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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...

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Autores principales: Méndez-Rojas, Miguel Angel, Bernès, Sylvain, Pérez-Benítez, Aarón, Romero Zarazúa, María Fernanda, Castellanos-Uribe, Adrián
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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.
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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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