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

Liu, B.-L.; Dong, D.-M.; Hua, X.-Y.; Zhu, J.-W.

doi:10.1107/S1600536811054316

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 (C-C) = 0.005 Å
R = 0.042
wR = 0.093
Data-to-parameter ratio = 12.3
Details

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

Bao-Lin Liu,^a De-Ming Dong,^a Xiu-Yi Hua ^a and Jian-Wei Zhu ^b ^*

^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 (L^2-), a Cu²⁺ cation, one 1,10-phenanthroline ligand and a methanol solvent molecule. The Cu^II ion adopts a CuO₂N₃ distorted square-pyramidal coordination. An O-HO hydrogen bond is formed between the methanol solvent molecule and the hydrazide O atom of the L^2- ligand.

Related literature

For details of the preparation of the Schiff base, see: Qiao et al. (2010). For applications of Schiff base compounds, see: Anford et al. (1998); Guo et al. (2010). For related structures, see: Huo et al. (2004); Liu et al. (2008); Sreeja et al. (2004).

Experimental

Crystal data

[Cu(C₁₈H₁₂N₂O₂)(C₁₂H₈N₂)]·CH₄O
M_r = 564.08
Monoclinic, P 2₁ /c
a = 20.388 (2) Å
b = 9.9707 (10) Å
c = 12.5268 (12) Å
= 105.035 (2)°
V = 2459.4 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.836, T_max = 0.858
12077 measured reflections
4352 independent reflections
2950 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.093
S = 1.02
4352 reflections
354 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_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-HA	D-H	HA	DA	D-HA
O3-H3AO1	0.84	1.99	2.820 (3)	167

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).

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.
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.
Huo, L.-H., Lu, Z.-Z., Gao, S., Zhao, H. & Zhao, J.-G. (2004). Acta Cryst. E60, m1636-m1638.
Liu, H.-Y., Lu, Z.-S. & Niu, D.-Z. (2008). J. Coord. Chem. 61, 4040-4046.
Qiao, Y., Ju, X., Gao, Z. & Kong, L. (2010). Acta Cryst. E66, o95.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sreeja, P. B., Prathapachandra Kurup, M. R., Kishore, A. & Jasmin, C. (2004). Polyhedron. 23, 575-581.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

metal-organic compounds