Synthesis, crystal structure and Hirshfeld surface analysis of 2-azido-N-(2,6-dimethylphenyl)acetamide

Abstract

The asymmetric unit of the title compound, C10H12N4O, consists of two independent molecules differing in the rotational orientation of the 2-azidoacetamido group. In the crystal, inspection of the contacts of the methyl groups shows an intramolecular H...O distance of 2.47 Å in one molecule and intermolecular H...N distances of 2.75 Å in both independent molecules. Both are definitely van der Waals contacts with the latter quite short as the H...O distance is 0.39 Å less than the sum of the respective van der Waals radii. A Hirshfeld surface analysis indicates that the H...H contacts make the largest contribution. In the absence of any specific C—H...N hydrogen bonds, the significant contribution of N...H/H...N contacts (24.7%) might seem surprising, but with the azide group projecting away from the rest of the molecule, there is considerable opportunity for such contacts to occur.

Keywords

• crystal structure
• azide
• phenylacetamide
• hydrogen bond
• c—h...π(ring) interaction