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Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(penta-fluoro-λ6-sulfan-yl)benzo-nitrile.

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The title compound, C7H3F5INS, a penta-fluoro-sulfanyl (SF5) containing arene, was synthesized from 4-(penta-fluoro-sulfan-yl)benzo-nitrile and lithium tetra-methyl-piperidide following a variation to the standard approach, which features simple and mild conditions that… Click to show full abstract

The title compound, C7H3F5INS, a penta-fluoro-sulfanyl (SF5) containing arene, was synthesized from 4-(penta-fluoro-sulfan-yl)benzo-nitrile and lithium tetra-methyl-piperidide following a variation to the standard approach, which features simple and mild conditions that allow direct access to tri-substituted SF5 inter-mediates that have not been demonstrated using previous methods. The mol-ecule displays a planar geometry with the benzene ring in the same plane as its three substituents. It lies on a mirror plane perpendicular to [010] with the iodo, cyano, and the sulfur and axial fluorine atoms of the penta-fluoro-sulfanyl substituent in the plane of the mol-ecule. The equatorial F atoms have symmetry-related counterparts generated by the mirror plane. The penta-fluoro-sulfanyl group exhibits a staggered fashion relative to the ring and the two hydrogen atoms ortho to the substituent. S-F bond lengths of the penta-fluoro-sulfanyl group are unequal: the equatorial bond facing the iodo moiety has a longer distance [1.572 (3) A] and wider angle compared to that facing the side of the mol-ecules with two hydrogen atoms [1.561 (4) A]. As expected, the axial S-F bond is the longest [1.582 (5) A]. In the crystal, in-plane C-H⋯F and N⋯I inter-actions as well as out-of-plane F⋯C inter-actions are observed. According to the Hirshfeld analysis, the principal inter-molecular contacts for the title compound are F⋯H (29.4%), F⋯I (15.8%), F⋯N (11.4%), F⋯F (6.0%), N⋯I (5.6%) and F⋯C (4.5%).

Keywords: plane; fluoro sulfanyl; penta fluoro; fluoro; fluoro sulfan

Journal Title: Acta Crystallographica Section E: Crystallographic Communications
Year Published: 2020

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