2,2'-(Disulfanedi-yl)di-benzoic acid N,N-di-methyl-formamide monosolvate: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The title 1:1 solvate, C14H10O4S2·C3H7NO, features a twisted mol-ecule of 2,2'-di-thiodi-benzoic acid (DTBA), with the central C-S-S-C torsion angle being -88.57?(6)°, and a mol-ecule of di-methyl-formamide (DMF). The carb-oxy-lic acid groups are, respectively, close to co-planar and twisted with respect to the benzene rings to which they are connected as seen in the CO2/C6 torsion angles of 1.03?(19) and 7.4?(2)°. Intra-molecular, hypervalent S?O inter-actions are noted [S?O = 2.6140?(9) and 2.6827?(9)?Å]. In the crystal, four-mol-ecule aggregates are formed via DTBA-O-H?O(DMF) and DTBA-O-H?O(DTBA) hydrogen bonding, the latter via an eight-membered {?OHCO}2 homosynthon. These are linked into supra-molecular layers parallel to (011) via benzene-C-H?O(DTBA) and DTBA-C=O??(benzene) inter-actions, with the connections between these, giving rise to a three-dimensional architecture, being of the type benzene-C-H??(benzene). An analysis of the calculated Hirshfeld surfaces indicates, in addition to the aforementioned inter-molecular contacts, the presence of stabilizing inter-actions between a benzene ring and a quasi-?-system defined by O-H?O hydrogen bonds between a DTBA dimer, i.e. the eight-membered {?OCOH}2 ring system, and between a benzene ring and a quasi-?(OCOH?OCH) system arising from the DTBA-O-H?O(DMF) hydrogen bond. The inter-centroid separations are 3.65 and 3.49?Å, respectively.

SUBMITTER: Tan SL 

PROVIDER: S-EPMC7336788 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature