Tetra­kis(1-benzyl-1H-imidazole)dichlorido­nickel(II)

Hongjuan Li; Jufeng Sun; Xianping Dai

doi:10.1107/S1600536809014494

. 2009 Apr 25;65(Pt 5):m564. doi: 10.1107/S1600536809014494

Tetrakis(1-benzyl-1H-imidazole)dichloridonickel(II)

Hongjuan Li ^a,^*, Jufeng Sun ^a, Xianping Dai ^a

PMCID: PMC2977609 PMID: 21583795

Abstract

In the title compound, [NiCl₂(C₁₀H₁₀N₂)₄], the Ni^II ion is located on an inversion center being coordinated by four N atoms from two pairs of symmetry-related 1-benzyl-1H-imidazole ligands and two chloride anions in a distorted octahedral geometry. Weak intermolecular C—H⋯Cl hydrogen bonds link the molecules into layers parallel to the ab plane.

Related literature

For general background to crystal engineering, see: Balamurugan et al. (2004 ▶); Desiraju (2007 ▶); Moulton & Zaworotko (2001 ▶). For applications of imidazole derivatives, see Lu et al. (2006 ▶); Huang et al. (2006 ▶). For details of the synthesis, see Owen et al. (2006 ▶).

Experimental

Crystal data

[NiCl₂(C₁₀H₁₀N₂)₄]
M _r = 762.41
Orthorhombic,
a = 7.296 (3) Å
b = 17.117 (4) Å
c = 29.651 (3) Å
V = 3703 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 292 K
0.48 × 0.32 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: spherical (modified interpolation procedure; Dwiggins, 1975 ▶) T _min = 0.743, T _max = 0.745
4699 measured reflections
3207 independent reflections
1518 reflections with I > 2σ(I)
R _int = 0.011
3 standard reflections every 200 reflections intensity decay: 1.8%

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.231
S = 1.14
3207 reflections
220 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −1.42 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014494/cv2549sup1.cif

e-65-0m564-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014494/cv2549Isup2.hkl

e-65-0m564-Isup2.hkl^{(157.4KB, 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
C1—H1⋯Cl1ⁱ	0.93	2.77	3.617 (8)	151
C14—H14B⋯Cl1ⁱ	0.97	2.68	3.579 (8)	153
C13—H13⋯Cl1ⁱⁱ	0.93	2.71	3.561 (9)	152

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

Acknowledgments

The authors are grateful to Binzhou Medical College for financial support (grant No. BY2007KJ13).

supplementary crystallographic information

Comment

Crystal engineering, the rational design of functional molecular solids, is currently an active area of investigation because of its importance in supramolecular chemistry, materials science, and solid-state chemistry (Desiraju, 2007; Moulton & Zaworotko, 2001). It is noteworthy that a promising strategy for inorganic crystal engineering through combining non-covalent bonds such as van der Waals, π···π stacking and hydrogen bonds with coordination chemistry has attracted increasing attention in recent years (Balamurugan et al., 2004). Organic ligands are often used to coordinate to transition metals via coordinate bonds to generate metal complexes as the building blocks of the assembly. Imidazole and its derivatives are ubiquitous in biological and biochemical structure and function and thus attracted special attention in the construction of some interesting metal-organic frameworks in recent years (Huang et al., 2006; Lu et al., 2006). Here, we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), each Ni^II ion displays a slightly distorted octahedral coordination geometry defined by four 1-benzyl-1H-imidazole ligands and two chloride anions. The Ni—N bond lengths are in the range of 2.070 (5) Å to 2.140 (3) Å and the Ni—Cl bond lengths is 2.468 (2) Å. Weak intermolecular C—H···Cl hydrogen bonds (Table 1) enhance the crystal packing stability.

Experimental

The 1-benzyl-1H-imidazole was prepared according to the literature (Owen et al., 2006). Nickel (II) chloride hexahydrate (1 mmol, 0.24 g) and 1-benzyl-1H-imidazole (4 mmol, 0.63 g) were mixed in chloroform (15 ml) and the mixture was stirred for 5 h at room temperature. After filtration, the solid was dissolved in methanol (8 ml). Green crystals suitable for X-ray analysis were obtained by slow evaporation of this solution over a period of six days.