González Espiet Jean C, Cintrón Cruz Juan A, Piñero Cruz Dalice M
Department of Chemistry, University of Puerto Rico-Rio Piedras Campus, PO Box 23346, San Juan, 00931-3346, Puerto Rico.
Department of Chemistry and the Molecular Sciences Research Center, University of Puerto Rico-Rio Piedras Campus, PO Box 23346, San Juan, 00931-3346, Puerto Rico.
Acta Crystallogr E Crystallogr Commun. 2020 Jan 17;76(Pt 2):231-234. doi: 10.1107/S2056989020000365. eCollection 2020 Feb 1.
The title compound, CHFINS, a penta-fluoro-sulfanyl (SF) 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 SF 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 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) Å] and wider angle compared to that facing the side of the mol-ecules 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 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%).
标题化合物CHFINS是一种含五氟硫基（SF）的芳烃，它由4-（五氟硫基）苯甲腈和四甲基哌啶锂按照对标准方法的一种改进合成而成，该方法具有简单温和的条件，能够直接得到三取代的SF中间体，而这是以前的方法所未能实现的。分子呈现平面几何构型，苯环与其三个取代基处于同一平面。它位于垂直于[010]的镜面平面上，碘、氰基以及五氟硫基取代基的硫和轴向氟原子在分子平面内。赤道面上的氟原子具有由镜面平面产生的对称相关对应原子。五氟硫基相对于环和取代基上的两个氢原子呈现出交错的构象。五氟硫基的S-F键长不相等：与碘部分相对的赤道面键距离更长[1.572 (3) Å]，角度也比与有两个氢原子的分子一侧相对的键更宽[1.561 (4) Å]。正如预期的那样，轴向S-F键最长[1.582 (5) Å]。在晶体中，观察到面内C-H⋯F和N⋯I相互作用以及面外F⋯C相互作用。根据Hirshfeld分析，该标题化合物的主要分子间接触为F⋯H（29.4%）、F⋯I（15.8%）、F⋯N（11.4%）、F⋯F（6.0%）、N⋯I（5.6%）和F⋯C（4.5%）。
