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Volume 69 
Part 11 
Page o1713  
November 2013  

Received 18 October 2013
Accepted 21 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.092
Data-to-parameter ratio = 18.9
Details
Open access

N,N,N-Tri­butyl­butan-1-aminium (T-4)-(cyano-[kappa]C)tri­hydro­borate

aDepartment of Chemistry, University of Montréal, CP 6128, Succ. Centre-ville, Montréal, Québec, H3C 3J7, Canada
Correspondence e-mail: thierry.maris@umontreal.ca

In the crystal structure of the title salt, C16H36N+·CH3BN-, the tetra-n-butyl­ammonium cations and [BH3(CN)]- anions are connected via weak C-H...N inter­actions, forming chains along the b-axis direction. The anion is almost linear with an N-C-B angle of 178.7 (2)°. The C-N-C angle values at the core of the tetra-n-butyl­ammonium cation range from 105.74 (11) to 111.35 (11)° with an average of 109.49 (11)°, close to the ideal tetra­hedral value.

Related literature

For the use of the title compound as a reducing agent, see: Hutchins & Kandasamy (1973[Hutchins, R. O. & Kandasamy, D. (1973). J. Am. Chem. Soc. 95, 6131-6132.]). It is also a selective reagent for reductive amination (Hutchins & Markovitz, 1981[Hutchins, R. O. & Markovitz, M. (1981). J. Org. Chem. 46, 3574-3575.]) and has been used as a radical mediator for hy­droxy­methyl­ation reactions (Kawamoto et al., 2012[Kawamoto, T., Fukuya, T. & Ryu, I. (2012). J. Am. Chem. Soc. 134, 875-877.]). For the structure of related borohydride salts, see: Jaron & Grochala (2011[Jaron, T. & Grochala, W. (2011). Acta Cryst. E67, o2171.]) (tetra­methyl­ammonium) and Jaron et al. (2012[Jaron, T., Wegner, W., Cyranski, M. K., Dobrzycki, L. & Grochala, W. (2012). J. Solid State Chem. 191, 279-282.]) (tetra-n-butyl­ammonium). For the ability of cyano­borohydride anions to form di­hydrogen bonds, see: Custelcean & Jackson (1998[Custelcean, R. & Jackson, J. E. (1998). J. Am. Chem. Soc. 120, 12935-12941.]). For the most usual conformations of quaternary ammonium cations, see: Alder et al. (1990[Alder, R. W., Maunder, C. M. & Orpen, A. G. (1990). Tetrahedron Lett. 31, 6717-6720.]).

[Scheme 1]

Experimental

Crystal data
  • C16H36N+·CH3BN-

  • Mr = 282.31

  • Monoclinic, P 21

  • a = 7.8312 (5) Å

  • b = 13.9334 (9) Å

  • c = 9.6313 (6) Å

  • [beta] = 112.269 (2)°

  • V = 972.54 (11) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.40 mm-1

  • T = 100 K

  • 0.25 × 0.2 × 0.15 mm

Data collection
  • Bruker Microstar X8 diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2012[Sheldrick, G. M. (2012). SADABS. University of Göttingen, Germany.]) Tmin = 0.590, Tmax = 0.753

  • 18043 measured reflections

  • 3520 independent reflections

  • 3510 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.03

  • 3520 reflections

  • 186 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack parameter determined using 1596 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.])

  • Absolute structure parameter: 0.14 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1B...N2i 0.97 2.58 3.515 (2) 162
C2-H2B...N2 0.97 2.58 3.523 (2) 165
C13-H13B...N2 0.97 2.59 3.474 (2) 152
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5361 ).


Acknowledgements

The Canada Foundation for Innovation, the Canada Research Chairs Program and the University of Montréal are acknowledged for financial support.

References

Alder, R. W., Maunder, C. M. & Orpen, A. G. (1990). Tetrahedron Lett. 31, 6717-6720.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Custelcean, R. & Jackson, J. E. (1998). J. Am. Chem. Soc. 120, 12935-12941.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hutchins, R. O. & Kandasamy, D. (1973). J. Am. Chem. Soc. 95, 6131-6132.  [CrossRef] [ChemPort] [Web of Science]
Hutchins, R. O. & Markovitz, M. (1981). J. Org. Chem. 46, 3574-3575.
Jaron, T. & Grochala, W. (2011). Acta Cryst. E67, o2171.  [CSD] [CrossRef] [IUCr Journals]
Jaron, T., Wegner, W., Cyranski, M. K., Dobrzycki, L. & Grochala, W. (2012). J. Solid State Chem. 191, 279-282.
Kawamoto, T., Fukuya, T. & Ryu, I. (2012). J. Am. Chem. Soc. 134, 875-877.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2012). SADABS. University of Göttingen, Germany.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1713  [ doi:10.1107/S1600536813028924 ]

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