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Volume 69 
Part 7 
Pages o1175-o1176  
July 2013  

Received 18 June 2013
Accepted 22 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.120
Data-to-parameter ratio = 15.6
Details
Open access

(E)-1-[2-(2-Cyanophenyl)diazen-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

There are two independent zwitterion molecules (A and B) in the asymmetric unit of the title compound, C17H11N3O, which belongs to the family of azo dyes. The dihedral angle between the benzene ring and the naphthalene ring system is 6.99 (6)° in molecule A and 4.38 (6)° in molecule B. The azo group adopts an E conformation with respect to the -N=N- bond and each of the independent molecules has an intramolecular N-H...O hydrogen bond. In the crystal, molecules are linked by C-H...O and C-H...N hydrogen bonds, forming ribbons propagating along [-110]. The ribbons are linked via [pi]-[pi] interactions involving the benzene and naphthalene rings of inversion-related A and inversion-related B molecules, forming a three-dimensional structure. The most significant centroid-centroid distances vary from 3.6599 (6) to 3.7538 (9) Å.

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 Pigments, 57, 77-86.]). For a related structure, see: Rãdulescu et al. (2006[Rãdulescu, C., Hossu, A. M. & Ionitã, I. (2006). Dyes Pigments, 71, 123-129.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C17H11N3O

  • Mr = 273.29

  • Triclinic, [P \overline 1]

  • a = 7.1296 (3) Å

  • b = 12.9532 (7) Å

  • c = 15.6181 (8) Å

  • [alpha] = 111.562 (2)°

  • [beta] = 90.536 (2)°

  • [gamma] = 100.779 (2)°

  • V = 1312.92 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.55 × 0.11 × 0.08 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.910, Tmax = 0.993

  • 18729 measured reflections

  • 6021 independent reflections

  • 3859 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.120

  • S = 1.06

  • 6021 reflections

  • 387 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.20 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
N2-H2...O1 0.92 (1) 1.80 (2) 2.5380 (16) 136 (2)
N5-H5...O2 0.90 (1) 1.72 (2) 2.5277 (17) 147 (2)
C21-H21...N3i 0.93 2.61 3.509 (2) 162
C30-H30...N3ii 0.93 2.60 3.487 (2) 159
C32-H32...O1iii 0.93 2.49 3.1994 (18) 133
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y-1, -z; (iii) x, y, z+1.

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: SU2616 ).


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 express our gratitude and thank Mr. L Ouahab, Director of Research at laboratory UMR LCSIM 6511, CNRS, Rennes I (France), for his valuable collaboration in the recording and interpretation of the XRD data.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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]
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 Pigments, 71, 123-129.
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
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]


Acta Cryst (2013). E69, o1175-o1176   [ doi:10.1107/S1600536813017261 ]

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