Topochemical bias in the hydrogen-bonded networks of guanidinium carboxybenzenesulfonates

Herein we describe the changes in the packing patterns and discuss the stru ctural modifications in guanidinium carboxybenzenesulfonates G . CBS [C(NH2 )(3)](+)[XC6H4SO3](-) (where X is the carboxylic group) compared with those in guanidinium benzenesulfonate G . BS. Generally, the one-dimensional arr angements in all three crystals comprise the same ribbon formations. Howeve r, the further organization of the ribbons is significantly different in G . CBS. We analyse the donor and acceptor efficacy of the additional functio nal group to disrupt some of the basic hydrogen bonds between the guanidini um and the sulfonium portions in G . BS. Since the carboxylic group introdu ces a mismatching of the sites on the counter ions, the changes in the symm etry relations essentially depend upon the topology of the substituent X, w hich results in modified packing patterns. All engineering peculiarities ar e analysed with respect to the symmetry constraints and geometrical demands of the packing forces.