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Volume 66 
Part 1 
Page o57  
January 2010  

Received 19 November 2009
Accepted 28 November 2009
Online 4 December 2009

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.096
Data-to-parameter ratio = 12.0
Details
Open access

1-Benzoyl-3,3-dinitroazetidine

Biao Yan,a,b Hai-Xia Ma,b* Jun-Feng Li,b Yu-Lei Guanb and Ji-Rong Songb

aSchool of Chemistry and Chemical Engineering, Yulin University, Yulin 719000 Shaanxi, People's Republic of China, and bSchool of Chemical Engineering, Northwest University, Xi'an 710069 Shaanxi, People's Republic of China
Correspondence e-mail: donghuhai@qq.com

In the title gem-dinitroazetidine derivative, C10H9N3O5, the azetidine ring is almost planar, the maximum value of the endocyclic torsion angle being 0.92 (14)°. The gem-dinitro groups are mutually perpendicular and the dihedral angle between the azetidine and benzene rings is 46.70 (10)°

Related literature

For energetic materials based on 3,3-dinitroazetidine, see: Archibald et al. (1990[ Archibald, T. G., Gilardi, R., Baum, K. & George, C. (1990). J. Org. Chem. 55, 2920-2924.]); Gao et al. (2009[ Gao, R., Ma, H. X., Yan, B., Song, J. R. & Wang, Y. H. (2009). Chem. J. Chin. Univ. 30, 577-582.]); Hiskey & Coburn (1994a[ Hiskey, M. A. & Coburn, M. D. (1994a). US Patent 5 336 784.],b[ Hiskey, M. A. & Coburn, M. D. (1994b). Chem. Abstr. 121, 300750s.]); Ma, Yan, Li, Guan et al. (2009[ Ma, H. X., Yan, B., Li, Z. N., Guan, Y. L., Song, J. R., Xu, K. Z. & Hu, R. Z. (2009). J. Hazard. Mater. 169, 1068-1073.]); Ma, Yan, Li, Song & Hu (2009[ Ma, H. X., Yan, B., Li, Z. N., Song, J. R. & Hu, R. Z. (2009). J. Therm. Anal. Calorim. 95, 437-444.]); Ma, Yan, Song et al. (2009[ Ma, H. X., Yan, B., Song, J. R., Lü, X. Q. & Wang, L. J. (2009). Chem. J. Chin. Univ. 30, 371-381.]).

[Scheme 1]

Experimental

Crystal data

  • C10H9N3O5

  • Mr = 251.20

  • Monoclinic, P 21 /c

  • a = 13.176 (4) Å

  • b = 6.2344 (19) Å

  • c = 13.522 (4) Å

  • [beta] = 92.612 (6)°

  • V = 1109.6 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.39 × 0.27 × 0.15 mm
Data collection

  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[ Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.954, Tmax = 0.981

  • 5306 measured reflections

  • 1975 independent reflections

  • 1210 reflections with I > 2[sigma](I)

  • Rint = 0.028
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.096

  • S = 0.98

  • 1975 reflections

  • 164 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Data collection: SMART (Bruker, 2003[ Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[ Bruker (2003). SMART and SAINT. 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: SHELXTL (Sheldrick, 2008[ Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2242 ).

Acknowledgements

We thank the National Natural Science Foundation of China (No. 20603026) and the Natural Science Foundation of Shaanxi Province, China (No. 2009JQ2002) for generously supporting this study.

References

Archibald, T. G., Gilardi, R., Baum, K. & George, C. (1990). J. Org. Chem. 55, 2920-2924.  [CrossRef] [ChemPort]
 Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
 Gao, R., Ma, H. X., Yan, B., Song, J. R. & Wang, Y. H. (2009). Chem. J. Chin. Univ. 30, 577-582.  [ChemPort]
 Hiskey, M. A. & Coburn, M. D. (1994a). US Patent 5 336 784.
 Hiskey, M. A. & Coburn, M. D. (1994b). Chem. Abstr. 121, 300750s.
 Ma, H. X., Yan, B., Li, Z. N., Guan, Y. L., Song, J. R., Xu, K. Z. & Hu, R. Z. (2009). J. Hazard. Mater. 169, 1068-1073.  [ISI] [CrossRef] [PubMed] [ChemPort]
 Ma, H. X., Yan, B., Li, Z. N., Song, J. R. & Hu, R. Z. (2009). J. Therm. Anal. Calorim. 95, 437-444.  [ISI] [CrossRef] [ChemPort]
 Ma, H. X., Yan, B., Song, J. R., Lü, X. Q. & Wang, L. J. (2009). Chem. J. Chin. Univ. 30, 371-381.
 Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2010). E66, o57  [ doi:10.1107/S1600536809051290 ]

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