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Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione
The title compounds, C(20)H(16)N(2)O(3)S, (I), and C(21)H(18)N(2)O(3)S, (II), differ by the presence of a methyl group in position 5 on the 1H-indole-2-one ring of compound (II). The two compounds have a structural overlap r.m.s. deviation of 0.48 Å. There is a significant difference in the conforma...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6362654/ https://www.ncbi.nlm.nih.gov/pubmed/30800460 http://dx.doi.org/10.1107/S2056989019000045 |
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author | Pangajavalli, S. Ranjithkumar, R. Srinivasan, N. Ramaswamy, S. Selvanayagam, S. |
author_facet | Pangajavalli, S. Ranjithkumar, R. Srinivasan, N. Ramaswamy, S. Selvanayagam, S. |
author_sort | Pangajavalli, S. |
collection | PubMed |
description | The title compounds, C(20)H(16)N(2)O(3)S, (I), and C(21)H(18)N(2)O(3)S, (II), differ by the presence of a methyl group in position 5 on the 1H-indole-2-one ring of compound (II). The two compounds have a structural overlap r.m.s. deviation of 0.48 Å. There is a significant difference in the conformation of the thiazolidine ring: it has a twisted conformation on the fused N—C bond in (I), but an envelope conformation in compound (II) with the S atom as the flap. The planar pyrrolidine ring of the indole ring system is normal to the mean plane of the five-membered pyrrolidine ring of the pyrrolothiazole unit in both compounds, with dihedral angles of 88.71 (9) and 84.59 (8)°. The pyran rings in both structures have envelope conformations with the methylene C atom adjacent to the C=O group as the flap. In both compounds, there is a short intramolecular C—H⋯O contact present. In the crystal of (I), molecules are linked by C—H⋯O hydrogen bonds forming chains propagating along the b-axis direction. The chains are linked by N—H⋯π interactions, forming layers parallel to (10[Image: see text]). In the crystal of (II), molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers which are linked by C—H⋯O hydrogen bonds to form a three-dimensional structure. |
format | Online Article Text |
id | pubmed-6362654 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-63626542019-02-22 Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione Pangajavalli, S. Ranjithkumar, R. Srinivasan, N. Ramaswamy, S. Selvanayagam, S. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, C(20)H(16)N(2)O(3)S, (I), and C(21)H(18)N(2)O(3)S, (II), differ by the presence of a methyl group in position 5 on the 1H-indole-2-one ring of compound (II). The two compounds have a structural overlap r.m.s. deviation of 0.48 Å. There is a significant difference in the conformation of the thiazolidine ring: it has a twisted conformation on the fused N—C bond in (I), but an envelope conformation in compound (II) with the S atom as the flap. The planar pyrrolidine ring of the indole ring system is normal to the mean plane of the five-membered pyrrolidine ring of the pyrrolothiazole unit in both compounds, with dihedral angles of 88.71 (9) and 84.59 (8)°. The pyran rings in both structures have envelope conformations with the methylene C atom adjacent to the C=O group as the flap. In both compounds, there is a short intramolecular C—H⋯O contact present. In the crystal of (I), molecules are linked by C—H⋯O hydrogen bonds forming chains propagating along the b-axis direction. The chains are linked by N—H⋯π interactions, forming layers parallel to (10[Image: see text]). In the crystal of (II), molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers which are linked by C—H⋯O hydrogen bonds to form a three-dimensional structure. International Union of Crystallography 2019-01-22 /pmc/articles/PMC6362654/ /pubmed/30800460 http://dx.doi.org/10.1107/S2056989019000045 Text en © Pangajavalli et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Pangajavalli, S. Ranjithkumar, R. Srinivasan, N. Ramaswamy, S. Selvanayagam, S. Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione |
title | Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione |
title_full | Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione |
title_fullStr | Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione |
title_full_unstemmed | Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione |
title_short | Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione |
title_sort | crystal structures of 6a,6b,7,11a-tetrahydro-6h,9h-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6h,9h-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6362654/ https://www.ncbi.nlm.nih.gov/pubmed/30800460 http://dx.doi.org/10.1107/S2056989019000045 |
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