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

Mindich, A.L.; Pavlishchuk, A.V.; Bokach, N.A.; Starova, G.L.; Zhizhin, K.Y.

doi:10.1107/S1600536812044984

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 (C-C) = 0.002 Å
R = 0.054
wR = 0.142
Data-to-parameter ratio = 28.0
Details

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

Aleksey L. Mindich,^a Anna V. Pavlishchuk,^b ^* Nadezhda A. Bokach,^a ^* Galina L. Starova ^a and Konstantin Yu. Zhizhin ^c

^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). For examples of substituted 1,2,4-oxadiazoles, their complexes and properties, see: Kritchenkov et al. (2012); Bokach et al. (2011a,b); Makarycheva-Mikhailova et al. (2007); Kukushkin & Pombeiro (2002); Kritchenkov et al. (2011); Bokach (2010); Sivaev et al. (2002, 2008). For propeties and structure examples of boron clusters, see: Dash et al. (2011); Dou et al. (1994).

Experimental

Crystal data

C₁₆H₃₆N⁺·C₁₀H₂₀B₁₀N₃O₃^-
M_r = 580.85
Monoclinic, P 2₁ /n
a = 8.7356 (4) Å
b = 15.8691 (6) Å
c = 24.7015 (10) Å
= 98.206 (1)°
V = 3389.2 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.161, T_max = 0.374
35977 measured reflections
10868 independent reflections
6806 reflections with I > 2(I)
R_int = 0.086

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.142
S = 0.94
10868 reflections
388 parameters
H-atom parameters constrained
_max = 0.55 e Å^-3
_min = -0.51 e Å^-3

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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

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organic compounds