Crystal structure and Hirshfeld surface analysis of 4-(2-chloroethyl)-5-methyl-1,2-dihydropyrazol-3-one

Abstract

In the crystal of the title compound, C6H9ClN2O, molecular pairs form dimers with an R 2 2(8) motif through N—H...O hydrogen bonds. These dimers are connect into ribbons parallel to the (100) plane with R 4 4(10) motifs by N—H...O hydrogen bonds along the c-axis direction. In addition, π–π [centroid-to-centroid distance = 3.4635 (9) Å] and C—Cl...π interactions between the ribbons form layers parallel to the (100) plane. The three-dimensional consolidation of the crystal structure is also ensured by Cl...H and Cl...Cl interactions between these layers. According to a Hirshfeld surface study, H...H (43.3%), Cl...H/H...Cl (22.1%) and O...H/H...O (18.7%) interactions are the most significant contributors to the crystal packing.