Dichloridobis(phenyl 2-pyridyl ketone oxime)nickel(II) acetone solvate

Jing-Zhou Yin; Guang-Xiang Liu

doi:10.1107/S1600536808043961

. 2009 Jan 8;65(Pt 2):m155. doi: 10.1107/S1600536808043961

Dichloridobis(phenyl 2-pyridyl ketone oxime)nickel(II) acetone solvate

Jing-Zhou Yin ^a,^*, Guang-Xiang Liu ^b

PMCID: PMC2968227 PMID: 21581767

Abstract

The Ni atom in the title compound, [NiCl₂(C₁₂H₁₀N₂O)₂]·C₃H₆O, adopts a distorted octahedral geometry, being ligated by four N atoms from two different phenyl 2-pyridyl ketone oxime ligands and two Cl atoms. In the crystal structure, intermolecular O—H⋯Cl hydrogen bonds link the molecules into a chain structure along [010]. There is a π–π contact between the pyridine rings [centroid–centroid distance = 3.824 (5) Å].

Related literature

For related structures, see: Korpi et al. (2005 ▶); Pearse et al. (1989 ▶); Afrati et al. (2005 ▶); Stamatatos et al. (2006 ▶); Papatriantafyllopoulou et al. (2007 ▶).

Experimental

Crystal data

[NiCl₂(C₁₂H₁₀N₂O)₂]·C₃H₆O
M _r = 584.13
Triclinic,
a = 9.0367 (11) Å
b = 12.9142 (16) Å
c = 13.0664 (16) Å
α = 105.4390 (10)°
β = 92.232 (2)°
γ = 108.183 (2)°
V = 1384.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 296 (2) K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.822, T _max = 0.866
6839 measured reflections
4761 independent reflections
4002 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.089
S = 1.05
4761 reflections
338 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536808043961/at2700sup1.cif

e-65-0m155-sup1.cif^{(25.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043961/at2700Isup2.hkl

e-65-0m155-Isup2.hkl^{(233.2KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Ni1—N3	2.0344 (18)
Ni1—N1	2.0418 (18)
Ni1—N4	2.0879 (17)
Ni1—N2	2.1188 (17)
Ni1—Cl1	2.3944 (6)
Ni1—Cl2	2.4153 (7)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl2	0.82	2.27	2.9582 (18)	142
O1—H1⋯Cl1ⁱ	0.82	2.91	3.4612 (16)	127
O1—H1⋯Cl1	0.82	2.37	3.0542 (16)	141

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 20731004), the Natural Science Foundation for Outstanding Scholars of Anhui Province, China (grant No. 044-J-04011) and the Natural Science Foundation of the Education Commission of Anhui Province, China (grant Nos. KJ2007B092 and KJ2008B004).

supplementary crystallographic information

Comment

Pyridine-2-carbaldehyde oxime ligands usually bind to metals in a bidentate fashion, either chelating one metal center or bridging two metals. Their complexes find application in diverse areas such as functional supramolecular design, magnetic materials and catalysis (Korpi et al., 2005; Pearse et al., 1989; Afrati et al., 2005; Stamatatos et al., 2006). The title compound is a new nickel complex from the reaction of NiCl₂ with phenyl-2-pyridyl ketone oxime (ppo). The compound consists of two N,N-chelating ligands and two chloride anion. The two ppo ligands are coordinated to Ni to form two five-membered NiC₂N₂ rings. The central Ni atom adopts a distorted octahedral geometry (Fig. 1), which are ligated by four N atoms from two different phenyl-2-pyridyl ketone oxime ligand and two Cl atoms. The bond distances Ni—N and Ni—Cl are in the expected ranges of 2.0344 (18)–2.1188 (17) and 2.3944 (6)–2.4153 (7) Å, respectively, and the coordination angles around Ni atom are in the range 76.84 (7)–170.18 (7)°, which are in agreement with the literature values (Papatriantafyllopoulou et al., 2007). In the crystal structure, intermolecular O—H···Cl hydrogen bonds link the molecules into one-dimensional chain structure (Table 2). There is a π–π contact between the pyridine rings, and the distance of centroid to centroid is 3.824 (5) Å.

Experimental

A colourless solution of phenyl-2-pyridyl ketone oxime (0.197 g, 1.00 mmol) in acetone (10 ml) was slowly added to a slurry of LiOH.H₂O (0.042 g, 1.00 mmol) in MeOH (5 ml); the hydroxide soon dissolved. The solution was then added to a slurry of NiCl2.6H2O (0.297 g, 1.00 mmol) in MeOH (10 ml) and the resulting green solution was stirred for 1 h at room temperature. A small quantity of undissolved material was removed by filtration. The filtrate was allowed to stand undisturbed in a closed flask for a period of 4–5 d. Dark cyan crystals appeared which were collected by filtration, washed with cold MeOH (1 ml) and ice-cold Et₂O (2 ml), and dried in air [Yield: 52%].