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, 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...
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International Union of Crystallography
2019-08-01
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Series: | Acta Crystallographica Section E: Crystallographic Communications |
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Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019009435 |
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author | S. Syed Abuthahir M. NizamMohideen S. Mayakrishnan N. Uma Maheswari V. Viswanathan |
author_facet | S. Syed Abuthahir M. NizamMohideen S. Mayakrishnan N. Uma Maheswari V. Viswanathan |
author_sort | S. Syed Abuthahir |
collection | DOAJ |
description | 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. |
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issn | 2056-9890 |
language | English |
last_indexed | 2024-12-20T11:25:26Z |
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publisher | International Union of Crystallography |
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series | Acta Crystallographica Section E: Crystallographic Communications |
spelling | doaj.art-17de71ea96894cf591cdb3da0c2ffaf12022-12-21T19:42:22ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-08-017581117112210.1107/S2056989019009435su5498Crystal 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-oneS. Syed Abuthahir0M. NizamMohideen1S. Mayakrishnan2N. Uma Maheswari3V. Viswanathan4PG & Research Department of Physics, The New College (Autonomous), University of Madras, Chennai 600 014, Tamil Nadu, IndiaPG & Research Department of Physics, The New College (Autonomous), University of Madras, Chennai 600 014, Tamil Nadu, IndiaOrganic & Bioorganic Chemistry, CSIR–Central Leather Research Institute, Chennai 600 020, Tamilnadu, IndiaOrganic & Bioorganic Chemistry, CSIR-Central Leather Research Institute, Chennai 600 020, Tamilnadu, IndiaDepartment of Biophysics, All India Institute of Medical Science, New Delhi 110 029, IndiaThe 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.http://scripts.iucr.org/cgi-bin/paper?S2056989019009435crystal structurechromenisochromenehydrogen bondingN—H...π interactionsC—H...π interactionsoffset π—π interactionsHirshfeld surface analysis |
spellingShingle | S. Syed Abuthahir M. NizamMohideen S. Mayakrishnan N. Uma Maheswari V. Viswanathan 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 Acta Crystallographica Section E: Crystallographic Communications crystal structure chromen isochromene hydrogen bonding N—H...π interactions C—H...π interactions offset π—π interactions Hirshfeld surface analysis |
title | 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 |
title_full | 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 |
title_fullStr | 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 |
title_full_unstemmed | 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 |
title_short | 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 |
title_sort | 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 |
topic | crystal structure chromen isochromene hydrogen bonding N—H...π interactions C—H...π interactions offset π—π interactions Hirshfeld surface analysis |
url | http://scripts.iucr.org/cgi-bin/paper?S2056989019009435 |
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