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4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one

In the title compound, C(16)H(15)BrN(2)O(4), the six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation with the disordered methyl­ene C atom as the flap. The pyran ring is almost orthogonal to the chloro­phenyl ring, making a dihedral angle of 87.11 (12)°. The amine-gr...

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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/PMC3685080/
https://www.ncbi.nlm.nih.gov/pubmed/23795099
http://dx.doi.org/10.1107/S1600536813012774
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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 In the title compound, C(16)H(15)BrN(2)O(4), the six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation with the disordered methyl­ene C atom as the flap. The pyran ring is almost orthogonal to the chloro­phenyl ring, making a dihedral angle of 87.11 (12)°. The amine-group N atom deviates significantly from the pyran ring [0.238 (3) Å]. 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, which generate C(8) chains running parallel to the b axis. The chains are linked by C—H⋯π inter­actions. The methyl­ene-group C atom of the chromene system that is disordered, along with its attached H atoms and the H atoms on the two adjacent C atoms, has an occupancy ratio of 0.791 (7):0.209 (7).
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spelling pubmed-36850802013-06-21 4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-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 In the title compound, C(16)H(15)BrN(2)O(4), the six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation with the disordered methyl­ene C atom as the flap. The pyran ring is almost orthogonal to the chloro­phenyl ring, making a dihedral angle of 87.11 (12)°. The amine-group N atom deviates significantly from the pyran ring [0.238 (3) Å]. 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, which generate C(8) chains running parallel to the b axis. The chains are linked by C—H⋯π inter­actions. The methyl­ene-group C atom of the chromene system that is disordered, along with its attached H atoms and the H atoms on the two adjacent C atoms, has an occupancy ratio of 0.791 (7):0.209 (7). International Union of Crystallography 2013-05-22 /pmc/articles/PMC3685080/ /pubmed/23795099 http://dx.doi.org/10.1107/S1600536813012774 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.
4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one
title 4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_full 4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_fullStr 4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_full_unstemmed 4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_short 4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one
title_sort 4-(4-bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4h-chromen-5-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685080/
https://www.ncbi.nlm.nih.gov/pubmed/23795099
http://dx.doi.org/10.1107/S1600536813012774
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