Crystal structure determination as part of an ongoing undergraduate organic laboratory project: 5-[(<i>E</i>)-styryl]-1,3,4-oxathiazol-2-one

Nason, Trevor R.; Schriver, Melbourne J.; Hendsbee, Arthur D.; Masuda, Jason Douglas, 1977-

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Crystal structure determination as part of an ongoing undergraduate organic laboratory project: 5-[(E)-styryl]-1,3,4-oxathiazol-2-one

Nason, Trevor R.; Schriver, Melbourne J.; Hendsbee, Arthur D.; Masuda, Jason Douglas, 1977-

Date: 2017-08-04

Type: Text

ISSN: 2056-9890

Source:

Acta Cryst E73, 1298–1301. (2017)

Abstract:

The title compound, C¹⁰H⁷NO²S, provides the first structure of an α-alkenyl oxathiazolone ring. The phenyl ring and the oxathiazolone groups make dihedral angles of 0.3 (3) and −2.8 (3)°, respectively, with the plane of the central alkene group; the dihedral angle between the rings is 2.68 (8)°. A careful consideration of bond lengths provides insight into the electronic structure and reactivity of the title compound. In the crystal, extended Π-stacking is observed parallel to the a-axis direction, consisting of cofacial head-to-tail dimeric units [centroid–centroid distance of 3.6191 (11) Å]. These dimeric units are separated by a slightly longer centroid–centroid distance of 3.8383 (12) Å, generating infinite stacks of molecules.