N-(3-Aminobicyclo[2.2.1]heptan-2-yl)-4-methylbenzenesulfonamide

In the title compound, C14H20N2O2S, the sulfonamide O atoms lie to one side of the benzene ring and the aminobicycloheptanyl to the other side [Car—S—N—C torsion angle = −57.93 (11)°; ar = aromatic]. An intramolecular N—H⋯N hydrogen bond is formed. In the crystal, a supramolecular chain is formed along the b axis via N—H⋯O and N—H⋯N hydrogen bonds.

In the title compound, C 14 H 20 N 2 O 2 S, the sulfonamide O atoms lie to one side of the benzene ring and the aminobicycloheptanyl to the other side [C ar -S-N-C torsion angle = À57.93 (11) ; ar = aromatic]. An intramolecular N-HÁ Á ÁN hydrogen bond is formed. In the crystal, a supramolecular chain is formed along the b axis via N-HÁ Á ÁO and N-HÁ Á ÁN hydrogen bonds.

Tiekink Comment
The title compound (I) was synthesized in the context of the development of chiral ligands for asymmetric catalytic reactions (Seo et al., 2001;Abdel-Aziz et al., 2004;Matsunaga et al., 2005;Yamakuchi et al. 2005).
In (I), Fig. 1, the two S-bound O atoms lie to one side of the adjacent benzene ring with the O1 and O2 atoms lying -0.466 (1) and -0.771 (1) Å out of the plane, respectively, and the aminobicycloheptanyl residue lying to the other side, the C8-S1-N2-C2 torsion being -57.93 (11)°. An intramolecular N-H···N hydrogen bond is noted, Table 1.
Molecules are connected into a supramolecular chain along the b axis via N-H···O and N-H···N hydrogen bonds that generate 12-membered {···HNC 2 NH···OSNC 2 N} synthons, Fig. 2 and Table 1. The chains pack into a three-dimensional architecture without specific interactions between them, Fig. 3.

Experimental
To the mixture of 2-imidazolidinone (2.0 ml), water (2 ml), ethanol (6 ml) and Ba(OH) 2 .8H 2 O (20 ml) were added. This was heated at 413 K in a glass sealed tube for 24 h. The solvents were evaporated and the precipitate extracted three times with chloroform (10 ml × 3). The organic extract was dried and crystallized from ethanol to afford the title compound.

Refinement
Carbon-bound H-atoms were placed in calculated positions [C-H = 0.95 to 1.00 Å, U iso (H) = 1.2-1.5U eq (C)] and were included in the refinement in the riding model approximation. The amino H-atoms were refined with N-H = 0.88±0.01 Å.