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

Yu-lin Yang; Rui-qing Fan; Wen-hui Li

doi:10.1107/S1600536808036842

. 2008 Nov 20;64(Pt 12):o2368. doi: 10.1107/S1600536808036842

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

Yu-lin Yang ^a,^*, Rui-qing Fan ^a, Wen-hui Li ^b

PMCID: PMC2959797 PMID: 21581340

Abstract

The title compound, C₂₉H₃₅N₃, is the product of the condensation reaction between 2,6-diacetylpyridine and 2,6-diethylaniline. In the molecule, the pyridyl ring is coplanar with the imino functional groups [torsion angles in the range 177.1 (2)–179.9 (2)°. The two 2,6-diethyl-substituted benzene rings are approximately perpendicular to the ethylidenepyridine central core, the dihedral angles being 88.7 (1) and 88.4 (1)°, respectively.

Related literature

For applications of pyridine derivatives, see: Tang & VanSlyke (1987 ▶); Wang (2001 ▶). For the synthesis of the title molecule, see: Fan et al. (2004 ▶). For structures of other imino derivatives, see: Mentes et al. (2001 ▶); Huang et al. (2006 ▶).

Experimental

Crystal data

C₂₉H₃₅N₃
M _r = 425.60
Monoclinic,
a = 7.9390 (8) Å
b = 12.3208 (13) Å
c = 25.998 (3) Å
β = 96.234 (2)°
V = 2528.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 193 (2) K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.983, T _max = 0.987
13906 measured reflections
4938 independent reflections
2362 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.101
S = 0.95
4938 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 global, I. DOI: 10.1107/S1600536808036842/bh2205sup1.cif

e-64-o2368-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036842/bh2205Isup2.hkl

e-64-o2368-Isup2.hkl^{(241.9KB, hkl)}

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

Table 1. Selected bond lengths (Å).

N1—C1	1.272 (3)
N1—C10	1.431 (3)
N2—C2	1.333 (2)
N2—C6	1.348 (2)
N3—C7	1.275 (2)
N3—C20	1.424 (3)

Open in a new tab

Acknowledgments

This work was supported by the National Natural Science Foundation of China (20671025 and 20771030), the Young Foundation of Heilongjiang Province in China (QC06C029), Heilongjiang Natural Science Foundation (B200603) and the Science Innovation Special Foundation of Harbin City, China (2006RFQXG037).

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 of 2,6-diacetylpyridine with the corresponding aniline in methanol (Fan et al., 2004). We report here the crystal structure of one of them, (I).

The molecular structure of (I) is shown in Fig. 1 and selected bond distances are given in Table 1. The pyridyl ring is coplanar with the two imino functional groups. The two imino C═N bonds have typical double-bond characteristics, with bond lengths of 1.272 (3) and 1.275 (2) Å, which are similar to that in BIP1, 1.266 (4) (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). Compound (I) possesses a structure which approximates C_s symmetry about a plane bisecting the central pyridyl ring. The two 2,6-diethyl-substituted phenyl rings are approximately perpendicular to the ethylidenepyridine ring, with the dihedral angles being 88.7° and 88.4°.

Experimental

The title compound was synthesized according to the literature method of Fan et al. (2004). To a solution of 2,6-diethylpyridine (1.5 g, 9.2 mmol) in absolute methanol (40 ml) was added 2,6-diethylaniline (4.6 ml, 27.7 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 a yellow powder. Pure (I) was obtained as yellow block crystals in 84% yield (3.3 g) upon recrystallization from methanol, giving single crystals suitable for X-ray diffraction.