Structure of Liquid Crystalline 1-Phenyl-3-{4-[4-(4-octyloxybenzoyloxy)phenyloxycarbonyl]phenyl}triazene-1-oxide at Low Temperature

Abstract

The molecular structure of 1-phenyl-3-{4-[4-(4-octyloxybenzoyloxy)-phenyloxycarbonyl]phenyl}triazene-1-oxide, a member of newly developed liquid crystalline homologous series, has been investigated by crystal X-ray crystallography at low temperature (100 K). The title compound crystallizes in the triclinic crystal class in the space group P with cell parameters a = 5.766(5) Å, b = 12.151(10) Å, c = 21.751(17) Å, α = 79.089(13)°, β = 88.646(14)°, γ = 84.278(14)°, V = 1489(2) Å³ for Z = 2. It establishes the N-oxide form of the triazene-1-oxide moiety. The overall molecule is not planar, the dihedral angles between pairs of adjacent benzene rings are 14.00 (10), 52.36 (07), and 50.57 (07)°. Intramolecular N–H…O hydrogen-bonding is present within the triazene-1-oxide moiety of the title compound. The compound forms inversion dimer via an intermolecular N–H…O and an intermolecular C–H…O links. The dimers are then linked into chains in a parallel fashion by C–H…O hydrogen bonds. The crystal packing is further stabilized by C–H…π interactions.

Keywords:

• hydrogen-bonding interaction
• liquid crystals
• triazene-1-oxide
• X-ray crystallography

ACKNOWLEDGMENTS

Financial support (SR/S1/IC-08/2007) from the DST, Government of India, is gratefully acknowledged. We thank the CSIR (India) for the award of a fellowship (ANB), and Professor A. Ramanan, IIT Delhi, for the X-ray crystallographic data collection.

Notes

Symmetry codes: (i) − x + 1, − y, − z; (ii) x − 1, y, z; (iii) x + 1, y, z; (iv) x, y + 1, z; (v) x − 1, y − 1, z.