The 1:2 co-crystal formed between N,N'-bis(pyridin-4-ylmeth-yl)ethanedi-amide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The crystal and mol-ecular structures of the title 1:2 co-crystal, C14H14N4O2·2C7H6O2, are described. The oxalamide mol-ecule has a (+)-anti-periplanar conformation with the 4-pyridyl residues lying to either side of the central, almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555?Å). The benzoic acid mol-ecules have equivalent, close to planar conformations [C6/CO2 dihedral angle = 6.33?(14) and 3.43?(10)°]. The formation of hy-droxy-O-H?N(pyrid-yl) hydrogen bonds between the benzoic acid mol-ecules and the pyridyl residues of the di-amide leads to a three-mol-ecule aggregate. Centrosymmetrically related aggregates assemble into a six-mol-ecule aggregate via amide-N-H?O(amide) hydrogen bonds through a 10-membered {?HNC2O}2 synthon. These are linked into a supra-molecular tape via amide-N-H?O(carbon-yl) hydrogen bonds and 22-membered {?HOCO?NC4NH}2 synthons. The contacts between tapes to consolidate the three-dimensional architecture are of the type methyl-ene-C-H?O(amide) and pyridyl-C-H?O(carbon-yl). These inter-actions are largely electrostatic in nature. Additional non-covalent contacts are identified from an analysis of the calculated Hirshfeld surfaces.

SUBMITTER: Tan SL 

PROVIDER: S-EPMC6944079 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature