[Journal logo]

Volume 69 
Part 5 
Page m240  
May 2013  

Received 13 March 2013
Accepted 21 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.042
wR = 0.109
Data-to-parameter ratio = 14.4
Details
Open access

Bis[2-(hydroxyimino)cyclohexan-1-one oximato-[kappa]2N,N']copper(II)

aInstitute of Applied Physics, Academy of Sciences of Moldova, Academiei str. 5, MD2028 Chisinau, Moldova, and bInstitute of Chemistry, Academy of Sciences of Moldova, Academiei str. 3, MD2028 Chisinau, Moldova
Correspondence e-mail: croitor.lilia@gmail.com

In the title compound, [Cu(C6H9N2O2)2], the CuII atom is located on an inversion center and has a square-planar environment. Two 2-(hydroxyimino)cyclohexan-1-one oximate monoanions chelate to the CuII atom and the Cu-N distances are 1.920 (3) and 1.930 (3) Å. There are two short intramolecular O-H...O hydrogen bonds between the ligands. The complex molecules stack into columns extended along the c axis, with a Cu...Cu distance between adjacent molecules of 3.3060 (3) Å.

Related literature

For complexes of copper(II) with 1,2-cyclohexanedionedioxime, see: Birkelbach et al. (1997[Birkelbach, F., Weyhermuller, T., Lengen, M., Gerdan, M., Trautwein, A. X., Wieghardt, K. & Chaudhuri, P. (1997). J. Chem. Soc. Dalton Trans. pp. 4529-4538.]); Cervera et al. (1997[Cervera, B., Ruiz, R., Lloret, F., Julve, M., Cano, J., Faus, J., Bois, C. & Mrozinski, J. (1997). J. Chem. Soc. Dalton Trans. pp. 395-401.]); Coropceanu et al. (2011[Coropceanu, E. B., Croitor, L., Botoshansky, M. M., Siminel, A. V. & Fonari, M. S. (2011). Polyhedron, 30, 2592-2598.]); Mégnamisi-Bélombé & Endres (1983[Mégnamisi-Bélombé, M. & Endres, H. (1983). Acta Cryst. C39, 707-709.]); Simonov et al. (1982[Simonov, Y. A., Dvorkin, A. A., Malinovskii, T. I., Batir, D. G., Bulgak, I. I. & Ozol, L. D. (1982). Proc. Natl. Acad. Sci. USSR, 263, 1135-1138.]). For the crystal structure of bis(dimethylglyoximato-[kappa]2N,N')nickel(II), see: Li et al. (2003[Li, D.-X., Xu, D.-J. & Xu, Y.-Z. (2003). Acta Cryst. E59, m1094-m1095.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C6H9N2O2)2]

  • Mr = 345.84

  • Monoclinic, C 2/c

  • a = 20.8009 (12) Å

  • b = 10.1124 (7) Å

  • c = 6.6121 (5) Å

  • [beta] = 100.787 (6)°

  • V = 1366.26 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.62 mm-1

  • T = 293 K

  • 0.40 × 0.08 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.878, Tmax = 1.000

  • 2458 measured reflections

  • 1459 independent reflections

  • 1013 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.109

  • S = 1.00

  • 1459 reflections

  • 101 parameters

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O1...O2i 0.88 (6) 1.69 (6) 2.564 (4) 168 (6)
Symmetry code: (i) -x, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2564 ).


References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Birkelbach, F., Weyhermuller, T., Lengen, M., Gerdan, M., Trautwein, A. X., Wieghardt, K. & Chaudhuri, P. (1997). J. Chem. Soc. Dalton Trans. pp. 4529-4538.  [CrossRef]
Cervera, B., Ruiz, R., Lloret, F., Julve, M., Cano, J., Faus, J., Bois, C. & Mrozinski, J. (1997). J. Chem. Soc. Dalton Trans. pp. 395-401.  [CrossRef]
Coropceanu, E. B., Croitor, L., Botoshansky, M. M., Siminel, A. V. & Fonari, M. S. (2011). Polyhedron, 30, 2592-2598.  [ISI] [CSD] [CrossRef] [ChemPort]
Li, D.-X., Xu, D.-J. & Xu, Y.-Z. (2003). Acta Cryst. E59, m1094-m1095.  [CSD] [CrossRef] [ChemPort] [details]
Mégnamisi-Bélombé, M. & Endres, H. (1983). Acta Cryst. C39, 707-709.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Simonov, Y. A., Dvorkin, A. A., Malinovskii, T. I., Batir, D. G., Bulgak, I. I. & Ozol, L. D. (1982). Proc. Natl. Acad. Sci. USSR, 263, 1135-1138.  [ChemPort]


Acta Cryst (2013). E69, m240  [ doi:10.1107/S160053681300785X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.