trans-Bis(2-benzoyl­benzoato-κO 1)bis­(ethanol-κO)bis­(1H-imidazole-κN 3)nickel(II)

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

doi:10.1107/S160053680902621X

. 2009 Jul 11;65(Pt 8):m907–m908. doi: 10.1107/S160053680902621X

trans-Bis(2-benzoylbenzoato-κO ¹)bis(ethanol-κO)bis(1H-imidazole-κN ³)nickel(II)

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

PMCID: PMC2977203 PMID: 21583367

Abstract

In the title centrosymmetric mononuclear nickel(II) complex, [Ni(C₁₄H₉O₃)₂(C₃H₄N₂)₂(CH₃CH₂OH)₂], the central Ni^II ion lies on an inversion centre and is octahedrally coordinated. The equatorial plane is formed by two O atoms from two symmetry-related 2-benzoylbenzoate ligands and two N atoms from two symmetry-related imidazole ligands, whereas the axial positions are occupied by two O atoms from two ethanol ligands. Intramolecular O---H...O hydrogen bonds stabilize this arrangement. The molecules are linked into chains running along the b axis by N—H⋯O hydrogen bonds.

Related literature

For crystal structures with 2-benzoylbenzoate ligands, 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 ▶); Yıldırım et al. (2009 ▶). For the crystal structure of 2-benzoylbenzoic acid, see: Lalancette et al. (1990 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Ni(C₁₄H₉O₃)₂(C₃H₄N₂)₂(C₂H₆O)₂]
M _r = 737.43
Monoclinic,
a = 12.8914 (8) Å
b = 8.3908 (5) Å
c = 16.4590 (11) Å
β = 90.832 (5)°
V = 1780.17 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 296 K
0.43 × 0.25 × 0.14 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.809, T _max = 0.921
15078 measured reflections
3889 independent reflections
2704 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.150
S = 1.11
3889 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 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/S160053680902621X/ci2845sup1.cif

e-65-0m907-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902621X/ci2845Isup2.hkl

e-65-0m907-Isup2.hkl^{(186.8KB, 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
O1—H1⋯O3	0.78 (5)	1.86 (5)	2.627 (4)	170 (6)
N2—H2⋯O3ⁱ	0.86	2.02	2.837 (5)	159

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Professor Dr Orhan Büyükgüngör for his help with the data collection and acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe II diffractometer (purchased under grant No. F279 of the University Research Fund).

supplementary crystallographic information

Comment

We have previously reported the crystal structure of [Cu(2-byba)₂(bim)₂] (bim = benzimidazole, 2-byba = 2-benzoylbenzoate) (Yıldırım et al., 2009). As an extension of this study, we now report the structure of a new nickel(II) complex with the 2-byba ligand.

In the title complex, the Ni^II ion lies on a centre of symmetry and has a octahedral coordination geometry formed by 2-byba, imidazole (im), ethanol ligands and their symmetry-related equivalents. All ligands are monodentate with the 2-byba coordinates through a carboxylate O atom, im coordinates through the aromatic N atom and ethanol coordinates through the O atom. Intramolecular O—H···O hydrogen bonds are observed.

The molecular packing is mainly stabilized by strong intermolecular N—H···O hydrogen bonds (Table 2 and Fig. 2). Atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H2, to atom O3 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).

Experimental

A solution of 2-benzoylbenzoate (0.45 g, 2 mmol) in ethanol (10 ml) was added to a solution of nickel acetate tetrahydrate (0.25 g, 1 mmol) in ethanol (10 ml) and the solution was stirred for 15 min at 333 K. To this solution, a solution of imidazole (0.23 g, 2 mmol) in ethanol (10 ml) was added and the resultant solution was left to evaporate slowly at room temperature. After one week, single crystals of the title complex were isolated.