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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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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. |
format | Online Article Text |
id | pubmed-3884480 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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