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Volume 69 
Part 8 
Pages o1322-o1323  
August 2013  

Received 8 July 2013
Accepted 21 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.068
wR = 0.202
Data-to-parameter ratio = 16.7
Details
Open access

1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, 25000 Constantine, Algeria
Correspondence e-mail: issam.boudraa@gmail.com

The title zwitterion, C17H14N2O2, crystallizes with two independent molecules in the asymmetric unit, both of which are approximately planar, the dihedral angles between the benzene ring and the naphthalene ring system being 4.39 (12)° in one molecule and 5.83 (12)° in the other, and show an E conformation with respect to the azo double bond. An intramolecular N-H...O hydrogen bond in each molecule helps to establish their near planar conformation. In the crystal, molecules are linked through O-H...O hydrogen bonds into infinite chains running along the a-axis direction. In addition, the chains are stacked along the b axis via [pi]-[pi] interactions between the benzene and the naphthalene rings of adjacent molecules, the centroid-centroid distances being 3.722 (3) and 3.823 (4) 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.]). For details of azo pigments, see: Herbst & Hunger (2004[Herbst, W. & Hunger, K. (2004). Industrial Organic Pigments, pp. 183-419. Weinheim: VCH.]). For related structures of hydrazone derivatives, see: Olivieri et al. (1989[Olivieri, A. C., Wilson, R. B., Paul, I. C. & Curtin, D. Y. (1989). J. Am. Chem. Soc. 111, 5525-5532.]); Oakes (2002[Oakes, J. (2002). Rev. Prog. Color. pp. 32-63.]). For bond-length data, see: Yazici et al. (2010[Yazici, S., Albayrak, Ç., Gümrükçüoglu, I., Senel, I. & Büyükgüngör, O. (2010). Acta Cryst. E66, o559-o560.]); Karadayi et al. (2006[Karadayi, N., Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o3695-o3696.]). Many azo compounds have been synthesized by diazotization and diazo coupling reactions, see: Wang et al. (2003[Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigments, 57, 77-86.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14N2O2

  • Mr = 278.31

  • Monoclinic, P 21 /a

  • a = 14.541 (5) Å

  • b = 6.052 (5) Å

  • c = 32.633 (5) Å

  • [beta] = 101.871 (5)°

  • V = 2810 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.03 × 0.02 × 0.02 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.853, Tmax = 0.995

  • 20440 measured reflections

  • 6447 independent reflections

  • 3301 reflections with I > 2[sigma](I)

  • Rint = 0.078

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.202

  • S = 1.05

  • 6447 reflections

  • 386 parameters

  • 2 restraints

  • All H-atom parameters refined

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.88 (2) 1.82 (3) 2.536 (4) 138 (2)
O2-H2...O6 0.82 1.85 2.631 (3) 159
O5-H5...O1i 0.82 1.81 2.622 (3) 168
N6-H6...O6 0.88 (2) 1.82 (3) 2.546 (4) 138 (2)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2112 ).


Acknowledgements

We thank all researchers of the CHEMS Research Unit, University of Constantine, Algeria, for their valuable assistance. Thanks are due to the MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique -Algérie) for financial support. We also express our gratitude to Professor L. Ouahab, Director of Research at the Laboratory UMR LCSIM 6511, CNRS, Rennes I (France), for recording the diffraction data and help with the structure determination.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Herbst, W. & Hunger, K. (2004). Industrial Organic Pigments, pp. 183-419. Weinheim: VCH.
Karadayi, N., Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o3695-o3696.  [CSD] [CrossRef] [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]
Oakes, J. (2002). Rev. Prog. Color. pp. 32-63.
Olivieri, A. C., Wilson, R. B., Paul, I. C. & Curtin, D. Y. (1989). J. Am. Chem. Soc. 111, 5525-5532.  [CrossRef] [ChemPort] [Web of Science]
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigments, 57, 77-86.  [CrossRef] [ChemPort]
Yazici, S., Albayrak, Ç., Gümrükçüoglu, I., Senel, I. & Büyükgüngör, O. (2010). Acta Cryst. E66, o559-o560.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1322-o1323   [ doi:10.1107/S160053681302014X ]

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