Formation of nitrobenzene dimers in racemic and chiral salts of 2-amino-1-(4-nitrophenyl)-1,3-propanediol (ANPD) with oxalic and fumaric acids

Abstract

This study aimed to investigate the effect of chirality on the formation of nitrobenzene dimers and crystal packing in multicomponent crystals. Four multicomponent crystals, [APPD+]½[FUM2−]·FUM (1), [ANPD+]½[FUM2−]·FUM (2), [ANPD+]½[OX2−] (3) and [(R,R)-ANPD+]½[OX2−] (4) were prepared by crystallizing 2-amino-1-phenyl-1,3-propanediol (APPD) or its nitro derivative, 2-amino-1-(4-nitrophenyl)-1,3- propanediol (ANPD) with either oxalic acid (OX) or fumaric acid (FUM). The crystals were characterized using single crystal X-ray diffraction (SCXRD) and differential scanning calorimetry (DSC). The interaction in the nitrobenzene dimers was investigated by Functional group Symmetry-Adapted Perturbation Theory (F-SAPT) and Hirshfeld surface analysis. A search of the Cambridge Structural Database was conducted on crystals that contain nitrobenzene moieties, and the results were analyzed.