2-Methyl-N′-(4-nitro­benzyl­idene)benzohydrazide

Tang, C.-B.

doi:10.1107/S1600536810038869

Volume 66
Part 11
Page o2715
November 2010

Received 21 September 2010
Accepted 29 September 2010
Online 2 October 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.059
wR = 0.140
Data-to-parameter ratio = 15.2
Details

2-Methyl-N'-(4-nitrobenzylidene)benzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
Correspondence e-mail: tangchunbao@yahoo.com.cn

The title hydrazone compound, C₁₅H₁₃N₃O₃, was prepared by the condensation of 4-nitrobenzaldehyde with 2-methylbenzohydrazide in methanol. The dihedral angle between the two benzene rings is 14.8 (2)°. In the crystal, molecules are linked through intermolecular N-HO hydrogen bonds, forming chains along the a axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010); Pyta et al. (2010); Angelusiu et al. (2010); Fun et al. (2008); Singh & Singh (2010); Ahmad et al. (2010). For bond-length data, see: Allen et al. (1987). For a similar hydrazone compound reported recently by the author, see: Tang (2010).

Experimental

Crystal data

C₁₅H₁₃N₃O₃
M_r = 283.28
Monoclinic, P 2₁ /n
a = 7.416 (1) Å
b = 26.198 (3) Å
c = 7.860 (2) Å
= 114.206 (1)°
V = 1392.8 (4) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.981, T_max = 0.983
7336 measured reflections
2941 independent reflections
1696 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.140
S = 1.01
2941 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O3ⁱ	0.90 (1)	1.99 (1)	2.870 (2)	167 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2493 ).

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055-2062.
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Sujith, K. V., Patil, P. S., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1961-o1962.
Pyta, K., Przybylski, P., Huczynski, A., Hoser, A., Wozniak, K., Schilf, W., Kamienski, B., Grech, E. & Brzezinski, B. (2010). J. Mol. Struct. 970, 147-154.
Rasras, A. J. M., Al-Tel, T. H., Al-Aboudi, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307-2313.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172.
Tang, C.-B. (2010). Acta Cryst. E66, o2482.

organic compounds