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Volume 66 
Part 1 
Page o47  
January 2010  

Received 25 November 2009
Accepted 1 December 2009
Online 4 December 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.129
Data-to-parameter ratio = 15.2
Details
Open access

5-Methyl-N'-(3-nitrobenzylidene)isoxazole-4-carbohydrazide

aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China
Correspondence e-mail: snowflakej@gmail.com

The molecule of the title compound, C12H10N4O4, displays an E configuration about the C=N bond. The dihedral angle between the benzene and isoxazole rings is 1.36 (5)° and the molecular conformation is stabilized by the an intramolecular C-H...N hydrogen bond. In the crystal structure, centrosymmetrically related molecules are connected by pairs of N-H...O hydrogen bonds into dimers, which are further linked into a three-dimensional network by intermolecular C-H...O hydrogen bonds and by [pi]...[pi] stacking interactions involving adjacent benzene and isoxazole rings, with a centroid-centroid separation of 3.861 (3) Å.

Related literature

For the biological activity and coordination ability of hydrazone compounds, see: Khattab (2005[Khattab, S. N. (2005). Molecules, 10, 1218-1228.]); Reiter et al. (1985[Reiter, J., Somoral, T. & Dvortsak, P. (1985). Heterocycl. Chem. 22, 385-394.]). For the properties of isoxazole derivatives, see: Stevens & Albizati (1984[Stevens, R. V. & Albizati, K. F. (1984). Tetrahedron Lett. 25, 4587-4591.]). For examples of crystal structures of hydrazone compounds, see: Fun et al. (2008[Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.]); Wei et al. (2009[Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o688.]); Khaledi et al. (2008[Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2481.]). For reference bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N4O4

  • Mr = 274.24

  • Monoclinic, P 21 /c

  • a = 4.8668 (8) Å

  • b = 25.202 (4) Å

  • c = 10.257 (2) Å

  • [beta] = 100.721 (12)°

  • V = 1236.1 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.66 × 0.30 × 0.14 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.971

  • 10436 measured reflections

  • 2828 independent reflections

  • 1943 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.129

  • S = 1.10

  • 2828 reflections

  • 186 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...N3 0.93 2.43 2.930 (2) 114
C12-H12...O4i 0.93 2.58 3.240 (2) 128
N2-H2...O2ii 0.90 (1) 1.95 (1) 2.855 (2) 179 (1)
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2400 ).


Acknowledgements

The author acknowledges financial support by the Zhejiang Provincial Natural Science Foundation of China (No. Y406049).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.  [CSD] [CrossRef] [details]
Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2481.  [CSD] [CrossRef] [details]
Khattab, S. N. (2005). Molecules, 10, 1218-1228.  [CrossRef] [PubMed] [ChemPort]
Reiter, J., Somoral, T. & Dvortsak, P. (1985). Heterocycl. Chem. 22, 385-394.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stevens, R. V. & Albizati, K. F. (1984). Tetrahedron Lett. 25, 4587-4591.  [CrossRef] [ChemPort] [ISI]
Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o688.  [CSD] [CrossRef] [details]


Acta Cryst (2010). E66, o47  [ doi:10.1107/S1600536809051733 ]

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