Synthesis, crystal structure and Hirshfeld surface analysis of (3Z)-4-[(4-amino-1,2,5-oxadiazol-3-yl)amino]-3-bromo-1,1,1-trifluorobut-3-en-2-one

Abstract

In the title compound, C6H4BrF3N4O2, the oxadiazole ring is essentially planar with a maximum deviation of 0.003 (2) Å. In the crystal, molecular pairs are connected by N—H...N hydrogen bonds, forming dimers with an R22(8) motif. The dimers are linked into layers parallel to the (10\overline{4}) plane by N—H...O hydrogen bonds. In addition, C—O...π and C—Br...π interactions connect the molecules, forming a three-dimensional network. The F atoms of the trifluoromethyl group are disordered over two sites in a 0.515 (6): 0.485 (6) ratio. The intermolecular interactions in the crystal structure were investigated and quantified using Hirshfeld surface analysis.

Keywords

• crystal structure
• α-haloketone
• diaminofurazan
• non-covalent interactions
• oxadiazole ring
• disorder
• hirshfeld surface analysis