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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 [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.104
Data-to-parameter ratio = 15.2
Details
Open access

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

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-H...O 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[Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005). Bioorg. Med. Chem. 13, 4638-4644.]); Liu et al. (2006[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.]). For the synthesis and structure of ethyl(4-chlorophenoxy)acetate, see: Dutkiewicz et al. (2009[Dutkiewicz, G., Chidan Kumar, C. S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2009). Acta Cryst. E65, o3189.]). For graph-set motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]) and for classification of hydrogen bonds, see: Gilli & Gilli (2009[Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond, p. 61. New York: Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClN3O2

  • Mr = 289.72

  • Monoclinic, P 21 /n

  • a = 13.059 (4) Å

  • b = 5.3567 (16) Å

  • c = 19.175 (6) Å

  • [beta] = 104.586 (5)°

  • V = 1298.2 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.927, Tmax = 0.959

  • 7114 measured reflections

  • 2796 independent reflections

  • 2437 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.885 (19) 1.96 (2) 2.8423 (19) 172.9 (18)
C2-H2A...Cg2ii 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[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). 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: 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.  [CSD] [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005). Bioorg. Med. Chem. 13, 4638-4644.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o28  [ doi:10.1107/S1600536812045989 ]

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