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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 [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.129
Data-to-parameter ratio = 14.9
Details
Open access

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

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-H...O, O-H...N, O-H...O and C-H...O 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[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 et al. (2009[Horiuchi, T., Nagata, M., Kitagawa, M., Akahane, K. & Uoto, K. (2009). Bioorg. Med. Chem. 17, 7850-7860.]). For coordination compounds of benzohydrazide derivatives, see: El-Dissouky et al. (2010[El-Dissouky, A., Al-Fulaij, O., Awad, M. K. & Rizk, S. (2010). J. Coord. Chem. 63, 330-345.]); Zhang et al. (2010[Zhang, S.-P., Wei, Y. & Shao, S.-C. (2010). Acta Cryst. E66, m1635.]). For standard bond lengths, see: Allen et al. (1987[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.]). For similar structures, see: Liu et al. (2011[Liu, W.-H., Song, S.-J. & Ma, J.-J. (2011). Acta Cryst. E67, o2198.]); Zhou et al. (2011[Zhou, X., Gao, S.-T. & Ma, J.-J. (2011). Acta Cryst. E67, o2275.]); Meng et al. (2011[Meng, X.-F., Wang, D.-Y. & Ma, J.-J. (2011). Acta Cryst. E67, o3109.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11N3O4

  • Mr = 285.26

  • Monoclinic, P 21 /n

  • a = 10.362 (2) Å

  • b = 12.178 (3) Å

  • c = 10.468 (2) Å

  • [beta] = 91.666 (2)°

  • V = 1320.3 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.982, Tmax = 0.984

  • 10464 measured reflections

  • 2884 independent reflections

  • 2017 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.82 2.02 2.8341 (18) 170
O1-H1...N1i 0.82 2.58 3.0757 (19) 120
N2-H2A...O1ii 0.89 (1) 2.53 (2) 3.0597 (19) 119 (2)
C5-H5...O1iii 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[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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: 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.  [ISI] [CrossRef] [ChemPort]
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.  [ChemPort] [PubMed]
Horiuchi, T., Nagata, M., Kitagawa, M., Akahane, K. & Uoto, K. (2009). Bioorg. Med. Chem. 17, 7850-7860.  [CrossRef] [PubMed] [ChemPort]
Liu, W.-H., Song, S.-J. & Ma, J.-J. (2011). Acta Cryst. E67, o2198.  [CSD] [CrossRef] [details]
Meng, X.-F., Wang, D.-Y. & Ma, J.-J. (2011). Acta Cryst. E67, o3109.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhang, S.-P., Wei, Y. & Shao, S.-C. (2010). Acta Cryst. E66, m1635.  [CSD] [CrossRef] [details]
Zhou, X., Gao, S.-T. & Ma, J.-J. (2011). Acta Cryst. E67, o2275.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o20  [ doi:10.1107/S1600536811051233 ]

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