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Volume 69 
Part 10 
Page o1498  
October 2013  

Received 22 August 2013
Accepted 27 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.154
Data-to-parameter ratio = 20.4
Details
Open access

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

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

In the title zwitterion, C17H12N2O2, the dihedral angle between the benzene ring and naphthalene ring system is 11.76 (7)° and an intramolecular N-H...O hydrogen bond exists. In the crystal, molecules are linked via pairs of C-H...O hydrogen bonds, forming inversion dimers.

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.]). For a related structure, see: Xu et al. (2010[Xu, J.-J., Li, J., Pi, M. & Jin, C.-M. (2010). Acta Cryst. E66, o1752.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12N2O2

  • Mr = 276.29

  • Monoclinic, P 21 /c

  • a = 5.601 (4) Å

  • b = 7.780 (5) Å

  • c = 29.70 (2) Å

  • [beta] = 94.624 (16)°

  • V = 1290.0 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.09 × 0.04 × 0.01 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 16470 measured reflections

  • 3964 independent reflections

  • 2155 reflections with I > 2[sigma](I)

  • Rint = 0.078

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.154

  • S = 1.01

  • 3963 reflections

  • 194 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.97 (3) 1.83 (3) 2.577 (3) 133 (3)
C6-H6...O1i 0.93 2.41 3.327 (4) 168
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: KappaCCD Server Software (Nonius, 1999[Nonius (1999). KappaCCD Server Software. 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: XU5735 ).


References

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 (1999). KappaCCD Server Software. 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]
Xu, J.-J., Li, J., Pi, M. & Jin, C.-M. (2010). Acta Cryst. E66, o1752.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1498  [ doi:10.1107/S1600536813024112 ]

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