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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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Detalles Bibliográficos
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
Descripción
Sumario: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.