[Journal logo]

Volume 66 
Part 3 
Page o561  
March 2010  

Received 26 January 2010
Accepted 2 February 2010
Online 6 February 2010

[bt5184sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.141
Data-to-parameter ratio = 10.0
Details
Open access

(S)-Perillaldehyde azine

Li-Lu Han,a Jiang-Hua Shi,b De-Peng Yanb and Seik Weng Ngc*

aHunan Yongzhou Vocational College, Yongzhou, Hunan 425100, People's Republic of China,bDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425100, People's Republic of China, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The C=N-N=C linkage [torsion angle -172.5 (2)°] in the title azine, C20H28N2, adopts a trans conformation. The six-membered rings adopt sofa conformations.

Related literature

A previous study reported the oxime derivative of S-perillaldehyde; see Yuan et al. (2009[Yuan, X.-Y., Zhang, M. & Ng, S. W. (2009). Acta Cryst. E65, o2149.]). Only few crystal structures of azines have been reported, see: Berthou et al. (1970[Berthou, J., Marzin, C., Rérat, B., Rérat, C. & Uesu, Y. (1970). C. R. Acad. Sci. Ser. C, pp. 918-921.]); Kim & Lee (2008[Kim, S. H. & Lee, S. W. (2008). Inorg. Chim. Acta, 361, 137-144.]); Marek et al. (1997[Marek, R., St'astná-Sedlácková, I., Tousek, J., Marek, J. & Potacek, M. (1997). Bull. Soc. Chim. Belg. 106, 645-649.]); Rizal et al. (2008[Rizal, M. R., Ali, H. M. & Ng, S. W. (2008). Acta Cryst. E64, o555.]); Sanz et al. (1999[Sanz, D., Ponce, M. J., Claramunt, R. M., Fernández-Castaño, C., Foces-Foces, C. & Elguero, J. (1999). J. Phys. Org. Chem. 12, 455-469.]).

[Scheme 1]

Experimental

Crystal data

  • C20H28N2

  • Mr = 296.44

  • Monoclinic, P 21

  • a = 8.8200 (5) Å

  • b = 9.7603 (6) Å

  • c = 10.1710 (6) Å

  • [beta] = 94.970 (1)°

  • V = 872.29 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 173 K

  • 0.48 × 0.46 × 0.21 mm
Data collection

  • Bruker SMART APEX diffractometer

  • 7179 measured reflections

  • 2013 independent reflections

  • 1802 reflections with I > 2[sigma](I)

  • Rint = 0.035
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.141

  • S = 1.12

  • 2013 reflections

  • 201 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Data collection: SMART (Bruker, 2003[Bruker (2003). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5184 ).

Acknowledgements

We thank the Key Subject Construction Project of Hunan Province (No. 2006-180), the Key Scientific Research Project of Hunan Provincial Education Department (No. 08 A023, 05 C736), the NSF of Hunan Province (09 J J3028) and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Berthou, J., Marzin, C., Rérat, B., Rérat, C. & Uesu, Y. (1970). C. R. Acad. Sci. Ser. C, pp. 918-921.
Bruker (2003). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Kim, S. H. & Lee, S. W. (2008). Inorg. Chim. Acta, 361, 137-144.  [ISI] [CSD] [CrossRef] [ChemPort]
Marek, R., St'astná-Sedlácková, I., Tousek, J., Marek, J. & Potacek, M. (1997). Bull. Soc. Chim. Belg. 106, 645-649.  [ChemPort]
Rizal, M. R., Ali, H. M. & Ng, S. W. (2008). Acta Cryst. E64, o555.  [CSD] [CrossRef] [details]
Sanz, D., Ponce, M. J., Claramunt, R. M., Fernández-Castaño, C., Foces-Foces, C. & Elguero, J. (1999). J. Phys. Org. Chem. 12, 455-469.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). publCIF. In preparation.
Yuan, X.-Y., Zhang, M. & Ng, S. W. (2009). Acta Cryst. E65, o2149.  [CSD] [CrossRef] [details]

Acta Cryst (2010). E66, o561  [ doi:10.1107/S1600536810004071 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.