catena-Poly[[[[2-(2-pyridyl-κN)-1H-benzimidazole-κN 3]copper(II)]-μ-l-methio­ninato-κ3 N,O:O′] perchlorate]

Yan-Mei Lu; Xue-Yi Le

doi:10.1107/S1600536811014000

. 2011 Apr 29;67(Pt 5):m642–m643. doi: 10.1107/S1600536811014000

catena-Poly[[[[2-(2-pyridyl-κN)-1H-benzimidazole-κN ³]copper(II)]-μ-l-methioninato-κ³ N,O:O′] perchlorate]

Yan-Mei Lu ^a, Xue-Yi Le ^b,^*

PMCID: PMC3089275 PMID: 21754350

Abstract

The structure of the title compound, {[Cu(C₅H₁₀NO₂S)(C₁₂H₉N₃)]ClO₄}_n, has orthorhombic symmetry. The chain structure is constructed from square-pyramidally coordinated Cu^II atoms linked through l-methionate ligands. The chains propagate along the a-axis direction and are linked to perchlorate anions via N—H⋯O hydrogen bonds.

Related literature

For the biological activity of benzimidazole derivatives and their metal complexes, see: Devereux et al. (2004 ▶, 2007 ▶); El-Sherif & Jeragh (2007 ▶). For metal complexes of l-α-amino acids, see: Lin et al. (2006 ▶), Yamauchi et al. (1992 ▶); Zhou et al. (2005 ▶).

Experimental

Crystal data

[Cu(C₅H₁₀NO₂S)(C₁₂H₉N₃)]ClO₄
M _r = 506.41
Orthorhombic,
a = 6.9718 (4) Å
b = 11.8902 (6) Å
c = 24.7024 (13) Å
V = 2047.73 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 293 K
0.45 × 0.35 × 0.13 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.583, T _max = 0.845
12781 measured reflections
4464 independent reflections
3557 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.111
S = 1.05
4464 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 1874 Friedel pairs
Flack parameter: −0.001 (17)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014000/ff2004sup1.cif

e-67-0m642-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014000/ff2004Isup2.hkl

e-67-0m642-Isup2.hkl^{(218.7KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Cu1—O2ⁱ	2.272 (3)
Cu1—O1	1.929 (3)
Cu1—N1	1.996 (2)
Cu1—N3	2.023 (3)
Cu1—N4	1.985 (3)
O2—Cu1ⁱⁱ	2.272 (3)

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2a⋯O3ⁱⁱⁱ	0.86	2.06	2.904 (6)	168
N4—H4a⋯O5^iv	0.90	2.53	3.370 (7)	155
N4—H4b⋯O4	0.90	2.31	3.064 (7)	141

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Symmetry codes: (iii) Inline graphic ; (iv) .

Acknowledgments

This work was supported by the Science and Technology Plan Project of Guangdong (No. 2009B020312010), the Natural Science Foundation of Guangdong (No. 10151064201000016) and the 211 Project Program Foundation of South China Agricultural University (No. 2009B010100001).

supplementary crystallographic information

Comment

In recent years, structure investigations of benzimidazole derivatives and their metal complexes have attracted an interest due to their antioxidant, antimycobacterium, antiparasitic activity and cytotoxicity (Devereux et al., 2004, 2007; El-Sherif & Jeragh, 2007). Furthermore, L-α-amino acids are important biological ligands, taking flexible coordination modes with metal ions (Lin et al.., 2006, Yamauchi et al., 1992, Zhou et al., 2005). With L-α-amino acids being involved, the biological activities of complexes can be improved. We report herein the synthesis and crystal structure of the title complex.

The crystal structure of the title complex consists of [Cu(C₁₂H₉N₃)(C₅H₁₀NO₂S)]_n polymeric chains (Fig. 2). The Cu(II) atom is in a slightly distorted square–pyramidal geometry (Fig. 1). The equatorial plane is occupied by two nitrogen atoms of 2-(2-pyridyl)benzimidazole ligand and one nitrogen atom and one oxygen atom of L-methionate ligand, while the apical position is occupied by another carboxylate oxygen atom from a symmetry-related neighboring L-methioninate ligand. The chains are connected by N—H···O hydrogen bonds to the perchlorate anions.

Experimental

To a stirred ethanol solution (20 ml) containing 2-(2-pyridyl) benzimidazole (HPB) (0.098 g, 0.5 mmol) was added an aqueous solution(1 ml) of Cu(ClO₄)₂ 6H₂O (0.188 g,0.5 mmol). An aqueous solution of L-Met(0.075 g, 0.5 mmol) and NaOH (0.020 g, 0.5 mmol) was then added to the mixture. After stirring continuously at 333 K for 1 h, the resulting green solution was filtered. The single crystals were obtained from the filtrate after two weeks (yield 67% based on Cu).