Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-meth­oxy­phen­yl)picolinamide

Abstract

The mol­ecular and crystal structure of N-(4-meth­oxy­phen­yl)picolinamide were studied and Hirshfeld surfaces and fingerprint plots were generated to investigate various inter­molecular inter­actions.

The synthesis, crystal structure, and Hirshfeld surface analysis of N-(4-meth­oxy­phen­yl)picolinamide (MPPA), C₁₃H₁₂N₂O₂, are presented. MPPA crystallizes in the monoclinic space group P2₁/n, with a single mol­ecule in the asymmetric unit. Structural analysis reveals that all non-hydrogen atoms are nearly coplanar, and the mol­ecule exhibits two intra­molecular hydrogen bonds that stabilize its conformation. Supra­molecular features include significant inter­molecular inter­actions, primarily C—H⋯π and various hydrogen bonds, contributing to the overall crystal cohesion, as confirmed by energy framework calculations yielding a total inter­action energy of −138.3 kJ mol⁻¹. Hirshfeld surface analysis indicates that H⋯H inter­actions dominate, followed by C⋯H and O⋯H inter­actions, highlighting the role of van der Waals forces and hydrogen bonding in crystal packing.