Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses

A hydrogen sulfate salt, C15H18NSe+·HSO4−·H2O or [BnSeCH2CH(Ph)NH3+](HSO4−), of a chiral selenated amine (R)-2-(benzylselanyl)-1-phenylethanamine (BnSeCH2CH(Ph)NH2) has been synthesized and characterized by elemental analysis,1H and 13C{1H} NMR, FT–IR analysis, and single-crystal X-ray diffraction s...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	H. R. Rajegowda, P. A. Suchetan, R. J. Butcher, P. Raghavendra Kumar
Formato:	article
Lenguaje:	EN
Publicado:	International Union of Crystallography 2021
Materias:	crystal structure chiral absolute structure selenium sbis hirshfeld surface Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/65cfe9e28e2d4680a2b6d095d31dd529
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:65cfe9e28e2d4680a2b6d095d31dd529
record_format	dspace
spelling	oai:doaj.org-article:65cfe9e28e2d4680a2b6d095d31dd5292021-11-12T11:16:09ZSynthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses2056-989010.1107/S2056989021010409https://doaj.org/article/65cfe9e28e2d4680a2b6d095d31dd5292021-11-01T00:00:00Zhttp://scripts.iucr.org/cgi-bin/paper?S2056989021010409https://doaj.org/toc/2056-9890A hydrogen sulfate salt, C15H18NSe+·HSO4−·H2O or [BnSeCH2CH(Ph)NH3+](HSO4−), of a chiral selenated amine (R)-2-(benzylselanyl)-1-phenylethanamine (BnSeCH2CH(Ph)NH2) has been synthesized and characterized by elemental analysis,1H and 13C{1H} NMR, FT–IR analysis, and single-crystal X-ray diffraction studies. The title salt crystallizes in the monohydrate form in the non-centrosymmetric monoclinic P21 space group. The cation is somewhat W shaped with the dihedral angle between the two aromatic rings being 60.9 (4)°. The carbon atom attached to the amine nitrogen atom is chiral and in the R configuration, and, the –C—C– bond of the –CH2—CH– fragment has a staggered conformation. In the crystal structure, two HSO4− anions and two water molecules form an R44(12) tetrameric type of assembly comprised of alternating HSO4− anions and water molecules via discrete D(2) O—H...O hydrogen bonds. This tetrameric assembly aggregates along the b-axis direction as an infinite one-dimensional tape. Adjacent tapes are interconnected via discrete D(2) N—H...O hydrogen bonds between the three amino hydrogen atoms of the cation sandwiched between the two tapes and the three HSO4− anions of the nearest asymmetric units, resulting in a complex two-dimensional sheet along the ab plane. The pendant arrangement of the cations is stabilized by C—H...π interactions between adjacent cations running as chains down the [010] axis. Secondary Se...O [3.1474 (4) Å] interactions are also observed in the crystal structure. A Hirshfeld surface analysis, including dnorm, shape-index and fingerprint plots of the cation, anion and solvent molecule, was carried out to confirm the presence of various interactions in the crystal structure.H. R. RajegowdaP. A. SuchetanR. J. ButcherP. Raghavendra KumarInternational Union of Crystallographyarticlecrystal structurechiralabsolute structureseleniumsbishirshfeld surfaceChemistryQD1-999ENActa Crystallographica Section E: Crystallographic Communications, Vol 77, Iss 11, Pp 1062-1066 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	crystal structure chiral absolute structure selenium sbis hirshfeld surface Chemistry QD1-999
spellingShingle	crystal structure chiral absolute structure selenium sbis hirshfeld surface Chemistry QD1-999 H. R. Rajegowda P. A. Suchetan R. J. Butcher P. Raghavendra Kumar Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses
description	A hydrogen sulfate salt, C15H18NSe+·HSO4−·H2O or [BnSeCH2CH(Ph)NH3+](HSO4−), of a chiral selenated amine (R)-2-(benzylselanyl)-1-phenylethanamine (BnSeCH2CH(Ph)NH2) has been synthesized and characterized by elemental analysis,1H and 13C{1H} NMR, FT–IR analysis, and single-crystal X-ray diffraction studies. The title salt crystallizes in the monohydrate form in the non-centrosymmetric monoclinic P21 space group. The cation is somewhat W shaped with the dihedral angle between the two aromatic rings being 60.9 (4)°. The carbon atom attached to the amine nitrogen atom is chiral and in the R configuration, and, the –C—C– bond of the –CH2—CH– fragment has a staggered conformation. In the crystal structure, two HSO4− anions and two water molecules form an R44(12) tetrameric type of assembly comprised of alternating HSO4− anions and water molecules via discrete D(2) O—H...O hydrogen bonds. This tetrameric assembly aggregates along the b-axis direction as an infinite one-dimensional tape. Adjacent tapes are interconnected via discrete D(2) N—H...O hydrogen bonds between the three amino hydrogen atoms of the cation sandwiched between the two tapes and the three HSO4− anions of the nearest asymmetric units, resulting in a complex two-dimensional sheet along the ab plane. The pendant arrangement of the cations is stabilized by C—H...π interactions between adjacent cations running as chains down the [010] axis. Secondary Se...O [3.1474 (4) Å] interactions are also observed in the crystal structure. A Hirshfeld surface analysis, including dnorm, shape-index and fingerprint plots of the cation, anion and solvent molecule, was carried out to confirm the presence of various interactions in the crystal structure.
format	article
author	H. R. Rajegowda P. A. Suchetan R. J. Butcher P. Raghavendra Kumar
author_facet	H. R. Rajegowda P. A. Suchetan R. J. Butcher P. Raghavendra Kumar
author_sort	H. R. Rajegowda
title	Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses
title_short	Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses
title_full	Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses
title_fullStr	Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses
title_full_unstemmed	Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses
title_sort	synthesis and absolute structure of (r)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and hirshfeld surface analyses
publisher	International Union of Crystallography
publishDate	2021
url	https://doaj.org/article/65cfe9e28e2d4680a2b6d095d31dd529
work_keys_str_mv	AT hrrajegowda synthesisandabsolutestructureofr2benzylselanyl1phenylethanaminiumhydrogensulfatemonohydratecrystalstructureandhirshfeldsurfaceanalyses AT pasuchetan synthesisandabsolutestructureofr2benzylselanyl1phenylethanaminiumhydrogensulfatemonohydratecrystalstructureandhirshfeldsurfaceanalyses AT rjbutcher synthesisandabsolutestructureofr2benzylselanyl1phenylethanaminiumhydrogensulfatemonohydratecrystalstructureandhirshfeldsurfaceanalyses AT praghavendrakumar synthesisandabsolutestructureofr2benzylselanyl1phenylethanaminiumhydrogensulfatemonohydratecrystalstructureandhirshfeldsurfaceanalyses
_version_	1718430622291066880

Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses

Ejemplares similares