Dichlorido[2,4-dimethyl-N-(pyridin-2-yl­methyl­idene)aniline-κ2 N,N′]dimethyl­tin(IV)

Sedigheh Loni; Mohamad Reza Talei Bavil Olyai; Fatemeh Roodbari; Behrouz Notash

doi:10.1107/S1600536811010439

. 2011 Mar 26;67(Pt 4):m489–m490. doi: 10.1107/S1600536811010439

Dichlorido[2,4-dimethyl-N-(pyridin-2-ylmethylidene)aniline-κ² N,N′]dimethyltin(IV)

Sedigheh Loni ^a, Mohamad Reza Talei Bavil Olyai ^b,^*, Fatemeh Roodbari ^a, Behrouz Notash ^c

PMCID: PMC3099817 PMID: 21754000

Abstract

The asymmetric unit of the title compound, [Sn(CH₃)₂Cl₂(C₁₄H₁₄N₂)], contains two crystallographically independent molecules. In each molecule, the Sn^IV atom is six-coordinated in a distorted octahedral geometry by one bidentate 2,4-dimethyl-N-(pyridin-2-ylmethylidene)aniline ligand, two methyl groups and two Cl atoms. In the crystal, intermolecular C—H⋯Cl hydrogen bonds link the molecules. There are π–π contacts between the pyridine rings of the ligands [centroid–centroid distance = 3.761 (4) Å].

Related literature

For applications of Schiff bases and their metal complexes, see: Azza & Abu (2006 ▶); Dudek & Dudek (1966 ▶); McAuliffe et al. (1986 ▶); Mladenova et al. (2002 ▶); Pandeya et al. (1999 ▶); Panneerselvam et al. (2005 ▶); Papić et al. (1994 ▶); Singh et al. (2006 ▶); Sridhar et al. (2001 ▶); Vlcek (2002 ▶); Walsh et al. (1996 ▶). For related structures, see: Ali et al. (2004 ▶); Fallah Nejad et al. (2010 ▶); Labisbal et al. (2006 ▶); Talei Bavil Olyai et al. (2008 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

[Sn(CH₃)₂Cl₂(C₁₄H₁₄N₂)]
M _r = 429.95
Orthorhombic,
a = 15.507 (3) Å
b = 7.3500 (15) Å
c = 32.175 (6) Å
V = 3667.2 (12) Å³
Z = 8
Mo Kα radiation
μ = 1.68 mm⁻¹
T = 298 K
0.30 × 0.28 × 0.20 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T _min = 0.607, T _max = 0.711
25085 measured reflections
9838 independent reflections
7280 reflections with I > 2σ(I)
R _int = 0.080

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.116
S = 0.97
9838 reflections
387 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ▶), 4819 Friedel pairs
Flack parameter: 0.19 (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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010439/hy2416sup1.cif

e-67-0m489-sup1.cif^{(27.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010439/hy2416Isup2.hkl

e-67-0m489-Isup2.hkl^{(481.1KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Sn1—C15	2.126 (8)
Sn1—C16	2.118 (7)
Sn1—N1	2.470 (5)
Sn1—N2	2.468 (8)
Sn1—Cl1	2.5213 (19)
Sn1—Cl2	2.4859 (19)
Sn2—C31	2.124 (7)
Sn2—C32	2.130 (7)
Sn2—N3	2.456 (5)
Sn2—N4	2.449 (8)
Sn2—Cl3	2.4908 (19)
Sn2—Cl4	2.5170 (19)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cl2ⁱ	0.93	2.73	3.608 (6)	157
C25—H25⋯Cl3ⁱⁱ	0.93	2.70	3.570 (7)	155

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

Acknowledgments

The authors acknowledge the Islamic Azad University, Karaj Branch, for financial support.

supplementary crystallographic information

Comment

Compounds with an azomethine group, C═N, are known as Schiff bases, which are usually synthesized from the condensation of primary amines and active carbonyl groups. The Schiff bases and their metal complexes are an important class of compounds in medicinal and pharmaceutical field. They show biological applications including antibacterial (Azza & Abu, 2006; Dudek & Dudek, 1966), antifungal (Pandeya et al., 1999; Panneerselvam et al., 2005; Singh et al., 2006; Sridhar et al. 2001) and antitumor activities (Mladenova et al., 2002; Walsh et al., 1996) and industrial uses, especially in catalysis (McAuliffe et al., 1986), dying (Papić et al., 1994), electronic and optic (Vlcek, 2002). In our ongoing studies on the synthesis and structural determination of transition metal complexes with iminopyridine ligands (Fallah Nejad et al., 2010; Talei Bavil Olyai et al., 2008, 2010a,b), we report here the crystal structure of the title compound, derived from the Schiff base ligand, 2,4-dimethyl-N-(pyridin-2-ylmethylene)aniline.

The title compound consists of two crystallographically independent molecules in the asymmetric unit, both with a similar six-coordinated environment. The Sn^IV atom is surrounded by two (one imino and one pyridine) N atoms belonging to the bidentate chelating iminopyridine ligand, two methyl groups and two Cl atoms (Fig. 1). The Sn—N, Sn—C and Sn—Cl bond distances (Table 1) are within normal ranges, which are similar to those reported in literature (Ali et al., 2004; Labisbal et al., 2006). The bond lengths and angles around the Sn^IV atoms show deviation from an ideal octahedral geometry. The Sn1—N2 and Sn2—N4 imine distances [2.468 (8) and 2.449 (8) Å] are approximately close to the Sn1—N1 and Sn2—N3 pyridine distances [2.470 (5) and 2.456 (5) Å]. The N2—C9 and N4—C25 bond lengths of 1.254 (10) and 1.277 (10) Å are typical for the C═N double bond.

In the crystal, intermolecular C—H···Cl hydrogen bonds (Table 2, Fig. 2) link the molecules, which may be effective in the stabilization of the structure. π–π contacts between the pyridine rings, Cg2ⁱ···Cg5 [Cg2 and Cg5 are the centroids of N1, C10—C14 and N3, C26—C30 rings, respectively; symmetry code: (i) 1/2+x, 3/2-y, z], further stabilize the structure, with centroid–centroid distance of 3.761 (4) Å (Fig. 3).

Experimental

For the preparation of the title compound, a solution of 2,4-dimethyl-N-(pyridin-2-ylmethylene)aniline (0.210 g, 1 mmol) in ethanol (10 ml) was added to a solution of Sn(CH₃)₂Cl₂ (0.220 g, 1 mmol) in methanol (10 ml). The resulting colorless solution was stirred for 2 hra at room temperature and then left to evaporate slowly at 3–5°C. After two weeks, yellow crystals of the title compound were isolated (yield: 0.329 g, 76.4%; m.p.: 416–419 K).