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Volume 68 
Part 1 
Page o17  
January 2012  

Received 18 November 2011
Accepted 25 November 2011
Online 3 December 2011

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Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.034
wR = 0.086
Data-to-parameter ratio = 42.5
Details
Open access

1-Hexyl-1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecan-1-ium iodide

Augusto Rivera,a* John Sadat-Bernal,a Jaime Ríos-Motta,a Karla Fejfarováb and Michal Dusekb

aDepartamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Bogotá, Colombia, and bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

In the title compound, C13H27N4+·I-, the ethylene bridge is distorted from the ideal D2d symmetry wherein an N-C-C-N planar bridge, around whose C-C bond the C-N and C-H bonds are exactly eclipsed, is disordered over two sites with equal occupancies. In both disorder components, the hexyl chain adopts an ideal all-trans conformation. In the crystal, adjacent ions are connected by C-H...I hydrogen bonds, forming ionic pairs that are further linked into chains along [101] via a second C-H...I interaction.

Related literature

For related structures, see: Rivera et al. (2011a[Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2011a). Acta Cryst. E67, o2629.],b[Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Dusek, M. & Palatinus, L. (2011b). Chem. Cent. J. 5, article number 55.]). For the preparation of the title compound, see: Rivera et al. (2011b[Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Dusek, M. & Palatinus, L. (2011b). Chem. Cent. J. 5, article number 55.]). For synthetic applications of quaternary ammonium salts, see: Starks (1971[Starks, C. M. (1971). J. Am. Chem. Soc. 93, 195-199.]). 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

  • C13H27N4+·I-

  • Mr = 366.3

  • Monoclinic, P 21 /n

  • a = 8.4914 (4) Å

  • b = 16.1497 (6) Å

  • c = 11.8673 (6) Å

  • [beta] = 102.690 (5)°

  • V = 1587.65 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.01 mm-1

  • T = 120 K

  • 0.21 × 0.19 × 0.11 mm
Data collection

  • Agilent Xcalibur Atlas Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), Tmin = 0.930, Tmax = 1.000

  • 6803 measured reflections

  • 6795 independent reflections

  • 4959 reflections with I > 3[sigma](I)

  • Rint = 0.028
Refinement

  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.086

  • S = 1.23

  • 6795 reflections

  • 160 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1a...I1i 0.96 2.98 3.913 (3) 164
C3-H3b...I1ii 0.96 3.04 3.925 (2) 154
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: JANA2006.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2384 ).

Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work, as well as the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences of the Czech Republic.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
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.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Dusek, M. & Palatinus, L. (2011b). Chem. Cent. J. 5, article number 55.  [CrossRef]
Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2011a). Acta Cryst. E67, o2629.  [CSD] [CrossRef] [details]
Starks, C. M. (1971). J. Am. Chem. Soc. 93, 195-199.  [CrossRef] [ChemPort] [ISI]

Acta Cryst (2012). E68, o17  [ doi:10.1107/S1600536811050781 ]

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