[Journal logo]

Volume 66 
Part 8 
Page m881  
August 2010  

Received 26 June 2010
Accepted 29 June 2010
Online 3 July 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.057
wR = 0.163
Data-to-parameter ratio = 14.4
Details
Open access

Bis[2-(cyclopentyliminomethyl)-5-methoxyphenolato]copper(II)

aSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723000, People's Republic of China
Correspondence e-mail: jiufulu@163.com

The title compound, [Cu(C13H16NO2)2], is a mononuclear copper(II) complex derived from the Schiff base ligand 2-(cyclopentyliminomethyl)-5-methoxyphenol and copper acetate. The CuII atom is four-coordinated by the phenolate O atoms and imine N atoms from two Schiff base ligands, in a highly distorted square-planar geometry. The O- and N-donor atoms are mutually trans and the dihedral angle between the two benzene rings is 55.8 (3)°.

Related literature

For background to complexes with Schiff bases, see: Hamaker et al. (2010[Hamaker, C. G., Maryashina, O. S., Daley, D. K. & Wadler, A. L. (2010). J. Chem. Crystallogr. 40, 34-39.]); Wang et al. (2010[Wang, W., Zhang, F. X., Li, J. & Hu, W. B. (2010). Russ. J. Coord. Chem. 36, 33-36.]); Mirkhani et al. (2010[Mirkhani, V., Kia, R., Milic, D., Vartooni, A. R. & Matkovic-Calogovic, D. (2010). Transition Met. Chem. 35, 81-87.]); Liu & Yang (2009[Liu, Y.-C. & Yang, Z.-Y. (2009). Eur. J. Med. Chem. 44, 5080-5089.]); Keypour et al. (2009[Keypour, H., Azadbakht, R., Rudbari, H. A., Heydarinekoo, A. & Khavasi, H. (2009). Transition Met. Chem. 34, 835-839.]); Adhikary et al. (2009[Adhikary, C., Sen, R., Bocelli, G., Cantoni, A., Solzi, M., Chaudhuri, S. & Koner, S. (2009). J. Coord. Chem. 62, 3573-3582.]); Peng et al. (2009[Peng, S.-J., Hou, H.-Y. & Zhou, C.-S. (2009). Synth. React. Inorg. Met. Org. Nano-Met. Chem. 39, 462-466.]). For similar copper complexes, see: Friscic et al. (2002[Friscic, T., Lough, A. J., Ferguson, G. & Kaitner, B. (2002). Acta Cryst. C58, m313-m315.]); Marsh & Spek (2001[Marsh, R. E. & Spek, A. L. (2001). Acta Cryst. B57, 800-805.]); Han et al. (2001[Han, Q.-F., Jian, F.-F., Lu, L.-D., Yang, X.-J. & Wang, X. (2001). J. Chem. Crystallogr. 31, 247-255.]); Akitsu & Einaga (2004[Akitsu, T. & Einaga, Y. (2004). Acta Cryst. E60, m436-m438.]); Dhar et al. (2003[Dhar, S., Senapati, D., Das, P. K., Chattopadhyay, P., Nethaji, M. & Chakravarty, A. R. (2003). J. Am. Chem. Soc. 125, 12118-12124.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C13H16NO2)2]

  • Mr = 500.08

  • Monoclinic, P 21 /n

  • a = 8.496 (1) Å

  • b = 14.054 (2) Å

  • c = 20.442 (2) Å

  • [beta] = 100.236 (3)°

  • V = 2402.0 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.94 mm-1

  • T = 298 K

  • 0.23 × 0.21 × 0.21 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.812, Tmax = 0.826

  • 12222 measured reflections

  • 4333 independent reflections

  • 3131 reflections with I > 2[sigma](I)

  • Rint = 0.081

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.163

  • S = 1.00

  • 4333 reflections

  • 300 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.69 e Å-3

  • [Delta][rho]min = -1.16 e Å-3

Table 1
Selected geometric parameters (Å, °)

Cu1-O1 1.890 (2)
Cu1-O3 1.891 (2)
Cu1-N2 1.967 (3)
Cu1-N1 1.978 (3)
O1-Cu1-O3 144.60 (13)
O1-Cu1-N2 93.93 (11)
O3-Cu1-N2 95.32 (11)
O1-Cu1-N1 95.40 (11)
O3-Cu1-N1 94.20 (11)
N2-Cu1-N1 148.66 (12)

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: 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: SJ5030 ).


Acknowledgements

The authors thank the Scientific Research Foundation of Shaanxi University of Technology (project No. SLGQD0708) for financial support.

References

Adhikary, C., Sen, R., Bocelli, G., Cantoni, A., Solzi, M., Chaudhuri, S. & Koner, S. (2009). J. Coord. Chem. 62, 3573-3582.  [ISI] [CSD] [CrossRef] [ChemPort]
Akitsu, T. & Einaga, Y. (2004). Acta Cryst. E60, m436-m438.  [CrossRef] [details]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dhar, S., Senapati, D., Das, P. K., Chattopadhyay, P., Nethaji, M. & Chakravarty, A. R. (2003). J. Am. Chem. Soc. 125, 12118-12124.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Friscic, T., Lough, A. J., Ferguson, G. & Kaitner, B. (2002). Acta Cryst. C58, m313-m315.  [CSD] [CrossRef] [details]
Hamaker, C. G., Maryashina, O. S., Daley, D. K. & Wadler, A. L. (2010). J. Chem. Crystallogr. 40, 34-39.  [ISI] [CSD] [CrossRef] [ChemPort]
Han, Q.-F., Jian, F.-F., Lu, L.-D., Yang, X.-J. & Wang, X. (2001). J. Chem. Crystallogr. 31, 247-255.  [ISI] [CSD] [CrossRef] [ChemPort]
Keypour, H., Azadbakht, R., Rudbari, H. A., Heydarinekoo, A. & Khavasi, H. (2009). Transition Met. Chem. 34, 835-839.  [ISI] [CrossRef] [ChemPort]
Liu, Y.-C. & Yang, Z.-Y. (2009). Eur. J. Med. Chem. 44, 5080-5089.  [ISI] [CrossRef] [PubMed] [ChemPort]
Marsh, R. E. & Spek, A. L. (2001). Acta Cryst. B57, 800-805.  [CrossRef] [details]
Mirkhani, V., Kia, R., Milic, D., Vartooni, A. R. & Matkovic-Calogovic, D. (2010). Transition Met. Chem. 35, 81-87.  [ISI] [CrossRef] [ChemPort]
Peng, S.-J., Hou, H.-Y. & Zhou, C.-S. (2009). Synth. React. Inorg. Met. Org. Nano-Met. Chem. 39, 462-466.  [ChemPort]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, W., Zhang, F. X., Li, J. & Hu, W. B. (2010). Russ. J. Coord. Chem. 36, 33-36.  [CrossRef]


Acta Cryst (2010). E66, m881  [ doi:10.1107/S1600536810025481 ]

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.