2,6-Dibromo-3,5-dimethylpyridine and 2,6-diiodo-3,5-dimethylpyridine
Acta Crystallographica Section C Crystal Structure Communications, 62, (10), . (doi:10.1107/S0108270106032732).
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The title compounds 2,6-dibromo-3,5-dimethyl-pyridine, C7H7Br2N, (I), and 2,6-diiodo-3,5-dimethyl-pyridine, C7H7I2N, (II), constitute the first structurally characterized examples of 2,6-dihalo-3,5-dimethyl-pyridines. 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 pi-stacking in the solid state, although there are no other long-range inter-actions. In (I), alternate molecules are oriented at 90 degrees, resulting in X-shaped columns, while in (II), molecules pack in a parallel fashion, leading to a zigzag array.
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