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Volume 68 
Part 12 
Page o3376  
December 2012  

Received 29 October 2012
Accepted 9 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.021
wR = 0.055
Data-to-parameter ratio = 11.4
Details
Open access

3,3-Dinitroazetidinium chloride

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-dinitroazetidinium chloride salt, C3H6N3O4+·Cl-, the cations and anions lie on a mirror plane. The azetidine ring is virtually planar, with a mean deviation from the plane of 0.0569 Å. The dihedral angle between the two nitro groups is 90.00 (5)°. In the crystal, the ions are linked by N-H...Cl interactions, forming a chain along the c-axis direction, and C-H...O interactions, forming a layer parallel to (010).

Related literature

For 1,3,3-trinitroazetidine and compounds prepared from its derivative 3,3-dinitroazetidine, see: Archibald et al. (1990[Archibald, T. G., Gilardi, R., Baum, K. & George, C. (1990). J. Org. Chem. 55, 2920-2924.]); Hiskey et al. (1992[Hiskey, M. A., Coburn, M. D., Mitchell, M. A. & Benicewicz, B. C. (1992). J. Heterocycl. Chem. 29, 1855-1856.]); Ma et al. (2009a[Ma, H. X., Yan, B., Li, Z. N., Guan, Y. L., Song, J. R., Xu, K. Z. & Hu, R. Z. (2009a). J. Hazard. Mater. 169, 1068-1073.],b[Ma, H. X., Yan, B., Li, Z. N., Song, J. R. & Hu, R. Z. (2009b). J. Therm. Anal. Calorim. 95, 437-444.], 2011[Ma, H. X., Yan, B., Ren, Y. H., Guan, Y. L., Zhao, F. Q., Song, J. R. & Hu, R. Z. (2011). J. Therm. Anal. Calorim. 103, 569-575.]); Yan et al. (2009[Yan, B., Ma, H.-X., Hu, Y., Guan, Y.-L. & Song, J.-R. (2009). Acta Cryst. E65, o3215.], 2010[Yan, B., Ma, H.-X., Li, J.-F., Guan, Y.-L. & Song, J.-R. (2010). Acta Cryst. E66, o57.]); 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.]). For related structures, see: Gao et al. (2010[Gao, R., Yan, B., Mai, T., Hu, Y. & Guan, Y.-L. (2010). Acta Cryst. E66, o3036.]); Ma et al. (2010[Ma, H. X., Yan, B., Li, J. F., Ren, Y. H., Chen, Y. S., Zhao, F. Q., Song, J. R. & Hu, R. Z. (2010). J. Mol. Struct. 981, 103-110.]). For the synthesis, see: Li et al. (2004[Li, H. Z., Shu, Y. J., Huang, Y. G., Liu, S. J. & Jiang, Q. (2004). Chin. J. Org. Chem. 24, 775-777.]).

[Scheme 1]

Experimental

Crystal data
  • C3H6N3O4+·Cl-

  • Mr = 183.56

  • Orthorhombic, C m c 21

  • a = 6.6807 (17) Å

  • b = 10.4409 (17) Å

  • c = 9.9707 (19) Å

  • V = 695.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 293 K

  • 0.35 × 0.34 × 0.30 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS . University of Göttingen, Germany.]) Tmin = 0.839, Tmax = 0.860

  • 1968 measured reflections

  • 708 independent reflections

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

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.021

  • wR(F2) = 0.055

  • S = 1.10

  • 708 reflections

  • 62 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 252 Friedel pairs

  • Flack parameter: 0.09 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1C...Cl 0.90 2.35 3.087 (2) 139
N1-H1D...Cli 0.90 2.19 3.0575 (19) 163
C1-H1B...O4ii 0.97 2.58 3.543 (2) 172
Symmetry codes: (i) [-x, -y+1, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2003[Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). APEX2 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: ZQ2187 ).


Acknowledgements

We thank the National Natural Science Foundation of China (grant No. 21073141), the Education Committee Foundation of Shaanxi Province (grant Nos. 11 JK0564 and 11J K0582) and the Project sponsored by SRF for AT, YLU (No. 09GK019) 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). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gao, R., Ma, H. X., Yan, B., Song, J. R. & Wang, Y. H. (2009). Chem. J. Chin. Univ. 30, 577-582.  [ChemPort]
Gao, R., Yan, B., Mai, T., Hu, Y. & Guan, Y.-L. (2010). Acta Cryst. E66, o3036.  [CSD] [CrossRef] [details]
Hiskey, M. A., Coburn, M. D., Mitchell, M. A. & Benicewicz, B. C. (1992). J. Heterocycl. Chem. 29, 1855-1856.  [CrossRef] [ChemPort]
Li, H. Z., Shu, Y. J., Huang, Y. G., Liu, S. J. & Jiang, Q. (2004). Chin. J. Org. Chem. 24, 775-777.  [ChemPort]
Ma, H. X., Yan, B., Li, Z. N., Guan, Y. L., Song, J. R., Xu, K. Z. & Hu, R. Z. (2009a). J. Hazard. Mater. 169, 1068-1073.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ma, H. X., Yan, B., Li, J. F., Ren, Y. H., Chen, Y. S., Zhao, F. Q., Song, J. R. & Hu, R. Z. (2010). J. Mol. Struct. 981, 103-110.  [ISI] [CSD] [CrossRef] [ChemPort]
Ma, H. X., Yan, B., Li, Z. N., Song, J. R. & Hu, R. Z. (2009b). J. Therm. Anal. Calorim. 95, 437-444.  [ISI] [CrossRef] [ChemPort]
Ma, H. X., Yan, B., Ren, Y. H., Guan, Y. L., Zhao, F. Q., Song, J. R. & Hu, R. Z. (2011). J. Therm. Anal. Calorim. 103, 569-575.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2000). SADABS . University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yan, B., Ma, H.-X., Hu, Y., Guan, Y.-L. & Song, J.-R. (2009). Acta Cryst. E65, o3215.  [CSD] [CrossRef] [details]
Yan, B., Ma, H.-X., Li, J.-F., Guan, Y.-L. & Song, J.-R. (2010). Acta Cryst. E66, o57.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3376  [ doi:10.1107/S1600536812046302 ]

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