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Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one

The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C(22)H(17)NO(2), (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C(14)H(17)NO(2), (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent m...

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Detalles Bibliográficos
Autores principales: Syed Abuthahir, S., NizamMohideen, M., Mayakrishnan, S., Uma Maheswari, N., Viswanathan, V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6690470/
https://www.ncbi.nlm.nih.gov/pubmed/31417776
http://dx.doi.org/10.1107/S2056989019009435
Descripción
Sumario:The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C(22)H(17)NO(2), (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C(14)H(17)NO(2), (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent mol­ecules (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 intra­molecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal of I, mol­ecules are linked by N—H⋯π inter­actions, forming chains along the b-axis direction. A C—H⋯π inter­action links the chains to form layers parallel to (100). The layers are then linked by a second C—H⋯π inter­action, forming a three-dimensional structure. In the crystal of II, the two independent mol­ecules (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 inter­actions involving inversion-related A mol­ecules. The latter are linked by offset π–π inter­actions [inter­centroid distances vary from 3.506 (1) to 3.870 (2) Å], forming a three-dimensional structure.