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...

Full description

Bibliographic Details
Main Authors: S. Syed Abuthahir, M. NizamMohideen, S. Mayakrishnan, N. Uma Maheswari, V. Viswanathan
Format: Article
Language:English
Published: International Union of Crystallography 2019-08-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
Online Access:http://scripts.iucr.org/cgi-bin/paper?S2056989019009435
_version_ 1818958418542592000
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.
first_indexed 2024-12-20T11:25:26Z
format Article
id doaj.art-17de71ea96894cf591cdb3da0c2ffaf1
institution Directory Open Access Journal
issn 2056-9890
language English
last_indexed 2024-12-20T11:25:26Z
publishDate 2019-08-01
publisher International Union of Crystallography
record_format Article
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
work_keys_str_mv AT ssyedabuthahir crystalstructuresoftwonewisocoumarinderivatives8amino6methyl34diphenyl1hisochromen1oneand8amino34diethyl6methyl1hisochromen1one
AT mnizammohideen crystalstructuresoftwonewisocoumarinderivatives8amino6methyl34diphenyl1hisochromen1oneand8amino34diethyl6methyl1hisochromen1one
AT smayakrishnan crystalstructuresoftwonewisocoumarinderivatives8amino6methyl34diphenyl1hisochromen1oneand8amino34diethyl6methyl1hisochromen1one
AT numamaheswari crystalstructuresoftwonewisocoumarinderivatives8amino6methyl34diphenyl1hisochromen1oneand8amino34diethyl6methyl1hisochromen1one
AT vviswanathan crystalstructuresoftwonewisocoumarinderivatives8amino6methyl34diphenyl1hisochromen1oneand8amino34diethyl6methyl1hisochromen1one