Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N?-bis­(pyridin-4-ylmeth­yl)ethane­diamide and 4-chloro­benzoic acid.

ABSTRACT: The asymmetric unit of the title 1:2 co-crystal, C14H14N4O2·2C7H5ClO2, comprises two half mol­ecules of oxalamide (4 LH2), as each is disposed about a centre of inversion, and two mol­ecules of 4-chloro­benzoic acid (CBA), each in general positions. Each 4 LH2 mol­ecule has a (+)anti­periplanar conformation with the pyridin-4-yl residues lying to either side of the central, planar C2N2O2 chromophore with the dihedral angles between the respective central core and the pyridyl rings being 68.65?(3) and 86.25?(3)°, respectively, representing the major difference between the independent 4 LH2 mol­ecules. The anti conformation of the carbonyl groups enables the formation of intra­molecular amide-N—H?O(amide) hydrogen bonds, each completing an S(5) loop. The two independent CBA mol­ecules are similar and exhibit C6/CO2 dihedral angles of 8.06?(10) and 17.24?(8)°, indicating twisted conformations. In the crystal, two independent, three-mol­ecule aggregates are formed via carb­oxy­lic acid-O—H?N(pyrid­yl) hydrogen bonding. These are connected into a supra­molecular tape propagating parallel to [100] through amide-N—H?O(amide) hydrogen bonding between the independent aggregates and ten-membered {?HNC2O}2 synthons. The tapes assemble into a three-dimensional architecture through pyridyl- and methyl­ene-C—H?O(carbon­yl) and CBA-C—H?O(amide) inter­actions. As revealed by a more detailed analysis of the mol­ecular packing by calculating the Hirshfeld surfaces and computational chemistry, are the presence of attractive and dispersive Cl?C=O inter­actions which provide inter­action energies approximately one-quarter of those provided by the amide-N—H?O(amide) hydrogen bonding sustaining the supra­molecular tape.

SUBMITTER: Tan SL 

PROVIDER: S-EPMC7001830 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature