Abstract

The title mol­ecule, C24H23N3, shows some delocalization of charge based on the small [8.0 (2)°] angle between the indolin-2-yl­idene ring system and the link methyl­diazene C2N2 atom plane. A further twist of 17.2 (3)° is subtended between the C2N2 plane and its attached benzene ring. The dihedral angle between the biphenyl rings is 47.96(14)°. In the crystal, the mol­ecules pack via C—H⋯π attractive inter­actions.

Highlights

  • The title molecule, C24H23N3, shows some delocalization of charge based on the small [8.0 (2) ] angle between the indolin2-ylidene ring system and the link methyldiazene C2N2 atom plane

  • The molecules pack via C—H attractive interactions

  • Dyes based on azobenzene typically exhibit high extinction coefficients and their absorption maxima can usually be tailored to lie anywhere in the visible region via appropriate substitution onto the phenyl rings. Due to their geometrically rigid structures and large aspect ratios, azobenzene compounds are ideal as mesogens (Möhlmann & van der Vorst, 1989)

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Summary

Bruker APEXII CCD diffractometer

R factor = 0.037; wR factor = 0.086; data-to-parameter ratio = 7.2. The title molecule, C24H23N3, shows some delocalization of charge based on the small [8.0 (2) ] angle between the indolin2-ylidene ring system and the link methyldiazene C2N2 atom plane. A further twist of 17.2 (3) is subtended between the. C2N2 plane and its attached benzene ring. The dihedral angle between the biphenyl rings is 47.96(14). The molecules pack via C—H attractive interactions

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