N,N'-Bis(pyridin-4-ylmeth-yl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The asymmetric unit of the title 1:1 solvate, C₁₄H₁₄N₄O₂·C₆H₆ [systematic name of the oxalamide mol-ecule: N,N'-bis-(pyridin-4-ylmeth-yl)ethanedi-amide], comprises a half mol-ecule of each constituent as each is disposed about a centre of inversion. In the oxalamide mol-ecule, the central C₂N₂O₂ atoms are planar (r.m.s. deviation = 0.0006?Å). An intra-molecular amide-N-H?O(amide) hydrogen bond is evident, which gives rise to an S(5) loop. Overall, the mol-ecule adopts an anti-periplanar 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)°]. In the crystal, supra-molecular layers parallel to (10) are generated owing the formation of amide-N-H?N(pyrid-yl) hydrogen bonds. The layers stack encompassing benzene mol-ecules which provide the links between layers via methyl-ene-C-H??(benzene) and benzene-C-H??(pyrid-yl) inter-actions. 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?? contacts (dispersion forces).

SUBMITTER: Tan SL 

PROVIDER: S-EPMC6690468 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature