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Volume 69 
Part 6 
Pages o867-o868  
June 2013  

Received 26 April 2013
Accepted 5 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.052
wR = 0.154
Data-to-parameter ratio = 20.9
Details
Open access

1-(4-Hydroxyphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium methanol hemisolvate

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: mbenaouida@yahoo.fr

In the title compound, C16H12N2O2·0.5CH3OH, the H atom of the -OH group has been transfered to the N atom in the azo group, forming a zwitterion. Hence, there is an intramolecular N-H...O, rather than an O-H...N, hydrogen bond in the molecule. The molecule is almost planar, the dihedral angle between the benzene ring and the mean plane of the naphthalene ring system being 4.51 (6)°. In the crystal, molecules are linked to and bridged by O-H...O hydrogen bonds involving the methanol molecule, which is located about a twofold rotation axis, and hence half-occupied, forming zigzag chains along [001]. Molecules are also linked via C-H...[pi] and [pi]-[pi] interactions, the latter involving adjacent benzene and naphthalene rings and having a centroid-centroid distance of 3.6616 (13) Å, forming a three-dimensional network.

Related literature

For azo compounds in the fields of 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 the synthesis of azo compounds, see: Wang et al. (2003[Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm. 57, 77-86.]). For the structures of related compounds, see: Jin et al. (2008[Jin, C.-M., Li, H., Zhong, Z.-X. & Wu, L.-Y. (2008). Acta Cryst. E64, o218.]); Xu et al. (2010[Xu, J.-J., Li, J., Pi, M. & Jin, C.-M. (2010). Acta Cryst. E66, o1752.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12N2O2·0.5CH4O

  • Mr = 280.30

  • Monoclinic, C 2/c

  • a = 26.942 (7) Å

  • b = 6.3479 (17) Å

  • c = 17.579 (5) Å

  • [beta] = 113.985 (4)°

  • V = 2746.8 (13) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.26 × 0.06 × 0.05 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 12992 measured reflections

  • 4212 independent reflections

  • 2286 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.154

  • S = 1.03

  • 4212 reflections

  • 202 parameters

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C5-C10 and C11-C16 rings, respectively.

D-H...A D-H H...A D...A D-H...A
O1S-H1O...O1i 0.92 1.92 2.832 (3) 171
N2-H2A...O1 0.86 1.84 2.540 (2) 137
O2-H2B...O1S 0.82 2.03 2.841 (3) 172
O2-H2B...O1Sii 0.82 1.97 2.690 (3) 146
C1S-H1SA...Cg3iii 1.11 (6) 2.58 (5) 3.555 (2) 147 (4)
C7-H7A...Cg2iv 0.93 2.73 3.521 (2) 144
Symmetry codes: (i) -x, -y+3, -z; (ii) [-x, y, -z-{\script{1\over 2}}]; (iii) [-x, y+1, -z-{\script{1\over 2}}]; (iv) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX publication routines (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: SU2594 ).


Acknowledgements

The authors, particularly MB (PNR project), thank the MESRS (Algeria) for financial support. Thanks are also due to Professor 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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jin, C.-M., Li, H., Zhong, Z.-X. & Wu, L.-Y. (2008). Acta Cryst. E64, o218.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm. 57, 77-86.  [CrossRef] [ChemPort]
Xu, J.-J., Li, J., Pi, M. & Jin, C.-M. (2010). Acta Cryst. E66, o1752.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o867-o868   [ doi:10.1107/S1600536813012245 ]

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