A 1:1:1 co-crystal solvate comprising 2,2'-di-thiodi-benzoic acid, 2-chloro-benzoic acid and N,N-di-methyl-formamide: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The asymmetric unit of the three-component title compound, 2,2'-di-thiodi-benzoic acid-2-chloro-benzoic acid-N,N-di-methyl-formamide (1/1/1), C14H10O4S2·C7H5ClO2·C3H7NO, contains a mol-ecule each of 2,2'-di-thiodi-benzoic acid (DTBA), 2-chloro-benzoic acid (2CBA) and di-methyl-formamide (DMF). The DTBA mol-ecule is twisted [the C-S-S-C torsion angle is 88.37?(17)°] and each carb-oxy-lic 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 mol-ecule of 2CBA [CO2/C6 dihedral angle = 4.4?(4)°]. In the crystal, the three mol-ecules are connected by hydrogen bonds with the two carb-oxy-lic acid residues derived from DTBA and 2CBA forming a non-symmetric eight-membered {?HOCO}2 synthon, and the second carb-oxy-lic acid of DTBA linked to the DMF mol-ecule via a seven-membered {?HOCO?HCO} heterosynthon. The three-mol-ecule aggregates are connected into a supra-molecular chain along the a axis via DTBA-C-H?O(hydroxyl-2CBA), 2CBA-C-H?O(hydroxyl-DTBA) and DTBA-C-H?S(DTBA) inter-actions. Supra-molecular 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 ?-? contact between the delocalized eight-membered {?HOC=O}2 carb-oxy-lic dimer and the phenyl ring of 2CBA. The latter was confirmed by electrostatic potential (ESP) mapping.

SUBMITTER: Tan SL 

PROVIDER: S-EPMC6509673 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature