(E)-N′-(4-Hy­droxy­benzyl­idene)-3-nitro­benzohydrazide

Meng, X.-F.; Wang, D.-Y.; Ma, J.-J.

doi:10.1107/S1600536811051233

Volume 68
Part 1
Page o20
January 2012

Received 18 November 2011
Accepted 28 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.129
Data-to-parameter ratio = 14.9
Details

(E)-N'-(4-Hydroxybenzylidene)-3-nitrobenzohydrazide

Xu-Feng Meng,^a Dong-Yue Wang ^a and Jing-Jun Ma ^a ^*

^aHebei Key Laboratory of Bioinorganic Chemistry, College of Sciences, Agricultural University of Hebei, Baoding 071001, People's Republic of China
Correspondence e-mail: majingjun71@yahoo.cn

The molecule of the title compound, C₁₄H₁₁N₃O₄, assumes an E conformation about the C=N double bond. The benzene rings form a dihedral angle of 3.9 (2)°. The crystal structure is stabilized by N-HO, O-HN, O-HO and C-HO hydrogen bonds, forming layers parallel to (101). In addition, intralayer [pi] - [pi] stacking interactions [centroid-centroid distance = 3.635 (2) Å] are observed.

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011); Horiuchi et al. (2009). For coordination compounds of benzohydrazide derivatives, see: El-Dissouky et al. (2010); Zhang et al. (2010). For standard bond lengths, see: Allen et al. (1987). For similar structures, see: Liu et al. (2011); Zhou et al. (2011); Meng et al. (2011).

Experimental

Crystal data

C₁₄H₁₁N₃O₄
M_r = 285.26
Monoclinic, P 2₁ /n
a = 10.362 (2) Å
b = 12.178 (3) Å
c = 10.468 (2) Å
= 91.666 (2)°
V = 1320.3 (5) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.982, T_max = 0.984
10464 measured reflections
2884 independent reflections
2017 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.129
S = 1.03
2884 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	2.02	2.8341 (18)	170
O1-H1N1ⁱ	0.82	2.58	3.0757 (19)	120
N2-H2AO1ⁱⁱ	0.89 (1)	2.53 (2)	3.0597 (19)	119 (2)
C5-H5O1ⁱⁱⁱ	0.93	2.54	3.367 (2)	147
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: RZ2676 ).

Acknowledgements

This project was sponsored by the Natural Development Foundation of Hebei Province (B2011204051), the Development Foundation of the Department of Education of Hebei Province (2010137) and the Research Development Foundation of the Agricultural University of Hebei.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orphen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Dissouky, A., Al-Fulaij, O., Awad, M. K. & Rizk, S. (2010). J. Coord. Chem. 63, 330-345.
El-Sayed, M. A. A., Abdel-Aziz, N. I., Abdel-Aziz, A. A. M., El-Azab, A. S., Asiri, Y. A. & ElTahir, K. E. H. (2011). Bioorg. Med. Chem. 19, 3416-3424.
Horiuchi, T., Nagata, M., Kitagawa, M., Akahane, K. & Uoto, K. (2009). Bioorg. Med. Chem. 17, 7850-7860.
Liu, W.-H., Song, S.-J. & Ma, J.-J. (2011). Acta Cryst. E67, o2198.
Meng, X.-F., Wang, D.-Y. & Ma, J.-J. (2011). Acta Cryst. E67, o3109.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, S.-P., Wei, Y. & Shao, S.-C. (2010). Acta Cryst. E66, m1635.
Zhou, X., Gao, S.-T. & Ma, J.-J. (2011). Acta Cryst. E67, o2275.

organic compounds