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

Tan, Sang Loon * and Tiekink, Edward R. T. * (2019) A 1:1:1 co-crystal solvate comprising 2,2′-dithiodibenzoic acid, 2-chlorobenzoic acid and N,N-dimethylformamide: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 75 (4). pp. 475-481. ISSN 2056-9890 (In Press)

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Tiekink A 1 1 1 co crystal solvate Acta Cryst. (2019). E75 475.pdf - Accepted Version
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Official URL: http://doi.org/10.1107/S205698901900375X

Abstract

The asymmetric unit of the three-component title compound, 2,20 -dithiodibenzoic acid–2-chlorobenzoic acid–N,N-dimethylformamide (1/1/1), C14H10O4S2C7H5ClO2C3H7NO, contains a molecule each of 2,20 -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 nonsymmetric eight-membered {HOCO}2 synthon, and the second carboxylic acid of DTBA linked to the DMF molecule via a seven-membered {HOCOHCO} heterosynthon. The three-molecule aggregates are connected into a supramolecular chain along the a axis via DTBA-C—HO(hydroxyl-2CBA), 2CBA-C—HO(hydroxyl-DTBA) and DTBA-C—HS(DTBA) interactions. Supramolecular layers in the ab plane are formed as the chains are linked via DMF-C—HS(DTBA) contacts, and these interdigitate 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 OH(phenyl-DTBA), 2CBA-ClH(phenyl-DTBA), as well as a – 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.

Item Type: Article
Uncontrolled Keywords: crystal structure; dithiodibenzoic acid; chlorobenzoic acid; hydrogen bonding; Hirshfeld surface analysis; computational chemistry.
Subjects: Q Science > QD Chemistry
Divisions: Sunway University > School of Science and Technology > Research Centre for Crystalline Materials
Depositing User: Dr Janaki Sinnasamy
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Date Deposited: 29 Mar 2019 03:08
Last Modified: 22 Apr 2019 05:15
URI: http://eprints.sunway.edu.my/id/eprint/1007

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