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Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses
A hydrogen sulfate salt, C(15)H(18)NSe(+)·HSO(4) (−)·H(2)O or [BnSeCH(2)CH(Ph)NH(3) (+)](HSO(4) (−)), of a chiral selenated amine (R)-2-(benzylselanyl)-1-phenylethanamine (BnSeCH(2)CH(Ph)NH(2)) has been synthesized and characterized by elemental analysis,(1)H and (13)C{(1)H} NMR, FT–IR analysis,...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587982/ https://www.ncbi.nlm.nih.gov/pubmed/34868636 http://dx.doi.org/10.1107/S2056989021010409 |
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author | Rajegowda, H. R. Suchetan, P. A. Butcher, R. J. Raghavendra Kumar, P. |
author_facet | Rajegowda, H. R. Suchetan, P. A. Butcher, R. J. Raghavendra Kumar, P. |
author_sort | Rajegowda, H. R. |
collection | PubMed |
description | A hydrogen sulfate salt, C(15)H(18)NSe(+)·HSO(4) (−)·H(2)O or [BnSeCH(2)CH(Ph)NH(3) (+)](HSO(4) (−)), of a chiral selenated amine (R)-2-(benzylselanyl)-1-phenylethanamine (BnSeCH(2)CH(Ph)NH(2)) has been synthesized and characterized by elemental analysis,(1)H and (13)C{(1)H} NMR, FT–IR analysis, and single-crystal X-ray diffraction studies. The title salt crystallizes in the monohydrate form in the non-centrosymmetric monoclinic P2(1) 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 –CH(2)—CH– fragment has a staggered conformation. In the crystal structure, two HSO(4) (−) anions and two water molecules form an R (4) (4)(12) tetrameric type of assembly comprised of alternating HSO(4) (−) 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 HSO(4) (−) 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 d (norm), 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 | Online Article Text |
id | pubmed-8587982 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-85879822021-12-02 Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses Rajegowda, H. R. Suchetan, P. A. Butcher, R. J. Raghavendra Kumar, P. Acta Crystallogr E Crystallogr Commun Jerry P. Jasinski tribute A hydrogen sulfate salt, C(15)H(18)NSe(+)·HSO(4) (−)·H(2)O or [BnSeCH(2)CH(Ph)NH(3) (+)](HSO(4) (−)), of a chiral selenated amine (R)-2-(benzylselanyl)-1-phenylethanamine (BnSeCH(2)CH(Ph)NH(2)) has been synthesized and characterized by elemental analysis,(1)H and (13)C{(1)H} NMR, FT–IR analysis, and single-crystal X-ray diffraction studies. The title salt crystallizes in the monohydrate form in the non-centrosymmetric monoclinic P2(1) 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 –CH(2)—CH– fragment has a staggered conformation. In the crystal structure, two HSO(4) (−) anions and two water molecules form an R (4) (4)(12) tetrameric type of assembly comprised of alternating HSO(4) (−) 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 HSO(4) (−) 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 d (norm), 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. International Union of Crystallography 2021-10-19 /pmc/articles/PMC8587982/ /pubmed/34868636 http://dx.doi.org/10.1107/S2056989021010409 Text en © Rajegowda et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Jerry P. Jasinski tribute Rajegowda, H. R. Suchetan, P. A. Butcher, R. J. Raghavendra Kumar, P. Synthesis and absolute structure of (R)-2-(benzylselanyl)-1-phenylethanaminium hydrogen sulfate monohydrate: crystal structure and Hirshfeld surface analyses |
title | 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_short | 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 |
topic | Jerry P. Jasinski tribute |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587982/ https://www.ncbi.nlm.nih.gov/pubmed/34868636 http://dx.doi.org/10.1107/S2056989021010409 |
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