Acta Crystallographica Section C

Crystal Structure Communications

Volume 63, Part 8 (August 2007)

organic compounds

tr3017 scheme

Acta Cryst. (2007). C63, o477-o480 [ doi:10.1107/S0108270107031071 ]

4,6-Dimethyl-2-[(4-phenylpiperidin-1-yl)methyl]isothiazolo[5,4-b]pyridin-3(2H)-one and 4,6-dimethyl-2-[(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)methyl]isothiazolo[5,4-b]pyridin-3(2H)-one

Z. Karczmarzyk and W. Malinka

Abstract: In the crystal structures of the title compounds, C₂₀H₂₃N₃OS, (II), and C₂₀H₂₁N₃OS, (III), significant differences occur in the conformation of, respectively, the phenylpiperidine and phenyltetrahydropyridine substituents at the 2-position of the isothiazolopyridine system. The piperidine ring adopts a chair conformation, while the tetrahydropyridine ring assumes a half-chair form. The phenylpiperidine and phenyltetrahydropyridine fragments exhibit different conformations resulting from the steric and conjugation effects in the phenyl ring, respectively. Theoretical calculations show that both conformations are energetically stable and correspond to a minimum of energy for the analyzed systems. The molecular packing in (II) is influenced by [pi] - [pi] interactions of the isothiazolopyridine systems, with a shortest centroid-to-centroid separation of 3.5843 (11) Å between pyridine rings. In the crystal structure of (III), the molecules are linked by C-HO hydrogen bonds and C-H [pi] interactions.

Formula: C₂₀H₂₃N₃OS and C₂₀H₂₁N₃OS


	Structure factor file (CIF format) (166.9 kbytes) [ doi:10.1107/S0108270107031071/tr3017IIsup2.hkl ] Contains datablock II

	Structure factor file (CIF format) (157.6 kbytes) [ doi:10.1107/S0108270107031071/tr3017IIIsup3.hkl ] Contains datablock III

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