organic papers
Acta Cryst.(2005). E61, o4047–o4048 doi:10.1107/S1600536805035853 Klapo¨tkeet al. C
25H33ISi3Te
o4047
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
Tris(dimethylphenylsilyl)methanetellurenyl
iodide
Thomas M. Klapo¨tke,* Burkhard Krumm and Ingo Schwab
Department of Chemistry and Biochemistry, Ludwig-Maximilian University, Butenandtstrasse 5–13 (Haus D), D-81377 Munich, Germany
Correspondence e-mail: tmk@cup.uni-muenchen.de
Key indicators
Single-crystal X-ray study T= 200 K
Mean(C–C) = 0.005 A˚ Rfactor = 0.031 wRfactor = 0.073
Data-to-parameter ratio = 22.5
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
The crystal structure of TpsiTeI [Tpsi = tris(dimethylphenyl-silyl)methyl], C25H33ISi3Te, exhibits discrete molecules
without Te I, Te Te or I I intermolecular contacts. TpsiTeI was prepared by cleavage of its parent ditellane with iodine, and represents a kinetically stabilized alkanetellurenyl iodide with a very bulky substituent. The molecule possesses an angular C—Te—I arrangement [110.53 (7)] with a Te—I single bond [2.7178 (7) A˚ ].
Comment
During the course of our investigations of organotellurenyl azides (Klapo¨tke, Krumm, No¨thet al., 2005), we were able to determine the crystal structure of the benzenetellurenyl iodide Mes*TeI (Klapo¨tke, Krumm & Schwab, 2005) and the alkanetellurenyl derivative TpsiTeI, (I) (Fig. 1).
As can be seen, the crystal structures of both compounds feature kinetically stabilized monomers; neither the Te nor the I atoms show intermolecular secondary interactions.
The Te—I bonds in (I) and Mes*TeI (Klapo¨tke, Krumm & Schwab, 2005) are very similar [2.7178 (7) versus
2.7181 (6) A˚ ]; however, a large difference is found in the C— Te—I angles [110.53 (7) versus 95.75 (8)]. This can be attributed to the increased bulkiness of the trisilylmethyl compared to the 2,4,6-tri-tert-butylphenyl substituent. In between these two, the steric influence of the terphenyl derivative 2,6-Trip2C6H3TeI [Te—I = 2.617 (1) A˚ and C—Te—
I = 106.2 (2)] can be estimated (Klapo¨tke, Krumm, No¨thet al.
2005).
Experimental
To a green solution of 0.28 mmol bis[tris(phenyldimethylsilyl)methyl] ditellane (TpsiTe)2(Klapo¨tke, Krumm, No¨thet al. 2005) in 10 ml of
benzene were added 0.23 mmol of neat iodine. After stirring for 1 h at ambient temperature, the dark-blue–green solution was evaporated in vacuo. Recrystallization at 277 K from n-pentane yielded dark-green blocks of TpsiTeI after several days.
Crystal data
C25H33ISi3Te Mr= 672.28
Monoclinic,P21=c a= 16.076 (3) A˚ b= 17.248 (3) A˚ c= 9.995 (2) A˚
= 101.18 (3)
V= 2718.9 (9) A˚3 Z= 4
Dx= 1.642 Mg m
3 MoKradiation Cell parameters from 6375
reflections
= 3.1–27.5
= 2.37 mm1 T= 200 (2) K Block, dark green 0.080.050.04 mm
Data collection
Nonius KappaCCD diffractometer
’and!scans
Absorption correction: none 12153 measured reflections 6229 independent reflections 4995 reflections withI> 2(I)
Rint= 0.023
max= 27.5 h=20!20 k=22!21 l=12!12
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.031 wR(F2) = 0.073 S= 1.07 6229 reflections 277 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0278P)2 + 1.9905P]
whereP= (Fo 2
+ 2Fc 2
)/3 (/)max= 0.002
max= 0.79 e A˚
3 min=1.35 e A˚
[image:2.610.316.564.67.374.2]3
Table 1
Selected geometric parameters (A˚ ,).
I1—Te1 2.7178 (7) Te1—C1 2.212 (3) Si1—C2 1.869 (3) Si1—C3 1.870 (3) Si1—C4 1.898 (3) Si1—C1 1.942 (3) Si2—C11 1.865 (3)
Si2—C10 1.870 (3) Si2—C12 1.888 (3) Si2—C1 1.917 (3) Si3—C18 1.866 (3) Si3—C19 1.880 (3) Si3—C20 1.892 (3) Si3—C1 1.925 (3)
C1—Te1—I1 110.53 (7)
H atoms were placed in geometrically idealized positions (C—H = 0.95 A˚ and 0.98 A˚ for aromatic CH and methyl groups, respectively) and constrained to ride on their parent atoms, with Uiso(H) =
1.2Ueq(C). The methyl groups were allowed to rotate but not to tip.
The highest residual electron density is located 0.96 A˚ from Te1 and the deepest hole is located 0.75 A˚ from I1.
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:DIAMOND(Brandenburg, 1996); software used to prepare material for publication:SHELXL97.
The authors thank Dr P. Mayer for data collection and the Ludwig–Maximilian University for financial support of this work.
References
Brandenburg, K. (1996).DIAMOND. University of Bonn, Germany. Klapo¨tke, T. M., Krumm, B., No¨th, H., Galvez-Ruiz, J.-C., Polborn, K., Schwab,
I. & Suter, M. (2005).Inorg. Chem.44, 5254–5265.
Klapo¨tke, T. M., Krumm, B. & Schwab, I. (2005).Acta Cryst. E61, o4045– o4046.
Nonius (2000).COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Figure 1
supporting information
sup-1 Acta Cryst. (2005). E61, o4047–o4048
supporting information
Acta Cryst. (2005). E61, o4047–o4048 [https://doi.org/10.1107/S1600536805035853]
Tris(dimethylphenylsilyl)methanetellurenyl iodide
Thomas M. Klap
ö
tke, Burkhard Krumm and Ingo Schwab
Tris(dimethylphenylsilyl)methanetellurenyl iodide
Crystal data
C25H33ISi3Te
Mr = 672.28
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 16.076 (3) Å
b = 17.248 (3) Å
c = 9.995 (2) Å
β = 101.18 (3)°
V = 2718.9 (9) Å3
Z = 4
F(000) = 1320
Dx = 1.642 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6375 reflections
θ = 3.1–27.5°
µ = 2.37 mm−1
T = 200 K Block, dark green 0.08 × 0.05 × 0.04 mm
Data collection
Nonius KappaCCD diffractometer
Radiation source: fine-focus sealed tube Vertically mounted graphite crystal
monochromator
Detector resolution: 9 pixels mm-1
φ? ω? scans
12153 measured reflections
6229 independent reflections 4995 reflections with I > 2σ(I)
Rint = 0.023
θmax = 27.5°, θmin = 3.2°
h = −20→20
k = −22→21
l = −12→12
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.031
wR(F2) = 0.073
S = 1.07 6229 reflections 277 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0278P)2 + 1.9905P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.002
Δρmax = 0.79 e Å−3
Δρmin = −1.35 e Å−3
Special details
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)
x y z Uiso*/Ueq
I1 0.284758 (17) 0.587630 (13) 1.10898 (2) 0.05022 (8) Te1 0.332126 (12) 0.578803 (11) 0.862760 (19) 0.03246 (7) Si1 0.35690 (5) 0.47194 (5) 0.62668 (8) 0.02888 (17) Si2 0.16234 (4) 0.49684 (4) 0.67015 (8) 0.02599 (16) Si3 0.28857 (5) 0.38037 (4) 0.85767 (8) 0.03015 (17) C1 0.27788 (16) 0.47408 (15) 0.7510 (3) 0.0248 (5) C2 0.30891 (19) 0.42521 (18) 0.4610 (3) 0.0380 (7)
H2A 0.2922 0.3720 0.4777 0.046*
H2B 0.3505 0.4245 0.4011 0.046*
H2C 0.2588 0.4547 0.4173 0.046*
C3 0.45965 (19) 0.4231 (2) 0.6991 (4) 0.0442 (8)
H3A 0.4496 0.3679 0.7126 0.053*
H3B 0.4845 0.4469 0.7868 0.053*
H3C 0.4988 0.4290 0.6358 0.053*
C4 0.38904 (17) 0.57411 (16) 0.5877 (3) 0.0303 (6) C5 0.4650 (2) 0.6069 (2) 0.6573 (3) 0.0420 (7)
H5A 0.5002 0.5779 0.7269 0.050*
C6 0.4901 (2) 0.6805 (2) 0.6271 (4) 0.0528 (9)
H6A 0.5411 0.7018 0.6778 0.063*
C7 0.4418 (2) 0.7231 (2) 0.5245 (4) 0.0551 (10)
H7A 0.4590 0.7738 0.5046 0.066*
C8 0.3681 (2) 0.69155 (19) 0.4505 (4) 0.0453 (8)
H8A 0.3351 0.7202 0.3780 0.054*
C9 0.34221 (18) 0.61822 (18) 0.4817 (3) 0.0343 (6)
H9A 0.2914 0.5974 0.4297 0.041*
C10 0.10913 (19) 0.40948 (17) 0.5811 (3) 0.0368 (7)
H10A 0.1020 0.3701 0.6487 0.044*
H10B 0.1440 0.3884 0.5195 0.044*
H10C 0.0534 0.4242 0.5284 0.044*
C11 0.09993 (18) 0.52935 (19) 0.7989 (3) 0.0381 (7)
H11A 0.1012 0.4889 0.8682 0.046*
H11B 0.0411 0.5391 0.7538 0.046*
H11C 0.1247 0.5771 0.8426 0.046*
C12 0.14905 (17) 0.57639 (16) 0.5380 (3) 0.0289 (6) C13 0.12082 (17) 0.56005 (18) 0.3996 (3) 0.0333 (6)
H13A 0.1122 0.5075 0.3717 0.040*
C14 0.10502 (19) 0.6179 (2) 0.3018 (3) 0.0432 (8)
H14A 0.0858 0.6050 0.2086 0.052*
C15 0.1174 (2) 0.6949 (2) 0.3409 (4) 0.0482 (9)
supporting information
sup-3 Acta Cryst. (2005). E61, o4047–o4048
C16 0.1442 (2) 0.71287 (19) 0.4762 (4) 0.0463 (8)
H16A 0.1524 0.7656 0.5033 0.056*
C17 0.15953 (19) 0.65457 (17) 0.5739 (3) 0.0373 (7)
H17A 0.1775 0.6682 0.6671 0.045*
C18 0.38399 (19) 0.3821 (2) 0.9977 (3) 0.0433 (8)
H18A 0.4342 0.3948 0.9600 0.052*
H18B 0.3915 0.3310 1.0415 0.052*
H18C 0.3764 0.4213 1.0653 0.052*
C19 0.2935 (2) 0.29505 (17) 0.7424 (3) 0.0408 (7)
H19A 0.2427 0.2943 0.6702 0.049*
H19B 0.2964 0.2470 0.7955 0.049*
H19C 0.3440 0.2994 0.7015 0.049*
C20 0.19685 (18) 0.35774 (16) 0.9447 (3) 0.0327 (6) C21 0.1909 (2) 0.39005 (19) 1.0709 (3) 0.0436 (8)
H21A 0.2332 0.4255 1.1132 0.052*
C22 0.1249 (2) 0.3717 (2) 1.1353 (4) 0.0511 (9)
H22A 0.1223 0.3950 1.2205 0.061*
C23 0.0631 (2) 0.3203 (2) 1.0787 (4) 0.0472 (8)
H23A 0.0170 0.3091 1.1224 0.057*
C24 0.0689 (2) 0.28527 (19) 0.9570 (4) 0.0431 (8)
H24A 0.0274 0.2483 0.9179 0.052*
C25 0.13443 (19) 0.30339 (17) 0.8913 (3) 0.0377 (7)
H25A 0.1373 0.2783 0.8076 0.045*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C17 0.0360 (16) 0.0334 (16) 0.0418 (17) 0.0077 (12) 0.0055 (13) −0.0023 (14) C18 0.0344 (17) 0.0511 (19) 0.0408 (18) 0.0071 (14) −0.0014 (14) 0.0134 (15) C19 0.0436 (18) 0.0301 (15) 0.050 (2) 0.0063 (13) 0.0113 (15) 0.0029 (14) C20 0.0336 (16) 0.0297 (14) 0.0338 (16) 0.0022 (12) 0.0042 (12) 0.0054 (12) C21 0.052 (2) 0.0395 (17) 0.0402 (18) −0.0113 (15) 0.0124 (15) −0.0025 (15) C22 0.059 (2) 0.050 (2) 0.049 (2) −0.0040 (17) 0.0229 (18) −0.0051 (17) C23 0.0422 (19) 0.052 (2) 0.052 (2) −0.0004 (15) 0.0188 (16) 0.0137 (17) C24 0.0352 (17) 0.0426 (18) 0.049 (2) −0.0062 (14) 0.0023 (15) 0.0115 (15) C25 0.0441 (18) 0.0362 (16) 0.0307 (16) −0.0021 (13) 0.0024 (13) 0.0046 (13)
Geometric parameters (Å, º)
I1—Te1 2.7178 (7) C10—H10C 0.9800
Te1—C1 2.212 (3) C11—H11A 0.9800
Si1—C2 1.869 (3) C11—H11B 0.9800
Si1—C3 1.870 (3) C11—H11C 0.9800
Si1—C4 1.898 (3) C12—C17 1.397 (4)
Si1—C1 1.942 (3) C12—C13 1.398 (4)
Si2—C11 1.865 (3) C13—C14 1.386 (4)
Si2—C10 1.870 (3) C13—H13A 0.9500
Si2—C12 1.888 (3) C14—C15 1.387 (5)
Si2—C1 1.917 (3) C14—H14A 0.9500
Si3—C18 1.866 (3) C15—C16 1.373 (5)
Si3—C19 1.880 (3) C15—H15A 0.9500
Si3—C20 1.892 (3) C16—C17 1.390 (4)
Si3—C1 1.925 (3) C16—H16A 0.9500
C2—H2A 0.9800 C17—H17A 0.9500
C2—H2B 0.9800 C18—H18A 0.9800
C2—H2C 0.9800 C18—H18B 0.9800
C3—H3A 0.9800 C18—H18C 0.9800
C3—H3B 0.9800 C19—H19A 0.9800
C3—H3C 0.9800 C19—H19B 0.9800
C4—C9 1.400 (4) C19—H19C 0.9800
C4—C5 1.403 (4) C20—C21 1.399 (5)
C5—C6 1.382 (5) C20—C25 1.401 (4)
C5—H5A 0.9500 C21—C22 1.380 (5)
C6—C7 1.373 (5) C21—H21A 0.9500
C6—H6A 0.9500 C22—C23 1.369 (5)
C7—C8 1.381 (5) C22—H22A 0.9500
C7—H7A 0.9500 C23—C24 1.378 (5)
C8—C9 1.386 (4) C23—H23A 0.9500
C8—H8A 0.9500 C24—C25 1.381 (4)
C9—H9A 0.9500 C24—H24A 0.9500
C10—H10A 0.9800 C25—H25A 0.9500
C10—H10B 0.9800
C1—Te1—I1 110.53 (7) Si2—C10—H10C 109.5
supporting information
sup-5 Acta Cryst. (2005). E61, o4047–o4048
C2—Si1—C4 107.50 (14) H10B—C10—H10C 109.5
C3—Si1—C4 104.01 (14) Si2—C11—H11A 109.5
C2—Si1—C1 111.50 (13) Si2—C11—H11B 109.5
C3—Si1—C1 113.53 (14) H11A—C11—H11B 109.5
C4—Si1—C1 110.59 (12) Si2—C11—H11C 109.5
C11—Si2—C10 108.24 (15) H11A—C11—H11C 109.5
C11—Si2—C12 105.15 (13) H11B—C11—H11C 109.5
C10—Si2—C12 105.86 (13) C17—C12—C13 116.7 (3)
C11—Si2—C1 112.17 (13) C17—C12—Si2 122.0 (2)
C10—Si2—C1 110.61 (13) C13—C12—Si2 121.1 (2)
C12—Si2—C1 114.38 (12) C14—C13—C12 122.2 (3)
C18—Si3—C19 110.22 (15) C14—C13—H13A 118.9
C18—Si3—C20 105.00 (14) C12—C13—H13A 118.9
C19—Si3—C20 104.46 (14) C13—C14—C15 119.6 (3)
C18—Si3—C1 111.99 (13) C13—C14—H14A 120.2
C19—Si3—C1 109.12 (13) C15—C14—H14A 120.2
C20—Si3—C1 115.72 (12) C16—C15—C14 119.6 (3)
Si2—C1—Si3 112.36 (13) C16—C15—H15A 120.2
Si2—C1—Si1 115.75 (14) C14—C15—H15A 120.2
Si3—C1—Si1 109.82 (13) C15—C16—C17 120.5 (3)
Si2—C1—Te1 107.49 (12) C15—C16—H16A 119.7
Si3—C1—Te1 114.96 (12) C17—C16—H16A 119.7
Si1—C1—Te1 95.50 (11) C16—C17—C12 121.4 (3)
Si1—C2—H2A 109.5 C16—C17—H17A 119.3
Si1—C2—H2B 109.5 C12—C17—H17A 119.3
H2A—C2—H2B 109.5 Si3—C18—H18A 109.5
Si1—C2—H2C 109.5 Si3—C18—H18B 109.5
H2A—C2—H2C 109.5 H18A—C18—H18B 109.5
H2B—C2—H2C 109.5 Si3—C18—H18C 109.5
Si1—C3—H3A 109.5 H18A—C18—H18C 109.5
Si1—C3—H3B 109.5 H18B—C18—H18C 109.5
H3A—C3—H3B 109.5 Si3—C19—H19A 109.5
Si1—C3—H3C 109.5 Si3—C19—H19B 109.5
H3A—C3—H3C 109.5 H19A—C19—H19B 109.5
H3B—C3—H3C 109.5 Si3—C19—H19C 109.5
C9—C4—C5 116.4 (3) H19A—C19—H19C 109.5
C9—C4—Si1 122.2 (2) H19B—C19—H19C 109.5
C5—C4—Si1 121.2 (2) C21—C20—C25 116.2 (3)
C6—C5—C4 121.7 (3) C21—C20—Si3 121.9 (2)
C6—C5—H5A 119.2 C25—C20—Si3 121.8 (2)
C4—C5—H5A 119.2 C22—C21—C20 121.5 (3)
C7—C6—C5 120.5 (3) C22—C21—H21A 119.3
C7—C6—H6A 119.7 C20—C21—H21A 119.3
C5—C6—H6A 119.7 C23—C22—C21 121.2 (3)
C6—C7—C8 119.4 (3) C23—C22—H22A 119.4
C6—C7—H7A 120.3 C21—C22—H22A 119.4
C8—C7—H7A 120.3 C22—C23—C24 118.8 (3)
C7—C8—H8A 119.9 C24—C23—H23A 120.6
C9—C8—H8A 119.9 C23—C24—C25 120.6 (3)
C8—C9—C4 121.7 (3) C23—C24—H24A 119.7
C8—C9—H9A 119.2 C25—C24—H24A 119.7
C4—C9—H9A 119.2 C24—C25—C20 121.7 (3)
Si2—C10—H10A 109.5 C24—C25—H25A 119.1
Si2—C10—H10B 109.5 C20—C25—H25A 119.1
H10A—C10—H10B 109.5
