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

Mao, F.-L.; Dai, C.-H.

doi:10.1107/S1600536810049482

Volume 67
Part 1
Page o7
January 2011

Received 25 November 2010
Accepted 26 November 2010
Online 4 December 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.144
Data-to-parameter ratio = 14.0
Details

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

Fu-Lin Mao ^a ^* and Chun-Hua Dai ^a

^aDepartment of Chemistry, Yancheng Teachers University, Yancheng 224002, People's Republic of China
Correspondence e-mail: xpzhougroup@163.com

The title compound, C₁₄H₁₁N₃O₄, was prepared by the reaction of 3-nitrobenzohydrazide with 3-hydroxybenzaldehyde. The molecule adopts an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 32.3 (2)°. In the crystal, the molecules are linked through intermolecular N-HO, O-HN, and O-HO hydrogen bonds, forming chains in the a-axis direction.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010); Zhang et al. (2010); Angelusiu et al. (2010). For related structures, see: Huang & Wu (2010); Khaledi et al. (2010); Zhou & Yang (2010); Ji & Lu (2010); Singh & Singh (2010); Ahmad et al. (2010). For similar compounds that we have reported recently, see: Dai & Mao (2010a,b).

Experimental

Crystal data

C₁₄H₁₁N₃O₄
M_r = 285.26
Monoclinic, C 2/c
a = 16.154 (3) Å
b = 13.295 (3) Å
c = 13.537 (2) Å
= 120.324 (2)°
V = 2509.5 (8) Å³
Z = 8
Mo K radiation
= 0.11 mm^-1
T = 298 K
0.28 × 0.27 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.969, T_max = 0.974
6631 measured reflections
2738 independent reflections
1588 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.144
S = 1.03
2738 reflections
196 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1ⁱ	0.85 (1)	2.58 (3)	2.986 (2)	111 (2)
O1-H1O2ⁱ	0.85 (1)	1.91 (1)	2.758 (2)	174 (3)
N2-H2AO4ⁱⁱ	0.89 (1)	2.47 (1)	3.354 (3)	171 (2)
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5070 ).

Acknowledgements

We acknowledge the Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection for financial support (Project No. JLCBE07026).

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022.
Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.
Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055-2062.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dai, C.-H. & Mao, F.-L. (2010a). Acta Cryst. E66, o2942.
Dai, C.-H. & Mao, F.-L. (2010b). Acta Cryst. E66, o3004-o3005.
Huang, H.-T. & Wu, H.-Y. (2010). Acta Cryst. E66, o2729-o2730.
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Khaledi, H., Alhadi, A. A., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o105-o106.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172.
Zhang, Y.-H., Zhang, L., Liu, L., Guo, J.-X., Wu, D.-L., Xu, G.-C., Wang, X.-H. & Jia, D.-Z. (2010). Inorg. Chim. Acta, 363, 289-293.
Zhou, C.-S. & Yang, T. (2010). Acta Cryst. E66, o290.

organic compounds