2-Iodopyridin-3-yl acetate

The title compound 2-iodopyridin-3-yl acetate was obtained by acetylation of the OH group of 2-iodo-3-hydroxypyridine. Knowing that the hydroxyl group, as a strong H-bond donor in halogenated hydroxypyridines, usually directs supramolecular packing and might enforce possible halogen–halogen contacts, we crystallized 2-iodo-3-acetoxypyridine with the aim of disrupting the most important H-bond donor and assessing the propensity of the iodine for halogen bond formation. Indeed, in the compound 2-iodopyridin-3-yl acetate, the crystal packing is characterized by infinite 3D chains bonded through I···O=C and C-H···I contacts between adjacent molecules. These chains are interconnected by weak C-H···O contacts, implying the presence of oxygen in the ester. The I···H contact with the C-H axis perpendicular to the electron belt of the iodine atom can enhance the σ-hole of the iodine and act cooperatively in crystal cohesion. No halogen–halogen contacts were present.