2,6‐Dibromo‐3,5‐dimethyl­pyridine and 2,6‐diiodo‐3,5‐dimethyl­pyridine

The title compounds 2,6‐dibromo‐3,5‐dimethyl­pyridine, C 7 H 7 Br 2 N, (I), and 2,6‐diiodo‐3,5‐dimethyl­pyridine, C 7 H 7 I 2 N, (II), constitute the first structurally characterized examples of 2,6‐dihalo‐3,5‐dimethyl­pyridines. Compound (I) crystallizes as a racemic twin with two symmetry‐independent mol­ecules in the asymmetric unit, while (II) is non‐planar with the pyridine ring slightly deformed into a saddle shape, and exhibits crystallographically imposed twofold symmetry. Both (I) and (II) exhibit aromatic face‐to‐face π‐stacking in the solid state, although there are no other long‐range inter­actions. In (I), alternate mol­ecules are oriented at 90°, resulting in X‐shaped columns, while in (II), mol­ecules pack in a parallel fashion, leading to a zigzag array.