Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 10 (October 2004)

organic compounds

Acta Cryst. (2004). C60, o744-o750 [ doi:10.1107/S0108270104020414 ]

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

J. N. Low, J. Cobo, M. Nogueras, P. Cuervo, R. Abonia and C. Glidewell

Abstract: 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-HO 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-HO and one C-H [pi] (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 $\overline 1$ . In (IIa), intra- and intermolecular N-HO hydrogen bonds generate a helical chain of rings, and these chains are linked into sheets by simple helical chains built from a C-H [pi] (arene) hydrogen bond, while in (IIb), the molecules are linked into simple chains by a C-HO hydrogen bond. In (III), where Z' = 2, each type of molecule forms a simple N-HO hydrogen-bonded chain generated by translation and the two types of chain are linked by a single [pi] - [pi] stacking interaction.

Formula: C₁₇H₁₅NO₃, two polymorphs of C₁₇H₁₅NO₄, and C₁₇H₁₂F₃NO₃


	Structure factor file (CIF format) (150.3 kbytes) Contains datablock I

	Structure factor file (CIF format) (155.6 kbytes) Contains datablock IIa

	Structure factor file (CIF format) (318.7 kbytes) Contains datablock IIb

	Structure factor file (CIF format) (323.5 kbytes) Contains datablock III

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