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Volume 69 
Part 7 
Page o1021  
July 2013  

Received 15 May 2013
Accepted 30 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.059
wR = 0.185
Data-to-parameter ratio = 14.1
Details
Open access

(E)-1-(3-Chlorophenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium

aUnité de recherche de Chimie de l'Environnement et Moléculaire Structurale, Faculté du sciences exactes, Université Mentouri de Constantine 1, 25000 Constantine, Algeria
Correspondence e-mail: king.ali@hotmail.fr

The title zwitterion,, C16H11ClN2O, is approximately planar, the dihedral angle between the benzene ring and naphthalene ring system is 1.55 (13)°; an intramolecular N-H...O hydrogen bond stabilizes the planar conformation. In the crystal, [pi]-[pi] stacking between the benzene ring and the naphthalene ring system of adjacent molecules links the molecules into supramolecular chains running along the b axis, the centroid-centroid distance being 3.765 (2) Å.

Related literature

For general background to the use of azo compounds as dyes, pigments and advanced materials, see: Lee et al. (2004[Lee, S. H., Kim, J. Y., Ko, J., Lee, J. Y. & Kim, J. S. (2004). J. Org. Chem. 69, 2902-2905.]); Oueslati et al. (2004[Oueslati, F., Dumazet-Bonnamour, I. & Lamartine, R. (2004). New J. Chem. 28, 1575-1578.]). Many azo compounds have been synthesized by diazotization and diazo-coupling reactions; for information, see: Wang et al. (2003[Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm. 57, 77-86.]). For a related structure, see: Elmali et al. (2001[Elmali, A., Elerman, Y. & Svoboda, I. (2001). Acta Cryst. C57, 485-486.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11ClN2O

  • Mr = 282.72

  • Monoclinic, P 21 /c

  • a = 16.340 (2) Å

  • b = 5.7665 (4) Å

  • c = 15.632 (2) Å

  • [beta] = 113.604 (4)°

  • V = 1349.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.09 × 0.04 × 0.02 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 4488 measured reflections

  • 2418 independent reflections

  • 1289 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.185

  • S = 1.01

  • 2418 reflections

  • 171 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.94 1.82 2.564 (4) 135

Data collection: KappaCCD Reference Manual (Nonius, 1998[Nonius (1998). KappaCCD Reference Manual. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5708 ).


Acknowledgements

We are grateful to Mr L. Ouahab (University of Rennes, France) for his collaboration in the recording and interpretation of XRD data and express our gratitude for the valuable assistance he has provided throughout the realisation of this work.

References

Elmali, A., Elerman, Y. & Svoboda, I. (2001). Acta Cryst. C57, 485-486.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Lee, S. H., Kim, J. Y., Ko, J., Lee, J. Y. & Kim, J. S. (2004). J. Org. Chem. 69, 2902-2905.  [CrossRef] [PubMed] [ChemPort]
Nonius (1998). KappaCCD Reference Manual. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Oueslati, F., Dumazet-Bonnamour, I. & Lamartine, R. (2004). New J. Chem. 28, 1575-1578.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm. 57, 77-86.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1021  [ doi:10.1107/S1600536813014931 ]

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