.0304 (13)
C80.5925 (3)0.3310 (7)0.2984 (4)0.0314 (13)
H80.56890.32170.24520.038*
C90.6711 (4)0.3402 (8)0.3269 (4)0.0421 (16)
H90.70040.33670.29240.051*
C100.7064 (4)0.3543 (8)0.4039 (4)0.0426 (16)
H100.75960.36060.42250.051*
C110.6628 (4)0.3593 (8)0.4542 (4)0.0402 (15)
H110.68670.36950.50730.048*
C120.5858 (4)0.3494 (8)0.4276 (4)0.0370 (15)
H120.55730.35190.46270.044*
C130.4096 (3)0.1588 (7)0.3471 (4)0.0312 (13)
C140.3318 (3)0.1342 (7)0.3281 (4)0.0327 (13)
H140.29770.20320.30120.039*
C150.3040 (4)0.0106 (9)0.3482 (4)0.0431 (17)
H150.25130.00480.33470.052*
C160.3533 (4)0.0902 (7)0.3881 (4)0.0382 (15)
H160.33540.17540.40240.046*
C170.4277 (5)0.0635 (8)0.4059 (4)0.0456 (18)
H170.46140.13310.43270.055*
C180.4574 (4)0.0556 (7)0.3882 (4)0.0355 (14)
H180.51030.06890.40360.043*
Br20.09145 (4)0.23720 (9)0.11290 (5)0.0511 (3)
Si20.05044 (9)0.06392 (18)0.17217 (10)0.0290 (4)
C190.0543 (3)0.0792 (6)0.1436 (4)0.0301 (12)
C200.0925 (3)0.0806 (7)0.1995 (3)0.0310 (13)
H200.06500.07290.25190.037*
C210.1708 (4)0.0932 (8)0.1780 (4)0.0419 (16)
H210.19630.09210.21580.050*
C220.2112 (4)0.1073 (7)0.1022 (4)0.0375 (14)
H220.26430.11690.08790.045*
C230.1737 (4)0.1074 (8)0.0466 (4)0.0404 (15)
H230.20140.11830.00560.048*
C240.0975 (4)0.0918 (8)0.0668 (4)0.0377 (15)
H240.07310.08940.02810.045*
C250.0929 (3)0.0861 (6)0.2773 (4)0.0291 (12)
C260.0895 (4)0.0262 (7)0.3249 (4)0.0371 (14)
H260.06620.11060.30320.044*
C270.1195 (5)0.0154 (9)0.4025 (4)0.0481 (18)
H270.11690.09240.43410.058*
C280.1542 (4)0.1087 (9)0.4358 (4)0.0438 (17)
H280.17470.11630.48960.053*
C290.1577 (4)0.2189 (8)0.3892 (4)0.0414 (16)
H290.18120.30280.41130.050*
C300.1278 (4)0.2103 (7)0.3101 (4)0.0373 (14)
H300.13090.28730.27880.045*
C310.0848 (3)0.1019 (7)0.1422 (3)0.0315 (13)
C320.1619 (4)0.1250 (8)0.1564 (4)0.0355 (14)
H320.19620.05300.17910.043*
C330.1895 (4)0.2494 (9)0.1384 (4)0.0460 (17)
H330.24210.26120.14820.055*
C340.1420 (4)0.3557 (8)0.1065 (4)0.0428 (16)
H340.16170.44140.09520.051*
C350.0630 (4)0.3379 (8)0.0904 (4)0.0444 (17)
H350.02910.41060.06800.053*
C360.0370 (4)0.2111 (7)0.1083 (4)0.0360 (14)
H360.01560.19780.09690.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0467 (5)0.0495 (5)0.0644 (5)0.0007 (3)0.0268 (4)0.0178 (4)
Si10.0234 (8)0.0314 (9)0.0324 (8)0.0019 (6)0.0098 (6)0.0012 (7)
C10.020 (3)0.028 (3)0.041 (3)0.003 (2)0.009 (2)0.001 (3)
C20.028 (3)0.035 (3)0.051 (4)0.000 (3)0.010 (3)0.009 (3)
C30.034 (4)0.049 (4)0.052 (4)0.006 (3)0.004 (3)0.017 (3)
C40.054 (4)0.061 (5)0.029 (3)0.020 (4)0.001 (3)0.014 (3)
C50.073 (6)0.051 (5)0.034 (4)0.015 (4)0.013 (4)0.009 (3)
C60.051 (4)0.035 (4)0.041 (4)0.001 (3)0.013 (3)0.004 (3)
C70.022 (3)0.032 (3)0.036 (3)0.002 (2)0.007 (2)0.002 (2)
C80.027 (3)0.034 (3)0.035 (3)0.004 (2)0.012 (2)0.002 (3)
C90.033 (3)0.050 (4)0.051 (4)0.000 (3)0.023 (3)0.008 (3)
C100.029 (3)0.049 (4)0.049 (4)0.006 (3)0.010 (3)0.001 (3)
C110.033 (3)0.044 (4)0.038 (3)0.003 (3)0.002 (3)0.002 (3)
C120.030 (3)0.049 (4)0.033 (3)0.008 (3)0.011 (3)0.004 (3)
C130.029 (3)0.032 (3)0.033 (3)0.004 (2)0.010 (2)0.004 (2)
C140.026 (3)0.039 (3)0.033 (3)0.002 (3)0.008 (2)0.004 (3)
C150.030 (3)0.061 (5)0.040 (4)0.011 (3)0.012 (3)0.004 (3)
C160.047 (4)0.029 (3)0.045 (4)0.005 (3)0.024 (3)0.005 (3)
C170.053 (4)0.050 (4)0.046 (4)0.024 (4)0.033 (3)0.018 (3)
C180.026 (3)0.041 (4)0.041 (3)0.003 (3)0.013 (3)0.003 (3)
Br20.0459 (5)0.0498 (5)0.0634 (5)0.0038 (3)0.0250 (4)0.0172 (4)
Si20.0226 (8)0.0325 (9)0.0340 (8)0.0000 (6)0.0120 (6)0.0026 (7)
C190.027 (3)0.031 (3)0.034 (3)0.001 (2)0.013 (2)0.000 (2)
C200.027 (3)0.039 (3)0.027 (3)0.001 (2)0.009 (2)0.003 (2)
C210.032 (3)0.057 (4)0.041 (4)0.002 (3)0.017 (3)0.007 (3)
C220.029 (3)0.037 (4)0.047 (4)0.002 (3)0.012 (3)0.000 (3)
C230.037 (3)0.051 (4)0.032 (3)0.002 (3)0.008 (3)0.005 (3)
C240.038 (3)0.045 (4)0.034 (3)0.003 (3)0.017 (3)0.006 (3)
C250.019 (3)0.026 (3)0.043 (3)0.000 (2)0.010 (2)0.005 (2)
C260.043 (4)0.031 (3)0.037 (3)0.005 (3)0.011 (3)0.006 (3)
C270.055 (5)0.050 (4)0.039 (4)0.013 (4)0.014 (3)0.002 (3)
C280.037 (4)0.056 (4)0.034 (3)0.011 (3)0.003 (3)0.012 (3)
C290.033 (3)0.040 (4)0.046 (4)0.004 (3)0.005 (3)0.013 (3)
C300.031 (3)0.033 (3)0.047 (4)0.000 (3)0.010 (3)0.004 (3)
C310.025 (3)0.040 (3)0.031 (3)0.003 (3)0.011 (2)0.002 (3)
C320.030 (3)0.047 (4)0.033 (3)0.005 (3)0.013 (2)0.001 (3)
C330.042 (4)0.059 (5)0.038 (4)0.015 (3)0.014 (3)0.005 (3)
C340.051 (4)0.043 (4)0.041 (4)0.007 (3)0.023 (3)0.005 (3)
C350.050 (4)0.039 (4)0.048 (4)0.014 (3)0.020 (3)0.014 (3)
C360.036 (3)0.037 (3)0.039 (3)0.001 (3)0.019 (3)0.001 (3)
Geometric parameters (Å, º) top
Br1—Si12.2486 (18)Br2—Si22.2440 (18)
Si1—C131.863 (6)Si2—C311.861 (7)
Si1—C71.865 (6)Si2—C251.870 (7)
Si1—C11.870 (7)Si2—C191.870 (6)
C1—C61.393 (10)C19—C241.407 (9)
C1—C21.409 (9)C19—C201.412 (8)
C2—C31.379 (11)C20—C211.399 (9)
C2—H20.9500C20—H200.9500
C3—C41.384 (13)C21—C221.379 (10)
C3—H30.9500C21—H210.9500
C4—C51.406 (12)C22—C231.398 (10)
C4—H40.9500C22—H220.9500
C5—C61.383 (11)C23—C241.365 (10)
C5—H50.9500C23—H230.9500
C6—H60.9500C24—H240.9500
C7—C121.403 (9)C25—C261.401 (9)
C7—C81.412 (9)C25—C301.408 (9)
C8—C91.404 (9)C26—C271.373 (10)
C8—H80.9500C26—H260.9500
C9—C101.379 (11)C27—C281.408 (11)
C9—H90.9500C27—H270.9500
C10—C111.400 (10)C28—C291.376 (12)
C10—H100.9500C28—H280.9500
C11—C121.376 (9)C29—C301.395 (10)
C11—H110.9500C29—H290.9500
C12—H120.9500C30—H300.9500
C13—C181.397 (9)C31—C361.398 (9)
C13—C141.407 (8)C31—C321.401 (9)
C14—C151.389 (10)C32—C331.380 (10)
C14—H140.9500C32—H320.9500
C15—C161.387 (10)C33—C341.365 (11)
C15—H150.9500C33—H330.9500
C16—C171.351 (10)C34—C351.424 (11)
C16—H160.9500C34—H340.9500
C17—C181.353 (10)C35—C361.387 (10)
C17—H170.9500C35—H350.9500
C18—H180.9500C36—H360.9500
C13—Si1—C7112.1 (3)C31—Si2—C25109.0 (3)
C13—Si1—C1109.7 (3)C31—Si2—C19113.9 (3)
C7—Si1—C1112.6 (3)C25—Si2—C19111.6 (3)
C13—Si1—Br1108.3 (2)C31—Si2—Br2107.3 (2)
C7—Si1—Br1106.1 (2)C25—Si2—Br2108.4 (2)
C1—Si1—Br1107.8 (2)C19—Si2—Br2106.3 (2)
C6—C1—C2117.7 (6)C24—C19—C20117.7 (6)
C6—C1—Si1118.6 (5)C24—C19—Si2122.0 (5)
C2—C1—Si1123.7 (5)C20—C19—Si2120.3 (5)
C3—C2—C1121.2 (7)C21—C20—C19120.2 (6)
C3—C2—H2119.4C21—C20—H20119.9
C1—C2—H2119.4C19—C20—H20119.9
C2—C3—C4120.3 (7)C22—C21—C20120.4 (6)
C2—C3—H3119.8C22—C21—H21119.8
C4—C3—H3119.8C20—C21—H21119.8
C3—C4—C5119.6 (7)C21—C22—C23119.7 (6)
C3—C4—H4120.2C21—C22—H22120.2
C5—C4—H4120.2C23—C22—H22120.2
C6—C5—C4119.6 (8)C24—C23—C22120.4 (6)
C6—C5—H5120.2C24—C23—H23119.8
C4—C5—H5120.2C22—C23—H23119.8
C5—C6—C1121.6 (7)C23—C24—C19121.6 (6)
C5—C6—H6119.2C23—C24—H24119.2
C1—C6—H6119.2C19—C24—H24119.2
C12—C7—C8118.5 (5)C26—C25—C30119.1 (6)
C12—C7—Si1120.2 (5)C26—C25—Si2118.2 (5)
C8—C7—Si1121.4 (5)C30—C25—Si2122.6 (5)
C7—C8—C9119.5 (6)C27—C26—C25120.6 (7)
C7—C8—H8120.2C27—C26—H26119.7
C9—C8—H8120.2C25—C26—H26119.7
C10—C9—C8121.2 (6)C26—C27—C28120.6 (7)
C10—C9—H9119.4C26—C27—H27119.7
C8—C9—H9119.4C28—C27—H27119.7
C9—C10—C11119.1 (6)C29—C28—C27118.8 (7)
C9—C10—H10120.5C29—C28—H28120.6
C11—C10—H10120.5C27—C28—H28120.6
C12—C11—C10120.8 (6)C28—C29—C30121.6 (7)
C12—C11—H11119.6C28—C29—H29119.2
C10—C11—H11119.6C30—C29—H29119.2
C11—C12—C7121.0 (6)C29—C30—C25119.2 (7)
C11—C12—H12119.5C29—C30—H30120.4
C7—C12—H12119.5C25—C30—H30120.4
C18—C13—C14117.4 (6)C36—C31—C32116.5 (6)
C18—C13—Si1123.0 (5)C36—C31—Si2123.1 (5)
C14—C13—Si1119.5 (5)C32—C31—Si2120.3 (5)
C15—C14—C13121.1 (6)C33—C32—C31121.8 (7)
C15—C14—H14119.5C33—C32—H32119.1
C13—C14—H14119.5C31—C32—H32119.1
C14—C15—C16119.8 (6)C34—C33—C32120.8 (7)
C14—C15—H15120.1C34—C33—H33119.6
C16—C15—H15120.1C32—C33—H33119.6
C17—C16—C15117.9 (7)C33—C34—C35119.9 (7)
C17—C16—H16121.1C33—C34—H34120.0
C15—C16—H16121.1C35—C34—H34120.0
C16—C17—C18124.5 (8)C36—C35—C34117.9 (6)
C16—C17—H17117.7C36—C35—H35121.1
C18—C17—H17117.7C34—C35—H35121.1
C17—C18—C13119.3 (7)C35—C36—C31123.1 (6)
C17—C18—H18120.3C35—C36—H36118.5
C13—C18—H18120.3C31—C36—H36118.5
C13—Si1—C1—C650.7 (6)C31—Si2—C19—C2467.8 (6)
C7—Si1—C1—C674.9 (6)C25—Si2—C19—C24168.1 (5)
Br1—Si1—C1—C6168.4 (5)Br2—Si2—C19—C2450.1 (6)
C13—Si1—C1—C2129.0 (5)C31—Si2—C19—C20113.1 (5)
C7—Si1—C1—C2105.5 (5)C25—Si2—C19—C2010.9 (6)
Br1—Si1—C1—C211.2 (6)Br2—Si2—C19—C20129.0 (5)
C6—C1—C2—C30.1 (10)C24—C19—C20—C210.4 (10)
Si1—C1—C2—C3179.8 (5)Si2—C19—C20—C21179.5 (5)
C1—C2—C3—C40.8 (11)C19—C20—C21—C221.3 (11)
C2—C3—C4—C50.2 (12)C20—C21—C22—C230.7 (11)
C3—C4—C5—C61.2 (13)C21—C22—C23—C240.9 (11)
C4—C5—C6—C12.1 (13)C22—C23—C24—C191.8 (12)
C2—C1—C6—C51.6 (11)C20—C19—C24—C231.2 (10)
Si1—C1—C6—C5178.8 (7)Si2—C19—C24—C23177.9 (6)
C13—Si1—C7—C1266.3 (6)C31—Si2—C25—C2649.0 (6)
C1—Si1—C7—C12169.5 (5)C19—Si2—C25—C2677.8 (5)
Br1—Si1—C7—C1251.8 (6)Br2—Si2—C25—C26165.4 (4)
C13—Si1—C7—C8113.1 (5)C31—Si2—C25—C30131.0 (5)
C1—Si1—C7—C811.1 (6)C19—Si2—C25—C30102.3 (5)
Br1—Si1—C7—C8128.9 (5)Br2—Si2—C25—C3014.5 (6)
C12—C7—C8—C90.1 (10)C30—C25—C26—C270.3 (10)
Si1—C7—C8—C9179.5 (5)Si2—C25—C26—C27179.8 (6)
C7—C8—C9—C100.2 (11)C25—C26—C27—C280.1 (11)
C8—C9—C10—C110.1 (12)C26—C27—C28—C290.3 (11)
C9—C10—C11—C120.4 (12)C27—C28—C29—C300.2 (11)
C10—C11—C12—C70.7 (12)C28—C29—C30—C250.2 (10)
C8—C7—C12—C110.6 (10)C26—C25—C30—C290.4 (9)
Si1—C7—C12—C11180.0 (6)Si2—C25—C30—C29179.6 (5)
C7—Si1—C13—C183.8 (7)C25—Si2—C31—C36119.2 (5)
C1—Si1—C13—C18122.1 (6)C19—Si2—C31—C366.2 (7)
Br1—Si1—C13—C18120.5 (5)Br2—Si2—C31—C36123.6 (5)
C7—Si1—C13—C14177.9 (5)C25—Si2—C31—C3257.7 (6)
C1—Si1—C13—C1456.2 (6)C19—Si2—C31—C32176.9 (5)
Br1—Si1—C13—C1461.2 (5)Br2—Si2—C31—C3259.4 (5)
C18—C13—C14—C151.3 (10)C36—C31—C32—C330.5 (10)
Si1—C13—C14—C15177.1 (5)Si2—C31—C32—C33176.7 (5)
C13—C14—C15—C160.5 (10)C31—C32—C33—C340.7 (11)
C14—C15—C16—C170.1 (10)C32—C33—C34—C351.1 (11)
C15—C16—C17—C180.7 (11)C33—C34—C35—C360.2 (11)
C16—C17—C18—C131.6 (11)C34—C35—C36—C311.0 (11)
C14—C13—C18—C171.9 (10)C32—C31—C36—C351.3 (10)
Si1—C13—C18—C17176.5 (5)Si2—C31—C36—C35175.8 (6)

Experimental details

Crystal data
Chemical formulaC18H15BrSi
Mr339.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)18.6306 (13), 9.6160 (4), 18.3618 (13)
β (°) 107.174 (5)
V3)3142.9 (3)
Z8
Radiation typeMo Kα
µ (mm1)2.68
Crystal size (mm)0.31 × 0.25 × 0.19
Data collection
DiffractometerStoe IPDSII two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.491, 0.630
No. of measured, independent and
observed [I > 2σ(I)] reflections
47324, 6141, 4739
Rint0.073
(sin θ/λ)max1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.094, 0.288, 1.16
No. of reflections6141
No. of parameters362
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationLerner, H.-W., Bolte, M., Schurz, K., Wiberg, N., Baum, G., Fenske, D., Bats, J. W. & Wagner, M. (2006). Eur. J. Inorg. Chem. pp. 4998–5005.  Web of Science CSD CrossRef Google Scholar
First citationLerner, H.-W., Scholz, S. & Bolte, M. (2001). Z. Anorg. Allg. Chem. 627, 1638–1642.  Web of Science CSD CrossRef CAS Google Scholar
First citationLerner, H.-W., Wiberg, N. & Bats, J. W. (2005). J. Organomet. Chem. 690, 3898–3907.  Web of Science CSD CrossRef CAS Google Scholar
First citationLobkovskii, E. B., Fokin, V. N. & Semenenko, K. N. (1981). Zh. Strukt. Khim. 22, 152–155.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar

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