2,6-Bis(4-meth-oxy-phen-yl)-1,4-dithiine.

Sha-Sha Zhao,Qiong Su,Zhi-Hong Peng,De-Lie An

doi:10.1107/s1600536814000397

Sha-Sha Zhao, Qiong Su + Show 2 more

Open Access

https://doi.org/10.1107/s1600536814000397

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Abstract

The title molecule, C18H16O2S2, reveals crystallographic twofold rotation symmetry (with both S atoms lying on the axis) and one half-molecule defines an asymmetric unit. The dithiine ring is in a boat conformation. The aromatic ring and the C=C bond are nearly coplanar, with small torsion angles of −171.26 (19) and 8.5 (3)°. The two S—C bond lengths [1.7391 (19) and 1.7795 (18) Å] are shorter than single C—S bonds and longer than analogous C=S double bonds, which indicates a certain degree of conjugation between the lone pair on the S atom and π electrons of the C=C bond. The crystal packing only features van der Waals interactions.

Highlights

The title molecule, C18H16O2S2, reveals crystallographic twofold rotation symmetry and one half-molecule defines an asymmetric unit
The dithiine ring is in a boat conformation
Bonds and longer than analogous C S double bonds, which indicates a certain degree of conjugation between the lone pair on the S atom and electrons of the C C bond

Summary

Data collection

R factor = 0.038; wR factor = 0.102; data-to-parameter ratio = 14.8. The title molecule, C18H16O2S2, reveals crystallographic twofold rotation symmetry (with both S atoms lying on the axis) and one half-molecule defines an asymmetric unit. The dithiine ring is in a boat conformation. The aromatic ring and the C C bond are nearly coplanar, with small torsion angles of 171.26 (19) and 8.5 (3). The two S—C bond lengths [1.7391 (19) and 1.7795 (18) Å] are shorter than single C—S bonds and longer than analogous C S double bonds, which indicates a certain degree of conjugation between the lone pair on the S atom and electrons of the C C bond. The crystal packing only features van der Waals interactions. Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL

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