Crystal structure and Hirshfeld surface analysis of (E)-2-[2-(2-amino-1-cyano-2-oxoethylidene)hydrazin-1-yl]benzoic acid N,N-dimethylformamide monosolvate

Abstract

In the title compound, C10H8N4O3·C3H7NO, the asymmetric unit contains two crystallographically independent molecules A and B, each of which has one DMF solvate molecule. Molecules A and B both feature intramolecular N—H...O hydrogen bonds, forming S(6) ring motifs and consolidating the molecular configuration. In the crystal, N—H...O and O—H...O hydrogen bonds connect molecules A and B, forming R22(8) ring motifs. Weak C—H...O interactions link the molecules, forming layers parallel to the (\overline{2}12) plane. The DMF solvent molecules are also connected to the main molecules (A and B) by N—H...O hydrogen bonds. π–π stacking interactions [centroid-to-centroid distance = 3.8702 (17) Å] between the layers also increase the stability of the molecular structure in the third dimension. According to the Hirshfeld surface study, O...H/H...O interactions are the most significant contributors to the crystal packing (27.5% for molecule A and 25.1% for molecule B).

Keywords

• crystal structure
• hydrogen bonds
• ring motifs
• π–π stacking interactions
• hirshfeld surface analysis