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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...

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Autores principales: Pangajavalli, S., Ranjithkumar, R., Srinivasan, N., Ramaswamy, S., Selvanayagam, S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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.
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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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