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Volume 66 
Part 11 
Pages o2797-o2798  
November 2010  

Received 30 September 2010
Accepted 7 October 2010
Online 13 October 2010

[lh5143sup1]
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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.046
wR = 0.122
Data-to-parameter ratio = 23.2
Details
Open access

3,5-Bis(3-butylimidazolium-1-ylmethyl)toluene bis(hexafluorophosphate)

Rosenani A. Haque,a Abbas Washeel,a Siang Guan Teoh,a Ching Kheng Quahb+ and Hoong-Kun Funb*++

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound [systematic name: 3,3'-Dibutyl-1,1'-(5-methyl-m-phenylenedimethylene)diimidazol-1-ium bis(hexafluoridophosphate)], C23H34N42+·2PF6-, the imidazole rings are inclined at angles of 68.06 (7) and 75.05 (8)° with respect to the central benzene ring. In the crystal, molecules are linked into one-dimensional columns along [010] via weak intermolecular C-H...F hydrogen bonds. The crystal structure is further consolidated by weak C-H...[pi](arene) interactions. One of the n-butyl groups is disordered over two sites with refined occupancies of 0.694 (5) and 0.306 (5). In addition, four of the F atoms of one of the PF6- cations are disordered over two sites with occupancies of 0.64 (3) and 0.36 (3).

Related literature

For general background to imidazoline-2-ylidenes, see: Arduengo et al. (1991[Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.]). For the organometallic and coordination chemistry of N-heterocyclic carbene ligands, see: Chen et al. (2002[Chen, W., Wu, B. & Matsumoto, K. (2002). J. Organomet. Chem. 654, 233-236.]); Zhou et al. (2008[Zhou, Y., Zhang, X., Chen, W. & Qiu, H. (2008). J. Organomet. Chem. 693, 205-215.]); Hahn & Jahnke (2008[Hahn, F. E. & Jahnke, M. C. (2008). Angew. Chem. Int. Ed. Engl. 47, 3122-3172.]); Danopoulos et al. (2007[Danopoulos, A. A., Tsoureas, N., Macgregor, S. A. & Smith, C. (2007). Organometallics, 26, 253-263.]); Bourissou et al. (2000[Bourissou, D., Guerret, O., Gabbai, F. P. & Bertrand, G. (2000). Chem. Rev. 100, 39-91.]); McGuinness & Cavell (2000[McGuinness, D. S. & Cavell, K. J. (2000). Organometallics, 19, 741-748.]); Garrison et al. (2001[Garrison, J. C., Simons, R. S., Talley, J. M., Wesdemiotis, C., Tessier, C. A. & Youngs, W. J. (2001). Organometallics, 20, 1276-1278.]). For catalytic studies related to organic synthesis, see: Cavell & McGuinness (2004[Cavell, K. J. & McGuinness, D. S. (2004). Coord. Chem. Rev. 248, 671-681.]); Liu et al. (2007[Liu, Q.-X., Zhao, X.-J., Wu, X.-M., Guo, J.-H. & Wang, X.-G. (2007). J. Organomet. Chem. 692, 5671-5679.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C23H34N42+·2PF6-

  • Mr = 656.48

  • Monoclinic, P 21 /c

  • a = 9.6207 (1) Å

  • b = 11.1801 (1) Å

  • c = 27.9277 (3) Å

  • [beta] = 102.416 (1)°

  • V = 2933.66 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 100 K

  • 0.49 × 0.20 × 0.14 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.890, Tmax = 0.967

  • 45569 measured reflections

  • 10399 independent reflections

  • 7294 reflections with I > 2[sigma](I)

  • Rint = 0.040
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.122

  • S = 1.03

  • 10399 reflections

  • 448 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 phenyl ring.
D-H...A D-H H...A D...A D-H...A
C8-H8A...F4 0.93 2.42 3.0154 (16) 121
C8-H8A...F5 0.93 2.39 3.2700 (16) 157
C16-H16A...F3 0.93 2.31 3.1941 (16) 160
C16-H16A...F4 0.93 2.45 3.1677 (16) 134
C21A-H21B...F4 0.97 2.49 3.196 (2) 130
C3-H3A...F12i 0.93 2.44 3.3147 (16) 157
C5-H5A...F9Aii 0.93 2.55 3.420 (8) 156
C7-H7A...F10Aii 0.97 2.51 3.427 (6) 158
C9-H9A...F12iii 0.93 2.48 3.2805 (17) 144
C12-H12A...F3iv 0.97 2.53 3.3358 (18) 140
C18-H18A...F8Av 0.93 2.38 3.148 (11) 140
C22A-H22C...Cg1vi 0.96 2.76 3.535 (3) 138
C23-H23B...Cg1vii 0.96 2.59 3.487 (2) 155
C22B-H22E...Cg1vi 0.96 2.86 3.637 (8) 139
Symmetry codes: (i) x-1, y+1, z; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+2; (iv) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) -x+1, -y+2, -z+2; (vi) x+1, y, z; (vii) -x, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5143 ).

Acknowledgements

RAH, AW and SGT thank Universiti Sains Malaysia (USM) for the FRGS fund (203/PKIMIA/671115), the short term grant (304/PKIMIA/639001) and the Research University Grant (1001/PKIMIA/813023). HKF and CKQ thank USM for the Research University Grant (1001/PFIZIK/811160) and CKQ also thanks USM for a research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.  [CrossRef] [ChemPort] [ISI]
Bourissou, D., Guerret, O., Gabbai, F. P. & Bertrand, G. (2000). Chem. Rev. 100, 39-91.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cavell, K. J. & McGuinness, D. S. (2004). Coord. Chem. Rev. 248, 671-681.  [ISI] [CrossRef] [ChemPort]
Chen, W., Wu, B. & Matsumoto, K. (2002). J. Organomet. Chem. 654, 233-236.  [CSD] [CrossRef] [ChemPort]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Danopoulos, A. A., Tsoureas, N., Macgregor, S. A. & Smith, C. (2007). Organometallics, 26, 253-263.  [CSD] [CrossRef] [ChemPort]
Garrison, J. C., Simons, R. S., Talley, J. M., Wesdemiotis, C., Tessier, C. A. & Youngs, W. J. (2001). Organometallics, 20, 1276-1278.  [CrossRef] [ChemPort]
Hahn, F. E. & Jahnke, M. C. (2008). Angew. Chem. Int. Ed. Engl. 47, 3122-3172.  [ISI] [CrossRef] [PubMed] [ChemPort]
Liu, Q.-X., Zhao, X.-J., Wu, X.-M., Guo, J.-H. & Wang, X.-G. (2007). J. Organomet. Chem. 692, 5671-5679.  [CrossRef] [ChemPort]
McGuinness, D. S. & Cavell, K. J. (2000). Organometallics, 19, 741-748.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zhou, Y., Zhang, X., Chen, W. & Qiu, H. (2008). J. Organomet. Chem. 693, 205-215.  [CSD] [CrossRef] [ChemPort]

Acta Cryst (2010). E66, o2797-o2798   [ doi:10.1107/S1600536810040055 ]

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