Synthesis and structure of a 1:1 co-crystal of hexamethylenetetramine carboxyborane and acetaminophen

Hexamethylenetetramine carboacetaminophenborane, a molecule with two pharmacophores attached to a central carboxyborate moiety, was synthesized and crystals were grown with an acetaminophen co-crystal former to result in the title 1:1 co-crystal [hexamethylenetetramine 4-acetamidophenyl 2-boranylacetate-4-acetamidophenol (1/1)], C15H22BN5O3 center dot C8H9NO2. In the first of these molecules, both the borate-ester and acetylamino groups are considerably twisted away from the plane of the intervening benzene ring [dihedral angles = 76.89 (9) and 65.42 (9)degrees, respectively]. The extended structure of this co-crystal features N-H center dot center dot center dot O and O-H center dot center dot center dot O hydrogen bonds, which link the components into (100) sheets and weak C-H center dot center dot center dot O hydrogen bonds help to consolidate the structure.