A 1:1:1 co-crystal solvate comprising 22′-di­thiodi­benzoic acid 2-chloro­benzoic acid and NN-di­methyl­formamide: crystal structure Hirshfeld surface analysis and computational study

摘要

The asymmetric unit of the three-component title compound, 2,2′-di­thiodi­benzoic acid–2-chloro­benzoic acid–N,N-di­methyl­formamide (1/1/1), C14H10O4S2·C7H5ClO2·C3H7NO, contains a mol­ecule each of 2,2′-di­thiodi­benzoic acid (DTBA), 2-chloro­benzoic acid (2CBA) and di­methyl­formamide (DMF). The DTBA mol­ecule is twisted [the C—S—S—C torsion angle is 88.37 (17)°] and each carb­oxy­lic group is slightly twisted from the benzene ring to which it is connected [CO2/C6 dihedral angles = 7.6 (3) and 12.5 (3)°]. A small twist is evident in the mol­ecule of 2CBA [CO2/C6 dihedral angle = 4.4 (4)°]. In the crystal, the three mol­ecules are connected by hydrogen bonds with the two carb­oxy­lic acid residues derived from DTBA and 2CBA forming a non-symmetric eight-membered {⋯HOCO}2 synthon, and the second carb­oxy­lic acid of DTBA linked to the DMF mol­ecule via a seven-membered {⋯HOCO⋯HCO} heterosynthon. The three-mol­ecule aggregates are connected into a supra­molecular chain along the a axis via DTBA-C—H⋯O(hydroxyl-2CBA), 2CBA-C—H⋯O(hydroxyl-DTBA) and DTBA-C—H⋯S(DTBA) inter­actions. Supra­molecular layers in the ab plane are formed as the chains are linked via DMF-C—H⋯S(DTBA) contacts, and these inter-digitate along the c-axis direction without specific points of contact between them. A Hirshfeld surface analysis points to additional but, weak contacts to stabilize the three-dimensional architecture: DTBA-C=O⋯H(phenyl-DTBA), 2CBA-Cl⋯H(phenyl-DTBA), as well as a π–π contact between the delocalized eight-membered {⋯HOC=O}2 carb­oxy­lic dimer and the phenyl ring of 2CBA. The latter was confirmed by electrostatic potential (ESP) mapping.