(E)-2-(4-Chloro­phen­oxy)-N′-(pyridin-4-yl­methyl­idene)acetohydrazide

Rao, X.; Wu, W.-S.; Li, C.; Huang, Y.

doi:10.1107/S1600536812045989

Volume 69
Part 1
Page o28
January 2013

Received 16 October 2012
Accepted 7 November 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.104
Data-to-parameter ratio = 15.2
Details

(E)-2-(4-Chlorophenoxy)-N'-(pyridin-4-ylmethylidene)acetohydrazide

Xiao-jin Rao,^a Wen-Shi Wu,^a ^* Chuan-hui Li ^a and Yu-min Huang ^a

^aCollege of Materials Science and Engineering, Huaqiao University, Xiamen, Fujian 361021, People's Republic of China
Correspondence e-mail: wws@hqu.edu.cn

In the title compound, C₁₄H₁₂ClN₃O₂, the acylhydrazone base [C(=O)-N-N=C] is essentially planar, with an r.m.s. deviation of 0.0095 Å, and makes a dihedral angle of 12.52 (10)°with the pyridine ring. In the crystal, molecules are linked via pairs of N-HO hydrogen bonds, forming inversion dimers with an R₂²(8) graph-set motif. The dimers are linked via C-H [pi] interactions forming chains along [101].

Related literature

For chemical properties of hydrazides, see: Narayana et al. (2005); Liu et al. (2006). For the synthesis and structure of ethyl(4-chlorophenoxy)acetate, see: Dutkiewicz et al. (2009). For graph-set motifs, see: Etter et al. (1990) and for classification of hydrogen bonds, see: Gilli & Gilli (2009).

Experimental

Crystal data

C₁₄H₁₂ClN₃O₂
M_r = 289.72
Monoclinic, P 2₁ /n
a = 13.059 (4) Å
b = 5.3567 (16) Å
c = 19.175 (6) Å
= 104.586 (5)°
V = 1298.2 (7) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 173 K
0.53 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.927, T_max = 0.959
7114 measured reflections
2796 independent reflections
2437 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.104
S = 1.05
2796 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C3-C8 phenyl ring.

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.885 (19)	1.96 (2)	2.8423 (19)	172.9 (18)
C2-H2ACg2ⁱⁱ	0.97	2.88	3.676 (2)	140
Symmetry codes: (i) -x, -y+3, -z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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: FB2275 ).

Acknowledgements

We are grateful for financial support from the National Science Foundation of Fujian Province of China (No. 2010 J01288) and the Fundamental Research Funds for the Central Universities (No. JB-JC1003). We also thank Dr Zhan-bin Wei (Department of Chemistry, Xiamen University) for the data collection.

References

Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dutkiewicz, G., Chidan Kumar, C. S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2009). Acta Cryst. E65, o3189.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond, p. 61. New York: Oxford University Press.
Liu, F., Stephen, A. G., Adainson, C. S., Gousset, K., Aman, M. J., Freed, E. O., Fisher, R. J. & Burke, T. R. Jr (2006). Org. Lett. 8, 5165-5168.
Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005). Bioorg. Med. Chem. 13, 4638-4644.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds