Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(penta-fluoro-λ
| Autor: | Jean C, González Espiet, Juan A, Cintrón Cruz, Dalice M, Piñero Cruz |
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| Rok vydání: | 2019 |
| Předmět: | |
| Zdroj: | Acta Crystallographica Section E: Crystallographic Communications |
| ISSN: | 2056-9890 |
| Popis: | A novel trisubstituted arene compound bearing a pentafluorosulfanyl group (SF5) has been synthesized through a regioselective ortho lithiation, improved by the addition of a bidentate amine, followed by trapping with electrophilic I2. Incorporating the iodo group in 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrile strengthens the intermolecular interaction network with the cyano and pentafluoro substituents. The title compound, C7H3F5INS, a pentafluorosulfanyl (SF5) containing arene, was synthesized from 4-(pentafluorosulfanyl)benzonitrile and lithium tetramethylpiperidide following a variation to the standard approach, which features simple and mild conditions that allow direct access to tri-substituted SF5 intermediates that have not been demonstrated using previous methods. The molecule 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 pentafluorosulfanyl substituent in the plane of the molecule. The equatorial F atoms have symmetry-related counterparts generated by the mirror plane. The pentafluorosulfanyl group exhibits a staggered fashion relative to the ring and the two hydrogen atoms ortho to the substituent. S—F bond lengths of the pentafluorosulfanyl group are unequal: the equatorial bond facing the iodo moiety has a longer distance [1.572 (3) Å] and wider angle compared to that facing the side of the molecules with two hydrogen atoms [1.561 (4) Å]. As expected, the axial S—F bond is the longest [1.582 (5) Å]. In the crystal, in-plane C—H⋯F and N⋯I interactions as well as out-of-plane F⋯C interactions are observed. According to the Hirshfeld analysis, the principal intermolecular 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%). |
| Databáze: | OpenAIRE |
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