Aqua­{N-[1-(2-oxidophen­yl)ethyl­idene]-l-serinato}copper(II) monohydrate

Gan-Qing Zhao; Da-Ming Tian; Yong-Jun Han; Ling-Wei Xue; Qin-Long Peng

doi:10.1107/S1600536809045292

. 2009 Nov 4;65(Pt 12):m1505. doi: 10.1107/S1600536809045292

Aqua{N-[1-(2-oxidophenyl)ethylidene]-l-serinato}copper(II) monohydrate

Gan-Qing Zhao ^a,^*, Da-Ming Tian ^b, Yong-Jun Han ^a, Ling-Wei Xue ^a, Qin-Long Peng ^a

PMCID: PMC2972012 PMID: 21578556

Abstract

In the title compound, [Cu(C₁₁H₁₁NO₄)(H₂O)]·H₂O, each Cu^II ion is four-coordinated by one N and two O atoms from the tridentate Schiff base ligand, and by one O atom from the coordinated water molecule in a distorted square-planar geometry. Intermolecular O—H⋯O hydrogen bonds link complex molecules and solvent water molecules into flattened columns propagated in [100].

Related literature

For general background to the chemistry of transition metal complexes with Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, and α-amino acids, see: Casella & Guillotti (1983 ▶); Vigato & Tamburini (2004 ▶); Ganguly et al. (2008 ▶). For related structures, see: Usman et al. (2003 ▶); Parekh et al. (2006 ▶); Basu Baul et al. (2007 ▶). For details of the synthesis, see: Plesch et al. (1997 ▶). graphic file with name e-65-m1505-scheme1.jpg

Experimental

Crystal data

[Cu(C₁₁H₁₁NO₄)(H₂O)]·H₂O
M _r = 320.78
Orthorhombic,
a = 5.6701 (9) Å
b = 13.788 (2) Å
c = 15.536 (2) Å
V = 1214.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.82 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.659, T _max = 0.712
6314 measured reflections
2149 independent reflections
2038 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.022
wR(F ²) = 0.053
S = 1.09
2149 reflections
176 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), 869 Friedel pairs
Flack parameter: 0.011 (13)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045292/cv2643sup1.cif

e-65-m1505-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045292/cv2643Isup2.hkl

e-65-m1505-Isup2.hkl^{(105.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3ⁱ	0.82	1.84	2.651 (3)	171
O1W—H1WA⋯O2W ⁱⁱ	0.82	1.91	2.694 (3)	161
O1W—H1WB⋯O2ⁱⁱⁱ	0.85	1.92	2.740 (3)	162
O2W—H2WA⋯O4	0.85	2.04	2.837 (3)	156
O2W—H2WB⋯O1ⁱⁱ	0.85	2.02	2.817 (3)	157

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This research was supported by the National Sciences Foundation of China (grant No. 20877036) and High-Level Personnel Foundation of Pingdingshan University (grant No. 2009001).

supplementary crystallographic information

Comment

In the past decades, significant progress has been achieved in understanding the chemistry of transition metal complexes with Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, and α-amino acids (Vigato & Tamburini, 2004; Ganguly et al., 2008; Casella & Guillotti, 1983). A few stuctural studies have been performed on Schiff base complexes derived from 2-Hydroxyacetophenone and animo acids (Usman et al., 2003; Basu Baul et al., 2007; Parekh et al., 2006). We report here the crystal structure of the title compound (I).

The asymmetric unit of (I) contains a monomeric square-planar coordinated Cu^II complex and one solvate water molecule (Fig. 1). The Cu—N bond length is 1.9335 (19) Å, while Cu—O bond lengths lie in the range 1.8595 (18)-1.9677 (18) Å.

The crystal structure is stabilized by O—H···O type hydrogen bonds (Table 1), which link complex molecules and solvent water molecules into flattened columns propagated in direction [100].

Experimental

The title compound was synthesized as described in the literature (Plesch et al., 1997). To L-serine (1.00 mmol) and potassium hydroxide (1.00 mmol) in 10 ml of methanol was added 2-Hydroxyacetophenone (1.00 mmol in 10 ml of methanol) dropwise. The yellow solution was stirred for 2.0 h at 333 K. The resultant mixture was added dropwise to copper (II) acetate monohydrate (1.00 mmol) in an aqueous methanolic solution (20 ml, 1:1 v/v), and heated with stirring for 2.0 h at 333 K. The dark green solution was filtered and left for several days, dark green crystals had formed that were filtered off, washed with water, and dried under vacuum.