Acta Crystallographica Section E: Structure Reports Online

Acta Crystallogr Sect E Struct Rep Online. 64(Pt 5): o880-o880

Bromotriphenylsilane

Hannah Steinerta, Hans-Wolfram Lernera, Michael Boltea*

a. Institut 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

© Steinert et al. 2008

DOI: 10.1107/S1600536808010520

Published online: 23 April 2008

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

Δρmax = 2.34 e Å⁻³

Δρmin = −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

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2078).

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.

Refinement

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.

Figures

Fig. 1.View larger versionFig. 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.View larger versionFig. 2. Reaction scheme.

Crystal data

See full table

Data collection

See full table

Refinement

See full table

Special details

See full table

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

See full table

Atomic displacement parameters (Å²)

See full table

Geometric parameters (Å, °)

See full table

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References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

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.

Lerner, H.-W., Scholz, S. & Bolte, M. (2001). Z. Anorg. Allg. Chem.627, 1638–1642.

Lerner, H.-W., Wiberg, N. & Bats, J. W. (2005). J. Organomet. Chem.690, 3898–3907.

Lobkovskii, E. B., Fokin, V. N. & Semenenko, K. N. (1981). Zh. Strukt. Khim.22, 152–155.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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

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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.

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Fig. 2.

Reaction scheme.

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C₁₈H₁₅BrSi | F₀₀₀ = 1376
Mr = 339.30 | Dx = 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 = 2.4–26.3º
b = 9.6160 (4) Å | µ = 2.68 mm⁻¹
c = 18.3618 (13) Å | T = 173 (2) K
β = 107.174 (5)º | Block, colourless
V = 3142.9 (3) Å³ | 0.31 × 0.25 × 0.19 mm
Z = 8 |

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Stoe IPDSII two-circle diffractometer | 6141 independent reflections
Radiation source: fine-focus sealed tube | 4739 reflections with I > 2σ(I)
Monochromator: graphite | Rint = 0.073
T = 173(2) K | θmax = 26.1º
ω scans | θmin = 2.3º
Absorption correction: multi-scan(MULABS; Spek, 2003; Blessing, 1995) | h = −22→21
Tmin = 0.491, Tmax = 0.630 | k = 0→11
47324 measured reflections | l = 0→22

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Refinement on F² | Secondary atom site location: difference Fourier map
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.094 | H-atom parameters constrained
wR(F²) = 0.288 |   w = 1/[σ²(Fo²) + (0.2P)²] where P = (Fo² + 2Fc²)/3
S = 1.16 | (Δ/σ)max < 0.001
6141 reflections | Δρmax = 2.34 e Å⁻³
362 parameters | Δρmin = −2.22 e Å⁻³
Primary atom site location: structure-invariant direct methods | Extinction correction: none

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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.

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| x | y | z | Uiso*/Ueq |
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* |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
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)

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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)

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