Bis­(benzimidazole-κN 3)bis(2-benzoyl­benzoato-κO)copper(II)

M Hakkı Yıldırım; Zerrin Heren; Hümeyra Paşaoğlu; Derya Hıra; Orhan Büyükgüngör

doi:10.1107/S1600536809017139

. 2009 May 14;65(Pt 6):m638–m639. doi: 10.1107/S1600536809017139

Bis(benzimidazole-κN ³)bis(2-benzoylbenzoato-κO)copper(II)

M Hakkı Yıldırım ^a,^*, Zerrin Heren ^b, Hümeyra Paşaoğlu ^a, Derya Hıra ^b, Orhan Büyükgüngör ^a

PMCID: PMC2969713 PMID: 21583006

Abstract

In the title centrosymmetric mononuclear copper(II) compound, [Cu(C₁₄H₉O₃)₂(C₇H₆N₂)₂], the central Cu^II ion is coordinated by two N atoms from two symmetry-related benzimidazole (bim) ligands and two O atoms from two symmetry-related 2-benzoylbenzoate (2-byba) ligands in a square-planar geometry. The molecules are linked into chains running along the b axis by N—H⋯O hydrogen bonds and the chains are cross-linked by C—H⋯π interactions.

Related literature

For general background to 2-benzoylbenzoate, see: Diop et al. (2006 ▶, 2007 ▶); Foreman et al. (2001 ▶); Jones et al. (1996 ▶); Martin & Valente (1998 ▶); Prout et al. (1996 ▶); Song et al. (2005 ▶). For the crystal structure of 2-benzoylbenzoate, see: Lalancette et al. (1990 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Cu(C₁₄H₉O₃)₂(C₇H₆N₂)₂]
M _r = 750.24
Monoclinic,
a = 10.8692 (6) Å
b = 7.4521 (3) Å
c = 23.0874 (15) Å
β = 95.111 (5)°
V = 1862.61 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 296 K
0.41 × 0.39 × 0.23 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.550, T _max = 0.792
10706 measured reflections
3859 independent reflections
2987 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.103
S = 1.05
3859 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017139/ci2798sup1.cif

e-65-0m638-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017139/ci2798Isup2.hkl

e-65-0m638-Isup2.hkl^{(185.3KB, hkl)}

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

Table 1. Selected bond lengths (Å).

N1—Cu1	1.9916 (17)
O1—Cu1	1.9474 (13)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	1.90	2.747 (2)	169 (2)
C5—H5⋯Cg1ⁱⁱ	0.93	2.67	3.560 (2)	160 (2)
C11—H11⋯Cg2ⁱⁱⁱ	0.93	2.95	3.760 (2)	146 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are centroids of the C9–C14 and N1/C15/N2/C16/C21 rings, respectively.

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

supplementary crystallographic information

Comment

Altough the crystal structure of 2-byba was investigated in 1990 (Lalancette et al., 1990), only a limited number of articles have focused on 2-byba complexes. Consequently, this study, among with our ongoing study of characterization of mixed-ligand metal complexes, will provide a new example of copper(II) complexes with 2-byba.

In title compound, the Cu^II ion lying on a centre of symmetry, is in a square-planar coordination geometry formed by two symmetry related 2-byba and two symmetry related bim ligands. Both ligands are monodentate with the 2-byba coordinates through carboxylate O atom and bim coordinates through the aromatic N atom.

The molecular packing is mainly stabilized by strong intermolecular N—H···O hydrogen bonds (Table 2 and Fig. 2) and C—H···π interactions. Atom N2 in the molecule at (x, y, z) acts as hydrogen-bond donor, via H2, to atom O2 in the molecule at (x, y - 1, z) forming C(8) chains with R₂²(16) rings (Bernstein et al., 1995). These chains run parallel to the [010] (Fig. 2). The chains are inter-connected to each other by C5—H5···Cg1ⁱⁱⁱ and C11—H11···Cg2^iv interactions along the [001] and [101], respectively. Cg1 and Cg2 are centroids of the C9–C14 and N1/C15/N2/C16/C21 rings, respectively and symmetry codes (iii) and (iv) are as in Table 2.

Experimental

For the preparation of the title complex, a solution of cupric acetate (0.18 g, 1 mmol) in methanol (10 ml) was added to a solution of 2-byba (0.45 g, 2 mmol) in methanol (10 ml) and the solution was stirred for 15 min at 333 K. Solution of bim (0.23 g, 2 mmol) in methanol (10 ml) was added to the former solution. Final solution was left to evaporate slowly at room temperature. After one week, violet stick crystals of the title complex were isolated.