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Volume 69 
Part 7 
Page o1097  
July 2013  

Received 30 May 2013
Accepted 9 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.010 Å
R = 0.061
wR = 0.137
Data-to-parameter ratio = 22.0
Details
Open access

5-Bromo-4-(3,5-dibromo-2-hydroxyphenyl)-2-(piperidin-1-yl)-1,3-dithiol-2-ylium bromide

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: lbirsa@uaic.ro

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-H...Br hydrogen bond.

Related literature

For applications of 1,3-dithiolium salts, see: Narita & Pittman (1976[Narita, M. & Pittman, C. U. Jr (1976). Synthesis, pp. 489-514.]); Bryce (2000[Bryce, M. R. (2000). J. Mater. Chem. 10, 589-598.]); Birsa & Ganju (2003[Birsa, M. L. & Ganju, D. (2003). J. Phys. Org. Chem. 16, 207-212.]); For the structure of 2-ethylthio-4,5-bis(trifluoromethyl)-1,3-dithiol-2-ylium hexachlorostibiate, see: Frasch et al. (1993[Frasch, M., Mono, S., Pritzkow, H. & Sundermeyer, W. (1993). Chem. Ber. 126, 273-275.])

[Scheme 1]

Experimental

Crystal data
  • C14H13Br3NOS2+·Br-

  • Mr = 595.01

  • Monoclinic, P 21 /c

  • a = 10.484 (2) Å

  • b = 7.9240 (16) Å

  • c = 21.396 (4) Å

  • [beta] = 95.16 (3)°

  • V = 1770.4 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 9.33 mm-1

  • T = 153 K

  • 0.26 × 0.13 × 0.05 mm

Data collection
  • Stoe IPDS 2T area-detector diffractometer

  • Absorption correction: for a sphere [modified Dwiggins (1975[Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.])] Tmin = 0.047, Tmax = 0.073

  • 19422 measured reflections

  • 4399 independent reflections

  • 3413 reflections with I > 2[sigma](I)

  • Rint = 0.132

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.137

  • S = 1.08

  • 4399 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.52 e Å-3

  • [Delta][rho]min = -1.03 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O-H0...Br4 0.84 2.30 3.120 (5) 167

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2264 ).


Acknowledgements

Part of this work was supported by a grant of the Romanian National Authority for Scientific Research, CNDI- UEFISCDI, project No. 51/2012.

References

Birsa, M. L. & Ganju, D. (2003). J. Phys. Org. Chem. 16, 207-212.  [Web of Science] [CrossRef] [ChemPort]
Bryce, M. R. (2000). J. Mater. Chem. 10, 589-598.  [Web of Science] [CrossRef] [ChemPort]
Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.  [CrossRef] [IUCr Journals]
Frasch, M., Mono, S., Pritzkow, H. & Sundermeyer, W. (1993). Chem. Ber. 126, 273-275.  [CrossRef] [ChemPort]
Narita, M. & Pittman, C. U. Jr (1976). Synthesis, pp. 489-514.  [CrossRef] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2013). E69, o1097  [ doi:10.1107/S1600536813016048 ]

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