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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, 2,2′-di­thiodi­benzoic acid–2-chloro­benzoic acid–N,N-di­methyl­formamide (1/1/1), C(14)H(10)O(4)S(2)·C(7)H(5)ClO(2)·C(3)H(7)NO, contains a mol­ecule each of 2,2′-di­thiodi­benzoic acid (DTBA), 2-chloro­benzoic acid (2CBA) and di­methyl­form...

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Autores principales: Tan, Sang Loon, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6509673/
https://www.ncbi.nlm.nih.gov/pubmed/31161060
http://dx.doi.org/10.1107/S205698901900375X
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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
collection PubMed
description The asymmetric unit of the three-component title compound, 2,2′-di­thiodi­benzoic acid–2-chloro­benzoic acid–N,N-di­methyl­formamide (1/1/1), C(14)H(10)O(4)S(2)·C(7)H(5)ClO(2)·C(3)H(7)NO, contains a mol­ecule each of 2,2′-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 [CO(2)/C(6) dihedral angles = 7.6 (3) and 12.5 (3)°]. A small twist is evident in the mol­ecule of 2CBA [CO(2)/C(6) 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 non-symmetric eight-membered {⋯HOCO}(2) synthon, and the second carb­oxy­lic acid of DTBA linked to the DMF mol­ecule via a seven-membered {⋯HOCO⋯HCO} heterosynthon. The three-mol­ecule aggregates are connected into a supra­molecular chain along the a axis via DTBA-C—H⋯O(hydroxyl-2CBA), 2CBA-C—H⋯O(hydroxyl-DTBA) and DTBA-C—H⋯S(DTBA) inter­actions. Supra­molecular 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 π–π 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.
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spelling pubmed-65096732019-06-03 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. Acta Crystallogr E Crystallogr Commun Research Communications The asymmetric unit of the three-component title compound, 2,2′-di­thiodi­benzoic acid–2-chloro­benzoic acid–N,N-di­methyl­formamide (1/1/1), C(14)H(10)O(4)S(2)·C(7)H(5)ClO(2)·C(3)H(7)NO, contains a mol­ecule each of 2,2′-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 [CO(2)/C(6) dihedral angles = 7.6 (3) and 12.5 (3)°]. A small twist is evident in the mol­ecule of 2CBA [CO(2)/C(6) 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 non-symmetric eight-membered {⋯HOCO}(2) synthon, and the second carb­oxy­lic acid of DTBA linked to the DMF mol­ecule via a seven-membered {⋯HOCO⋯HCO} heterosynthon. The three-mol­ecule aggregates are connected into a supra­molecular chain along the a axis via DTBA-C—H⋯O(hydroxyl-2CBA), 2CBA-C—H⋯O(hydroxyl-DTBA) and DTBA-C—H⋯S(DTBA) inter­actions. Supra­molecular 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 π–π 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 2019-03-26 /pmc/articles/PMC6509673/ /pubmed/31161060 http://dx.doi.org/10.1107/S205698901900375X Text en © Tan and Tiekink 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
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
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_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_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_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
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6509673/
https://www.ncbi.nlm.nih.gov/pubmed/31161060
http://dx.doi.org/10.1107/S205698901900375X
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