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Volume 68 
Part 11 
Page o3066  
November 2012  

Received 6 September 2012
Accepted 28 September 2012
Online 3 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.036
wR = 0.070
Data-to-parameter ratio = 26.1
Details
Open access

3-(Ammoniomethyl)pyridinium dibromide

aDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan,bFaculty of Science and IT, Al-Balqa'a Applied University, Salt, Jordan, and cDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan
Correspondence e-mail: bfali@aabu.edu.jo

In the title salt, C6H10N22+·2Br-, the non-H atoms of the 3-methylpyridinium unit of the cation are almost coplanar (r.m.s. deviation = 0.0052 Å). In the crystal, the dications and Br anions are linked by a combination of six hydrogen bonds, viz. one Npy-H...Br, two C-H...Br and three H2N-H...Br, into supramolecular layers, parallel to the bc plane, composed of alternating R24(10) and R24(8) loops. Weak [pi]-[pi] interactions between cationic rings with centroid-centroid distances of 3.891 (2) Å are also observed.

Related literature

For non-covalent interactions, see: Allen et al. (1997[Allen, F. H., Hoy, V. J., Howard, J. A. K., Thalladi, V. R., Desiraju, G. R., Wilson, C. C. & McIntyre, G. J. (1997). J. Am. Chem. Soc. 119, 3477-3480.]); Desiraju (1997[Desiraju, G. R. (1997). Chem. Commun. pp. 1475-1482.]); Dolling et al. (2001[Dolling, B., Gillon, A. L., Orpen, A. G., Starbuck, J. & Wang, X. M. (2001). Chem. Commun. pp. 567-568.]); Gould et al. (1985[Gould, R. O., Gray, A. M., Taylor, P. & Walkinshaw, M. D. (1985). J. Am. Chem. Soc. 107, 5921-5927.]); Hunter (1994[Hunter, C. A. (1994). Chem. Soc. Rev. 23, 101-109.]); Hunter & Sanders (1990[Hunter, C. A. & Sanders, J. K. M. (1990). J. Am. Chem. Soc. 112, 5525-5534.]); Panunto et al. (1987[Panunto, T. W., Urbanczyk-Lipkowska, Z., Johnson, R. & Etter, M. C. (1987). J. Am. Chem. Soc. 109, 7786-7797.]); Robinson et al. (2000[Robinson, J. M. A., Philp, D., Harris, K. D. M. & Kariuki, B. M. (2000). New J. Chem. 24, 799-806.]); Singh & Thornton (1990[Singh, J. & Thornton, J. M. (1990). J. Mol. Biol. 211, 595-615.]). For standard bond lengths, 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.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C6H10N2+·2Br-

  • Mr = 269.96

  • Monoclinic, P 21 /c

  • a = 11.1588 (6) Å

  • b = 9.3902 (5) Å

  • c = 9.3833 (5) Å

  • [beta] = 113.092 (6)°

  • V = 904.44 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 8.90 mm-1

  • T = 293 K

  • 0.23 × 0.18 × 0.12 mm

Data collection
  • Agilent Xcalibur EOS diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.143, Tmax = 0.343

  • 4032 measured reflections

  • 2401 independent reflections

  • 1641 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.070

  • S = 1.02

  • 2401 reflections

  • 92 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2B...Br1 0.89 2.61 3.358 (3) 142
N2-H2C...Br1i 0.89 2.69 3.330 (3) 130
N2-H2D...Br1ii 0.89 2.49 3.348 (3) 161
N1-H1A...Br2 0.86 2.41 3.206 (3) 155
C5-H5A...Br2iii 0.93 2.91 3.793 (4) 160
C6-H6A...Br2iv 0.93 2.89 3.619 (4) 136
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x+2, -y+1, -z+2; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: IM2401 ).


Acknowledgements

The structure was determined at the Hamdi Mango Center for Scientific Research at the University of Jordan, Amman. RA-F would like to thank Al-Balqa'a Applied University (Jordan) for financial support (sabbatical leave).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Allen, F. H., Hoy, V. J., Howard, J. A. K., Thalladi, V. R., Desiraju, G. R., Wilson, C. C. & McIntyre, G. J. (1997). J. Am. Chem. Soc. 119, 3477-3480.  [CrossRef] [ChemPort] [ISI]
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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Desiraju, G. R. (1997). Chem. Commun. pp. 1475-1482.  [CrossRef]
Dolling, B., Gillon, A. L., Orpen, A. G., Starbuck, J. & Wang, X. M. (2001). Chem. Commun. pp. 567-568.  [CSD] [CrossRef]
Gould, R. O., Gray, A. M., Taylor, P. & Walkinshaw, M. D. (1985). J. Am. Chem. Soc. 107, 5921-5927.  [CrossRef] [ChemPort] [ISI]
Hunter, C. A. (1994). Chem. Soc. Rev. 23, 101-109.  [CrossRef] [ChemPort] [ISI]
Hunter, C. A. & Sanders, J. K. M. (1990). J. Am. Chem. Soc. 112, 5525-5534.  [CrossRef] [ChemPort] [ISI]
Panunto, T. W., Urbanczyk-Lipkowska, Z., Johnson, R. & Etter, M. C. (1987). J. Am. Chem. Soc. 109, 7786-7797.  [CrossRef] [ChemPort] [ISI]
Robinson, J. M. A., Philp, D., Harris, K. D. M. & Kariuki, B. M. (2000). New J. Chem. 24, 799-806.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, J. & Thornton, J. M. (1990). J. Mol. Biol. 211, 595-615.  [CrossRef] [ChemPort] [PubMed] [ISI]


Acta Cryst (2012). E68, o3066  [ doi:10.1107/S1600536812040937 ]

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