N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study

The asymmetric unit of the title 1:1 solvate, C14H4N4O2-C6H6 [systematic name of the oxalamide molecule: N,N'-bis(pyridin-4-ylmethyl)ethanediamide], comprises a half molecule of each constituent as each is disposed about a centre of inversion. In the oxalamide molecule, the central C2N2O2 atoms are planar (r.m.s. deviation = 0.0006 angstrom). An intramolecular amide-N - H center dot center dot center dot O(amide) hydrogen bond is evident, which gives rise to an S(5) loop. Overall, the molecule adopts an antiperiplanar disposition of the pyridyl rings, and an orthogonal relationship is evident between the central plane and each terminal pyridyl ring [dihedral angle = 86.89 (3)degrees]. In the crystal, supramolecular layers parallel to (10 (2) over bar) are generated owing the formation of amide-N - H center dot center dot center dot N(pyridyl) hydrogen bonds. The layers stack encompassing benzene molecules which provide the links between layers via methylene-C- H center dot center dot center dot pi(benzene) and benzene-C-H center dot center dot center dot pi(pyridyl) interactions. The specified contacts are indicated in an analysis of the calculated Hirshfeld surfaces. The energy of stabilization provided by the conventional hydrogen bonding (approximately 40 kJ mol(-1); electrostatic forces) is just over double that by the C-H center dot center dot center dot pi contacts (dispersion forces).