Polysulfonylamines. CXLV. N-Diethylcarbamoyl-o-benzenedisulfonimide, a urea with non-planar geometry at nitrogen and an amide single bond

The prominent features in the molecular structure of the title compound (al ternative name: 2-diethylcarbamoyl-1,1,3,3-tetraoxo-1,3,2-benzodithiazole), C11H14N2O5S2, arise in the urea moiety S2N-C(O)-N'C-2 : the sum of the ang les at N is 332.3 (1)degrees, the N-C(O)-N'C-2 unit is planar, and distance s N-C(O) = 1.494 (3) Angstrom, N'-C(O) = 1.325 (2) Angstrom and C-O = 1.215 (2) Angstrom. The molecules are associated via five C-H . . .O hydrogen bo nds to form layers parallel to the yz plane. This compound and its dimethyl homologue, which were synthesized by treating the silver salt of o-benzene disulfonimide with carbamoyl chlorides, are prone to rapid hydrolysis at th e weak N-C(O) bond. For both molecules, the rotational barrier about the pa rtial N'-C(O) double bond is ca 50 kJ mol(-1) at 250 K (from dynamic H-1 NM R experiments).