Supramolecular architectures of succinates of 1-hydroxypropan-2-aminium derivatives

Aminoalkanol and aroxyalkyl derivatives are known as potential anticonvulsants. Two new salts, namely bis{(R,S)-N-[2-(2,6-dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium} succinate (1s), C₁₃H₂₂NO₂⁺·0.5C₄H₄O₄^2-, and bis{(S)-(+)-N-[2-(2,6-dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium} succinate (2s), C₁₃H₂₂NO₂⁺·0.5C₄H₄O₄^2-, have been prepared and characterized by single-crystal X-ray diffraction. The N atoms are protonated by proton transfer from succinic acid. Salt 1s crystallizes in the space group P2₁/n with one cation and half an anion in the asymmetric unit across an inversion centre, while (2s) crystallizes in the space group P2₁ with four cations and two anions in the asymmetric unit. The hydroxy group of the cation of 1s is observed in two R/S disorder positions. The crystals of these two salts display similar supramolecular architectures (i.e. two-dimensional networks), built mainly by intermolecular N⁺-H...O^δ- and O-H...O^δ- hydrogen bonds, where `δ-' represents a partial charge. The succinate anions are engaged in hydrogen bonds, not only with protonated N atoms, but also with hydroxy groups.