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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...

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Detalles Bibliográficos
Autores principales: McAdam, C. John, Moratti, Stephen C., Simpson, Jim, Shi, Zheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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.
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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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AT shizheng ethyl5hydroxy6oxo4phenyl56dihydro4hcyclopentabthiophene5carboxylate