Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N'-bis-[(pyridin-4-yl)meth-yl]ethanedi-amide and 3-chloro-benzoic acid.

ABSTRACT: The asymmetric unit of the title 1:2 co-crystal, C14H14N4O2·2C7H5ClO2, comprises a half-mol-ecule of oxalamide (4 LH2), being located about a centre of inversion, and a mol-ecule of3-chloro-benzoic acid (3-ClBA) in a general position. From symmetry, the 4 LH2 mol-ecule has a (+)anti-periplanar conformation with the 4-pyridyl residues lying to either side of the central, planar C2N2O2 chromophore with the dihedral angle between the core and pyridyl ring being 74.69?(11)°; intra-molecular amide-N-H?O(amide) hydrogen bonds are noted. The 3-ClBA mol-ecule exhibits a small twist as seen in the C6/CO2 dihedral angle of 8.731?(12)°. In the mol-ecular packing, three-mol-ecule aggregates are formed via carb-oxy-lic acid-O-H?N(pyrid-yl) hydrogen bonding. These are connected into a supra-molecular tape along [111] through amide-N-H?O(carbon-yl) hydrogen bonding. Additional points of contact between mol-ecules include pyridyl and benzoic acid-C-H?O(amide), methyl-ene-C-H?O(carbon-yl) and C-Cl??(pyrid-yl) inter-actions so a three-dimensional architecture results. The contributions to the calculated Hirshfeld surface are dominated by H?H (28.5%), H?O/O?H (23.2%), H?C/C?H (23.3%), H?Cl/Cl?H (10.0%) and C?Cl/C?Cl (6.2%) contacts. Computational chemistry confirms the C-Cl?? inter-action is weak, and the importance of both electrostatic and dispersion terms in sustaining the mol-ecular packing despite the strong electrostatic term provided by the carb-oxy-lic acid-O-H?N(pyrid-yl) hydrogen bonds.

SUBMITTER: Tan SL 

PROVIDER: S-EPMC7274012 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature