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Volume 68 
Part 12 
Pages o3284-o3285  
December 2012  

Received 8 June 2012
Accepted 30 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.054
wR = 0.142
Data-to-parameter ratio = 28.0
Details
Open access

Tetrabutylammonium 2-[2,5-dimethyl-3-(4-nitrophenyl)-2,3-dihydro-1,2,4-oxadiazolium-4-yl]nonahydro-closo-decaborate

aDepartment of Chemistry, Saint-Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation,bDepartment of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska str. 62, Kiev 01601, Ukraine, and cN. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Pr., 119991 Moscow, Russian Federation
Correspondence e-mail: annpavlis@ukr.net,

The title ionic compound, C16H36N+·C10H20B10N3O3-, consists of a tetrabutylammonium cation and a closo-decaborate cluster anion, which is bound to the substituted 2,3-dihydro-1,2,4-oxadiazole ring through a B-N bond [1.540 (2) Å]. The distances between connected B atoms in the decaborate cluster range from 1.689 (2) to 1.844 (2) Å. The 2,3-dihydro-1,2,4-oxadiazole ring adopts an envelope conformation with the N atom as the flap atom.

Related literature

For related structures and background, see: Mindich et al. (2012[Mindich, A. L., Bokach, N. A., Dolgushin, F. M., Haukka, M., Lisitsyn, L. A., Zhdanov, A. P. & Zhizhin, K. Y. (2012). Organometallics, 31, 1716-1724.]). For examples of substituted 1,2,4-oxadiazoles, their complexes and properties, see: Kritchenkov et al. (2012[Kritchenkov, A. S., Bokach, N. A., Kuznetsov, M. L., Dolgushin, F. M., Tung, T. Q., Molchanov, A. P. & Kukushkin, V. Y. (2012). Organometallics, 31, 687-699.]); Bokach et al. (2011a[Bokach, N. A., Balova, I. A., Haukka, M. & Kukushkin, V. Y. (2011a). Organometallics, 30, 595-602.],b[Bokach, N. A., Kuznetsov, M. L. & Kukushkin, V. Y. (2011b). Coord. Chem. Rev. 255, 2946-2967.]); Makarycheva-Mikhailova et al. (2007[Makarycheva-Mikhailova, A. V., Golenetskaya, J. A., Bokach, N. A., Balova, I. A., Haukka, M. & Kukushkin, V. Y. (2007). Inorg. Chem. 46, 8323-8331.]); Kukushkin & Pombeiro (2002[Kukushkin, V. Y. & Pombeiro, A. J. L. (2002). Chem. Rev. 102, 1771-1802.]); Kritchenkov et al. (2011[Kritchenkov, A. S., Bokach, N. A., Haukka, M. & Kukushkin, V. Y. (2011). Dalton Trans. 40, 4175-4182.]); Bokach (2010[Bokach, N. A. (2010). Russ. Chem. Rev. 79, 89-100.]); Sivaev et al. (2002[Sivaev, I. B., Votinova, N. A., Bragin, V. I., Starikova, Z. A., Goeva, L. V., Bregadze, V. I. & Sjoberg, S. (2002). J. Organomet. Chem. 657, 163-170.], 2008[Sivaev, I. B., Kulikova, N. Y., Nizhnik, E. A., Vichuzhanin, M. V., Starikova, Z. A., Semioshkin, A. A. & Bregadze, V. I. (2008). J. Organomet. Chem. 693, 519-525.]). For propeties and structure examples of boron clusters, see: Dash et al. (2011[Dash, B. P., Satapathy, R., Maguire, J. A. & Hosmane, N. S. (2011). New J. Chem. 35, 1955-1972.]); Dou et al. (1994[Dou, D., Mavunkal, I. J., Bauer, J. A. K., Knobler, C. B., Hawthorne, M. F. & Shore, S. G. (1994). Inorg. Chem. 33, 6432-6434.]).

[Scheme 1]

Experimental

Crystal data
  • C16H36N+·C10H20B10N3O3-

  • Mr = 580.85

  • Monoclinic, P 21 /n

  • a = 8.7356 (4) Å

  • b = 15.8691 (6) Å

  • c = 24.7015 (10) Å

  • [beta] = 98.206 (1)°

  • V = 3389.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.35 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.161, Tmax = 0.374

  • 35977 measured reflections

  • 10868 independent reflections

  • 6806 reflections with I > 2[sigma](I)

  • Rint = 0.086

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.142

  • S = 0.94

  • 10868 reflections

  • 388 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2067 ).


Acknowledgements

This work was supported by the Russian Fund for Basic Research (grants11-03-00262 and 11-03-90417), the Federal Targeted Program Scientific and Scientific-Pedagogical Personnel of Innovative Russia in 2009-2013 (contract P1294 from 09/06/2010) and the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041). ALM expresses his gratitude to the Government of Saint-Petersburg for a grant for graduate and undergraduate students (2011). Financial support from the Visby Program through the Swedish Institute is gratefully acknowledged.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bokach, N. A. (2010). Russ. Chem. Rev. 79, 89-100.  [CrossRef] [ChemPort]
Bokach, N. A., Balova, I. A., Haukka, M. & Kukushkin, V. Y. (2011a). Organometallics, 30, 595-602.  [CSD] [CrossRef] [ChemPort]
Bokach, N. A., Kuznetsov, M. L. & Kukushkin, V. Y. (2011b). Coord. Chem. Rev. 255, 2946-2967.  [ISI] [CrossRef] [ChemPort]
Bruker (2005). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dash, B. P., Satapathy, R., Maguire, J. A. & Hosmane, N. S. (2011). New J. Chem. 35, 1955-1972.  [ISI] [CrossRef] [ChemPort]
Dou, D., Mavunkal, I. J., Bauer, J. A. K., Knobler, C. B., Hawthorne, M. F. & Shore, S. G. (1994). Inorg. Chem. 33, 6432-6434.  [CrossRef] [ChemPort] [ISI]
Kritchenkov, A. S., Bokach, N. A., Haukka, M. & Kukushkin, V. Y. (2011). Dalton Trans. 40, 4175-4182.  [CSD] [CrossRef] [ChemPort] [PubMed]
Kritchenkov, A. S., Bokach, N. A., Kuznetsov, M. L., Dolgushin, F. M., Tung, T. Q., Molchanov, A. P. & Kukushkin, V. Y. (2012). Organometallics, 31, 687-699.  [CSD] [CrossRef] [ChemPort]
Kukushkin, V. Y. & Pombeiro, A. J. L. (2002). Chem. Rev. 102, 1771-1802.  [ISI] [CrossRef] [PubMed] [ChemPort]
Makarycheva-Mikhailova, A. V., Golenetskaya, J. A., Bokach, N. A., Balova, I. A., Haukka, M. & Kukushkin, V. Y. (2007). Inorg. Chem. 46, 8323-8331.  [ISI] [PubMed] [ChemPort]
Mindich, A. L., Bokach, N. A., Dolgushin, F. M., Haukka, M., Lisitsyn, L. A., Zhdanov, A. P. & Zhizhin, K. Y. (2012). Organometallics, 31, 1716-1724.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sivaev, I. B., Kulikova, N. Y., Nizhnik, E. A., Vichuzhanin, M. V., Starikova, Z. A., Semioshkin, A. A. & Bregadze, V. I. (2008). J. Organomet. Chem. 693, 519-525.  [CSD] [CrossRef] [ChemPort]
Sivaev, I. B., Votinova, N. A., Bragin, V. I., Starikova, Z. A., Goeva, L. V., Bregadze, V. I. & Sjoberg, S. (2002). J. Organomet. Chem. 657, 163-170.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3284-o3285   [ doi:10.1107/S1600536812044984 ]

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