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Zwitterionic crystalline complexes between 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), a guanidine derivative, and two dicarboxylic acids (DCAs) (oxalic acid, adipic acid) as well as a special monocarboxylic acid (glycolic acid) have been analyzed by single crystal X-ray diffraction methods. In the solid state the carboxylic acid forms a monoanion by readily transferring an acidic proton to a TBD base, resulting in formation of strong +N–H⋯O− hydrogen-bonded R22(8) ring motifs, while O–H⋯O interactions expand the network into infinite one-dimensional supramolecular chains. Numerous C(sp3)–H⋯O interactions also contribute in crystal packing, including TBD as a weak donor and O atoms of carboxyl groups or co-crystallized water molecules as acceptors. The hydrogen bonding and crystal packing of all three complexes have been compared with the respective guanidine–carboxylate or related complexes reported previously.

Supramolecular 1D ribbons in complexes between a bicyclic-guanidine derivative and di- or monocarboxylic acids