The crystal structures of two isomers of 5-(phenyl- isothiazolyl)-1,3,4-oxathiazol-2-one

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dc.creator Zhu, Shuguang
dc.creator Schriver, Melbourne J.
dc.creator Hendsbee, Arthur D.
dc.creator Masuda, Jason D.
dc.date.accessioned 2022-06-20T14:03:59Z
dc.date.available 2022-06-20T14:03:59Z
dc.date.issued 2017-10-20
dc.identifier.issn 2056-9890
dc.identifier.uri http://library2.smu.ca/xmlui/handle/01/30984
dc.description Published Version en_CA
dc.description.abstract 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 Å) mol­ecules of isomer (I) in the asymmetric unit, which form centrosymmetric tetra­mers linked by strong S...N [3.072 (2) Å] and S...O contacts [3.089 (1) Å]. 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) Å] and S...C contacts [3.299 (2) Å] and the non-planar structure of the mol­ecule lead to a form of π-stacking not observed in isomer (I) or other oxa­thia­zolone derivatives. en_CA
dc.description.provenance Submitted by Sherry Briere (sherry.briere@smu.ca) on 2022-06-20T14:03:59Z No. of bitstreams: 1 Masuda_Jason_D_article_2017_d.pdf: 839386 bytes, checksum: 21e37bb226cb67c41e776fe3177521c9 (MD5) en
dc.description.provenance Made available in DSpace on 2022-06-20T14:03:59Z (GMT). No. of bitstreams: 1 Masuda_Jason_D_article_2017_d.pdf: 839386 bytes, checksum: 21e37bb226cb67c41e776fe3177521c9 (MD5) Previous issue date: 2017-10-16 en
dc.language.iso en_CA en_CA
dc.publisher International Union of Crystallography en_CA
dc.relation.uri https://doi.org/10.1107/S2056989017015067
dc.title The crystal structures of two isomers of 5-(phenyl- isothiazolyl)-1,3,4-oxathiazol-2-one en_CA
dc.type Text en_CA
dcterms.bibliographicCitation Acta Cryst. E73: 1726-1731. (2017) en_CA
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Published Version: https://doi.org/10.1107/S2056989017015067
 
 

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