Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis

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

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Official URL: http://dx.doi.org/10.1515/zkri-2015-1911

Abstract

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.

Item Type: Article
Additional Information: First and 2nd authors are with Universidade Federal de São Carlos, Laboratório de Cristalografia; 3rd author is with Universidade de São Paulo, Departamento de Farmácia, Faculdade de Ciências Farmacêuticas; 4th author is with Sunway University, Centre for Crystalline Materials, Faculty of Science and Technology
Uncontrolled Keywords: aryl-1,3-thianes; conformation; crystal structure analysis; DFT; X-ray diffraction
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Science and Technology > Research Centre for Crystalline Materials
Depositing User: Ms. Molly Chuah
Date Deposited: 31 Oct 2017 09:23
Last Modified: 14 Feb 2018 02:33
URI: http://eprints.sunway.edu.my/id/eprint/655

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