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Volume 69 
Part 8 
Page o1250  
August 2013  

Received 3 July 2013
Accepted 9 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.034
wR = 0.066
Data-to-parameter ratio = 19.3
Details
Open access

(E)-1-[(2,4,6-Tribromophenyl)diazenyl]naphthalen-2-ol

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 azo molecule, C16H9Br3N2O, adopts a trans conformation with respect to the azo N=N double bond. An intramolecular O-H...N hydrogen bond forms an S(6) ring motif. The dihedral angle between the naphthalene ring system and the benzene ring is 33.80 (16)°. In the crystal, molecules are stacked in columns along the a axis by [pi]-[pi] interactions [centroid-centroid distances = 3.815 (3) and 3.990 (3) Å].

Related literature

For applications of azo compounds, see: Gale et al. (1998[Gale, P. A., Chen, Z., Drew, M. G. B., Heath, J. A. & Beer, P. D. (1998). Polyhedron, 4, 405-412.]). For the synthesis of similar compounds, see: Wang et al. (2003[Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm. 57, 77-86.]); Heinrich et al. (2007[Heinrich, M. R., Blank, O. & Wetzel, A. (2007). J. Org. Chem. 72, 476-484.]). For bond lengths and angles in related azo compounds, see: Deveci et al. (2005[Deveci, O., Isik, S., Albayrak, C. & Agar, E. (2005). Acta Cryst. E61, o3226-o3227.]); El-Ghamry et al. (2008[El-Ghamry, H., Issa, R., El-Baradie, K., Isagai, K., Masaoka, S. & Sakai, K. (2008). Acta Cryst. E64, o1673-o1674.]).

[Scheme 1]

Experimental

Crystal data
  • C16H9Br3N2O

  • Mr = 484.98

  • Orthorhombic, P 21 21 21

  • a = 3.9904 (11) Å

  • b = 15.689 (4) Å

  • c = 24.580 (7) Å

  • V = 1538.8 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 7.87 mm-1

  • T = 293 K

  • 0.03 × 0.02 × 0.02 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.244, Tmax = 0.332

  • 13143 measured reflections

  • 3841 independent reflections

  • 2910 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.066

  • S = 0.96

  • 3841 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1553 Friedel pairs

  • Flack parameter: 0.004 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 1.85 2.561 (4) 144

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: 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: 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: IS5290 ).


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

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deveci, O., Isik, S., Albayrak, C. & Agar, E. (2005). Acta Cryst. E61, o3226-o3227.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
El-Ghamry, H., Issa, R., El-Baradie, K., Isagai, K., Masaoka, S. & Sakai, K. (2008). Acta Cryst. E64, o1673-o1674.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Gale, P. A., Chen, Z., Drew, M. G. B., Heath, J. A. & Beer, P. D. (1998). Polyhedron, 4, 405-412.  [Web of Science] [CrossRef]
Heinrich, M. R., Blank, O. & Wetzel, A. (2007). J. Org. Chem. 72, 476-484.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2004). 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 Pigm. 57, 77-86.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1250  [ doi:10.1107/S1600536813018977 ]

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