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

Author(s)

Zukerman-Schpector, Julio ^[1] ; Madureira, Lucas Sousa ^[1] ; Stefani, Helio A. ^[2] ; Gozhina, Olga ^[2] ; Tiekink, Edward R. T. ^[3]

Affiliation

^[1] Univ Fed Sao Carlos, Dept Quim, Lab Cristalog Estereodinam & Modelagem Mol, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, BR-05508900 Sao Paulo, SP - Brazil

^[3] Sunway Univ, Fac Sci & Technol, Res Ctr Crystalline Mat, Bandar Sunway 47500, Selangor Darul - Malaysia

• Document type: Journal article
• Source: ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS; v. 231, n. 6, p. 329-339, JUN 2016.
• Web of Science Citations: 0

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 center dot center dot center dot C linteractions in the putative transition state. The molecular packing in 1-3, while globally similar, are distinct, being based on combinations of identifiable C-H center dot center dot center dot pi(arene), C-H center dot center dot center dot S and C-Cl center dot center dot center dot pi(arene) interactions. The lack of isostructural relationships points to the significance of the identified intermolecular interactions to direct molecular packing. (AU)

• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants