N-(6-Bromomethyl-2-pyridyl)acetamide

The title acetamide compound, C8H9BrN2O, crystallizes with three crystallographically independent molecules (A, B and C) in the asymmetric unit. In molecule A, the mean plane through the acetamide unit is inclined at a dihedral angle of 4.40 (11)° with respect to the pyridine ring [10.31 (12) and 2.27 (11)°, respectively, for molecules B and C]. In the crystal structure, molecules are interconnected into sheets parallel to the ac plane by N—H⋯O, C—H⋯Br, C—H⋯O and C—H⋯N hydrogen bonds. The structure is further stabilized by weak intermolecular C—H⋯π interactions.

The title acetamide compound, C 8 H 9 BrN 2 O, crystallizes with three crystallographically independent molecules (A, B and C) in the asymmetric unit. In molecule A, the mean plane through the acetamide unit is inclined at a dihedral angle of 4.40 (11) with respect to the pyridine ring [10.31 (12) and 2.27 (11) , respectively, for molecules B and C]. In the crystal structure, molecules are interconnected into sheets parallel to the ac plane by N-HÁ Á ÁO, C-HÁ Á ÁBr, C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds. The structure is further stabilized by weak intermolecular C-HÁ Á Á interactions.

Experimental
The title compound was prepared according to literature procedures (Goswami et al., 2001(Goswami et al., , 2004 and was recrystallized from a mixture of CHCl 3 and CH 3 OH (9:1) by slow evaporation method.

Refinement
H atoms bound to N atoms are located in a difference Fourier map and allowed to refine freely [range of N-H = 0.73 The remaining H atoms were placed in their calculated positions, with C-H = 0.93-0.97 Å, and refined using a riding model, with U iso = 1.2 or 1.5 U eq (C). The rotating group model was applied to methyl groups. Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.    Glazer, 1986) operating at 100.0 (1)K.

N-(6-Bromomethyl-2-pyridyl)acetamide
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. 0.0389 (9) 0.0208 (7) 0.0268 (7 0.0555 (11) 0.0220 (7) 0.0271 (7) −0.0039 (7) −0.0182 (7) 0.0056 (6) N1B 0.0190 (7) 0.0172 (7) 0.0156 (6)