Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis
The crystal structure analysis of three aryl-1,3-dithiane derivatives, with aryl=4-methylphenyl (1), 4-chlorophenyl (2) and 2,4-dichlorophenyl (3), shows the three molecules to have very similar conformations, with the aryl ring lying on an approximate mirror plane that bisects the dithiane ring whi...
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my.sunway.eprints.6552020-10-07T10:02:40Z http://eprints.sunway.edu.my/655/ Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis Zukerman-Schpector, Julio Sousa Madureira, Lucas Stefani, Hélio A. Gozhina, Olga Tiekink, Edward R. T. * QD Chemistry The crystal structure analysis of three aryl-1,3-dithiane derivatives, with aryl=4-methylphenyl (1), 4-chlorophenyl (2) and 2,4-dichlorophenyl (3), shows the three molecules to have very similar conformations, with the aryl ring lying on an approximate mirror plane that bisects the dithiane ring which adopts a chair conformation; the energy-minimised structures are consistent with the experimental structures. The greater barrier to rotation about the methine-C–C(ipso) bond in 3, cf. 1 and 2, is related to unfavourable intramolecular S···Cl interactions in the putative transition state. The molecular packing in 1–3, while globally similar, are distinct, being based on combinations of identifiable C–H···π(arene), C–H···S and C–Cl···π(arene) interactions. The lack of isostructural relationships points to the significance of the identified intermolecular interactions to direct molecular packing. De Gruyter 2016 Article PeerReviewed text en http://eprints.sunway.edu.my/655/1/Z.%20Kristallogr.%202016%20231%20329.pdf Zukerman-Schpector, Julio and Sousa Madureira, Lucas and Stefani, Hélio A. and Gozhina, Olga and Tiekink, Edward R. T. * (2016) Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis. Zeitschrift für Kristallographie - Crystalline Materials, 231 (6). pp. 329-339. ISSN 2194-4946 http://dx.doi.org/10.1515/zkri-2015-1911 doi:10.1515/zkri-2015-1911 |
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QD Chemistry Zukerman-Schpector, Julio Sousa Madureira, Lucas Stefani, Hélio A. Gozhina, Olga Tiekink, Edward R. T. * Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis |
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The crystal structure analysis of three aryl-1,3-dithiane derivatives, with aryl=4-methylphenyl (1), 4-chlorophenyl (2) and 2,4-dichlorophenyl (3), shows the three molecules to have very similar conformations, with the aryl ring lying on an approximate mirror plane that bisects the dithiane ring which adopts a chair conformation; the energy-minimised structures are consistent with the experimental structures. The greater barrier to rotation about the methine-C–C(ipso) bond in 3, cf. 1 and 2, is related to unfavourable intramolecular S···Cl interactions in the putative transition state. The molecular packing in 1–3, while globally similar, are distinct, being based on combinations of identifiable C–H···π(arene), C–H···S and C–Cl···π(arene) interactions. The lack of isostructural relationships points to the significance of the identified intermolecular interactions to direct molecular packing. |
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Article |
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Zukerman-Schpector, Julio Sousa Madureira, Lucas Stefani, Hélio A. Gozhina, Olga Tiekink, Edward R. T. * |
author_facet |
Zukerman-Schpector, Julio Sousa Madureira, Lucas Stefani, Hélio A. Gozhina, Olga Tiekink, Edward R. T. * |
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Zukerman-Schpector, Julio |
title |
Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis |
title_short |
Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis |
title_full |
Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis |
title_fullStr |
Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis |
title_full_unstemmed |
Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis |
title_sort |
structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and hirshfeld surface analysis |
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De Gruyter |
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2016 |
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http://eprints.sunway.edu.my/655/1/Z.%20Kristallogr.%202016%20231%20329.pdf http://eprints.sunway.edu.my/655/ http://dx.doi.org/10.1515/zkri-2015-1911 |
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