The cover picture shows
a stereoview of the formation of tetramethylimidazoium
tetrazolide through the cycloaddition reaction of the azide anion to
the 2-cyano-1,3,4,5-tetramethylimidazolium cation. The tetrazolide moiety, an
isostere for carboxylate, builds strong, stable, hydrogen bonding
networks by incorporation of water molecules of crystallization into
solid-state packing motifs. Each molecule of tetramethylimidazoium
tetrazolide crystallizes with five water molecules of solvation that
encase the tetrazolide ring in an ice-like hydrogen-bond matrix. This
“ice” matrix extends throughout the crystal, and remains stable
and ordered under the influence of the tetrazolide group at room
temperature - well above the normal melting point of ice. This
depiction was created using Blender 3D. A dynamic view of the actual crystal packing is available here.