Cargando…
(1S,3′S,3a′R,6′S)-6′-(2-Chlorophenyl)-3′-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2H,2′H-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile
The molecular conformation of the title compound, C(41)H(29)ClN(4)O(3)S, is stabilized by intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds. The thiazole ring adopts an envelope conformation with the N atom as the flap, while the pyrrolidine ring has a twisted conformation on the N—C bond involving...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3648279/ https://www.ncbi.nlm.nih.gov/pubmed/23723899 http://dx.doi.org/10.1107/S1600536813009276 |
_version_ | 1782268808960933888 |
---|---|
author | Devi, Seenivasan Karthiga Srinivasan, Thothadri Rajesh, Raju Raghunathan, Raghavachary Velmurugan, Devadasan |
author_facet | Devi, Seenivasan Karthiga Srinivasan, Thothadri Rajesh, Raju Raghunathan, Raghavachary Velmurugan, Devadasan |
author_sort | Devi, Seenivasan Karthiga |
collection | PubMed |
description | The molecular conformation of the title compound, C(41)H(29)ClN(4)O(3)S, is stabilized by intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds. The thiazole ring adopts an envelope conformation with the N atom as the flap, while the pyrrolidine ring has a twisted conformation on the N—C bond involving the spiro C atom. The β lactam ring makes dihedral angles of 39.74 (15) and 16.21 (16)° with the mean planes of the thiazole and pyrrolidine rings, respectively. The thiazole ring mean plane makes dihedral angles of 23.79 (13) and 70.88 (13) ° with the pyrrolidine and cyclopentane rings, respectively, while the pyrrolidine ring makes a dihedral angle of 85.63 (13)° with the cyclopentane ring. The O atom attached to the β lactam ring deviates from its mean plane by 0.040 (2) Å, while the O atom attached to the cyclopentane ring deviates from its mean plane by 0.132 (2) Å. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains along [010], and C—H⋯π and π-π interactions [centroid-centroid distance = 3.6928 (17) Å]. |
format | Online Article Text |
id | pubmed-3648279 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-36482792013-05-30 (1S,3′S,3a′R,6′S)-6′-(2-Chlorophenyl)-3′-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2H,2′H-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile Devi, Seenivasan Karthiga Srinivasan, Thothadri Rajesh, Raju Raghunathan, Raghavachary Velmurugan, Devadasan Acta Crystallogr Sect E Struct Rep Online Organic Papers The molecular conformation of the title compound, C(41)H(29)ClN(4)O(3)S, is stabilized by intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds. The thiazole ring adopts an envelope conformation with the N atom as the flap, while the pyrrolidine ring has a twisted conformation on the N—C bond involving the spiro C atom. The β lactam ring makes dihedral angles of 39.74 (15) and 16.21 (16)° with the mean planes of the thiazole and pyrrolidine rings, respectively. The thiazole ring mean plane makes dihedral angles of 23.79 (13) and 70.88 (13) ° with the pyrrolidine and cyclopentane rings, respectively, while the pyrrolidine ring makes a dihedral angle of 85.63 (13)° with the cyclopentane ring. The O atom attached to the β lactam ring deviates from its mean plane by 0.040 (2) Å, while the O atom attached to the cyclopentane ring deviates from its mean plane by 0.132 (2) Å. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains along [010], and C—H⋯π and π-π interactions [centroid-centroid distance = 3.6928 (17) Å]. International Union of Crystallography 2013-04-17 /pmc/articles/PMC3648279/ /pubmed/23723899 http://dx.doi.org/10.1107/S1600536813009276 Text en © Devi et al. 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Devi, Seenivasan Karthiga Srinivasan, Thothadri Rajesh, Raju Raghunathan, Raghavachary Velmurugan, Devadasan (1S,3′S,3a′R,6′S)-6′-(2-Chlorophenyl)-3′-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2H,2′H-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile |
title | (1S,3′S,3a′R,6′S)-6′-(2-Chlorophenyl)-3′-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2H,2′H-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile |
title_full | (1S,3′S,3a′R,6′S)-6′-(2-Chlorophenyl)-3′-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2H,2′H-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile |
title_fullStr | (1S,3′S,3a′R,6′S)-6′-(2-Chlorophenyl)-3′-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2H,2′H-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile |
title_full_unstemmed | (1S,3′S,3a′R,6′S)-6′-(2-Chlorophenyl)-3′-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2H,2′H-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile |
title_short | (1S,3′S,3a′R,6′S)-6′-(2-Chlorophenyl)-3′-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2H,2′H-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile |
title_sort | (1s,3′s,3a′r,6′s)-6′-(2-chlorophenyl)-3′-[(2r,3s)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetrahydro-2h,2′h-spiro[acenaphthylene-1,1′-pyrrolo[1,2-c][1,3]thiazole]-2′,2′-dicarbonitrile |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3648279/ https://www.ncbi.nlm.nih.gov/pubmed/23723899 http://dx.doi.org/10.1107/S1600536813009276 |
work_keys_str_mv | AT deviseenivasankarthiga 1s3s3ar6s62chlorophenyl32r3s14methoxyphenyl4oxo3phenylazetidin2yl2oxo33a46tetrahydro2h2hspiroacenaphthylene11pyrrolo12c13thiazole22dicarbonitrile AT srinivasanthothadri 1s3s3ar6s62chlorophenyl32r3s14methoxyphenyl4oxo3phenylazetidin2yl2oxo33a46tetrahydro2h2hspiroacenaphthylene11pyrrolo12c13thiazole22dicarbonitrile AT rajeshraju 1s3s3ar6s62chlorophenyl32r3s14methoxyphenyl4oxo3phenylazetidin2yl2oxo33a46tetrahydro2h2hspiroacenaphthylene11pyrrolo12c13thiazole22dicarbonitrile AT raghunathanraghavachary 1s3s3ar6s62chlorophenyl32r3s14methoxyphenyl4oxo3phenylazetidin2yl2oxo33a46tetrahydro2h2hspiroacenaphthylene11pyrrolo12c13thiazole22dicarbonitrile AT velmurugandevadasan 1s3s3ar6s62chlorophenyl32r3s14methoxyphenyl4oxo3phenylazetidin2yl2oxo33a46tetrahydro2h2hspiroacenaphthylene11pyrrolo12c13thiazole22dicarbonitrile |