Crystallographic evidence for unintended benziso­thia­zolinone 1-oxide formation from benzo­thia­zinones through oxidation

1,3-Benzo­thia­zin-4-ones (BTZs) are a promising new class of drugs with activity against Mycobacterium tuberculosis, which have already reached clinical trials. A product obtained in low yield upon treatment of 8-nitro-2-(piperidin-1-yl)-6-(tri­fluoro­meth­yl)-4H-benzo­thia­zin-4-one with 3-chloro­perbenzoic acid, in ana­logy to a literature report describing the formation of sulfoxide and sulfone derived from BTZ043 [Tiwari et al. (2015 ▸). ACS Med. Chem. Lett. 6, 128–133], is a ring-contracted benziso­thia­zolinone (BIT) 1-oxide, namely, 7-nitro-2-(piperi­dine-1-carbon­yl)-5-(tri­fluoro­meth­yl)benzo[d]iso­thia­zol-3(2H)-one 1-oxide, C(14)H(12)F(3)N(3)O(5)S, as revealed by X-ray crystallography. Single-crystal X-ray analysis of the oxidation product originally assigned as BTZ043 sulfone provides clear evidence that the structure of the purported BTZ043 sulfone is likewise the corresponding BIT 1-oxide, namely, 2-[(S)-2-methyl-1,4-dioxa-8-aza­spiro­[4.5]decane-8-carbon­yl]-7-nitro-5-(tri­fluoro­meth­yl)benzo[d]iso­thia­zol-3(2H)-one 1-oxide, C(17)H(16)F(3)N(3)O(7)S. A possible mechanism for the ring contraction affording the BIT 1-oxides instead of the anti­cipated constitutionally isomeric BTZ sulfones and anti­mycobacterial activities thereof are discussed.