2,6-Bis[1-(2-methyl­phenyl­imino)eth­yl]pyridine

Rui-Qing Fan; Xiao-Dong Ding; Guang-Peng Zhou; Yu-Lin Yang

doi:10.1107/S1600536809020522

. 2009 Jun 6;65(Pt 7):o1480. doi: 10.1107/S1600536809020522

2,6-Bis[1-(2-methylphenylimino)ethyl]pyridine

Rui-Qing Fan ^a,^*, Xiao-Dong Ding ^a, Guang-Peng Zhou ^a, Yu-Lin Yang ^a

PMCID: PMC2969280 PMID: 21582782

Abstract

The molecule of the title compound, C₂₃H₂₃N₃, which was synthesized by the condensation reaction between 2,6-diacetylpyridine and 2-dimethylaniline, adopts an E configuration about both C=N imine bonds. The dihedral angles formed by the benzene rings with the pyridine ring are 89.68 (5) and 53.62 (6)°.

Related literature

For the applications of pyridine-based ligands in sensor technologies and electro-luminescent devices, see: Tang & Vanslyke (1987 ▶); Wang (2001 ▶). For the crystal structures of related compounds, see: Mentes et al. (2001 ▶); Huang et al. (2006 ▶). For the synthesis, see: Fan et al. (2004 ▶).

Experimental

Crystal data

C₂₃H₂₃N₃
M _r = 341.44
Monoclinic,
a = 12.966 (3) Å
b = 11.304 (2) Å
c = 14.767 (3) Å
β = 115.62 (3)°
V = 1951.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 193 K
0.56 × 0.41 × 0.36 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.960, T _max = 0.972
18526 measured reflections
4435 independent reflections
2804 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.157
S = 1.06
4435 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 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. DOI: 10.1107/S1600536809020522/rz2329sup1.cif

e-65-o1480-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020522/rz2329Isup2.hkl

e-65-o1480-Isup2.hkl^{(217.3KB, hkl)}

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant Nos. 20771030 and 20671025), the Youthful Foundation of Heilongjiang Province of China (grant No. QC06C029) and the Research Fund for the Doctoral Program of Higher Education (grant No. 20070213005).

supplementary crystallographic information

Comment

Luminescent coordination compounds based on pyridine-type ligands have attracted intensive attention due to their potential application in areas of sensor technologies and electro-luminescent devices (Tang & Vanslyke, 1987; Wang, 2001). In order to explore potential luminescent complexes of this type, we prepared a series of bis(iminoalkyl)pyridine ligands by the condensation reaction of 2,6-diacetylpyridine with the corresponding aniline in methanol (Fan et al., 2004). It is still challenging to design and rationally synthesize ligands with unique structures and functions. In this regard, we report herein the synthesis and crystal structure of the title compound.

The molecule of the title compound (Fig. 1) possesses an approximate C_s symmetry about a plane bisecting the pyridine ring. The pyridine ring is coplanar with the two imino groups, which show typical C═N double bond character (1.2606 (18) and 1.2674 (19) Å for N1═C1 and N3═C7, respectively). These values are in good agreement with those observed in 2,6-bis[1-(phenylimino)ethyl]pyridine (1.266 (4) Å; Mentes et al., 2001) and in 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine (1.265 (2) and 1.271 (2) Å; Huang et al., 2006). The dihedral angles between the C10–C15 and C17–C22 benzene rings and the pyridine ring are 89.68 (5) and 53.62 (6)°, respectively. The crystal packing (Fig. 2) is stabilized only by van der Waals interactions.

Experimental

The title compound was synthesized according to the literatute method (Fan et al., 2004). To a solution of 2,6-diacetylpyridine (1.1 g, 6.7 mmol) in absolute methanol (25 ml) was added 2-dimethylaniline (2.2 ml, 20.5 mmol). After the addition of several drops of formic acid, the reaction mixture was refluxed for 24 h and then allowed to cool down to room temperature. The crude product precipitated as yellow powder. Yellow block crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a methanol solution in 85% yield (1.96 g).