A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

Tan, Sang Loon * and Tiekink, Edward R. T. * (2019) A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 75 (1). pp. 1-7. ISSN 2056-9890

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Official URL: http://doi.org/10.1107/S2056989018017097

Abstract

The asymmetric unit of the title 1:2 co-crystal, C14H10O4S2-2C7H6O2, comprises half a molecule of dithiodibenzoic acid [systematic name: 2-[(2-carboxyphenyl)disulfanyl]benzoic acid, DTBA], as the molecule is located about a twofold axis of symmetry, and a molecule of benzoic acid (BA). The DTBA molecule is twisted about the disulfide bond [the C—S—S—C torsion angle is -83.19 (8)⁰] resulting in a near perpendicular relationship between the benzene rings [dihedral angle = 71.19 (4)⁰]. The carboxylic acid group is almost co-planar with the benzene ring to which it is bonded [dihedral angle = 4.82 (12)⁰]. A similar near co-planar relationship pertains for the BA molecule [dihedral angle = 3.65 (15)⁰]. Three-molecule aggregates are formed in the crystal whereby two BA molecules are connected to a DTBA molecule via hydroxyO—H...O(hydroxy) hydrogen bonds and eight-membered {...HOC=O}2 synthons. These are connected into a supramolecular layer in the ab plane through C—H...O interactions. The interactions between layers to consolidate the three-dimensional architecture are π–π stacking interactions between DTBA and BA rings [inter-centroid separation = 3.8093 (10) A ˚ ] and parallel DTBA-hydroxy-O...π(BA) contacts [O...ring centroid separation = 3.9049 (14) A ˚ ]. The importance of the specified interactions as well as other weaker contacts, e.g. π–π and C—H...S, are indicated in the analysis of the calculated Hirshfeld surface and interaction energies.

Item Type: Article
Uncontrolled Keywords: crystal structure; dithiodibenzoic acid; benzoic acid; hydrogen bonding; 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
Related URLs:
Date Deposited: 09 Dec 2018 06:02
Last Modified: 22 Apr 2019 05:15
URI: http://eprints.sunway.edu.my/id/eprint/955

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