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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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Autores principales: Rajegowda, H. R., Suchetan, P. A., Butcher, R. J., Raghavendra Kumar, P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
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.
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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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