Interplay of carbonyl–carbonyl, CH⋯O and CH⋯π interactions in hierarchical supramolecular assembly of tartaric anhydrides – Tartaric acid and its O-acyl derivatives: Part 11

Abstract

► Relation between conformation of acyl groups and weak intramolecular interactions. ► Hirshfeld surfaces analysis of intermolecular C=O···C=O, C–H···O, C–H···π interactions. ► Primary ribbon structure of p 2 1 symmetry directed by weak intermolecular forces. ► Pseudo-hexagonal packing of ribbons. The detailed analysis of molecular and crystal structure of the O -acyltartaric anhydrides is presented. The role of both intra- and intermolecular weak interactions is discussed. The Hirshfeld surfaces analysis in form of d norm representation and decomposed finger print plots was used to find out the types of weak but directional carbonyl–carbonyl, C H⋯O and C H⋯π interactions. The major interactions at the subsequent levels of the crystal architecture were identified. The interplay between carbonyl–carbonyl interactions and C H⋯O hydrogen bonds both at the molecular level as well as in basic supramolecular motives was analyzed. In all cases the primary supramolecular motif was found to be the ribbon showing the p 2 1 rod group symmetry. The key role of the ribbon motif is reflected in the hexagonal packing of rods.