2-Chloro-N′-(5-hydr­oxy-2-nitro­benzyl­idene)benzohydrazide

Zhou, C.-S.; Yang, T.

doi:10.1107/S1600536810001303

Volume 66
Part 2
Page o365
February 2010

Received 10 January 2010
Accepted 11 January 2010
Online 16 January 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.103
Data-to-parameter ratio = 14.3
Details

2-Chloro-N'-(5-hydroxy-2-nitrobenzylidene)benzohydrazide

Cong-Shan Zhou ^a and Tao Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan 414006, People's Republic of China
Correspondence e-mail: zhoucongsh@gmail.com

The molecule of the title Schiff base compound, C₁₄H₁₀ClN₃O₄, exists in a trans configuration with respect to the acyclic C=N bond. The dihedral angle between the two benzene rings is 62.37 (9)°. An intramolecular C-HO hydrogen bond is observed. In the crystal structure, adjacent molecules are linked into a ribbon along [1 $[\overline{1}]$ 0] by O-HO and N-HO hydrogen bonds.

Related literature

For the biological properties of Schiff bases, see: Mohamed et al. (2009); Ritter et al. (2009); Bagihalli et al. (2008). For related structures, see: Fun et al. (2008); Shafiq et al. (2009); Goh et al. (2010); Zhou et al. (2009); Zhou & Yang (2009).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₄
M_r = 319.70
Triclinic, $[P \overline 1]$
a = 7.2490 (2) Å
b = 9.4719 (3) Å
c = 10.4749 (4) Å
= 100.623 (2)°
= 97.433 (2)°
= 96.127 (2)°
V = 694.64 (4) Å³
Z = 2
Mo K radiation
= 0.30 mm^-1
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.951, T_max = 0.957
4097 measured reflections
2900 independent reflections
2332 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.103
S = 1.03
2900 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O2ⁱ	0.89 (1)	2.09 (1)	2.9591 (18)	165 (2)
O4-H4O1ⁱⁱ	0.82	1.85	2.6708 (17)	176
C7-H7O2	0.93	2.22	2.817 (2)	122
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+2, -z+1.

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: CI5018 ).

Acknowledgements

The authors acknowledge the Hunan Provincial Natural Science Foundation of China (grant No. 09 J J6022) and the Scientific Research Fund of Hunan Provincial Education Department (grant No. 08B031), China, for financial support.

References

Bagihalli, G. B., Avaji, P. G., Patil, S. A. & Badami, P. S. (2008). Eur. J. Med. Chem. 43, 2639-2649.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Chantrapromma, S., Jana, S., Hazra, A. & Goswami, S. (2008). Acta Cryst. E64, o175-o176.
Goh, J. H., Fun, H.-K., Vinayaka, A. C. & Kalluraya, B. (2010). Acta Cryst. E66, o24.
Mohamed, G. G., Omar, M. M. & Ibrahim, A. A. (2009). Eur. J. Med. Chem. 44, 4801-4812.
Ritter, E., Przybylski, P., Brzezinski, B. & Bartl, F. (2009). Curr. Org. Chem. 13, 241-249.
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2501.
Sheldrick, G. M. (1996). SADABS. University of Goöttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhou, C.-S., Hou, H.-Y. & Yang, T. (2009). Z. Kristallogr. New Cryst. Struct. 224, 37-38.
Zhou, C.-S. & Yang, T. (2009). Z. Kristallogr. New Cryst. Struct. 224, 39-40.

organic compounds