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Volume 69 
Part 7 
Page o1052  
July 2013  

Received 19 May 2013
Accepted 30 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.043
wR = 0.120
Data-to-parameter ratio = 12.8
Details
Open access

1-(3-Acetylphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium

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

The title compound, C18H14N2O2, crystallized with two independent zwitterion molecules (A and B) in the asymmetric unit. They are both close to planar, the dihedral angle between the benzene ring and naphthalene ring system being 4.30 (9)° in A and 4.69 (9)° in B. Each molecule has an E conformation with respect to the azo double bond. In each of the independent molecules, an intramolecular N-H...O hydrogen bond forms an S(6) ring motif. In the crystal, molecules are linked via C-H...O hydrogen bonds, forming -A-A-A- and -B-B-B- chains parallel to one another and propagating along the a-axis direction. There are also [pi]-[pi] interactions between adjacent molecules involving benzene and naphthalene rings [centroid-centroid distance of 3.626 (3) Å for adjacent A molecules and 3.652 (3) Å for adjacent B molecules].

Related literature

For general background to azo compounds and their use in 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, see: Wang et al. (2003[Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm. 57, 77-86.]). For a related structure, see: Rãdulescu et al. (2006[Rãdulescu, C., Hossu, A. M. & Ionitã, I. (2006). Dyes Pigm. 71, 123-129.]).

[Scheme 1]

Experimental

Crystal data
  • C18H14N2O2

  • Mr = 290.31

  • Orthorhombic, P c a 21

  • a = 15.965 (5) Å

  • b = 5.807 (5) Å

  • c = 30.185 (5) Å

  • V = 2798 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.26 × 0.22 × 0.17 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.830, Tmax = 0.985

  • 13123 measured reflections

  • 5097 independent reflections

  • 4621 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.120

  • S = 1.03

  • 5097 reflections

  • 399 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N13-H13...O1 0.86 1.91 2.580 (3) 134
N43-H43...O31 0.86 1.90 2.575 (3) 134
C15-H15...O22i 0.93 2.36 3.256 (4) 162
C45-H45...O52ii 0.93 2.36 3.256 (4) 162
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+1, z]; (ii) [x+{\script{1\over 2}}, -y+2, z].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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: SU2604 ).


Acknowledgements

We thank all researchers of the CHEMS Research Unit of the University of Constantine, Algeria, for the valuable assistance they have provided us throughout the realisation of this work. We also thank Dr. L. Ouahab, Director of Research at the Laboratory UMR LCSIM 6511, CNRS, Rennes I (France), for his valuable collaboration in the data collection and analysis.

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, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Oueslati, F., Dumazet-Bonnamour, I. & Lamartine, R. (2004). New J. Chem. 28, 1575-1578.  [Web of Science] [CrossRef] [ChemPort]
Rãdulescu, C., Hossu, A. M. & Ionitã, I. (2006). Dyes Pigm. 71, 123-129.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm. 57, 77-86.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1052  [ doi:10.1107/S1600536813014918 ]

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