1,3-Bis(pyridin-2-yl)-1H-benzimidazol-3-ium tetra­fluoridoborate

Grieco, G.; Blacque, O.; Berke, H.

doi:10.1107/S1600536811027942

Volume 67
Part 8
Pages o2066-o2067
August 2011

Received 29 June 2011
Accepted 12 July 2011
Online 16 July 2011

Key indicators
Single-crystal X-ray study
T = 183 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.042
wR = 0.117
Data-to-parameter ratio = 15.5
Details

1,3-Bis(pyridin-2-yl)-1H-benzimidazol-3-ium tetrafluoridoborate

Gabriele Grieco,^a Olivier Blacque ^a ^* and Heinz Berke ^a

^aInstitute of Inorganic Chemistry, University of Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland
Correspondence e-mail: oblacque@aci.uzh.ch

The asymmetric unit of the title compound, C₁₇H₁₃N₄⁺·BF₄^-, contains one half of the benzimidazolium cation and one half of the tetrafluoridoborate anion, with crystallographic mirror planes bisecting the molecules. One F atom of the tetrafluoridoborate is equally disordered about a crystallographic mirror plane. In the crystal, C-HF interactions link the cations and anions into layers parallel to (100). The crystal packing is further stabilized by F [pi] contacts involving the tetrafluoridoborate anions and the five-membered rings [Fcentroid = 2.811 (2) Å].

Related literature

For applications of N,N'-bis(2-pyridyl)aryldiamines, see: Stoessel et al. (2010); Goldfarb (2009) and of imidazolium salts, see: Berlin et al. (2007); Bold et al. (2005); Huang et al. (2005); Murakami et al. (2007); Teles et al. (1996). For pharmaceuticals based on the aniline-pyridine scaffold, see: Kim et al. (1996); Wu et al. (2001). For the synthesis of the starting material N,N'-bis(pyridin-2-yl)benzene-1,2-diamine, see: Gdaniec et al. (2004).

Experimental

Crystal data

C₁₇H₁₃N₄⁺·BF₄^-
M_r = 360.12
Orthorhombic, P n m a
a = 7.3412 (2) Å
b = 17.5051 (5) Å
c = 12.2426 (3) Å
V = 1573.28 (7) Å³
Z = 4
Mo K radiation
= 0.13 mm^-1
T = 183 K
0.44 × 0.31 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby detector
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) based on Clark & Reid (1995)] T_min = 0.964, T_max = 0.991
8816 measured reflections
2014 independent reflections
1543 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.117
S = 1.08
2014 reflections
130 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1F3	0.95 (2)	2.14 (2)	3.094 (2)	178 (2)
C9-H9F1ⁱ	0.93	2.62	3.4759 (19)	154
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006), ORTEP-3 for Windows (Farrugia, 1997) and POV-RAY for Windows (Cason, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2291 ).

References

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organic compounds