Ethyl 2-(3,5-dimethyl-1,1-dioxo-2H-1λ⁶,2,6-thiadiazin-4-yl)benzoate

Abstract

In the title compound, C14H16N2O4S, the thia­diazine ring is in a half-boat conformation. The aromatic ring deviates from the plane of this moiety at an angle of 74.6 (2)°. The structure displays inter­molecular N—H⋯O hydrogen bonding [N⋯O = 2.8157 (16) Å], creating ribbons along the [010] axis. There are also weak C—H⋯O inter­actions in the crystal but no π–π stacking.

2-(3,5-Dimethyl-1,1-dioxo-2H-1λ6,2,6-thiadiazin-4-yl)benzoic acid

“…For synthetic background and applications of 1,2,6-thiadiazine-1,1-dioxide derivatives, see: Wright (1964); Breining et al (1995). For a related structure, see: Bhatt et al (2012) Experimental H atoms treated by a mixture of independent and constrained refinement Á max = 0.37 e Å À3 Á min = À0.42 e Å À3 Table 1 Hydrogen-bond geometry (Å , ).…”

“…It is the second 3,5-dimethyl based structure reported with an aromatic ring at position 4 of the thiadiazine ring. Previously we have reported the phenyl ethyl and methyl ester (Bhatt et al, 2012). It is the first containing an acid functional group in the broader family of 1,2,6-thiadiazine-1,1dioxides.…”