{5,5′-Dimeth­oxy-2,2′-[4,5-dimethyl-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}nickel(II)

Atefeh Sahraei; Hadi Kargar; Reza Kia; Muhammad Nawaz Tahir

doi:10.1107/S1600536810051834

. 2010 Dec 15;67(Pt 1):m82–m83. doi: 10.1107/S1600536810051834

{5,5′-Dimethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II)

Atefeh Sahraei ^a, Hadi Kargar ^a, Reza Kia ^b,^c,^*, Muhammad Nawaz Tahir ^d,^*

PMCID: PMC3050280 PMID: 21522599

Abstract

In the title Schiff base complex, [Ni(C₂₄H₂₂N₂O₄)], the Ni^II atom shows a square-planar geometry. The dihedral angles between the central benzene ring and the two outer rings are 4.79 (15) and 7.54 (15)°. In the crystal, molecules are connected through intermolecular C—H⋯O hydrogen bond, resulting in chains extending along the c axis. The crystal structure is further stabilized by intermolecular π–π interactions, with centroid–centroid distances in the range 3.3760 (15)–3.7196 (17) Å.

Related literature

For background to Schiff base–metal complexes, see: Granovski et al. (1993 ▶); Blower et al. (1998 ▶). For related structures, see: Elmali et al. (2000 ▶); Kargar et al. (2010 ▶).

Experimental

Crystal data

[Ni(C₂₄H₂₂N₂O₄)]
M _r = 461.15
Monoclinic,
a = 11.3244 (10) Å
b = 16.5528 (19) Å
c = 12.1622 (11) Å
β = 113.261 (6)°
V = 2094.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 296 K
0.24 × 0.12 × 0.08 mm

Data collection

Stoe IPDS II Image Plate diffractometer
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009 ▶) T _min = 0.872, T _max = 1.000
13361 measured reflections
4799 independent reflections
3241 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.092
S = 0.98
4799 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051834/pv2367sup1.cif

e-67-00m82-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051834/pv2367Isup2.hkl

e-67-00m82-Isup2.hkl^{(235.1KB, 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
C7—H7A⋯O2ⁱ	0.93	2.41	3.173 (3)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

HK and AS thank PNU for financial support. RK thanks Islamic Azad University. MNT thanks GC University of Sargodha, Pakistan, for the research facilities.

supplementary crystallographic information

Comment

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with the ease of preparation and structural variations (Granovski et al., 1993). Metal derivatives of the Schiff bases have been studied extensively, and Ni(II) and Cu(II) complexes play a major role in both synthetic and structurel research (Kargar et al., 2010; Elmali et al., 2000; Blower et al., 1998).

In the title compound (Fig. 1), the geometry around the Ni(II) atom is square-planar which is coordinated by O1/O2/N1/N2 donor atoms of the tetradenate Schiff base ligand. The dihedral angles between the central benzene ring (C8–C13), and the two outer rings (C1–C6 and C15–C20) are 4.79 (15) and 7.54 (15)°. The crystal structure is furhter stabilized by intermolecular π–π interactions [Cg1···Cg2ⁱ = 3.4737 (17)Å; Cg2···Cg3ⁱ = 3.7196 (17)Å; Cg3···Cg3ⁱ = 3.3760 (15)Å; Cg1, Cg2, and Cg3 are the centroids of the Ni1/N1/C8/C13/N2, C15–C20, and Ni1/O2/C20/C15/C14/N2 rings, respectively].

Experimental

The title compound was synthesized by adding bis(4-methoxysalicylidene)-4,5-dimethyl phenylenediamine (2 mmol) to a solution of NiCl₂. 6 H₂O (2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant red solution was filtered. Dark-red plate single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvent at room temperature over several days.