Received 18 October 2013
In the crystal structure of the title salt, C16H36N+·CH3BN-, the tetra-n-butylammonium cations and [BH3(CN)]- anions are connected via weak C-HN 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.
For the use of the title compound as a reducing agent, see: Hutchins & Kandasamy (1973). It is also a selective reagent for reductive amination (Hutchins & Markovitz, 1981) and has been used as a radical mediator for hydroxymethylation reactions (Kawamoto et al., 2012). For the structure of related borohydride salts, see: Jaron & Grochala (2011) (tetramethylammonium) and Jaron et al. (2012) (tetra-n-butylammonium). For the ability of cyanoborohydride anions to form dihydrogen bonds, see: Custelcean & Jackson (1998). For the most usual conformations of quaternary ammonium cations, see: Alder et al. (1990).
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5361 ).
The Canada Foundation for Innovation, the Canada Research Chairs Program and the University of Montréal are acknowledged for financial support.
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