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

Jin, Y.-X.

doi:10.1107/S1600536809051733

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 (C-C) = 0.003 Å
R = 0.049
wR = 0.129
Data-to-parameter ratio = 15.2
Details

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

Yan-Xian Jin ^a ^*

^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-HN hydrogen bond. In the crystal structure, centrosymmetrically related molecules are connected by pairs of N-HO hydrogen bonds into dimers, which are further linked into a three-dimensional network by intermolecular C-HO 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); Reiter et al. (1985). For the properties of isoxazole derivatives, see: Stevens & Albizati (1984). For examples of crystal structures of hydrazone compounds, see: Fun et al. (2008); Wei et al. (2009); Khaledi et al. (2008). For reference bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₂H₁₀N₄O₄
M_r = 274.24
Monoclinic, P 2₁ /c
a = 4.8668 (8) Å
b = 25.202 (4) Å
c = 10.257 (2) Å
= 100.721 (12)°
V = 1236.1 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.951, T_max = 0.971
10436 measured reflections
2828 independent reflections
1943 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(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
_max = 0.32 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3AN3	0.93	2.43	2.930 (2)	114
C12-H12O4ⁱ	0.93	2.58	3.240 (2)	128
N2-H2O2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: 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.
Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2481.
Khattab, S. N. (2005). Molecules, 10, 1218-1228.
Reiter, J., Somoral, T. & Dvortsak, P. (1985). Heterocycl. Chem. 22, 385-394.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stevens, R. V. & Albizati, K. F. (1984). Tetrahedron Lett. 25, 4587-4591.
Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o688.

organic compounds