Crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one

In the title compound, C(17)H(13)NO(5), the coumarin ring system is essentially planar (r.m.s. deviation = 0.008 Å). The nitro­phenyl ring makes a dihedral angle of 25.27 (9)° with the coumarin ring plane. The nitro group is almost coplanar with the phenyl ring to which it is attached, making a dihe...

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Autores principales: Walki, Shashikanth, Naveen, S., Kenchanna, S., Mahadevan, K. M., Kumara, M. N., Lokanath, N. K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Data Reports
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645040/
https://www.ncbi.nlm.nih.gov/pubmed/26594565
http://dx.doi.org/10.1107/S2056989015019325
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author Walki, Shashikanth
Naveen, S.
Kenchanna, S.
Mahadevan, K. M.
Kumara, M. N.
Lokanath, N. K.
author_facet Walki, Shashikanth
Naveen, S.
Kenchanna, S.
Mahadevan, K. M.
Kumara, M. N.
Lokanath, N. K.
author_sort Walki, Shashikanth
collection PubMed
description In the title compound, C(17)H(13)NO(5), the coumarin ring system is essentially planar (r.m.s. deviation = 0.008 Å). The nitro­phenyl ring makes a dihedral angle of 25.27 (9)° with the coumarin ring plane. The nitro group is almost coplanar with the phenyl ring to which it is attached, making a dihedral angle of 4.3 (3)°. The eth­oxy group is inclined to the coumarin ring plane by 4.1 (2)°. Electron delocalization was found at the short bridging C—C bond with a bond length of 1.354 (2) Å. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming sheets in the bc plane. The sheets are linked via π–π stacking [centroid–centroid distances = 3.5688 (13) and 3.7514 (13) Å], forming a three-dimensional structure.
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spelling pubmed-46450402015-11-20 Crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one Walki, Shashikanth Naveen, S. Kenchanna, S. Mahadevan, K. M. Kumara, M. N. Lokanath, N. K. Acta Crystallogr E Crystallogr Commun Data Reports In the title compound, C(17)H(13)NO(5), the coumarin ring system is essentially planar (r.m.s. deviation = 0.008 Å). The nitro­phenyl ring makes a dihedral angle of 25.27 (9)° with the coumarin ring plane. The nitro group is almost coplanar with the phenyl ring to which it is attached, making a dihedral angle of 4.3 (3)°. The eth­oxy group is inclined to the coumarin ring plane by 4.1 (2)°. Electron delocalization was found at the short bridging C—C bond with a bond length of 1.354 (2) Å. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming sheets in the bc plane. The sheets are linked via π–π stacking [centroid–centroid distances = 3.5688 (13) and 3.7514 (13) Å], forming a three-dimensional structure. International Union of Crystallography 2015-10-17 /pmc/articles/PMC4645040/ /pubmed/26594565 http://dx.doi.org/10.1107/S2056989015019325 Text en © Walki et al. 2015 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 Data Reports
Walki, Shashikanth
Naveen, S.
Kenchanna, S.
Mahadevan, K. M.
Kumara, M. N.
Lokanath, N. K.
Crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one
title Crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one
title_full Crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one
title_fullStr Crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one
title_full_unstemmed Crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one
title_short Crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2H-chromen-2-one
title_sort crystal structure of 8-eth­oxy-3-(4-nitro­phen­yl)-2h-chromen-2-one
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645040/
https://www.ncbi.nlm.nih.gov/pubmed/26594565
http://dx.doi.org/10.1107/S2056989015019325
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