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

Rivera, A.; Sadat-Bernal, J.; Ríos-Motta, J.; Fejfarová, K.; Dušek, M.

doi:10.1107/S1600536811036403

Volume 67
Part 10
Page o2629
October 2011

Received 31 August 2011
Accepted 6 September 2011
Online 14 September 2011

Key indicators
Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.004 Å
R = 0.027
wR = 0.065
Data-to-parameter ratio = 24.2
Details

1-Heptyl-1,3,6,8-tetraazatricyclo[4.3.1.1^3,8]undecan-1-ium iodide

Augusto Rivera,^a ^* John Sadat-Bernal,^a Jaime Ríos-Motta,^a Karla Fejfarová ^b and Michal Dusek ^b

^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

The title compound C₁₄H₂₉N₄⁺·I^- salt, was obtained by the reaction of cage adamanzane-type aminal 1,3,6,8-tetraazatricyclo[4.3.1.1^3,8]undecane with heptyl iodide. In the cation, the bond lengths and angles are within normal ranges, except for one N-C(ring) bond distance of 1.542 (3) Å, which is unexpectedly long compared with related compounds. In the crystal, ions are linked through C-HI hydrogen bonds. The crystal studied was a non-merohedral twin with a minor twin domain of 6.56 (5)%.

Related literature

For the preparation of the title compound, see: Rivera et al. (2011). For synthetic applications of quaternary ammonium salts, see: Starks (1971). For related structures, see: Betz & Klüfers (2007); Lee et al. (2011).

Experimental

Crystal data

C₁₄H₂₉N₄⁺·I^-
M_r = 380.3
Monoclinic, P 2₁ /n
a = 8.8325 (2) Å
b = 15.3276 (3) Å
c = 12.4792 (2) Å
= 100.072 (2)°
V = 1663.41 (6) Å³
Z = 4
Mo K radiation
= 1.92 mm^-1
T = 160 K
0.31 × 0.24 × 0.16 mm

Data collection

Agilent Xcalibur diffractometer with Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.871, T_max = 1
22619 measured reflections
4183 independent reflections
3517 reflections with I > 3(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.065
S = 1.61
4183 reflections
173 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2aI1ⁱ	0.96	2.94	3.858 (2)	161
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006); molecular graphics: Diamond (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2371 ).

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 the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the project Praemium Academiae of the Academy of Science of the Czech Republic. JS-B acknowledges the Facultad de Ciencias de la Universidad Nacional de Colombia for a fellowship.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Betz, R. & Klüfers, P. (2007). Acta Cryst. E63, o4279.
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.
Lee, J.-D., Han, W.-S., Suh, I.-H. & Kang, S. O. (2011). Acta Cryst. E67, o2148.
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. (2011). Chem. Cent. J. Submitted.
Starks, C. M. (1971). J. Am. Chem. Soc. 93, 195-199.

organic compounds

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