Crystal structure and Hirshfeld surface analysis of 3,3′-(sulfanedi­yl)bis­(2-iodo-1-methyl-1H-indole)

Abstract

The title compound consists of two N-methyl-2-iodo­indole units linked by a thio­ether bridge in a gauche conformation. In the crystal, short I⋯C and I⋯π contacts dominate the packing and generate a herringbone motif.

The title compound, C₁₈H₁₄I₂N₂S, comprises two N-methyl-2-iodo­indole fragments linked at the 3-positions by a thio­ether bridge. The sulfur atom adopts a typical thio­ether geometry, and the C—S—C linkage is gauche on both sides, with C—S—C—C torsion angles of −64.1 (11) and −48.3 (10)°. The indole units are essentially planar and are strongly inclined to one another, with an inter­planar angle of 103.3 (3)°. The compound crystallizes in the ortho­rhom­bic space group Fdd2; the mol­ecule lacks classical hydrogen-bond donors, and no significant hydrogen bonding or π–π stacking is observed. The packing is dominated by van der Waals inter­actions together with short I⋯C and I⋯π contacts, giving a herringbone arrangement and forming chains along the b axis. Hirshfeld surface analysis indicates that H⋯H (33.1%), H⋯C/C⋯H (25.5%) and H⋯I/I⋯H (24.4%) contacts make the largest contributions to the crystal packing.