1,4-Bis(4-nitro­styr­yl)benzene

Phuong-Truc T Pham

doi:10.1107/S1600536809024751

. 2009 Jul 11;65(Pt 8):o1806. doi: 10.1107/S1600536809024751

1,4-Bis(4-nitrostyryl)benzene

Phuong-Truc T Pham ^a,^*

PMCID: PMC2977189 PMID: 21583510

Abstract

The complete molecule of the title compound, C₂₂H₁₆N₂O₄, is generated by a crystallographic centre of inversion. The plane of the central aromatic ring is tilted by 11.85 (4)° with respect to the outer aromatic ring. The crystal packing is determined by van der Waals interactions, with stair-like stacking between adjacent aromatic rings. The stacks are staggered and each layer is approximately 3.8 Å from the next. The closest intermolecular contact (approximately 2.42 Å) is between an O atom and a vinyl H atom.

Related literature

For background information on photonic materials, see: He et al. (2008 ▶). For stilbenes, see: Moreno-Fuquen et al. (2008 ▶, 2009 ▶). For the synthesis, see: Borsche (1912 ▶); Nakatsuji et al. (1991 ▶). For a related structure, see: Bazan et al. (2000 ▶).

Experimental

Crystal data

C₂₂H₁₆N₂O₄
M _r = 372.37
Monoclinic,
a = 7.4689 (12) Å
b = 16.615 (3) Å
c = 7.3917 (12) Å
β = 108.824 (3)°
V = 868.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.40 × 0.18 × 0.12 mm

Data collection

Bruker SMART Platform CCD diffractometer
Absorption correction: none
10088 measured reflections
2001 independent reflections
1486 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.116
S = 1.02
2001 reflections
159 parameters
All H-atom parameters refined
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024751/ng2592sup1.cif

e-65-o1806-sup1.cif^{(14.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024751/ng2592Isup2.hkl

e-65-o1806-Isup2.hkl^{(98.5KB, 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. The author also acknowledges Benjamin E. Kucera, Victor G. Young Jr, and the X-Ray Crystallographic Laboratory at the University of Minnesota.

supplementary crystallographic information

Comment

Distyrylbenzene derivatives have been studied as laser dyes, components of organic light-emitting diodes, and as model compounds for the study of conductivity and molecular properties in substituted p-phenylenevinylene (PPV) polymers. For background information on photonic materials, see: He et al. (2008). For related systems of stilbene, see: Moreno-Fuquen et al. (2008, 2009). For literature related to the synthesis, see: Borsche (1912).

Experimental

Synthesis was carried out following literature procedures (Nakatsuj) by standard Wittig synthesis. To a mixture of p-phenylenedimethylene- bis(tripheny1phosphonium chloride) (1.00 g, 1.43 mmol) and p-nitrobenzaldehyde (0.432 g 2.86 mmol) in EtOH (10 ml) was added 0.2 mol/L EtOLi(20 ml, 4.0 mmol) and the mixture was stirred overnight. The resulting reaction mixture was poured into water to give a yellow precipitate (0.4 g, 75%) which was filtered off, washed with EtOH, dried under reduced pressure, m.p. 289–290. Crystallization attempts from various solvents yielded only powders. Yellowish orange crystals however were grown by sublimation.