Abstract
The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C22H17NO2, (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C14H17NO2, (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In I, the two phenyl rings are inclined to each other by 56.41 (7)° and to the mean plane of the 1H-isochromene ring system by 67.64 (6) and 44.92 (6)°. In both compounds, there is an intra-molecular N-H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal of I, mol-ecules are linked by N-H⋯π inter-actions, forming chains along the b-axis direction. A C-H⋯π inter-action links the chains to form layers parallel to (100). The layers are then linked by a second C-H⋯π inter-action, forming a three-dimensional structure. In the crystal of II, the two independent mol-ecules (A and B) are linked by N-H⋯O hydrogen bonds, forming -A-B-A-B- chains along the [101] direction. The chains are linked into ribbons by C-H⋯π inter-actions involving inversion-related A mol-ecules. The latter are linked by offset π-π inter-actions [inter-centroid distances vary from 3.506 (1) to 3.870 (2) Å], forming a three-dimensional structure.
Highlights
The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C22H17NO2, (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C14H17NO2, (II), are new isocoumarin derivatives in which the isochromene ring systems are planar
In the crystal of I, molecules are linked by N—HÁ Á Á interactions, forming chains along the b-axis direction
The layers are linked by a second C—HÁ Á Á interaction, forming a three-dimensional structure
Summary
There has been growing interest in the synthesis of natural products, since they are a tremendous and trustworthy source for the development of new drugs. Isocoumarins and their derivatives are secondary metabolites of an extensive range of microbial plant and insect sources and in the creation of other medicinal compounds (Manivel et al, 2008; Basvanag et al, 2009) Depending on their chemical composition and concentration, they can be active either as inhibitors or stimulators in these processes. The synthesis and pharmacological and other properties of coumarin and isocoumarin derivatives have been studied intensely and reviewed (Jain et al, 2012; Pal et al, 2011) Against this background and in view of the importance of their natural occurrence, biological activities, pharmacological activities, medicinal activities and utility as synthetic intermediates, we have synthesized the title compounds, and report on their crystal structures. Symmetry codes: (i) Àx þ 12; y À 12; Àz À 12; (ii) Àx þ 12; y þ 12; Àz þ 12; (iii) Àx þ 1; Ày þ 1; Àz
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