The crystal structures of two isomers of 5-(phenyl-iso-thia-zol-yl)-1,3,4-oxa-thia-zol-2-one.
Acta crystallographica. Section E, Crystallographic communications(2017)
摘要
The syntheses and crystal structures of two isomers of phenyl isothiazolyl oxathiazolone, C11H6N2O2S2, are described [systematic names: 5-(3-phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one, (I), and 5-(3-phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one, (II)]. There are two almost planar (r.m.s. deviations = 0.032 and 0.063 A) molecules of isomer (I) in the asymmetric unit, which form centrosymmetric tetramers linked by strong S⋯N [3.072 (2) A] and S⋯O contacts [3.089 (1) A]. The tetramers are π-stacked parallel to the a-axis direction. The single molecule in the asymmetric unit of isomer (II) is twisted into a non-planar conformation by steric repulsion [dihedral angles between the central isothiazolyl ring and the pendant oxathiazolone and phenyl rings are 13.27 (6) and 61.18 (7)°, respectively], which disrupts the π-conjugation between the heteroaromatic isothiazoloyl ring and the non-aromatic oxathiazolone heterocycle. In the crystal of isomer (II), the strong S⋯O [3.020 (1) A] and S⋯C contacts [3.299 (2) A] and the non-planar structure of the molecule lead to a form of π-stacking not observed in isomer (I) or other oxathiazolone derivatives.
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关键词
conjugation,crystal structure,isothiazoyl,nitrile sulfide,oxathiazolone,π-stacking
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