Synthesis, crystal structure and Hirshfeld surface analysis of 2-{4-[(2-chloro­phen­yl)meth­yl]-3-methyl-6-oxopyridazin-1-yl}-N-phenyl­acetamide

Abstract

The phenyl­acetamide moiety is nearly planar due to a weak, intra­molecular C—H⋯O hydrogen bond and its nitro­gen lone pair appears involved in N→C π bonding. In the crystal, N—H⋯O hydrogen bonds and π-stacking inter­actions between pyridazine and phenyl rings form helical chains of mol­ecules, which are linked by C—H⋯O hydrogen bonds and C—H⋯π(ring) inter­actions.

In the title mol­ecule, C₂₀H₁₈ClN₃O₂, the 2-chloro­phenyl group is disordered to a small extent [occupancies 0.875 (2)/0.125 (2)]. The phenyl­acetamide moiety is nearly planar due to a weak, intra­molecular C—H⋯O hydrogen bond. In the crystal, N—H⋯O hydrogen bonds and π-stacking inter­actions between pyridazine and phenyl rings form helical chains of mol­ecules in the b-axis direction, which are linked by C—H⋯O hydrogen bonds and C—H⋯π(ring) inter­actions. A Hirshfeld surface analysis was performed, which showed that H⋯H, C⋯H/H⋯C and O⋯H/H⋯O inter­actions to dominate the inter­molecular contacts in the crystal.