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

Abstract

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·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)°, respectively]. The extended structure of this co-crystal features N - H⋯O and O - H⋯O hydrogen bonds, which link the components into (100) sheets and weak C - H⋯O hydrogen bonds help to consolidate the structure.