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1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one

The piperidone ring in the title compound, C(18)H(19)NOS(2), is in a distorted half-chair conformation, distorted towards a twisted boat, with the central methyl­ene C atom of the propyl backbone lying 0.606 (2) Å out of the plane defined by the other five atoms (r.m.s. deviation = 0.1197 Å). One of...

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Autores principales: Caracelli, Ignez, Olivato, Paulo R., Cerqueira Jr, Carlos R., Santos, Jean M. M., Ng, Seik Weng, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379371/
https://www.ncbi.nlm.nih.gov/pubmed/22719569
http://dx.doi.org/10.1107/S1600536812021277
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author Caracelli, Ignez
Olivato, Paulo R.
Cerqueira Jr, Carlos R.
Santos, Jean M. M.
Ng, Seik Weng
Tiekink, Edward R. T.
author_facet Caracelli, Ignez
Olivato, Paulo R.
Cerqueira Jr, Carlos R.
Santos, Jean M. M.
Ng, Seik Weng
Tiekink, Edward R. T.
author_sort Caracelli, Ignez
collection PubMed
description The piperidone ring in the title compound, C(18)H(19)NOS(2), is in a distorted half-chair conformation, distorted towards a twisted boat, with the central methyl­ene C atom of the propyl backbone lying 0.606 (2) Å out of the plane defined by the other five atoms (r.m.s. deviation = 0.1197 Å). One of the S-bound phenyl rings is almost perpendicular to the least-squares plane through the piperidone ring, whereas the other is splayed [dihedral angles = 75.97 (6) and 44.21 (7)°, respectively]. The most prominent feature of the crystal packing is the formation of helical supra­molecular chains along the b axis sustained by C—H⋯O inter­actions. The chains are consolidated into a three-dimensional architecture via C—H⋯π inter­actions whereby one S-bound phenyl ring accepts two C—H⋯π contacts.
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spelling pubmed-33793712012-06-20 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one Caracelli, Ignez Olivato, Paulo R. Cerqueira Jr, Carlos R. Santos, Jean M. M. Ng, Seik Weng Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers The piperidone ring in the title compound, C(18)H(19)NOS(2), is in a distorted half-chair conformation, distorted towards a twisted boat, with the central methyl­ene C atom of the propyl backbone lying 0.606 (2) Å out of the plane defined by the other five atoms (r.m.s. deviation = 0.1197 Å). One of the S-bound phenyl rings is almost perpendicular to the least-squares plane through the piperidone ring, whereas the other is splayed [dihedral angles = 75.97 (6) and 44.21 (7)°, respectively]. The most prominent feature of the crystal packing is the formation of helical supra­molecular chains along the b axis sustained by C—H⋯O inter­actions. The chains are consolidated into a three-dimensional architecture via C—H⋯π inter­actions whereby one S-bound phenyl ring accepts two C—H⋯π contacts. International Union of Crystallography 2012-05-19 /pmc/articles/PMC3379371/ /pubmed/22719569 http://dx.doi.org/10.1107/S1600536812021277 Text en © Caracelli et al. 2012 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
Caracelli, Ignez
Olivato, Paulo R.
Cerqueira Jr, Carlos R.
Santos, Jean M. M.
Ng, Seik Weng
Tiekink, Edward R. T.
1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one
title 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one
title_full 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one
title_fullStr 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one
title_full_unstemmed 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one
title_short 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one
title_sort 1-methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379371/
https://www.ncbi.nlm.nih.gov/pubmed/22719569
http://dx.doi.org/10.1107/S1600536812021277
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