The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)-oxy]acet-yl}piperazin-1-yl)acetamide and N-(2,4-di-meth-oxy-benz-yl)-2-[(2-oxo-2H-chromen-4-yl)-oxy]acetamide.

ABSTRACT: The title compounds, 2-(4-{2-[(2-oxo-2H-chromen-4-yl)-oxy]acet-yl}piperazin-1-yl)acetamide, C₁₇H₁₉N₃O₅, (I), and N-(2,4-di-meth-oxy-benz-yl)-2-[(2-oxo-2H-chromen-4-yl)-oxy]acetamide, C₂₀H₁₉NO₆, (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 intra-molecular contacts in both mol-ecules 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, mol-ecules are linked by N-H?O hydrogen bonds, forming chains along [10] 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?? and offset ?-? inter-actions [inter-centroid distance = 3.691?(1)?Å] present within the layers. In the crystal of (II), there are only weak offset ?-? inter-actions [inter-centroid distance = 3.981?(6)?Å] present within the layers. The inter-molecular contacts in the crystals of both compounds have been analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

SUBMITTER: Syed Abuthahir S 

PROVIDER: S-EPMC6509693 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature