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Polarized molecular–electronic ­structures and supramolecular ­aggregation in 1-(6-amino-1,3-benzodioxol-5-yl)-3-aryl­prop-2-en-1-ones

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Molecules of 1-(6-amino-1,3-benzodioxol-5-yl)-3-(4-methyl­phenyl)­prop-2-en-1-one, C17H15NO3, (I), 1-(6-amino-1,3-benzodioxol-5-yl)-3-(4-methoxy­phenyl)­prop-2-en-1-one, C17H15NO4, (II), and 1-(6-amino-1,3-benzodioxol-5-yl)-3-[4-(tri­fluoro­methyl)­phenyl]­prop-2-en-1-one, C17H12F3NO3, (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…(arene) hydrogen bond. Compound (II) crystallizes as two concomitant polymorphs, viz. (IIa), with Z′ = 1 in P21/c, and (IIb), with Z′ = 2 in P . In (IIa), 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…(arene) hydrogen bond, while in (IIb), 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 – stacking interaction.
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Document Type: Research Article

Publication date: 2004-10-01

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