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Volume 69 
Part 2 
Page m95  
February 2013  

Received 30 December 2012
Accepted 3 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.027
wR = 0.050
Data-to-parameter ratio = 22.2
Details
Open access

3,5-Diphenyl-1,2,4-dithiazolium tetrabromidoferrate(III)

aDepartment of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, Alberta, Canada T1K 3M4
Correspondence e-mail: boere@uleth.ca

The cation of the title salt, (C14H10NS2)[FeBr4], contains a flat central NC2S2 ring (r.m.s. deviation = 0.005 Å), with two attached phenyl rings that are almost coplanar [the dihedral angles between the mean planes are 2.4 (1) and 7.7 (1)° for the two phenyl rings]. The [FeBr4]- anion makes short Br...S contacts [Br...S = 3.4819 (8), 3.6327 (9) and 3.5925 (9) Å] and also bridges by way of short contacts to ring H atoms of a second cation held parallel to the first by [pi]-stacking, with a separation between the mean 1,2,4-dithiazolium rings of 3.409 Å. The closest contacts are between a phenyl ring centroid of one cation and the ipso C atom of the phenyl ring of another cation, for which the distance is 3.489 Å. The discrete dimers are linked laterally by further Br...H short contacts, resulting in double sheets located parallel to the b axis and to the bisector of a and c.

Related literature

For synthesis details, see: Corsaro et al. (1984[Corsaro, A., Compagnini, A., Perrini, G. & Purrello, G. (1984). J. Chem. Soc. Perkin Trans. 1, pp. 897-900.]); Liebscher & Hartmann (1977[Liebscher, J. & Hartmann, H. (1977). Liebigs Ann. Chem. pp. 1005-1012.]). For related structures, see: Clegg et al. (1996[Clegg, W., Elsegood, M. R. J., Banister, A. J. & Hibbert, T. G. (1996). Acta Cryst. C52, 2148-2150.]); Neels et al. (1986[Neels, J., Ziemer, B., Meisel, M. & Leibnitz, P. (1986). Z. Anorg. Allg. Chem. 542, 123-130.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For bond lengths in tetrabromidoferrate complexes, see: Maithufi & Otto (2011[Maithufi, N. & Otto, S. (2011). Acta Cryst. C67, m279-m283.]); Bhattacharya & Sarkar (2010[Bhattacharya, D. & Sarkar, S. (2010). Eur. J. Inorg. Chem. pp. 3429-3435.]). For short-contact distances between stacked aryl rings, see: Martinez & Iverson (2012[Martinez, C. R. & Iverson, B. L. (2012). Chem. Sci. 3, 2191-2201.]); McGaughey et al. (1998[McGaughey, G. B., Gagné, M. & Rappé, A. M. (1998). J. Biol. Chem. 273, 15458-15463.]).

[Scheme 1]

Experimental

Crystal data
  • (C14H10NS2)[FeBr4]

  • Mr = 631.84

  • Monoclinic, P 21 /c

  • a = 10.6492 (5) Å

  • b = 11.4005 (6) Å

  • c = 15.8046 (8) Å

  • [beta] = 96.482 (1)°

  • V = 1906.51 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 9.39 mm-1

  • T = 173 K

  • 0.22 × 0.13 × 0.07 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.556, Tmax = 0.746

  • 27655 measured reflections

  • 4426 independent reflections

  • 3497 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.050

  • S = 1.02

  • 4426 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2091 ).


Acknowledgements

The Natural Sciences and Engineering Research Council of Canada (NSERC) is gratefully acknowledged for a Discovery Grant. The diffractometer was purchased with the help of NSERC and the University of Lethbridge.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bhattacharya, D. & Sarkar, S. (2010). Eur. J. Inorg. Chem. pp. 3429-3435.  [ISI] [CrossRef]
Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Clegg, W., Elsegood, M. R. J., Banister, A. J. & Hibbert, T. G. (1996). Acta Cryst. C52, 2148-2150.  [CSD] [CrossRef] [details]
Corsaro, A., Compagnini, A., Perrini, G. & Purrello, G. (1984). J. Chem. Soc. Perkin Trans. 1, pp. 897-900.  [CrossRef]
Liebscher, J. & Hartmann, H. (1977). Liebigs Ann. Chem. pp. 1005-1012.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Maithufi, N. & Otto, S. (2011). Acta Cryst. C67, m279-m283.  [CSD] [CrossRef] [details]
Martinez, C. R. & Iverson, B. L. (2012). Chem. Sci. 3, 2191-2201.  [CrossRef] [ChemPort]
McGaughey, G. B., Gagné, M. & Rappé, A. M. (1998). J. Biol. Chem. 273, 15458-15463.  [CrossRef] [ChemPort] [PubMed]
Neels, J., Ziemer, B., Meisel, M. & Leibnitz, P. (1986). Z. Anorg. Allg. Chem. 542, 123-130.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m95  [ doi:10.1107/S1600536813000275 ]

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