(3aR,6S,7aR)-7a-Bromo-2-methylsulfonyl-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole

In the title compound, C9H12BrNO3S, the two tetrahydrofuran rings adopt envelope conformations, the pyrrolidine ring adopts a half-chair conformation and the six-membered ring is in a boat conformation. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into R 2 2(8) and R 2 2(14) rings along the b-axis direction.

In the title compound, C 9 H 12 BrNO 3 S, the two tetrahydrofuran rings adopt envelope conformations, the pyrrolidine ring adopts a half-chair conformation and the six-membered ring is in a boat conformation. In the crystal, weak intermolecular C-HÁ Á ÁO hydrogen bonds link the molecules into R 2 2 (8) and R 2 2 (14) rings along the b-axis direction.

Comment
Sulfonamides are one of the most important groups of compounds for the medical purposes (Kleemann et al., 1999). They have mostly been applied for the treatment of bacterial infection (Cremlyn, 1996). Sulfonamide is not only an early class of antibiotics, also, has showed different functionality such as a protease inhibitor amprenavir, the analgesic celecoxib, sildenafil for erectile dysfunction, and the antimigraine agent sumatriptan. The most sulfonamides have been synthesized from a reaction between a sulfonyl chloride and ammonia or primary or secondary amines or via related transformations (Anderson, 1979).
Several thermal intramolecular Diels Alder reaction of furans (IMDAF) cycloadditon were performed including a nitrogen linked side chain of furan and already reported by Demircan and his co-workers (Demircan and Parsons, 2002;Arslan et al., 2008). We would like to report here a newly synthesized sulfonamide, I.
In continuation of our interest, mesyl group in the structure is normally chosen as a protective group for nitrogen, but at the same time, accelerates the cycloaddition process for IMDAF (Greene, 1981;Choony et al., 1997). This facile, versatile and environmentally friendly reaction was accomplished in aqueous condition and stirred for two days at 372 K.

Refinement
H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.96, 0.97, 0.98 and 0.93 Å for CH 3 , CH 2 , CH and CH(aromatic), respectively. The displacement parameters of the H atoms were constrained with U iso (H) = 1.2U eq (aromatic, methylene or methine C) or 1.5U eq (methyl C). Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.