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Volume 69 
Part 6 
Page o843  
June 2013  

Received 17 April 2013
Accepted 2 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.148
Data-to-parameter ratio = 21.5
Details
Open access

3-(Ammoniomethyl)pyridinium bis(perchlorate)

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Tunisia, and bCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal
Correspondence e-mail: cherif_bennasr@yahoo.fr

In the title molecular salt, C6H10N22+·2ClO4-, the Cl-O bond lengths [anion 1: 1.369 (3)-1.415 (3); anion 2: 1.420 (2)-1.441 (2) Å] and the O-Cl-O angles [anion 1: 105.4 (2)-111.8 (4); anion 2: 107.8 (1)-110.3 (1)°] indicate a slight distortion of the perchlorate anions from regular tetrahedral symmetry. In the crystal, the components are linked into columns along the a-axis direction via N-H...O and C-H...O hydrogen bonds, with stacks of the organic molecules being surrounded by stacks of perchlorate anions.

Related literature

For general background to perchlorate salts with organic cations, see: Czarnecki et al. (1994[Czarnecki, P., Nawrocik, W., Pajaxk, Z. & Nawrocik, J. (1994). J. Phys. Condens. Matter, 6, 4955-4960.]); Czupinski et al. (2002[Czupinski, O., Bator, G., Ciunik, Z., Jakubas, R., Medycki, W. & Wiergiel, J. S. (2002). J. Phys. Condens. Matter, 14, 8497-8512.], 2006[Czupinski, O., Wojtas, M., Zaleski, J., Jakubas, R. & Medycki, W. (2006). J. Phys. Condens. Matter, 88, 3307-3324.]). For related structures, see: Kapplinger & Keutel (1999[Kapplinger, E.-G. J. I. & Keutel, H. (1999). Inorg. Chim. Acta, C291, 190-206.]); Ye et al. (2002[Ye, M.-D., Hu, M.-L. & Ye, C.-P. (2002). Z. Kristallogr. New Cryst. Struct. 217, 501-502.])

[Scheme 1]

Experimental

Crystal data
  • C6H10N22+·2ClO4-

  • Mr = 309.06

  • Monoclinic, P 21 /c

  • a = 5.1947 (1) Å

  • b = 12.1221 (3) Å

  • c = 18.2724 (5) Å

  • [beta] = 98.067 (1)°

  • V = 1139.24 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.61 mm-1

  • T = 293 K

  • 0.44 × 0.33 × 0.22 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.765, Tmax = 0.875

  • 26338 measured reflections

  • 3509 independent reflections

  • 3007 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.148

  • S = 1.06

  • 3509 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.75 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O5 0.86 2.16 2.901 (3) 144
N1-H1...O7i 0.86 2.36 2.945 (3) 125
N2-H2A...O2ii 0.89 2.09 2.866 (3) 146
N2-H2A...O6iii 0.89 2.54 3.166 (3) 128
N2-H2B...O6ii 0.89 2.10 2.925 (3) 155
N2-H2B...O3iv 0.89 2.47 2.922 (4) 112
N2-H2C...O1v 0.89 2.08 2.933 (3) 160
C5-H5...O1vi 0.93 2.54 3.350 (4) 145
C6-H6A...O8vii 0.97 2.50 3.137 (3) 123
Symmetry codes: (i) x-1, y, z; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) x+1, y, z; (vii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2003[Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). 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: 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: LR2104 ).


Acknowledgements

We would like to acknowledge the support provided by the Secretary of State for Scientific Research and Technology of Tunisia. PSPS acknowledges support by the Fundação para a Ciência e a Tecnologia (FCT), under scholarship SFRH/BPD/84173/2012.

References

Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Czarnecki, P., Nawrocik, W., Pajaxk, Z. & Nawrocik, J. (1994). J. Phys. Condens. Matter, 6, 4955-4960.  [CrossRef] [ChemPort] [ISI]
Czupinski, O., Bator, G., Ciunik, Z., Jakubas, R., Medycki, W. & Wiergiel, J. S. (2002). J. Phys. Condens. Matter, 14, 8497-8512.  [ISI] [CSD] [CrossRef] [ChemPort]
Czupinski, O., Wojtas, M., Zaleski, J., Jakubas, R. & Medycki, W. (2006). J. Phys. Condens. Matter, 88, 3307-3324.  [ISI] [CSD] [CrossRef]
Kapplinger, E.-G. J. I. & Keutel, H. (1999). Inorg. Chim. Acta, C291, 190-206.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
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]
Ye, M.-D., Hu, M.-L. & Ye, C.-P. (2002). Z. Kristallogr. New Cryst. Struct. 217, 501-502.  [ChemPort]


Acta Cryst (2013). E69, o843  [ doi:10.1107/S1600536813012038 ]

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