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Volume 68 
Part 1 
Page m17  
January 2012  

Received 5 August 2011
Accepted 1 December 2011
Online 7 December 2011

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Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.012 Å
R = 0.052
wR = 0.082
Data-to-parameter ratio = 19.3
Details
Open access

2-Bromo-1,3-diisopropyl-4,5-dimethyl-1H-imidazol-3-ium dicyanidoargentate

Eyad Mallah,a* Kamal Sweidan,b Qutaiba Abu-Salem,c Wael Abu Dayyiha and Manfred Steimannd

aFaculty of Pharmacy and Medical Sciences, Petra University, PO Box 961343, Amman 11196, Jordan,bDepartment of Chemistry, Faculty of Science, The University of Jordan, Amman, Jordan,cDepartment of Chemistry, Faculty of Science, University of Al al-Bayt, Al-Mafraq, Jordan, and dInstitut für Anorganische Chemie der Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany
Correspondence e-mail: eyad782002@yahoo.com

The title structure, (C11H20BrN2)[Ag(CN)2)], is built up from an approximately C2v-symmetric imidazolium cation and a nearly linear dicyanidoargentate anion [N-Ag-N = 176.6 (9)° and Ag-C-N = 178.8 (9) and 177.2 (11)°]. These two constituents are linked by a remarkably short interaction between the Br atom of the imidazolium cation [C-Br = 1.85 (3) Å] and one N atom of the cyanidoargentate anion [Br...N = 2.96 (2) Å], which is much less than the sum of the van der Waals radii (3.40 Å). The crystal studied was twinned by merohedry.

Related literature

For similar structures, see: Mallah et al. (2009[Mallah, E., Kuhn, N., Maichle-Mössmer, C., Steimann, M., Ströbele, M. & Zeller, K. P. (2009). Z. Naturforsch. Teil B, 64, 1176-1182.], 2011[Mallah, E., Abu-Salem, Q., Sweidan, K., Kuhn, N., Maichle-Mössmer, C., Steimann, M., Ströbele, M. & Walker, M. (2011). Z. Naturforsch. Teil B, 66, 545-548.]); Kuhn et al. (2009[Kuhn, N., Mallah, E., Maichle-Mössmer, C. & Steimann, M. (2009). Z. Naturforsch. Teil B, 64, 835-839.]); Potocenak & Chomic (2006[Potocenak, I. & Chomic, J. (2006). Transition Met. Chem. 31, 504-515.]); Mascal et al. (1996[Mascal, M., Richardson, J. L., Blake, A. J. & Li, W.-S. (1996). Tetrahedron Lett. 37, 3505-3506.]). For the synthesis of the starting material, see: Kuhn et al. (2004[Kuhn, N., Abu-Rayyan, A., Eichele, K., Schwarz, S. & Steimann, M. (2004). Inorg. Chim. Acta, 357, 1799-1804.]).

[Scheme 1]

Experimental

Crystal data

  • (C11H20BrN2)[Ag(CN)2)]

  • Mr = 420.11

  • Orthorhombic, P 21 21 21

  • a = 6.6986 (15) Å

  • b = 10.6222 (14) Å

  • c = 23.989 (4) Å

  • V = 1706.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.52 mm-1

  • T = 291 K

  • 0.40 × 0.20 × 0.20 mm
Data collection

  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: refined from [Delta]F (DIFABS; Walker & Stuart, 1983[Walker, N. & Stuart, D. (1983). Acta Cryst. A39, 158-166.]) Tmin = 0.41, Tmax = 1.00

  • 4327 measured reflections

  • 3475 independent reflections

  • 1781 reflections with I > 2[sigma](I)

  • Rint = 0.052

  • 3 standard reflections every 300 reflections intensity decay: 1.5%
Refinement

  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.082

  • S = 0.98

  • 3475 reflections

  • 180 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Data collection: CAD-4 Software; cell refinement: CELDIM (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software and CELDIM. Enraf-Nonius, Delft, The Netherlands.]); data reduction: HELENA/PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2020 ).

Acknowledgements

The authors are grateful to the Deutsche Forschungsgemeinschaft, the Higher Council for Science and Technology of Jordan and Petra University for financial support. We also thank Dr Cäcilia Maichle-Mössmer for helpful discussions.

References

Enraf-Nonius (1989). CAD-4 Software and CELDIM. Enraf-Nonius, Delft, The Netherlands.
Kuhn, N., Abu-Rayyan, A., Eichele, K., Schwarz, S. & Steimann, M. (2004). Inorg. Chim. Acta, 357, 1799-1804.  [ISI] [CSD] [CrossRef] [ChemPort]
Kuhn, N., Mallah, E., Maichle-Mössmer, C. & Steimann, M. (2009). Z. Naturforsch. Teil B, 64, 835-839.  [ChemPort]
Mallah, E., Abu-Salem, Q., Sweidan, K., Kuhn, N., Maichle-Mössmer, C., Steimann, M., Ströbele, M. & Walker, M. (2011). Z. Naturforsch. Teil B, 66, 545-548.  [ChemPort]
Mallah, E., Kuhn, N., Maichle-Mössmer, C., Steimann, M., Ströbele, M. & Zeller, K. P. (2009). Z. Naturforsch. Teil B, 64, 1176-1182.  [ChemPort]
Mascal, M., Richardson, J. L., Blake, A. J. & Li, W.-S. (1996). Tetrahedron Lett. 37, 3505-3506.  [CrossRef] [ChemPort] [ISI]
Potocenak, I. & Chomic, J. (2006). Transition Met. Chem. 31, 504-515.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Walker, N. & Stuart, D. (1983). Acta Cryst. A39, 158-166.  [CrossRef] [details]

Acta Cryst (2012). E68, m17  [ doi:10.1107/S1600536811051828 ]

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