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Volume 69 
Part 8 
Page o1325  
August 2013  

Received 18 July 2013
Accepted 22 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
Disorder in solvent or counterion
R = 0.077
wR = 0.247
Data-to-parameter ratio = 11.6
Details
Open access

1,3-Bis[(5-aminofuran-2-yl)methyl]-3,4,5,6-tetrahydropyrimidin-1-ium hexafluorophosphate

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cDepartment of Chemistry, Faculty of Arts and Sciences, Inönü University, 44280, Malatya, Turkey, and dDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The asymmetric unit of the title salt, C16H21N2O2+·PF6-, contains half of the whole ion pair, which has crystallographic mirror symmetry. Two F atoms related by the mirror plane are disordered over two sites of equal occupancy. The dihedral angle between the central ring and the furan ring is 59.3 ()°. In the crystal, the anions and cations are linked through C-H...F interactions, forming a three-dimensional network.

Related literature

N-heterocyclic carbene (NHC)-metal complexes have attracted much attention, particularly for their functions in catalytic reactions, see: Akkoç & Gök (2013[Akkoç, S. & Gök, Y. (2013). J. Coord. Chem. 66, 1396-1404.]); Arduengo et al. (1992[Arduengo, A. J., Rasika, H. V., Harlow, R. L. & Kline, M. J. (1992). J. Am. Chem. Soc. 114, 5530-5534.]); Bagherzadeh et al. (2012[Bagherzadeh, M., Amini, M., Ellero, A. & Woo, L. K. (2012). Inorg. Chim. Acta, 383, 46-51.]); Hermann (2002[Hermann, W. A. (2002). Angew. Chem. Int. Ed. 41, 1290-1309.]); Lee et al. (2013[Lee, C. S., Lai, Y. B., Lin, W. J., Zhuang, R. R. & Hwang, W. S. (2013). J. Organomet. Chem. 724, 235-243.]); Saba et al. (1991[Saba, S., Brescia, A. & Kaloustian, M. K. (1991). Tetrahedron Lett. 32, 5031-5034.]); Yigit et al. (2007[Yigit, M., Özdemir, I., Çetinkaya, E. & Çetinkaya, B. (2007). Transition Met. Chem. 32, 536-540.]); Özdemir et al. (2001[Özdemir, I., Yigit, B., Çetinkaya, B., Ülkü, D., Tahir, M. N. & Arici, C. (2001). J. Organomet. Chem. 633, 27-32.]); Çetinkaya et al. (1997[Çetinkaya, B., Özdemir, I., Bruneau, C. & Dixneuf, P. H. (1997). J. Mol. Catal. A Chem. 118, L1-L4.]). For 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
  • C16H21N2O2+·PF6-

  • Mr = 418.32

  • Monoclinic, P 21 /m

  • a = 6.0793 (6) Å

  • b = 18.879 (2) Å

  • c = 8.5750 (9) Å

  • [beta] = 100.747 (5)°

  • V = 966.90 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 296 K

  • 0.35 × 0.28 × 0.23 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: part of the refinement model ([Delta]F) (XABS2; Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) Tmin = 0.932, Tmax = 0.953

  • 1677 measured reflections

  • 1677 independent reflections

  • 1089 reflections with I > 2[sigma](I)

  • Rint = 0.000

Refinement
  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.247

  • S = 1.08

  • 1677 reflections

  • 144 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...F2i 0.93 2.40 3.312 (8) 167
C1-H1...F4ii 0.93 2.52 3.044 (8) 116
Symmetry codes: (i) x, y, z-1; (ii) x-1, y, z-1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5332 ).


Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Akkoç, S. & Gök, Y. (2013). J. Coord. Chem. 66, 1396-1404.
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., Rasika, H. V., Harlow, R. L. & Kline, M. J. (1992). J. Am. Chem. Soc. 114, 5530-5534.  [CrossRef] [ChemPort]
Bagherzadeh, M., Amini, M., Ellero, A. & Woo, L. K. (2012). Inorg. Chim. Acta, 383, 46-51.  [CrossRef] [ChemPort]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Çetinkaya, B., Özdemir, I., Bruneau, C. & Dixneuf, P. H. (1997). J. Mol. Catal. A Chem. 118, L1-L4.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hermann, W. A. (2002). Angew. Chem. Int. Ed. 41, 1290-1309.  [CrossRef]
Lee, C. S., Lai, Y. B., Lin, W. J., Zhuang, R. R. & Hwang, W. S. (2013). J. Organomet. Chem. 724, 235-243.  [CrossRef] [ChemPort]
Özdemir, I., Yigit, B., Çetinkaya, B., Ülkü, D., Tahir, M. N. & Arici, C. (2001). J. Organomet. Chem. 633, 27-32.
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Saba, S., Brescia, A. & Kaloustian, M. K. (1991). Tetrahedron Lett. 32, 5031-5034.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yigit, M., Özdemir, I., Çetinkaya, E. & Çetinkaya, B. (2007). Transition Met. Chem. 32, 536-540.


Acta Cryst (2013). E69, o1325  [ doi:10.1107/S1600536813020187 ]

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