Open AccessPolarized molecular–electronic structures and supramolecular aggregation in 1‐(6‐amino‐1,3‐benzodioxol‐5‐yl)‐3‐arylprop‐2‐en‐1‐ones
Author(s) -
Low John N.,
Cobo Justo,
Nogueras Manuel,
Cuervo Paola,
Abonia Rodrigo,
Glidewell Christopher
Publication year - 2004
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270104020414
Subject(s) - hydrogen bond , intramolecular force , chemistry , stacking , intermolecular force , crystallography , molecule , stereochemistry , supramolecular chemistry , crystal structure , organic chemistry
Molecules of 1‐(6‐amino‐1,3‐benzodioxol‐5‐yl)‐3‐(4‐methylphenyl)prop‐2‐en‐1‐one, C 17 H 15 NO 3 , (I), 1‐(6‐amino‐1,3‐benzodioxol‐5‐yl)‐3‐(4‐methoxyphenyl)prop‐2‐en‐1‐one, C 17 H 15 NO 4 , (II), and 1‐(6‐amino‐1,3‐benzodioxol‐5‐yl)‐3‐[4‐(trifluoromethyl)phenyl]prop‐2‐en‐1‐one, C 17 H 12 F 3 NO 3 , (III), all contain an intramolecular N—H⋯O hydrogen bond and all exhibit polarized molecular–electronic structures. The molecules of (I) are linked into simple sheets, generated by translation, by means of one N—H⋯O and one C—H⋯π(arene) hydrogen bond. Compound (II) crystallizes as two concomitant polymorphs, viz . (II a ), with Z ′ = 1 in P 2 1 / c , and (II b ), with Z ′ = 2 in P . In (II a ), intra‐ and intermolecular N—H⋯O hydrogen bonds generate a helical chain of rings, and these chains are linked into sheets by simple helical chains built from a C—H⋯π(arene) hydrogen bond, while in (II b ), the molecules are linked into simple chains by a C—H⋯O hydrogen bond. In (III), where Z ′ = 2, each type of molecule forms a simple N—H⋯O hydrogen‐bonded chain generated by translation and the two types of chain are linked by a single π–π stacking interaction.