Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Syed Abuthahir, S., NizamMohideen, M., Viswanathan, V., Govindhan, M., Subramanian, K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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
_version_ 1783417294267875328
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
work_keys_str_mv AT syedabuthahirs thecrystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT nizammohideenm thecrystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT viswanathanv thecrystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT govindhanm thecrystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT subramaniank thecrystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT syedabuthahirs crystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT nizammohideenm crystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT viswanathanv crystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT govindhanm crystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide
AT subramaniank crystalstructuresoftwonewcoumarinderivatives2422oxo2hchromen4yloxyacetylpiperazin1ylacetamideandn24dimethoxybenzyl22oxo2hchromen4yloxyacetamide