A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study
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 mole...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019
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| Online Access: | http://eprints.sunway.edu.my/955/ http://eprints.sunway.edu.my/955/1/Tiekink%20A%201%202%20co%20crystal%20Acta%20Cryst%20%282019%29%2075%201.pdf |
| _version_ | 1848801937248485376 |
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| author | Tan, Sang Loon * Tiekink, Edward R. T. * |
| author_facet | Tan, Sang Loon * Tiekink, Edward R. T. * |
| author_sort | Tan, Sang Loon * |
| building | SU Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T21:15:23Z |
| format | Article |
| id | sunway-955 |
| institution | Sunway University |
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| language | English |
| last_indexed | 2025-11-14T21:15:23Z |
| publishDate | 2019 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
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| spelling | sunway-9552020-10-12T07:21:42Z http://eprints.sunway.edu.my/955/ A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study Tan, Sang Loon * Tiekink, Edward R. T. * QD Chemistry 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. International Union of Crystallography 2019-12-01 Article PeerReviewed text en cc_by_4 http://eprints.sunway.edu.my/955/1/Tiekink%20A%201%202%20co%20crystal%20Acta%20Cryst%20%282019%29%2075%201.pdf 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 http://doi.org/10.1107/S2056989018017097 doi:10.1107/S2056989018017097 |
| spellingShingle | QD Chemistry Tan, Sang Loon * Tiekink, Edward R. T. * A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title | A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_full | A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_fullStr | A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_full_unstemmed | A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_short | A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_sort | 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, hirshfeld surface analysis and computational study |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/955/ http://eprints.sunway.edu.my/955/ http://eprints.sunway.edu.my/955/ http://eprints.sunway.edu.my/955/1/Tiekink%20A%201%202%20co%20crystal%20Acta%20Cryst%20%282019%29%2075%201.pdf |