Bis(1-methyl-1H-imidazole-κN 3)bis­[2-(naphthalen-1-yl)acetato-κO]copper(II) monohydrate

Fu-Jun Yin; Li-Jun Han; Shu-Ping Yang; Xing-You Xu; Yu Gu

doi:10.1107/S1600536811049439

. 2011 Nov 25;67(Pt 12):m1821. doi: 10.1107/S1600536811049439

Bis(1-methyl-1H-imidazole-κN ³)bis[2-(naphthalen-1-yl)acetato-κO]copper(II) monohydrate

Fu-Jun Yin ^a,^*, Li-Jun Han ^b, Shu-Ping Yang ^c, Xing-You Xu ^d, Yu Gu ^e

PMCID: PMC3238723 PMID: 22199600

Abstract

In the crystal structure of the title compound, [Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]·H₂O, the Cu^II atom is coordinated by two 2-(naphthalen-1-yl)acetate anions and two 1-methylimidazole ligands, giving monomeric complexes with a square-planar coordination environment. Two complex molecules and two water molecules form a centrosymmetric ring system via O—H⋯O hydrogen bonds.

Related literature

For the pharmacological potential of metal complexes with imidazole, see: Boiani & Gonzales (2005 ▶); Parshina & Trofimov (2011 ▶). For the coordination chemistry of 1-naphthylacetate ligands, see: Yin et al. (2010 ▶); Chen et al. (2004 ▶); Yang et al. (2008 ▶); Tang et al. (2006 ▶); Ji et al. (2011 ▶).

Experimental

Crystal data

[Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]·H₂O
M _r = 616.16
Triclinic,
a = 8.7213 (10) Å
b = 12.8689 (14) Å
c = 13.5787 (15) Å
α = 107.223 (1)°
β = 90.295 (2)°
γ = 90.931 (1)°
V = 1455.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.843, T _max = 0.843
11175 measured reflections
5094 independent reflections
3534 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.102
S = 1.03
5094 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049439/im2340sup1.cif

e-67-m1821-sup1.cif^{(35KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049439/im2340Isup2.hkl

e-67-m1821-Isup2.hkl^{(244.4KB, 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
O1W—H1WA⋯O1	0.85	1.97	2.789 (3)	163
O1W—H1WB⋯O3ⁱ	0.85	2.07	2.904 (3)	167

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Self-assembly of supramolecular architectures based on naphthalene-1-yl-acetate ligands has attracted much attention during recent decades (Yin et al., 2010; Chen et al., 2004; Yang et al., 2008; Tang et al.,2006; Ji et al., 2011). Recent studies reveal that metal complexes with substituted imidazole and carboxylate ligands are interesting for medicinal chemists who explore their various pharmacological potentials (Boiani & Gonzales, 2005; Parshina & Trofimov, 2011). The crystal structure of the title compound was determined as part of an ongoing study on the properties of copper complexes containing imidazole ligands.

In the crystal structure of the title compound [Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]H₂O, each copper cation is coordinated by two N atoms of different 1-methylimidazole ligands and by two carboxyl O atoms of distinct naphthalene-1-yl-acetate anions within a square planar coordination sphere (Fig. 1). The Cu—N and Cu—O bond lengths are 1.985 (3) and 1.974 (2) Å, respectively. The asymmetric unit consits of one Cu^II cation, two neutral imidazole ligands, two anionic carboxylate ligands and one lattic water in general positions. It is noteworthy that there exist strong hydrogen-bonding interactions (Table 1, Fig.2) involving the carboxy group oxygen atoms of 1-naphthylacetate ligands as well as water molecules. The molecules fomr centrosymmetric ring systems by O—H···O hydrogen bonds

Experimental

The title compound was synthesized by the reaction of Cu(NO₃)₂ × 3 H₂O (72.3 mg, 0.3 mmol), naphthalene-1-yl-acetic acid (93 mg, 0.5 mmol), 1-methylimidazole (32.8 mg, 0.4 mmol) and NaOH (20 mg, 0.5 mmol) in 6 mL of a water-ethanol (2:1) mixture under solvothermal conditions. The mixture was homogenized and transferred into a sealed Teflon-lined solvothermal bomb (volume: 25 ml) and heated to 140°C for three days. After cooling green crystals of the title compound were obtained, which were washed with distilled water and absolute ethanol (yield: 38.7% based on Cu(NO₃)₂ × 3 H₂O ).