Title of article :
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
Author/Authors :
Abuthahir, S. Syed PG & Research Department of Physics - The New College (Autonomous) - University of Madras, India , NizamMohideen, M. PG & Research Department of Physics - The New College (Autonomous) - University of Madras, India , Mayakrishnan, S. Organic & Bioorganic Chemistry - CSIR–Central Leather Research Institute, India , Uma Maheswari, N. Organic & Bioorganic Chemistry - CSIR-Central Leather Research Institute, India , Viswanathan, V. Department of Biophysics - All India Institute of Medical Science, India
Pages :
18
From page :
1
To page :
18
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 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.
Keywords :
crystal structure , chromen , isochromene , hydrogen bonding , N—H⋯π inter­actions , C—H⋯π inter­actions , offset π—π inter­actions , Hirshfeld surface analysis
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
Serial Year :
2019
Full Text URL :
Record number :
2625386
Link To Document :
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