Crystal structure and Hirshfeld surface analysis of supra­molecular aggregate of 2,2,6,6-tetra­methyl­piperidin-1-ium bromide with 1,2,3,4-tetra­fluoro-5,6-di­iodo­benzene

Abstract

The asymmetric unit of the title compound contains one 2,2,6,6 tetra­methyl­piperidine-1-ium cation, one 1,2,3,4-tetra­fluoro-5,6-di­iodo­benzene mol­ecule, and one uncoordinated bromide anion. In the crystal, the bromide anions link the 2,2,6,6-tetra­methyl­piperidine mol­ecules by inter­molecular C—H⋯Br and N—H⋯Br hydrogen bonds, leading to dimers, with the coplanar 1,2,3,4-tetra­fluoro-5, 6-di­iodo­benzene mol­ecules filling the space between them.

The asymmetric unit of the title compound, C₉H₂₀N⁺·Br⁻·C₆F₄I₂, contains one 2,2,6,6 tetra­methyl­piperidine-1-ium cation, one 1,2,3,4-tetra­fluoro-5,6-di­iodo­benzene mol­ecule, and one uncoordinated bromide anion. In the crystal, the bromide anions link the 2,2,6,6-tetra­methyl­piperidine mol­ecules by inter­molecular C—H⋯Br and N—H⋯Br hydrogen bonds, leading to dimers, with the coplanar 1,2,3,4-tetra­fluoro-5,6-di­iodo­benzene mol­ecules filling the space between them. There is a π–π interaction between the almost parallel benzene rings [dihedral angle = 10.5 (2)°] with a centroid-to-centroid distance of 3.838 (3) Å and slippage of 1.468 Å. No C—H⋯π(ring) inter­actions are observed. A Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯F/F⋯H (23.8%), H⋯H (22.6%), H⋯Br/Br⋯H (17.3%) and H⋯I/I⋯H (13.8%) inter­actions. Hydrogen bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing.