Crystal structure and Hirshfeld surface analysis of N-{N-[amino(dimethylamino)methyl]carbamimidoyl}-3-bromobenzenesulfonamide

Abstract

The title compound, C10H14BrN5O2S, is the bromobenzenesulfonamide derivative of the type 2 diabetes drug metformin. The asymmetric unit contains two molecules with almost identical conformations but a different orientation of the bromophenyl moiety. Both molecules exhibit intramolecular N—H...N and N—H...O hydrogen bonds. The molecular packing features chain formation in the a-axis direction by alternating N—H...N and N—H...O interactions. In addition, ring motifs consisting of four molecules and π–π interactions between the phenyl rings contribute to the three-dimensional architecture. A Hirshfeld surface analysis shows that the largest contributions to surface contacts arise from contacts in which H atoms are involved.

Keywords

• crystal structure
• metformin
• hydrogen-bond interactions
• π–π interactions
• hirshfeld surface analysis