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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

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 molecu...

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Main Authors: Tan, Sang Loon *, Tiekink, Edward R. T. *
Format: Article
Language:English
Published: International Union of Crystallography 2019
Subjects:
QD Chemistry
Online Access:http://eprints.sunway.edu.my/1007/1/Tiekink%20%20A%201%201%201%20co%20crystal%20solvate%20Acta%20Cryst.%20%282019%29.%20E75%20475.pdf
http://eprints.sunway.edu.my/1007/
http://doi.org/10.1107/S205698901900375X
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spelling my.sunway.eprints.10072020-10-12T07:25:29Z http://eprints.sunway.edu.my/1007/ 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 * Tiekink, Edward R. T. * QD Chemistry 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. International Union of Crystallography 2019-03-19 Article PeerReviewed text en cc_by_4 http://eprints.sunway.edu.my/1007/1/Tiekink%20%20A%201%201%201%20co%20crystal%20solvate%20Acta%20Cryst.%20%282019%29.%20E75%20475.pdf 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) http://doi.org/10.1107/S205698901900375X doi:10.1107/S205698901900375X
institution Sunway University
building Sunway Campus Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Sunway University
content_source Sunway Institutional Repository
url_provider http://eprints.sunway.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Tan, Sang Loon *
Tiekink, Edward R. T. *
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
description 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.
format Article
author Tan, Sang Loon *
Tiekink, Edward R. T. *
author_facet Tan, Sang Loon *
Tiekink, Edward R. T. *
author_sort Tan, Sang Loon *
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publisher International Union of Crystallography
publishDate 2019
url http://eprints.sunway.edu.my/1007/1/Tiekink%20%20A%201%201%201%20co%20crystal%20solvate%20Acta%20Cryst.%20%282019%29.%20E75%20475.pdf
http://eprints.sunway.edu.my/1007/
http://doi.org/10.1107/S205698901900375X
_version_ 1683233344237600768
score 13.211869

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