Received 30 May 2013
aDepartment of Chemistry, University of Craiova, 107I Calea Bucuresti, Craiova, Romania,bChemisches Institut der Otto-von-Guericke-Universität, Universitätsplatz 2, D-39116 Magdeburg, Germany, and cDepartment of Chemistry, "Al. I. Cuza" University Iasi, 11 Carol I Bvd, Iasi 700506, Romania
Correspondence e-mail: firstname.lastname@example.org
In the title salt, C14H13Br3NOS2+·Br-, synthesized by bromination of mesoionic 2-[2-(piperidin-1-yl)-1,3-dithiol-2-ylium-4-yl]phenolate in glacial acetic acid, the dihedral angle between the 1,3-dithiolium ring and the phenolic substituent ring is 45.9 (3)° due to the steric influence of the ortho-Br group on the 1,3-dithiolium ring. The piperidine ring adopts a chair conformation. In the crystal, the cation and anion are linked by an O-HBr hydrogen bond.
For applications of 1,3-dithiolium salts, see: Narita & Pittman (1976); Bryce (2000); Birsa & Ganju (2003); For the structure of 2-ethylthio-4,5-bis(trifluoromethyl)-1,3-dithiol-2-ylium hexachlorostibiate, see: Frasch et al. (1993)
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2264 ).
Part of this work was supported by a grant of the Romanian National Authority for Scientific Research, CNDI- UEFISCDI, project No. 51/2012.
Birsa, M. L. & Ganju, D. (2003). J. Phys. Org. Chem. 16, 207-212.
Bryce, M. R. (2000). J. Mater. Chem. 10, 589-598.
Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.
Frasch, M., Mono, S., Pritzkow, H. & Sundermeyer, W. (1993). Chem. Ber. 126, 273-275.
Narita, M. & Pittman, C. U. Jr (1976). Synthesis, pp. 489-514.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA. Stoe & Cie, Darmstadt, Germany.