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

Preview

Text Z. Kristallogr. 2016 231 329.pdf - Accepted Version Download (949kB) | Preview

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.

Actions (login required)

View Item