Aqua­[2-(5-ethyl-2-pyridyl-κN)-4-iso­propyl-4-methyl-5-oxo-4,5-dihydroxy­imidazol-1-ido-κN 1](5-methyl-1H-pyrazole-3-carboxyl­ato-κ2 N 2,O)copper(II) 1.33-hydrate

Ji-Chang Zhuang; Fei-Long Hu; Zhong-Jing Huang; Yue Zhuang; Feng Zhang

doi:10.1107/S1600536809053768

. 2009 Dec 19;66(Pt 1):m79. doi: 10.1107/S1600536809053768

Aqua[2-(5-ethyl-2-pyridyl-κN)-4-isopropyl-4-methyl-5-oxo-4,5-dihydroxyimidazol-1-ido-κN ¹](5-methyl-1H-pyrazole-3-carboxylato-κ² N ²,O)copper(II) 1.33-hydrate

Ji-Chang Zhuang ^a, Fei-Long Hu ^a, Zhong-Jing Huang ^a,^*, Yue Zhuang ^a, Feng Zhang ^a

PMCID: PMC2980135 PMID: 21579972

Abstract

In the title complex, [Cu(C₅H₅N₂O₂)(C₁₄H₁₈N₃O)(H₂O)]·1.33H₂O, the Cu^II ion is coordinated in a slightly distorted square-pyramidal environment. The basal plane is formed by two N atoms from a 2-(5-ethyl-2-pyridyl-κN)-4-isopropyl-4-methyl-5-oxo-4,5-dihydroxyimidazol-1-ide ligand and by one O atom and one N atom from a 5-methyl-1H-pyrazole-3-carboxylate ligand. The apical position is occupied by a water molecule. In the crystal structure, O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds lead to a three-dimensional supramolecular network.

Related literature

For general background to pyrazole and pyridine derivatives, see: Manna et al. (1992 ▶); Montoya et al. (2007 ▶); Perevalov et al. (2001 ▶).

Experimental

Crystal data

[Cu(C₅H₅N₂O₂)(C₁₄H₁₈N₃O)(H₂O)]·1.33H₂O
M _r = 475.01
Trigonal,
a = 26.7859 (3) Å
c = 16.6531 (5) Å
V = 10347.6 (4) Å³
Z = 18
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 296 K
0.50 × 0.40 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.638, T _max = 0.723
19606 measured reflections
5619 independent reflections
3406 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.168
S = 1.04
5619 reflections
279 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.29 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: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053768/hy2262sup1.cif

e-66-00m79-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053768/hy2262Isup2.hkl

e-66-00m79-Isup2.hkl^{(275.5KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Cu1—N1	1.962 (2)
Cu1—N3	1.946 (3)
Cu1—N5	2.008 (2)
Cu1—O4	1.973 (2)
Cu1—O6	2.265 (2)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.85	2.12	2.965 (10)	172
O2—H2A⋯O5	0.85	2.08	2.838 (7)	148
O2—H2B⋯O2ⁱ	0.85	2.41	3.246 (10)	168
O6—H6A⋯O3ⁱⁱ	0.85	2.14	2.807 (3)	135
O6—H6B⋯N4ⁱⁱⁱ	0.85	2.07	2.861 (3)	154
N2—H2⋯O5	0.83	2.01	2.733 (3)	144

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

Acknowledgments

This work was supported by the Innovation Project of Guangxi University for Nationalities (gxun-chx2009080).

supplementary crystallographic information

Comment

The chemical and pharmacological properties of heterocyclic derivatives, particularly pyrazole and pyridine derivatives have been investigated extensively because of their chelating ability with metal ions and their potentially beneficial chemical and biological activities (Manna et al., 1992; Montoya et al., 2007; Perevalov et al., 2001). During our research of these types of compounds, a new mixed-ligand copper(II) complex has been synthesized and characterized by single-crystal X-ray diffraction.

As illustrated in Fig. 1, the Cu^II ion is five-coordinated by three N atoms and two O atoms in a distorted square-pyramidal geometry (Table 1). The basal plane is formed by two N atoms from a 2-(5-ethylpyridin-2-yl)-5-isopropyl-5-methyl-imidazol-4-one ligand and by one O atom and one N atom from a 5-methyl-1H-pyrazole-3-carboxylate ligand. The apical position is occupied by the O atom from a water molecule. The complex molecules and uncoordinated water molecules are held together by hydrogen bonds (Table 2), generating a three-dimensional supramolecular network (Fig. 2).

Experimental

All reagents were available commercially and were used without further purification. A mixture of 5-methyl-1H-pyrazole-3-carboxylatic acid (0.126 g, 1.0 mmol), 2-(5-ethyl-pyridin-2-yl)-5-isopropyl-5-methyl-3,5-dihydro-imidazol-4-one (0.245 g, 1.0 mmol), CuCl₂.2H₂O (0.170 g, 1.0 mmol), EtOH (10 ml) and H₂O (10 ml) was sealed in a 25 ml Teflon-lined bomb and heated to 393 K for 3 d, and then cooled to room temperature. Blue crystals were obtained (yield 32% based on Cu).