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2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione
The title molecule, C(13)H(4)O(2)S(5), is folded by 47.83 (6)° along the S⋯S vector of the [1,4]dithiine six-membered ring, with the naphthoquinone and [1,3]dithiole-2-thione moieties being nearly planar [largest deviations from least-squares planes = 0.028 (2) and 0.016 (1) Å, respectively]. This...
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/PMC3247576/ https://www.ncbi.nlm.nih.gov/pubmed/22219881 http://dx.doi.org/10.1107/S1600536811039079 |
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author | Méndez-Rojas, Miguel Angel Bernès, Sylvain Pérez-Benítez, Aarón Romero Zarazúa, María Fernanda Castellanos-Uribe, Adrián |
author_facet | Méndez-Rojas, Miguel Angel Bernès, Sylvain Pérez-Benítez, Aarón Romero Zarazúa, María Fernanda Castellanos-Uribe, Adrián |
author_sort | Méndez-Rojas, Miguel Angel |
collection | PubMed |
description | The title molecule, C(13)H(4)O(2)S(5), is folded by 47.83 (6)° along the S⋯S vector of the [1,4]dithiine six-membered ring, with the naphthoquinone and [1,3]dithiole-2-thione moieties being nearly planar [largest deviations from least-squares planes = 0.028 (2) and 0.016 (1) Å, respectively]. This boat conformation is close to that observed in the analogous compound [Mendez-Rojas et al. (2001). J. Chem. Crystallogr. 31, 17–28] including a 2-oxo group [folding angle: 42.3 (1)° at 213 (2) K]. Both compounds are indeed isomorphous, and the small difference in the folding angle probably results from the involvement of the thioxo group of the title compound in intermolecular S⋯S contacts [3.5761 (13) Å]. In the crystal structure, molecules are stacked in the [100] direction, with dithiole rings making π–π interactions. In a stack, alternating short and long separations are observed between the centroids of dithiole rings, 3.5254 (17) and 4.7010 (18) Å. |
format | Online Article Text |
id | pubmed-3247576 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32475762012-01-04 2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione Méndez-Rojas, Miguel Angel Bernès, Sylvain Pérez-Benítez, Aarón Romero Zarazúa, María Fernanda Castellanos-Uribe, Adrián Acta Crystallogr Sect E Struct Rep Online Organic Papers The title molecule, C(13)H(4)O(2)S(5), is folded by 47.83 (6)° along the S⋯S vector of the [1,4]dithiine six-membered ring, with the naphthoquinone and [1,3]dithiole-2-thione moieties being nearly planar [largest deviations from least-squares planes = 0.028 (2) and 0.016 (1) Å, respectively]. This boat conformation is close to that observed in the analogous compound [Mendez-Rojas et al. (2001). J. Chem. Crystallogr. 31, 17–28] including a 2-oxo group [folding angle: 42.3 (1)° at 213 (2) K]. Both compounds are indeed isomorphous, and the small difference in the folding angle probably results from the involvement of the thioxo group of the title compound in intermolecular S⋯S contacts [3.5761 (13) Å]. In the crystal structure, molecules are stacked in the [100] direction, with dithiole rings making π–π interactions. In a stack, alternating short and long separations are observed between the centroids of dithiole rings, 3.5254 (17) and 4.7010 (18) Å. International Union of Crystallography 2011-10-05 /pmc/articles/PMC3247576/ /pubmed/22219881 http://dx.doi.org/10.1107/S1600536811039079 Text en © Méndez-Rojas 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 Méndez-Rojas, Miguel Angel Bernès, Sylvain Pérez-Benítez, Aarón Romero Zarazúa, María Fernanda Castellanos-Uribe, Adrián 2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione |
title | 2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione |
title_full | 2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione |
title_fullStr | 2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione |
title_full_unstemmed | 2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione |
title_short | 2-Sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione |
title_sort | 2-sulfanylidene-1,3-dithiolo[4,5-b]naphtho[2,3-e][1,4]dithiine-5,10-dione |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247576/ https://www.ncbi.nlm.nih.gov/pubmed/22219881 http://dx.doi.org/10.1107/S1600536811039079 |
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