N-Benzylpyridine-2-sulfonamide

The title compound, C12H12N2O2S, was obtained by the reaction of 2-mercaptopyridine and benzylamine. The dihedral angle between the benzene and pyridine rings is 75.75 (9)°. In the crystal, molecules are linked into chains along the c axis by N—H⋯O and N—H⋯N hydrogen bonds; the chains are cross-linked into a two-dimensional network parallel to the bc plane via C—H⋯O hydrogen bonds.

The title compound, C 12 H 12 N 2 O 2 S, was obtained by the reaction of 2-mercaptopyridine and benzylamine. The dihedral angle between the benzene and pyridine rings is 75.75 (9) . In the crystal, molecules are linked into chains along the c axis by N-HÁ Á ÁO and N-HÁ Á ÁN hydrogen bonds; the chains are cross-linked into a two-dimensional network parallel to the bc plane via C-HÁ Á ÁO hydrogen bonds.
Hydrogen bonding plays a significant role in stabilizing the crystal structure; see Table 1 for geometric parameters and symmetry operations. The molecules are linked into a chain along the c axis by N-H···O and N-H···N hydrogen bonds.
The chains are cross-linked via C-H···O hydrogen bonds to form a two-dimensional network parallel to the bc plane.

Experimental
The title compound was synthesized using a similar synthetic method for the preparation of heteroaryl sulfonamides (Wright et al., 2006). 2-Mercaptopyridine (0.56 g, 5 mmol) was stirred in a mixture of 25 mL of dichloromethane and 25 mL of 1 M HCl in a 125 ml flask for 8 min at 263 to 268 K. Cold sodium hypochlorite (6% solution, 0.68 M, 26 ml, 18 mmol, 3.3 equiv) was then added dropwise with very rapid stirring, maintaining the internal temperature at 263 to 268 K. The mixture was stirred for 30 min at 263 to 268 K after the addition was completed, the mixture was transferred to a separatory funnel (pre-cooled with ice water) and the dichloromethane layer was rapidly separated and collected in a clean 125 ml flask cooled in a ice-salt bath. Benzylamine (1.1 ml, 10 mmol) was added with stirring, when the dichloromethane layer became a white suspension, the flask was removed to an ice-water bath and the suspension was stirred for 30 min at 273 K. The suspension was then washed with 1 M HCl, then with water and brine. Drying (MgSO 4 ) and concentration afforded the title compound as a white solid with 81% yield. Single crystals of the title compound were grown in a petroleum ether-ethyl acetate solution (3:1 v/v) by slow evaporation.

Refinement
Atom H1 was located in a difference map and its positional parameters were refined. The remaining H atoms were positioned geometrically [C-H = 0.95 Å (aromatic) and 0.99 Å (methylene)] and were included in the refinement in the riding-model approximation. The isotropic displacement parameters were set at 1.2 times U eq of the parent atoms. as those based on F, and R-factors based on ALL data will be even larger.