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The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide
The title compounds, 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide, C(17)H(19)N(3)O(5), (I), and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide, C(20)H(19)NO(6), (II), are new coumarin derivatives. In compound (I), the six-membered piperazine adopts a ch...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6509693/ https://www.ncbi.nlm.nih.gov/pubmed/31161061 http://dx.doi.org/10.1107/S2056989019003736 |
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author | Syed Abuthahir, S. NizamMohideen, M. Viswanathan, V. Govindhan, M. Subramanian, K. |
author_facet | Syed Abuthahir, S. NizamMohideen, M. Viswanathan, V. Govindhan, M. Subramanian, K. |
author_sort | Syed Abuthahir, S. |
collection | PubMed |
description | The title compounds, 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide, C(17)H(19)N(3)O(5), (I), and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide, C(20)H(19)NO(6), (II), are new coumarin derivatives. In compound (I), the six-membered piperazine adopts a chair conformation. The dihedral angles between the mean planes of the chromene ring and amide plane is 82.65 (7)° in (I) and 26.2 (4)° in (II). The dihedral angles between the mean planes of the chromene ring and the four planar C atoms of the piperazine ring in (I) and the benzene ring in (II) are 87.66 (6) and 65.0 (4)°, respectively. There are short intramolecular contacts in both molecules forming S(5) ring motifs, viz. N—H⋯N and C—H⋯O in (I), and N—H⋯O and C—H⋯N in (II). In the crystals of both compounds, molecules are linked by N—H⋯O hydrogen bonds, forming chains along [1[Image: see text]0] in (I) and [010] in (II). The chains are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ab plane in the crystals of both compounds. In the crystal of (I), there are also C—H⋯π and offset π–π interactions [intercentroid distance = 3.691 (1) Å] present within the layers. In the crystal of (II), there are only weak offset π–π interactions [intercentroid distance = 3.981 (6) Å] present within the layers. The intermolecular contacts in the crystals of both compounds have been analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots. |
format | Online Article Text |
id | pubmed-6509693 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-65096932019-06-03 The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide Syed Abuthahir, S. NizamMohideen, M. Viswanathan, V. Govindhan, M. Subramanian, K. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide, C(17)H(19)N(3)O(5), (I), and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide, C(20)H(19)NO(6), (II), are new coumarin derivatives. In compound (I), the six-membered piperazine adopts a chair conformation. The dihedral angles between the mean planes of the chromene ring and amide plane is 82.65 (7)° in (I) and 26.2 (4)° in (II). The dihedral angles between the mean planes of the chromene ring and the four planar C atoms of the piperazine ring in (I) and the benzene ring in (II) are 87.66 (6) and 65.0 (4)°, respectively. There are short intramolecular contacts in both molecules forming S(5) ring motifs, viz. N—H⋯N and C—H⋯O in (I), and N—H⋯O and C—H⋯N in (II). In the crystals of both compounds, molecules are linked by N—H⋯O hydrogen bonds, forming chains along [1[Image: see text]0] in (I) and [010] in (II). The chains are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ab plane in the crystals of both compounds. In the crystal of (I), there are also C—H⋯π and offset π–π interactions [intercentroid distance = 3.691 (1) Å] present within the layers. In the crystal of (II), there are only weak offset π–π interactions [intercentroid distance = 3.981 (6) Å] present within the layers. The intermolecular contacts in the crystals of both compounds have been analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots. International Union of Crystallography 2019-03-26 /pmc/articles/PMC6509693/ /pubmed/31161061 http://dx.doi.org/10.1107/S2056989019003736 Text en © Syed Abuthahir et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Syed Abuthahir, S. NizamMohideen, M. Viswanathan, V. Govindhan, M. Subramanian, K. The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide |
title | The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide |
title_full | The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide |
title_fullStr | The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide |
title_full_unstemmed | The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide |
title_short | The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide |
title_sort | crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2h-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and n-(2,4-dimethoxybenzyl)-2-[(2-oxo-2h-chromen-4-yl)oxy]acetamide |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6509693/ https://www.ncbi.nlm.nih.gov/pubmed/31161061 http://dx.doi.org/10.1107/S2056989019003736 |
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