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Volume 68 
Part 1 
Page m86  
January 2012  

Received 3 December 2011
Accepted 17 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 185 K
Mean [sigma](C-C) = 0.005 Å
R = 0.042
wR = 0.093
Data-to-parameter ratio = 12.3
Details
Open access

{N'-[(2-Oxidonaphthalen-1-yl)methylidene]benzohydrazidato}(1,10-phenanthroline)copper(II) methanol monosolvate

aCollege of Environment and Resources, Jilin University, Changchun 130012, People's Republic of China, and bCollege of Earth Sciences, Jilin University, Changchun 130061, People's Republic of China
Correspondence e-mail: jianweizhu1905@163.com

The title mononuclear complex, [Cu(C18H12N2O2)(C12H8N2)]·CH3OH, contains one N'-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidate ligand (L2-), a Cu2+ cation, one 1,10-phenanthroline ligand and a methanol solvent molecule. The CuII ion adopts a CuO2N3 distorted square-pyramidal coordination. An O-H...O hydrogen bond is formed between the methanol solvent molecule and the hydrazide O atom of the L2- ligand.

Related literature

For details of the preparation of the Schiff base, see: Qiao et al. (2010[Qiao, Y., Ju, X., Gao, Z. & Kong, L. (2010). Acta Cryst. E66, o95.]). For applications of Schiff base compounds, see: Anford et al. (1998[Anford, J. D., Vittal, J. J. & Wang, Y. M. (1998). Inorg. Chem. 37, 1226-1231.]); Guo et al. (2010[Guo, Y.-N., Xu, G.-F., Gamez, P., Zhao, L., Lin, S.-Y., Deng, R., Tang, J.-K. & Zhang, H.-J. (2010). J. Am. Chem. Soc. 132, 8538-8539.]). For related structures, see: Huo et al. (2004[Huo, L.-H., Lu, Z.-Z., Gao, S., Zhao, H. & Zhao, J.-G. (2004). Acta Cryst. E60, m1636-m1638.]); Liu et al. (2008[Liu, H.-Y., Lu, Z.-S. & Niu, D.-Z. (2008). J. Coord. Chem. 61, 4040-4046.]); Sreeja et al. (2004[Sreeja, P. B., Prathapachandra Kurup, M. R., Kishore, A. & Jasmin, C. (2004). Polyhedron. 23, 575-581.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C18H12N2O2)(C12H8N2)]·CH4O

  • Mr = 564.08

  • Monoclinic, P 21 /c

  • a = 20.388 (2) Å

  • b = 9.9707 (10) Å

  • c = 12.5268 (12) Å

  • [beta] = 105.035 (2)°

  • V = 2459.4 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.93 mm-1

  • T = 185 K

  • 0.20 × 0.18 × 0.17 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.836, Tmax = 0.858

  • 12077 measured reflections

  • 4352 independent reflections

  • 2950 reflections with I > 2[sigma](I)

  • Rint = 0.059

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

  • wR(F2) = 0.093

  • S = 1.02

  • 4352 reflections

  • 354 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Selected bond lengths (Å)

Cu1-O2 1.913 (2)
Cu1-N2 1.914 (2)
Cu1-O1 1.984 (2)
Cu1-N4 2.023 (3)
Cu1-N3 2.321 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O1 0.84 1.99 2.820 (3) 167

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010)[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.].


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2374 ).


Acknowledgements

The authors thank the Natural Science Foundation of Jilin University.

References

Anford, J. D., Vittal, J. J. & Wang, Y. M. (1998). Inorg. Chem. 37, 1226-1231.  [ISI] [CrossRef] [PubMed]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Guo, Y.-N., Xu, G.-F., Gamez, P., Zhao, L., Lin, S.-Y., Deng, R., Tang, J.-K. & Zhang, H.-J. (2010). J. Am. Chem. Soc. 132, 8538-8539.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Huo, L.-H., Lu, Z.-Z., Gao, S., Zhao, H. & Zhao, J.-G. (2004). Acta Cryst. E60, m1636-m1638.  [CSD] [CrossRef] [details]
Liu, H.-Y., Lu, Z.-S. & Niu, D.-Z. (2008). J. Coord. Chem. 61, 4040-4046.  [CrossRef] [ChemPort]
Qiao, Y., Ju, X., Gao, Z. & Kong, L. (2010). Acta Cryst. E66, o95.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sreeja, P. B., Prathapachandra Kurup, M. R., Kishore, A. & Jasmin, C. (2004). Polyhedron. 23, 575-581.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, m86  [ doi:10.1107/S1600536811054316 ]

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