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The structure of the title compound, C18H16N2O4S, with a new chiral pyrido[3′,2′:5,6][1,2]thia­zino[3,2-c][1,4]oxazine ring system, is described. Both partially saturated thia­zine and oxazine rings adopt diplanar conformations. The mol­ecular packing is influenced by weak C—H...O and π–π inter­actions.

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In the structure of the title compound, C19H21N5O3S, the piperazine ring adopts a slightly deformed chair conformation, with puckering parameters Q = 0.534 (2) Å and θ = 22.2 (2)° and an almost flat configuration of the piperazine N atom bonded to the benzene ring. This deformation is caused by the strong conjugation effect of the lone pair of the N atom with the π-electron system of the benzene ring in the aryl­piperazine part of the mol­ecule. The mol­ecular packing is influenced by weak π–π inter­actions of the isothia­zolopyridine systems, with a shortest centroid-to-centroid separation of 3.5113 (14) Å between pyridine rings.
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