4-[(1E,3E,5E)-6-(4-Pyrid­yl)hexa-1,3,5-trien­yl]pyridine

Mamoun M Bader

doi:10.1107/S1600536809029092

. 2009 Jul 29;65(Pt 8):o2006. doi: 10.1107/S1600536809029092

4-[(1E,3E,5E)-6-(4-Pyridyl)hexa-1,3,5-trienyl]pyridine

Mamoun M Bader ^a,^*

PMCID: PMC2977225 PMID: 21583677

Abstract

The two independent molecules in the asymmetric unit of the title compound, C₁₆H₁₄N₂, are planar [dihedral angle between the terminal pyridine rings = 1.76 (2)°] and each display an all-trans configuration of C=C double bonds. One of the two molecules lies about a center of inversion. The dihedral angle between the two pyridine rings in the molecule lying on a general position is 1.65 (2)°.

Related literature

For acceptor-terminated polyenes, see: Gao et al. (2004 ▶). For the synthesis, see: Woitellier et al. (1989 ▶). For a related structure, see: Pham (2009 ▶).

Experimental

Crystal data

C₁₆H₁₄N₂
M _r = 234.29
Monoclinic,
a = 5.837 (1) Å
b = 17.171 (4) Å
c = 19.227 (4) Å
β = 97.685 (4)°
V = 1909.8 (7) Å³
Z = 6
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 K
0.44 × 0.24 × 0.22 mm

Data collection

Bruker SMART Platform CCD diffractometer
Absorption correction: none
18771 measured reflections
3366 independent reflections
2460 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.089
S = 1.01
3366 reflections
328 parameters
All H-atom parameters refined
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029092/ng2615sup1.cif

e-65-o2006-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029092/ng2615Isup2.hkl

e-65-o2006-Isup2.hkl^{(165.1KB, hkl)}

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

Acknowledgments

This work was supported in part by Research Development grants from the Pennsylvania State University and partially by the MRSEC Program of the National Science Foundation under award No. DMR-0819885. The author also acknowledges William W. Brennessel, Victor G. Young Jr and the X-ray Crystallographic Laboratory at the University of Minnesota.

supplementary crystallographic information

Comment

Pyridyl-terminated polyenes have been investigated for studying electron reactions with applications in biology, inorganic reaction mechanisms and molecular electronics. They have also been used in the synthesis of coordination polymers as well as template for solid state reactions.

For related systems of acceptor terminated polyenes, see: Gao et al. (2004); Pham (2009). For literature related to the synthesis, see: Woitellier et al. (1989).

Experimental

Synthesis was carried out following literature procedures (Woitellier et al., 1989) as follows: a solution of potassium tert-butoxide (1 2. l g in 200 ml of glyme) was added dropwise to a solution of tetraethyl ((E)-2-butene-1,4-diyl)diphosphonate (16.4 g, 0.05 mol) and pyridine-4-carboxaldehyde (10.70 g, 0.10 mol) in 100 ml of glyme at room temperature. After the addition of the base was complete, the resulting mixture was stirred at room temperature for 16 h. Cold water (ca 300–400 ml) was added and the product isolated by vacuum filtration (3.5 g, 30% crude yield) and recrystallized from acetone (2.3 g, 19%): mp 196–197. Crystals were grown from DMF.