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Volume 69 
Part 8 
Pages o1335-o1336  
August 2013  

Received 3 July 2013
Accepted 20 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.054
wR = 0.144
Data-to-parameter ratio = 12.4
Details
Open access

(E)-1-(2-Phenyldiazen-2-ium-1-yl)naphthalen-2-olate

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Département de Chimie, Université Mentouri de Constantine 1, 25000 Constantine, Algeria
Correspondence e-mail: bougueriahassiba@gmail.com

In the title zwitterionic compound, C16H12N2O, the dihedral angle between the phenyl ring and the naphthalene ring system is 17.85 (8)°; an intramolecular N-H...O hydrogen bond occurs. In the crystal, [pi]-[pi] stacking is observed between naphthalene ring systems of adjacent molecules, the centroid-centroid distance being 3.6486 (11) Å.

Related literature

For general background to azo compounds and their applications in the fields of dyes, pigments and advanced materials, see: Biswas & Umapathy (2000[Biswas, N. & Umapathy, S. (2000). J. Phys. Chem. A, 104, 2734-2745.]); Willner & Rubin (1996[Willner, I. & Rubin, S. (1996). Angew. Chem. Int. Ed. Engl. 35, 367-385.]); Hunger (2003[Hunger, K. (2003). Industrial Dyes, Chemistry, Properties and Applications, edited by K. Hunger, pp. 20-35. Weinheim: Wiley-VCH.]); Catino & Farris (1985[Catino, S. C. & Farris, R. E. (1985). Azo dyes, in Concise Encyclopedia of Chemical Technology, edited by M. Grayson, pp. 142-144. New York: John Wiley and Sons.]); Zollinger (2003[Zollinger, H. (2003). Colour Chemistry: Synthesis, Properties and Applications of Organic Dyes and Pigments, edited by H. Zollinger, 3rd rev. ed. Weinheim: Wiley-VCH.]); Bahatti & Seshadri (2004[Bahatti, H. S. & Seshadri, S. (2004). Color. Technol. 120, 151-155.]); Taniike et al. (1996[Taniike, K., Matsumoto, T., Sato, T., Ozaki, Y., Nakashima, K. & Iriyama, K. (1996). J. Phys. Chem. 100, 15508-15516.]); Fadda et al. (1994[Fadda, A. A., Etmen, H. A., Amer, F. A., Barghout, M. & Mohammed, K. S. J. (1994). J. Chem. Technol. Biotechnol. 61, 343-349.]); Bach et al. (1996[Bach, H., Anderle, K., Fuhrmann, Th. & Wendorff, J. H. (1996). J. Phys. Chem. 100, 4135-4140.]); Clark & Hester (1993[Clark, R. J. H. & Hester, R. E. (1993). Spectroscopy of New Materials: Advances in Spectroscopy, edited by R. J. H. Clark & R. E. Hester. New York: John Wiley and Sons.]). For the synthesis, see: Wang et al. (2003[Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigments, 57, 77-86.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12N2O

  • Mr = 248.28

  • Monoclinic, P 21 /c

  • a = 13.0800 (12) Å

  • b = 13.5170 (13) Å

  • c = 7.0080 (4) Å

  • [beta] = 94.140 (6)°

  • V = 1235.80 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.26 × 0.22 × 0.17 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 4092 measured reflections

  • 2139 independent reflections

  • 1546 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.144

  • S = 1.06

  • 2139 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 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 1.73 2.5346 (19) 141

Data collection: KappaCCD Server Software (Nonius, 1999[Nonius (1999). KappaCCD Server Software. Nonius BV, Delft, The Nertherlands.]); cell refinement: KappaCCD Server Software; data reduction: 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.]); program(s) used to solve structure: SHELXS86 (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: 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: XU5718 ).


Acknowledgements

The authors would like to thank Professor L. Ouahab, University of Rennes (France), for his valuable collaboration in the recording and interpretation of the XRD data and Professor S. E. Bouaoud, University of Constantine (Algeria) for providing laboratory facilities and encouragement.

References

Bach, H., Anderle, K., Fuhrmann, Th. & Wendorff, J. H. (1996). J. Phys. Chem. 100, 4135-4140.  [CrossRef] [ChemPort] [Web of Science]
Bahatti, H. S. & Seshadri, S. (2004). Color. Technol. 120, 151-155.
Biswas, N. & Umapathy, S. (2000). J. Phys. Chem. A, 104, 2734-2745.  [CrossRef] [ChemPort]
Catino, S. C. & Farris, R. E. (1985). Azo dyes, in Concise Encyclopedia of Chemical Technology, edited by M. Grayson, pp. 142-144. New York: John Wiley and Sons.
Clark, R. J. H. & Hester, R. E. (1993). Spectroscopy of New Materials: Advances in Spectroscopy, edited by R. J. H. Clark & R. E. Hester. New York: John Wiley and Sons.
Fadda, A. A., Etmen, H. A., Amer, F. A., Barghout, M. & Mohammed, K. S. J. (1994). J. Chem. Technol. Biotechnol. 61, 343-349.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hunger, K. (2003). Industrial Dyes, Chemistry, Properties and Applications, edited by K. Hunger, pp. 20-35. Weinheim: Wiley-VCH.
Nonius (1999). KappaCCD Server Software. Nonius BV, Delft, The Nertherlands.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Taniike, K., Matsumoto, T., Sato, T., Ozaki, Y., Nakashima, K. & Iriyama, K. (1996). J. Phys. Chem. 100, 15508-15516.  [CrossRef] [ChemPort] [Web of Science]
Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigments, 57, 77-86.  [CrossRef] [ChemPort]
Willner, I. & Rubin, S. (1996). Angew. Chem. Int. Ed. Engl. 35, 367-385.  [CrossRef] [ChemPort] [Web of Science]
Zollinger, H. (2003). Colour Chemistry: Synthesis, Properties and Applications of Organic Dyes and Pigments, edited by H. Zollinger, 3rd rev. ed. Weinheim: Wiley-VCH.


Acta Cryst (2013). E69, o1335-o1336   [ doi:10.1107/S1600536813020102 ]

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