(E)-6-Chloro-N′-(3,5-dichloro-2-hydroxy­benzyl­idene)­nicotinohydrazide

Ren, C.

doi:10.1107/S1600536809007272

Volume 65
Part 4
Page o678
April 2009

Received 26 February 2009
Accepted 27 February 2009
Online 6 March 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R = 0.049
wR = 0.114
Data-to-parameter ratio = 13.0
Details

(E)-6-Chloro-N'-(3,5-dichloro-2-hydroxybenzylidene)nicotinohydrazide

Chun-yan Ren ^a ^*

^aCollege of Chemistry and Pharmacy, Qingdao Agricultural University, Shandong 266109, People's Republic of China
Correspondence e-mail: furbear01@163.com

The title Schiff base compound, C₁₃H₈Cl₃N₃O₂, was synthesized by the condensation reaction of 3,5-dichlorosalicylaldehyde with 6-chloronicotinic acid hydrazide in 95% ethanol. The molecule is nearly planar, with a dihedral angle of 1.9 (2)° between the aromatic ring planes, and an intramolecular O-HN hydrogen bond is observed. In the crystal, the molecules are connected by intermolecular N-HO hydrogen bonds into infinite chains propagating in [100].

Related literature

For general background, see: Kim et al. (2005); Fan et al. (2007). For background on the biological activities of Schiff bases, see: Ren et al. (2002); Takeuchi et al. (1998). For a related structure, see: Zhi (2008). For reference structural data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₃H₈Cl₃N₃O₂
M_r = 344.57
Monoclinic, P 2₁ /c
a = 4.8920 (10) Å
b = 18.014 (4) Å
c = 16.112 (3) Å
= 97.90 (3)°
V = 1406.4 (5) Å³
Z = 4
Mo K radiation
= 0.66 mm^-1
T = 298 K
0.27 × 0.23 × 0.23 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996) T_min = 0.842, T_max = 0.864
7275 measured reflections
2478 independent reflections
1323 reflections with I > 2(I)
R_int = 0.078

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.114
S = 1.01
2478 reflections
191 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O2ⁱ	0.86	2.20	2.930 (4)	142
O1-H1N1	0.82	1.82	2.540 (4)	147
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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: HB2920 ).

References

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.
Fan, Y. H., He, X. T., Bi, C. F., Guo, F., Bao, Y. & Chen, R. (2007). Russ. J. Coord. Chem. 33, 535-538.
Kim, H.-J., Kim, W., Lough, A. J., Kim, B. M. & Chin, J. (2005). J. Am. Chem. Soc. 127, 16776-16777.
Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Takeuchi, T., Bottcher, A., Quezada, C. M., Simon, M. I., Meade, T. J. & Gray, H. B. (1998). J. Am. Chem. Soc. 120 . 8555-8556.
Zhi, F. (2008). Acta Cryst. E64, o150.

organic compounds