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 R22(8) motif through N—H...O hydrogen bonds. These dimers are connect into ribbons parallel to the (100) plane with R44(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.

Keywords

• crystal structure
• hydrogen bonds
• dimers
• pyrazole ring
• hirshfeld surface analysis