Cargando…

N (2)-(4-Meth­oxy­salicyl­idene)arginine hemihydrate

The title compound, C(14)H(20)N(4)O(4)·0.5H(2)O [systematic name: (2S)-5-{[amino­(iminium­yl)meth­yl]amino}-2-{[(1Z)-4-meth­oxy-2-oxido­benzyl­idene]aza­nium­yl}penta­noate hemihydrate], has been synthesized by the reaction of l-arginine and 4-meth­oxy­salicyl­aldehyde and crystallizes with two inde...

Descripción completa

Detalles Bibliográficos
Autores principales: Sethuram, M., Bhargavi, G., Dhandapani, M., Amirthaganesan, G., NizamMohideen, M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793792/
https://www.ncbi.nlm.nih.gov/pubmed/24109379
http://dx.doi.org/10.1107/S1600536813019727
_version_ 1782287118578483200
author Sethuram, M.
Bhargavi, G.
Dhandapani, M.
Amirthaganesan, G.
NizamMohideen, M.
author_facet Sethuram, M.
Bhargavi, G.
Dhandapani, M.
Amirthaganesan, G.
NizamMohideen, M.
author_sort Sethuram, M.
collection PubMed
description The title compound, C(14)H(20)N(4)O(4)·0.5H(2)O [systematic name: (2S)-5-{[amino­(iminium­yl)meth­yl]amino}-2-{[(1Z)-4-meth­oxy-2-oxido­benzyl­idene]aza­nium­yl}penta­noate hemihydrate], has been synthesized by the reaction of l-arginine and 4-meth­oxy­salicyl­aldehyde and crystallizes with two independent substituted l-arginine mol­ecules and one water mol­ecule of solvation in the asymmetric unit. Each mol­ecule exists as a zwitterion and adopts a Z configuration about the central C=N. The mol­ecular conformation is stabilized by strong intra­molecular N—H⋯O hydrogen bonds that generate S(6) and S(10) ring motifs. Inter­molecular N—H⋯O and O—H⋯O hydrogen bonds involving also the water mol­ecule and weak inter­molecular C—H⋯O(water) inter­actions link the mol­ecules into an infinite one-dimensional ribbon structure extending along the b axis. The known (2S) absolute configuration for l-arginine was invoked. Weak intermolecular C—H⋯π interactions are also present.
format Online
Article
Text
id pubmed-3793792
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-37937922013-10-09 N (2)-(4-Meth­oxy­salicyl­idene)arginine hemihydrate Sethuram, M. Bhargavi, G. Dhandapani, M. Amirthaganesan, G. NizamMohideen, M. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(14)H(20)N(4)O(4)·0.5H(2)O [systematic name: (2S)-5-{[amino­(iminium­yl)meth­yl]amino}-2-{[(1Z)-4-meth­oxy-2-oxido­benzyl­idene]aza­nium­yl}penta­noate hemihydrate], has been synthesized by the reaction of l-arginine and 4-meth­oxy­salicyl­aldehyde and crystallizes with two independent substituted l-arginine mol­ecules and one water mol­ecule of solvation in the asymmetric unit. Each mol­ecule exists as a zwitterion and adopts a Z configuration about the central C=N. The mol­ecular conformation is stabilized by strong intra­molecular N—H⋯O hydrogen bonds that generate S(6) and S(10) ring motifs. Inter­molecular N—H⋯O and O—H⋯O hydrogen bonds involving also the water mol­ecule and weak inter­molecular C—H⋯O(water) inter­actions link the mol­ecules into an infinite one-dimensional ribbon structure extending along the b axis. The known (2S) absolute configuration for l-arginine was invoked. Weak intermolecular C—H⋯π interactions are also present. International Union of Crystallography 2013-07-24 /pmc/articles/PMC3793792/ /pubmed/24109379 http://dx.doi.org/10.1107/S1600536813019727 Text en © Sethuram et al. 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Sethuram, M.
Bhargavi, G.
Dhandapani, M.
Amirthaganesan, G.
NizamMohideen, M.
N (2)-(4-Meth­oxy­salicyl­idene)arginine hemihydrate
title N (2)-(4-Meth­oxy­salicyl­idene)arginine hemihydrate
title_full N (2)-(4-Meth­oxy­salicyl­idene)arginine hemihydrate
title_fullStr N (2)-(4-Meth­oxy­salicyl­idene)arginine hemihydrate
title_full_unstemmed N (2)-(4-Meth­oxy­salicyl­idene)arginine hemihydrate
title_short N (2)-(4-Meth­oxy­salicyl­idene)arginine hemihydrate
title_sort n (2)-(4-meth­oxy­salicyl­idene)arginine hemihydrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793792/
https://www.ncbi.nlm.nih.gov/pubmed/24109379
http://dx.doi.org/10.1107/S1600536813019727
work_keys_str_mv AT sethuramm n24methoxysalicylideneargininehemihydrate
AT bhargavig n24methoxysalicylideneargininehemihydrate
AT dhandapanim n24methoxysalicylideneargininehemihydrate
AT amirthaganesang n24methoxysalicylideneargininehemihydrate
AT nizammohideenm n24methoxysalicylideneargininehemihydrate