Syntheses and structures of spontaneously resolved (2S)-2-phenyl-3-(thia-zol-2-yl)-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one and racemic 2-(furan-2-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one

自发拆分的 (2S)-2-苯基-3-(噻唑-2-基)-2,3,5,6-四氢-4H-1,3-噻嗪-4-酮和外消旋 2-(呋喃-2-基)-3-苯基-2,3,5,6-四氢-4H-1,3-噻嗪-4-酮的合成及结构

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Abstract

The title compounds, one a thia-zole derivative: (2S)-2-phenyl-3-(thia-zol-2-yl)-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one, C(13)H(12)N(2)OS(2), and the second a furan derivative: (rac)-2-(furan-2-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one, C(14)H(13)NO(2)S, crystallize in space-groups P2(1)2(1)2(1) and P2(1)/c, respectively, with a single mol-ecule in their asymmetric units. The crystal of the thia-zole derivative chosen for data collection was found to consist of the S enanti-omer [Flack parameter 0.013 (9)]. The crystal of the furan derivative in the centrosymmetric space group is a racemic mixture. The puckering of the thia-zine ring in both the structures is a half-chair. The extended structure of the thia-zole derivative shows two weak C-H⋯O type inter-actions, but no aromatic ring inter-actions. In the structure of the furan derivative, an extensive and continuous network of C-H⋯O hydrogen bonds between the furan and the substituted thia-zine ring, and also between symmetry-related furan rings, results in a continuous amphiphilic layer lying parallel to the (100) plane. Adjacent to this plane is the layer of hydro-phobic phenyl rings. Thus, the extended structure comprises alternating layers of amphiphilic and hydro-phobic regions, stacked in the a-axis direction. A C-H⋯O inter-action between the phenyl ring and the thia-zin-4-one moiety and the π-π stacking of the phenyl rings between pairs of symmetry-related mol-ecules further consolidates the extended structure.

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