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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...

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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
Descripción
Sumario: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.