organic compounds
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
The title compound, C18H15BrSi, crystallizes with two almost identical molecules (r.m.s. deviation for all non-H atoms = 0.074 Å) in the It is isomorphous with chlorotriphenylsilane.
Related literature
For related literature, see: Lerner et al. (2001, 2005, 2006); Lobkovskii et al. (1981).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2001); cell 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
10.1107/S1600536808010520/pv2078sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010520/pv2078Isup2.hkl
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.
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.
Data collection: X-AREA (Stoe & Cie, 2001); cell
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).C18H15BrSi | F(000) = 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 = 2.4–26.3° |
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 |
Stoe IPDSII two-circle diffractometer | 6141 independent reflections |
Radiation source: fine-focus sealed tube | 4739 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
ω scans | θmax = 26.1°, θmin = 2.3° |
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 |
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(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
6141 reflections | (Δ/σ)max < 0.001 |
362 parameters | Δρmax = 2.34 e Å−3 |
0 restraints | Δρmin = −2.22 e Å−3 |
C18H15BrSi | V = 3142.9 (3) Å3 |
Mr = 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)° |
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 = 0.630 | Rint = 0.073 |
47324 measured reflections |
R[F2 > 2σ(F2)] = 0.094 | 0 restraints |
wR(F2) = 0.288 | H-atom parameters constrained |
S = 1.16 | Δρmax = 2.34 e Å−3 |
6141 reflections | Δρmin = −2.22 e Å−3 |
362 parameters |
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. |
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* |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.491, 0.630 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 47324, 6141, 4739 |
Rint | 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 |
Δρmax, Δρmin (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
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
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. Web of Science CSD CrossRef Google Scholar
Lerner, H.-W., Scholz, S. & Bolte, M. (2001). Z. Anorg. Allg. Chem. 627, 1638–1642. Web of Science CSD CrossRef CAS Google Scholar
Lerner, H.-W., Wiberg, N. & Bats, J. W. (2005). J. Organomet. Chem. 690, 3898–3907. Web of Science CSD CrossRef CAS Google Scholar
Lobkovskii, E. B., Fokin, V. N. & Semenenko, K. N. (1981). Zh. Strukt. Khim. 22, 152–155. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
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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).