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Volume 69 
Part 6 
Page o884  
June 2013  

Received 29 April 2013
Accepted 7 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.004 Å
R = 0.023
wR = 0.053
Data-to-parameter ratio = 18.5
Details
Open access

1-Allyl-2-aminopyridin-1-ium bromide

aDepartment of Physics, Government Arts College (Autonomous), Karur 639 005, India,bSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, India,cFaculty of Health and Life Sciences, Coventry University, Coventry CV1 5FB, England, and dDepartment of Bioinformatics, School of Chemical and Biotechnology, SASTRA University, Thanjavur 613 401, India
Correspondence e-mail: thamu@scbt.sastra.edu

In the cation of the title salt, C8H11N2+·Br-, the dihedral angle between the planes of the pyridinium ring and the allyl group is 79.4 (3)°. In the crystal, N-H...Br and weak C-H...Br hydrogen bonds link the cations and anions, forming chains of alternating R21(7) and R42(8) rings, which run parallel to the c-axis direction. The crystal studied was an inversion twin with components in a 0.753 (12):0.247 (12) ratio.

Related literature

For related structures, see: Seethalakshmi et al. (2006a[Seethalakshmi, T., Kaliannan, P., Venkatesan, P., Fronczek, F. R. & Thamotharan, S. (2006a). Acta Cryst. E62, o2353-o2355.],b[Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006b). Acta Cryst. E62, o2560-o2562.],c[Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006c). Acta Cryst. E62, o3389-o3390.], 2007[Seethalakshmi, T., Manivannan, S., Lynch, D. E., Dhanuskodi, S. & Kaliannan, P. (2007). Acta Cryst. E63, o599-o601.], 2013[Seethalakshmi, T., Manivannan, S., Dhanuskodi, S., Lynch, D. E. & Thamotharan, S. (2013). Acta Cryst. E69, o835-o836.]). For the biolgical activity of alkyl-pyridinium salts, see: Sundararaman et al. (2013[Sundararaman, M., Rajesh Kumar, R., Venkatesan, P. & Ilangovan, A. (2013). J. Med. Microbiol. 62, 241-248.]); Ilangovan et al. (2012[Ilangovan, A., Venkatesan, P., Sundararaman, M. & Rejesh Kumar, R. (2012). Med. Chem. Res. 21, 694-702.]). For hydrogen-bond graph-set motifs, 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
  • C8H11N2+·Br-

  • Mr = 215.10

  • Orthorhombic, P n a 21

  • a = 7.8205 (2) Å

  • b = 13.3560 (3) Å

  • c = 8.5621 (2) Å

  • V = 894.32 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.53 mm-1

  • T = 120 K

  • 0.30 × 0.14 × 0.03 mm

Data collection
  • Bruker-Nonius 95mm CCD camera on [kappa]-goniostat diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.343, Tmax = 0.876

  • 14540 measured reflections

  • 2033 independent reflections

  • 1960 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.023

  • wR(F2) = 0.053

  • S = 1.06

  • 2033 reflections

  • 110 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 945 Friedel pairs

  • Flack parameter: 0.247 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...Br1i 0.84 (2) 2.61 (2) 3.412 (2) 160 (4)
N2-H2B...Br1ii 0.85 (2) 2.51 (2) 3.357 (2) 175 (3)
C6-H6A...Br1iii 0.99 2.91 3.668 (3) 134
C6-H6B...Br1i 0.99 2.84 3.810 (3) 167
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5611 ).


Acknowledgements

The authors thank the EPSRC National Crystallography Service (University of Southampton, UK) for the X-ray data collection and Professor P. Kaliannan for his help. ST thanks the management of SASTRA University for their encouragement.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Ilangovan, A., Venkatesan, P., Sundararaman, M. & Rejesh Kumar, R. (2012). Med. Chem. Res. 21, 694-702.  [ISI] [CrossRef] [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307-326. New York: Academic Press.
Seethalakshmi, T., Kaliannan, P., Venkatesan, P., Fronczek, F. R. & Thamotharan, S. (2006a). Acta Cryst. E62, o2353-o2355.  [CSD] [CrossRef] [ChemPort] [details]
Seethalakshmi, T., Manivannan, S., Dhanuskodi, S., Lynch, D. E. & Thamotharan, S. (2013). Acta Cryst. E69, o835-o836.  [CrossRef] [details]
Seethalakshmi, T., Manivannan, S., Lynch, D. E., Dhanuskodi, S. & Kaliannan, P. (2007). Acta Cryst. E63, o599-o601.  [CSD] [CrossRef] [ChemPort] [details]
Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006b). Acta Cryst. E62, o2560-o2562.  [CSD] [CrossRef] [ChemPort] [details]
Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006c). Acta Cryst. E62, o3389-o3390.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Sundararaman, M., Rajesh Kumar, R., Venkatesan, P. & Ilangovan, A. (2013). J. Med. Microbiol. 62, 241-248.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o884  [ doi:10.1107/S1600536813012452 ]

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