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Two (E)‐2‐({[4‐(dialkylamino)phenyl]imino}methyl)‐4‐nitrophenols

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Abstract:

The slow evaporation of analytical NMR samples resulted in the formation of crystals of (E)‐2‐({[4‐(dimethylamino)phenyl]imino}methyl)‐4‐nitrophenol, C15H15N3O3, (I), and (E)‐2‐({[4‐(diethylamino)phenyl]imino}methyl)‐4‐nitrophenol, C17H19N3O3, (II). Despite the small structural difference between these two N‐salicylideneaniline derivatives, they show different space groups and diverse molecular packing. The molecules of both compounds are close to being planar due to an intramolecular O—H...N hydrogen bond. The 4‐alkylamino‐substituted benzene ring is inclined at an angle of 13.44 (19)° in (I) and 2.57 (8)° in (II) with respect to the 4‐nitro‐substituted phenol ring. Only very weak intermolecular π–π stacking and C—H...O interactions were found in these structures.

Document Type: Research Article

DOI: https://doi.org/10.1107/S0108270112025589

Publication date: 2012-08-15

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