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(4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one

The title compound, C(16)H(15)N(3)O(6), is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The six-membered carbocyclic ring adopts an envelope conformation with the central CH(2) C atom as the flap. The amine N atom deviates from the mean plane of the pyran...

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Autores principales: Narayanan, P., Kamalraja, Jayabal, Perumal, Paramasivam T., Sethusankar, K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884480/
https://www.ncbi.nlm.nih.gov/pubmed/24427023
http://dx.doi.org/10.1107/S1600536813021181
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author Narayanan, P.
Kamalraja, Jayabal
Perumal, Paramasivam T.
Sethusankar, K.
author_facet Narayanan, P.
Kamalraja, Jayabal
Perumal, Paramasivam T.
Sethusankar, K.
author_sort Narayanan, P.
collection PubMed
description The title compound, C(16)H(15)N(3)O(6), is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The six-membered carbocyclic ring adopts an envelope conformation with the central CH(2) C atom as the flap. The amine N atom deviates from the mean plane of the pyran ring by 0.1365 (15) Å. The nitro­phenyl ring is almost orthogonal to the pyran ring and the mean plane of the six-membered carbocyclic ring, the dihedral angle between their mean planes being 88.30 (7) and 87.61 (8)°, respectively. The mol­ecular structure is stabilized by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming infinite bands lying parallel to (-110) and composed of alternate R (2) (2)(24) and R (2) (4)(12) graph-set ring motifs. The crystal structure is further stabilized by C—H⋯π inter­actions, forming a three-dimensional structure.
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spelling pubmed-38844802014-01-14 (4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one Narayanan, P. Kamalraja, Jayabal Perumal, Paramasivam T. Sethusankar, K. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(16)H(15)N(3)O(6), is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The six-membered carbocyclic ring adopts an envelope conformation with the central CH(2) C atom as the flap. The amine N atom deviates from the mean plane of the pyran ring by 0.1365 (15) Å. The nitro­phenyl ring is almost orthogonal to the pyran ring and the mean plane of the six-membered carbocyclic ring, the dihedral angle between their mean planes being 88.30 (7) and 87.61 (8)°, respectively. The mol­ecular structure is stabilized by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming infinite bands lying parallel to (-110) and composed of alternate R (2) (2)(24) and R (2) (4)(12) graph-set ring motifs. The crystal structure is further stabilized by C—H⋯π inter­actions, forming a three-dimensional structure. International Union of Crystallography 2013-08-03 /pmc/articles/PMC3884480/ /pubmed/24427023 http://dx.doi.org/10.1107/S1600536813021181 Text en © Narayanan 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
Narayanan, P.
Kamalraja, Jayabal
Perumal, Paramasivam T.
Sethusankar, K.
(4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one
title (4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_full (4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_fullStr (4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_full_unstemmed (4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_short (4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_sort (4s*)-2-methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4h-chromen-5-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884480/
https://www.ncbi.nlm.nih.gov/pubmed/24427023
http://dx.doi.org/10.1107/S1600536813021181
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