trans-Bis(N′-isopropyl­idene­benzo­hydrazidato-κ2 N′,O)bis­(pyridine-κN)nickel(II)

Chang-Zheng Zheng; Liang Wang; Juan Liu

doi:10.1107/S1600536811024214

. 2011 Jun 25;67(Pt 7):m978. doi: 10.1107/S1600536811024214

trans-Bis(N′-isopropylidenebenzohydrazidato-κ² N′,O)bis(pyridine-κN)nickel(II)

Chang-Zheng Zheng ^a, Liang Wang ^a,^*, Juan Liu ^a

PMCID: PMC3152089 PMID: 21836952

Abstract

The complex molecule of the title compound, [Ni(C₁₀H₁₁N₂O)₂(C₅H₅N)₂], has a crystallographically imposed centre of symmetry. The Ni^II atom is coordinated in a distorted octahedral geometry by the O and N atoms of two trans arranged anionic bidentate hydrazone ligands forming the equatorial plane and by the N atoms of two pyridine molecules at the axial positions. In the crystal, intermolecular C—H⋯N hydrogen bonds link the molecules into columns parallel to the b axis.

Related literature

For the biological and coordination properties of aroylhydrazones, see: Ali et al. (2004 ▶); Carcelli et al. (1995 ▶); Cheng et al. (1996 ▶); Zhang et al. (2011 ▶).

Experimental

Crystal data

[Ni(C₁₀H₁₁N₂O)₂(C₅H₅N)₂]
M _r = 567.33
Monoclinic,
a = 15.419 (5) Å
b = 9.242 (3) Å
c = 21.295 (9) Å
β = 109.924 (5)°
V = 2853.1 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 298 K
0.23 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.852, T _max = 0.919
7093 measured reflections
2514 independent reflections
2285 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.078
S = 1.10
2514 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024214/rz2613sup1.cif

e-67-0m978-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024214/rz2613Isup2.hkl

e-67-0m978-Isup2.hkl^{(123.6KB, 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
C13—H13⋯N1ⁱ	0.93	2.50	3.382 (3)	157

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the National Natural Science Foundation of Shaanxi Province, China (2009JM2012) for financial support.

supplementary crystallographic information

Comment

Hydrazones are an important class of Schiff bases compounds which has attracted much attention because of their biological activities (Carcelli et al., 1995), chemical and industrial versatility, and strong tendency to chelate to transition metals (Zhang et al., 2011; Ali et al., 2004; Cheng et al., 1996). As an extension of our work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here.

In the title compound, the complex molecule has crystallographically imposed centre of symmetry (Fig. 1). The coordination polyhedron about the nickel metal is distorted octahedral, with the N, O atoms of two trans-arranged anionic bidentate hydrazone ligands at the equatorial plane and by the N atoms of two pyridine molecules occupying the axial positions. In the crystal structure, complex molecules are linked by intermolecular C—H···N hydrogen bonds (Table 1) into columns parallel to the b axis.

Experimental

Ethyl benzoate (6.00 g, 0.04 mol) was dissolved in ethnol (30 ml) at room temperature and heated at 363 K, followed by the addition of hydrazine hydrate (2.40 g, 0.048 mol). Subsequently, the mixture was refluxed for 9 h, and then cooled to room temperature. The crystals precipitated were collected by filtration. The product was recrystallized from ethanol and dried under reduced pressure to give benzoylhydrazine. Benzoylhydrazine (3.40 g, 0.025 mol) was dissolved in ethanol (20 ml) at room temperature and heated at 363 K, followed by the addition of dimethyl ketone (1.45 g, 0.025 mol). Subsequently, the mixture was refluxed for 10 h, and then cooled to room temperature. The solid phase precipitated was collected by filtration. The product was recrystallized from ethanol and dried under reduced pressure to give N'-[(E)- dimethylketone]-benzohydrazide. A mixture of N'-[(E)-dimethylketone]-benzohydrazide (0.018 g, 0.10 mmol), NiC_l2.6H₂O (0.024 g, 0.10 mmol), pyridine (0.0079 g, 0.10 mmol), H₂O (5.00 ml) and several drop of methanol was placed in a Parr Teflon-lined stainless steel vessel (25 ml), and then the vessel was sealed and heated at 393 K for 3 d. After the mixture was slowly cooled to room temperature, red crystals suitable for X-ray analysis were obtained (yield 37%).