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Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate
In the title molecule, C(16)H(14)O(4)S, the dihydrocyclopentathiophenone ring system is almost planar, with an r.m.s. deviation of 0.060 Å from the best fit plane through all nine non-H atoms. The cyclopentanone ring adopts a severely flattened envelope conformation with the C atom carrying t...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201281/ https://www.ncbi.nlm.nih.gov/pubmed/22058815 http://dx.doi.org/10.1107/S1600536811037032 |
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author | McAdam, C. John Moratti, Stephen C. Simpson, Jim Shi, Zheng |
author_facet | McAdam, C. John Moratti, Stephen C. Simpson, Jim Shi, Zheng |
author_sort | McAdam, C. John |
collection | PubMed |
description | In the title molecule, C(16)H(14)O(4)S, the dihydrocyclopentathiophenone ring system is almost planar, with an r.m.s. deviation of 0.060 Å from the best fit plane through all nine non-H atoms. The cyclopentanone ring adopts a severely flattened envelope conformation with the C atom carrying the OH and ethylcarboxylate substituents at the flap. This atom lies only 0.185 (3) Å from the plane through the other four C atoms. The phenyl substituent is inclined at 43.37 (5)° to the dihydrocyclopentathiophenone mean plane. In the crystal, molecules are linked by pairs of O—H⋯O hydrogen bonds, forming inversion dimers with R (2) (2)(10) ring motifs. Weak C—H⋯O hydrogen bonds also link molecules into chains along c, while an approximately orthogonal set of C—H⋯O contacts form chains along b, resulting in layers lying parallel to (100). Inversion dimers also form through weaker R (2) (2)(12) C—H⋯S contacts, which combine with C—H⋯O contacts to form stacks along b. |
format | Online Article Text |
id | pubmed-3201281 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32012812011-11-06 Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate McAdam, C. John Moratti, Stephen C. Simpson, Jim Shi, Zheng Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title molecule, C(16)H(14)O(4)S, the dihydrocyclopentathiophenone ring system is almost planar, with an r.m.s. deviation of 0.060 Å from the best fit plane through all nine non-H atoms. The cyclopentanone ring adopts a severely flattened envelope conformation with the C atom carrying the OH and ethylcarboxylate substituents at the flap. This atom lies only 0.185 (3) Å from the plane through the other four C atoms. The phenyl substituent is inclined at 43.37 (5)° to the dihydrocyclopentathiophenone mean plane. In the crystal, molecules are linked by pairs of O—H⋯O hydrogen bonds, forming inversion dimers with R (2) (2)(10) ring motifs. Weak C—H⋯O hydrogen bonds also link molecules into chains along c, while an approximately orthogonal set of C—H⋯O contacts form chains along b, resulting in layers lying parallel to (100). Inversion dimers also form through weaker R (2) (2)(12) C—H⋯S contacts, which combine with C—H⋯O contacts to form stacks along b. International Union of Crystallography 2011-09-30 /pmc/articles/PMC3201281/ /pubmed/22058815 http://dx.doi.org/10.1107/S1600536811037032 Text en © McAdam et al. 2011 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 McAdam, C. John Moratti, Stephen C. Simpson, Jim Shi, Zheng Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate |
title | Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate |
title_full | Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate |
title_fullStr | Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate |
title_full_unstemmed | Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate |
title_short | Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate |
title_sort | ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4h-cyclopenta[b]thiophene-5-carboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201281/ https://www.ncbi.nlm.nih.gov/pubmed/22058815 http://dx.doi.org/10.1107/S1600536811037032 |
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