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(+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea
The title compound, C(11)H(20)N(2)O(2)S, is an enantiomerically pure heterocycle-substituted thiourea synthesized under solvent-free conditions. The thiourea unit adopts a ZZ conformation, with the HN—(C=S)—NH core almost planar and the tetrahydrofurfuryl groups placed below and above this plan...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968003/ https://www.ncbi.nlm.nih.gov/pubmed/21581734 http://dx.doi.org/10.1107/S1600536808040373 |
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author | Peña, Úlises Bernès, Sylvain Gutiérrez, René |
author_facet | Peña, Úlises Bernès, Sylvain Gutiérrez, René |
author_sort | Peña, Úlises |
collection | PubMed |
description | The title compound, C(11)H(20)N(2)O(2)S, is an enantiomerically pure heterocycle-substituted thiourea synthesized under solvent-free conditions. The thiourea unit adopts a ZZ conformation, with the HN—(C=S)—NH core almost planar and the tetrahydrofurfuryl groups placed below and above this plane. The whole molecule thus approximates to noncrystallographic C (2) symmetry. Unexpectedly, the C=S group is not involved in intermolecular hydrogen bonding, as generally observed in homodisubstituted thioureas. Instead, molecules form a one-dimensional network based on weak N—H⋯O(heterocycle) hydrogen bonding, resulting in a zigzag ribbon-like structure around the crystallographic 2(1) screw axis along [100]. |
format | Text |
id | pubmed-2968003 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29680032010-12-30 (+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea Peña, Úlises Bernès, Sylvain Gutiérrez, René Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(11)H(20)N(2)O(2)S, is an enantiomerically pure heterocycle-substituted thiourea synthesized under solvent-free conditions. The thiourea unit adopts a ZZ conformation, with the HN—(C=S)—NH core almost planar and the tetrahydrofurfuryl groups placed below and above this plane. The whole molecule thus approximates to noncrystallographic C (2) symmetry. Unexpectedly, the C=S group is not involved in intermolecular hydrogen bonding, as generally observed in homodisubstituted thioureas. Instead, molecules form a one-dimensional network based on weak N—H⋯O(heterocycle) hydrogen bonding, resulting in a zigzag ribbon-like structure around the crystallographic 2(1) screw axis along [100]. International Union of Crystallography 2008-12-13 /pmc/articles/PMC2968003/ /pubmed/21581734 http://dx.doi.org/10.1107/S1600536808040373 Text en © Peña et al. 2009 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 Peña, Úlises Bernès, Sylvain Gutiérrez, René (+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea |
title | (+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea |
title_full | (+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea |
title_fullStr | (+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea |
title_full_unstemmed | (+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea |
title_short | (+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea |
title_sort | (+)-(s,s)-1,3-bis[(tetrahydrofuran-2-yl)methyl]thiourea |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968003/ https://www.ncbi.nlm.nih.gov/pubmed/21581734 http://dx.doi.org/10.1107/S1600536808040373 |
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