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Volume 69 
Part 7 
Page m405  
July 2013  

Received 13 June 2013
Accepted 15 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.004 Å
R = 0.034
wR = 0.082
Data-to-parameter ratio = 12.3
Details
Open access

Bis{1-[(E)-(2-chlorophenyl)diazenyl]naphthalen-2-olato}copper(II)

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, Algeria
Correspondence e-mail: mbenaouida@yahoo.fr

The CuII atom in the title compound, [Cu(C16H10ClN2O)2], is located on an inversion center and is tetracoordinated by two N and two O atoms from two bidentate 1-[(E)-(2-chlorophenyl)diazenyl]naphthalen-2-olate ligands, forming a square-planar complex. In the crystal, molecules are linked via weak C-H...O and C-H...Cl hydrogen bonds, forming chains propagating along [010]. There are also [pi]-[pi] interactions present involving adjacent naphthalene rings [centroid-centroid distance = 3.661 (13) 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.]). For related structures, see: Tai et al. (2010[Tai, W.-J., Li, C.-H., Li, C.-Y. & Ko, B.-T. (2010). Acta Cryst. E66, m1315.]); Lin et al. (2010[Lin, M.-L., Tsai, C.-Y., Li, C.-Y., Huang, B.-H. & Ko, B.-T. (2010). Acta Cryst. E66, m1022.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C16H10ClN2O)2]

  • Mr = 626.99

  • Monoclinic, P 21 /c

  • a = 10.2218 (4) Å

  • b = 7.8348 (3) Å

  • c = 17.5678 (6) Å

  • [beta] = 111.941 (2)°

  • V = 1305.03 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.08 mm-1

  • T = 273 K

  • 0.01 × 0.01 × 0.01 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 7327 measured reflections

  • 2299 independent reflections

  • 1979 reflections with I > 2[sigma](I)

  • Rint = 0.030

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

  • wR(F2) = 0.082

  • S = 1.04

  • 2299 reflections

  • 187 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O1i 0.93 2.62 3.300 (3) 130
C5-H5...Cl1i 0.93 2.94 3.682 (3) 138
Symmetry code: (i) x, y+1, z.

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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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: SU2613 ).


Acknowledgements

The authors thank the MESRS (Algeria) for financial support. MB especially thanks the Algerian MESRS for the financial support of a PNR project.

References

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]
Lin, M.-L., Tsai, C.-Y., Li, C.-Y., Huang, B.-H. & Ko, B.-T. (2010). Acta Cryst. E66, m1022.  [CSD] [CrossRef] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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]
Tai, W.-J., Li, C.-H., Li, C.-Y. & Ko, B.-T. (2010). Acta Cryst. E66, m1315.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, m405  [ doi:10.1107/S1600536813016681 ]

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