6-Chloro-N-(pyridin-4-ylmethyl)pyridine-3-sulfonamide

In the title sulfonamide derivative, C11H10ClN3O2S, the dihedral angle between the pyridine rings is 46.85 (12)°. The N atom of the chloropyridine ring is anti to the N—H bond. In the crystal, molecules are linked through N—H⋯N hydrogen bonds into zigzag chains parallel to [001] with a C(7) graph-set motif.

In the title sulfonamide derivative, C 11 H 10 ClN 3 O 2 S, the dihedral angle between the pyridine rings is 46.85 (12) . The N atom of the chloropyridine ring is anti to the N-H bond. In the crystal, molecules are linked through N-HÁ Á ÁN hydrogen bonds into zigzag chains parallel to [001] with a C(7) graph-set motif.
In the structure of compound (I) the dihedral angle between the two pyridine rings is 46.85(12°. The N-atom of the chloropyridine ring in the compound is anti to the N-H bond (Fig 1). In the crystal structure, the molecules are linked through N2-HN2···N3 hydrogen bonds (Table 1, Fig. 2) into zigzag chains with graph-set notation C(7) (Bernstein et al. 1995) running parallel to [001] .

Experimental
Pyridin-4-ylmethanamine (7.4 mmol) was taken in dry dichloromethane (10 ml) and cooled to 273 K. To this solution 6chloropyridine-3-sulfonyl chloride (7.4 mmol) in dichloromethane and triethylamine (1.48 mmol) was added slowly and the solution was heated to 323 K for 4 h. The reaction was monitored by TLC. The reaction mixture was cooled and washed with 10% sodium bicarbonate solution. The organic layer was separated, dried and concentrated to obtain the crude compound. It was purified by column chromatography using petroleum ether: ethyl acetate (7:3) as eluent.
Yellow prisms of the title compound suitable for diffraction studies were obtained from evapouration of the solution of the compound in a mixture of petroleum ether: ethyl acetate (7:3).

Refinement
The H atom of the NH group was located in a difference map and refined freely. The other H atoms were positioned with idealized geometry using a riding model with C-H = 0.93 Å (aromatic) and 0.97 Å (methylene). Isotropic displacement parameters for all H atoms were set to 1.2 times U eq of the parent atom.

Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008   Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. 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 > 2σ(F 2 ) is used only for calculating R-factors(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.