4-(Anthracen-9-yl)-2-phenyl-6-(pyridin-2-yl)pyridine

Hao-Wei Wang; Jun Ren; Wen-Bo Ye; Jia-Xiang Yang

doi:10.1107/S1600536812012299

. 2012 Mar 28;68(Pt 4):o1210. doi: 10.1107/S1600536812012299

4-(Anthracen-9-yl)-2-phenyl-6-(pyridin-2-yl)pyridine

Hao-Wei Wang ^a, Jun Ren ^a, Wen-Bo Ye ^a, Jia-Xiang Yang ^a,^*

PMCID: PMC3344146 PMID: 22606149

Abstract

In the title compound, C₃₀H₂₀N₂, the anthracene ring system is approximately planar [maximum deviation = 0.035 (2) Å] and is nearly perpendicular to the central pyridine ring, making a dihedral angle of 75.73 (7)°. The terminal pyridine ring and the phenyl ring are oriented at dihedral angles of 8.11 (10) and 13.22 (10)°, respectively, to the central pyridine ring.

Related literature

For applications of aromatic conjugated organic compounds, see: Nishihara et al. (1989 ▶); Mi et al. (2003 ▶); Roberto et al. (2000 ▶).

Experimental

Crystal data

C₃₀H₂₀N₂
M _r = 408.48
Monoclinic,
a = 12.6420 (3) Å
b = 14.8499 (4) Å
c = 11.8707 (3) Å
β = 104.006 (2)°
V = 2162.26 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
35644 measured reflections
4951 independent reflections
3128 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.215
S = 1.33
4951 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012299/xu5476sup1.cif

e-68-o1210-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012299/xu5476Isup2.hkl

e-68-o1210-Isup2.hkl^{(242.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012299/xu5476Isup3.cml

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

Acknowledgments

The work was supported by the National Natural Science Foundation of China (50873001, 21071001) and the Education Committee of Anhui Province, China (KJ2011Z338).

supplementary crystallographic information

Comment

The aromatic conjugated organic compounds are investigated with great interest due to their potential applications in optical image processing, all-optical switching, organic light emitting diodes (OLEDs) and integrated optical devices (Nishihara et al., 1989; Mi et al., 2003; Roberto et al., 2000). As a part of our continuing studies of the synthesis and characterization of optical materials, we have prepared a new anthracene derivative containing two pyridine rings and investigated its crystal structure.

The molecule structure of (I) is shown in Fig. 1. Two pyridine rings makes the dihedral angle of 8.11 (10)°. The anthracen moiety is almost planar, and make the dihedral angles of 75.73 (7)° and 67.84 (2)° with two pyridine rings, respectively.

Experimental

3-(Anthracen-9-yl)-1-phenylprop-2-en-1-one (1.54 g, 5.0 mmol), 2-acetylpyridine (1.82 g, 15 mmol) and NaOH (0.20 g, 5.0 mmol) were crashed together with a pestle and mortar for 3 h. The light yellow powder was added to a stirred solution of ammonium acetate (15.4 g, 200.0 mmol) in ethanol (200 ml). The reaction mixture was heated at reflux. Thin layer chromatography analysis tracking reaction, evaporated solvent, extracted with dichloromethane, and dried to afford the product. It was purified by flash column chromatography on silica. Elution with petroleum/ethyl acetate (10:1) gave a white solid (yield; 1.3 g, 65%). Single crystals of (I) were grown by slow evaporation of a dichloromethane/ethyl acetate (1:1) solution.