2-(Dimethyl­amino­meth­yl)phenyl phenyl telluride

Chakraborty, T.; Singh, H.B.; Butcher, R.J.

doi:10.1107/S1600536809038161

Volume 65
Part 10
Pages o2562-o2563
October 2009

Received 19 September 2009
Accepted 21 September 2009
Online 26 September 2009

Key indicators
Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.003 Å
R = 0.023
wR = 0.058
Data-to-parameter ratio = 31.0
Details

2-(Dimethylaminomethyl)phenyl phenyl telluride

Tapash Chakraborty,^a Harkesh B. Singh ^a ^* and Ray J. Butcher ^b

^aDepartment of Chemistry, Indian Institute of Technology Bombay, Powai 400 076, India, and ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: chhbsia@chem.iitb.ac.in

The title compound, C₁₅H₁₇NTe, is a heteroleptic Te, N-bidentate ligand having a short TeN contact [2.8079 (16) Å] involving a secondary bonding interaction between the amino N and Te^II atoms. The Te-C bond [2.136 (2) Å] trans to the amino group is slightly elongated compared to the other Te-C bond [2.1242 (18) Å] due to the hypervalent interaction. The bond angle for the trans N-Te-C atoms [164.92 (6)°] deviates significantly from linearity.

Related literature

For Heck and cross-coupling reactions, see: Cella et al. (2006); Nishibayashi et al. (1996a,b); Zeni & Comasseto (1999); Zeni et al. (2001). For intramolecularly coordinated tellurides, see: Detty et al. (1995); Drake et al. (2001); Engman et al. (2004); Kaur et al. (1995, 2009); Menon et al. (1996); Panda et al. (1999); Singh et al. (1990). For van der Waals and covalent radii, see: Bondi (1964); Cordero et al. (2008).

Experimental

Crystal data

C₁₅H₁₇NTe
M_r = 338.90
Monoclinic, P 2₁ /c
a = 8.5736 (3) Å
b = 13.2472 (5) Å
c = 12.6719 (4) Å
= 95.933 (3)°
V = 1431.52 (9) Å³
Z = 4
Mo K radiation
= 2.06 mm^-1
T = 110 K
0.49 × 0.41 × 0.27 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.728, T_max = 1.000
20642 measured reflections
4836 independent reflections
2926 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.023
wR(F²) = 0.058
S = 0.97
4836 reflections
156 parameters
H-atom parameters constrained
_max = 0.58 e Å^-3
_min = -0.47 e Å^-3

Table 1
Selected geometric parameters (Å, °)

Te-C1	2.1242 (18)
Te-C10	2.136 (2)
Te-N	2.8079 (16)

C1-Te-C10	94.19 (7)
C1-Te-N	70.77 (6)
C10-Te-N	164.92 (6)

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5068 ).

Acknowledgements

HSB is grateful to the Department of Science and Technology (DST) for the award of a Ramanna Fellowship. TC is grateful to the CSIR for a JRF/SRF fellowship. RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

Bondi, A. (1964). J. Phys. Chem. 68, 441-451.
Cella, R., Cunha, R. L. O., Reis, A. E. S., Pimenta, D. C., Klitzke, C. F. & Stefani, H. A. (2006). J. Org. Chem. 71, 244-250.
Cordero, B., Gómez, V., Platero-Prats, A. E., Revés, M., Echeverría, J., Cremades, E., Barragán, F. & Alvarez, S. (2008). Dalton Trans. pp. 2832-2838.
Detty, R. M., Friedman, A. E. & McMillan, M. (1995). Organometallics, 14, 1442-1449.
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Engman, L., Wojton, A., Oleksyn, B. J. & Sliwinski, J. (2004). Phosphorus Sulfur Silicon Relat. Elem. 179, 285-292.
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Kaur, R., Singh, H. B. & Butcher, R. J. (1995). Organometallics, 14, 4745-4763.
Menon, S. C., Singh, H. B., Jasinski, J. M., Jasinski, J. P. & Butcher, R. J. (1996). Organometallics, 15, 1707-1712.
Nishibayashi, Y., Cho, C. S., Ohe, K. & Uemura, S. (1996a). J. Organomet. Chem. 526, 335-339.
Nishibayashi, Y., Cho, C. S. & Uemura, S. (1996b). J. Organomet. Chem. 507, 197-200.
Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.
Panda, A., Mugesh, G., Singh, H. B. & Butcher, R. J. (1999). Organometallics, 18, 1986-1993.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, H. B., Sudha, N., West, A. A. & Hamor, T. A. (1990). J. Chem. Soc. Dalton Trans. pp. 907-913.
Zeni, C. & Comasseto, J. V. (1999). Tetrahedron Lett. 40, 4619-4622.
Zeni, G., Menezes, P. H., Moro, A. V., Braga, A. L., Silveira, C. C. & Stefani, H. A. (2001). Synlett, 9, 1473-1475.

organic compounds