Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrile
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-substitute...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2020-02-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989020000365 |
| _version_ | 1798018502466994176 |
|---|---|
| author | Jean C. González Espiet Juan A. Cintrón Cruz Dalice M. Piñero Cruz |
| author_facet | Jean C. González Espiet Juan A. Cintrón Cruz Dalice M. Piñero Cruz |
| author_sort | Jean C. González Espiet |
| collection | DOAJ |
| description | 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%). |
| first_indexed | 2024-04-11T16:25:06Z |
| format | Article |
| id | doaj.art-fcc05f31da48445f8ecd0a9a3ab4263b |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T16:25:06Z |
| publishDate | 2020-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-fcc05f31da48445f8ecd0a9a3ab4263b2022-12-22T04:14:12ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-02-0176223123410.1107/S2056989020000365dx2019Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrileJean C. González Espiet0Juan A. Cintrón Cruz1Dalice M. Piñero Cruz2Department of Chemistry, University of Puerto Rico-Rio Piedras Campus, PO Box 23346, San Juan, 00931-3346, Puerto RicoDepartment of Chemistry, University of Puerto Rico-Rio Piedras Campus, PO Box 23346, San Juan, 00931-3346, Puerto RicoDepartment of Chemistry and the Molecular Sciences Research Center, University of Puerto Rico-Rio Piedras Campus, PO Box 23346, San Juan, 00931-3346, Puerto RicoThe 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%).http://scripts.iucr.org/cgi-bin/paper?S2056989020000365substituted arenespentafluorothiofunctionalized aromatic ringsorganometallic synthesiscrystal structure |
| spellingShingle | Jean C. González Espiet Juan A. Cintrón Cruz Dalice M. Piñero Cruz Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrile Acta Crystallographica Section E: Crystallographic Communications substituted arenes pentafluorothio functionalized aromatic rings organometallic synthesis crystal structure |
| title | Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrile |
| title_full | Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrile |
| title_fullStr | Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrile |
| title_full_unstemmed | Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrile |
| title_short | Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(pentafluoro-λ6-sulfanyl)benzonitrile |
| title_sort | structural characterization and hirshfeld surface analysis of 2 iodo 4 pentafluoro λ6 sulfanyl benzonitrile |
| topic | substituted arenes pentafluorothio functionalized aromatic rings organometallic synthesis crystal structure |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989020000365 |
| work_keys_str_mv | AT jeancgonzalezespiet structuralcharacterizationandhirshfeldsurfaceanalysisof2iodo4pentafluorol6sulfanylbenzonitrile AT juanacintroncruz structuralcharacterizationandhirshfeldsurfaceanalysisof2iodo4pentafluorol6sulfanylbenzonitrile AT dalicempinerocruz structuralcharacterizationandhirshfeldsurfaceanalysisof2iodo4pentafluorol6sulfanylbenzonitrile |