3-(Ammonio­meth­yl)pyridinium dibromide

Ali, B.F.; Al-Far, R.; Haddad, S.F.

doi:10.1107/S1600536812040937

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 (C-C) = 0.005 Å
R = 0.036
wR = 0.070
Data-to-parameter ratio = 26.1
Details

3-(Ammoniomethyl)pyridinium dibromide

Basem F. Ali,^a ^* Rawhi Al-Far ^b and Salim F. Haddad ^c

^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 N_py-HBr, two C-HBr and three H₂N-HBr, 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); Desiraju (1997); Dolling et al. (2001); Gould et al. (1985); Hunter (1994); Hunter & Sanders (1990); Panunto et al. (1987); Robinson et al. (2000); Singh & Thornton (1990). For standard bond lengths, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₆H₁₀N₂⁺·2Br^-
M_r = 269.96
Monoclinic, P 2₁ /c
a = 11.1588 (6) Å
b = 9.3902 (5) Å
c = 9.3833 (5) Å
= 113.092 (6)°
V = 904.44 (9) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.143, T_max = 0.343
4032 measured reflections
2401 independent reflections
1641 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.070
S = 1.02
2401 reflections
92 parameters
H-atom parameters constrained
_max = 0.60 e Å^-3
_min = -0.50 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2BBr1	0.89	2.61	3.358 (3)	142
N2-H2CBr1ⁱ	0.89	2.69	3.330 (3)	130
N2-H2DBr1ⁱⁱ	0.89	2.49	3.348 (3)	161
N1-H1ABr2	0.86	2.41	3.206 (3)	155
C5-H5ABr2ⁱⁱⁱ	0.93	2.91	3.793 (4)	160
C6-H6ABr2^iv	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
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.
Desiraju, G. R. (1997). Chem. Commun. pp. 1475-1482.
Dolling, B., Gillon, A. L., Orpen, A. G., Starbuck, J. & Wang, X. M. (2001). Chem. Commun. pp. 567-568.
Gould, R. O., Gray, A. M., Taylor, P. & Walkinshaw, M. D. (1985). J. Am. Chem. Soc. 107, 5921-5927.
Hunter, C. A. (1994). Chem. Soc. Rev. 23, 101-109.
Hunter, C. A. & Sanders, J. K. M. (1990). J. Am. Chem. Soc. 112, 5525-5534.
Panunto, T. W., Urbanczyk-Lipkowska, Z., Johnson, R. & Etter, M. C. (1987). J. Am. Chem. Soc. 109, 7786-7797.
Robinson, J. M. A., Philp, D., Harris, K. D. M. & Kariuki, B. M. (2000). New J. Chem. 24, 799-806.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, J. & Thornton, J. M. (1990). J. Mol. Biol. 211, 595-615.

organic compounds