Insights into the supramolecular features in isopropylmalonic and n-butylmalonic acids: Inputs from PIXEL and Hirshfeld surface analysis

• Isopropylmalonic acid and n-butylmalonic acid.
• Aliphatic group guided supramolecular self-assembly.
• Existence of strong OH⋯O and CH⋯O hydrogen-bonding patterns in the solid-state.
• Quantitative investigation of different intermolecular interactions.
• Hirshfeld Surface analysis provides a fingerprint for the atom···atom contact in the crystalline environment.

In this study, we have investigated the supramolecular pattern in two dicarboxylic acids, namely isopropylmalonic acid (1) and n-butylmalonic acid (2), via the presence of different hydrogen bonding patterns and aliphatic chains associated with the respective acids. The crystal structure is formed via the presence of strong OH⋯O and CH⋯O H-bonds, in the solid-state. The nature and energetics of the different supramolecular architectures in these two molecules have been further analyzed quantitatively via the PIXEL method. Hirshfeld surface analysis and fingerprint plots help to evaluate the contribution of different types of intermolecular contacts in the crystal packing. MESP calculations have been done to delineate the negative and positive areas of the electrostatic potential in different regions of the molecule in the crystal environment.

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