[Journal logo]

Volume 68 
Part 6 
Page o1635  
June 2012  

Received 26 April 2012
Accepted 30 April 2012
Online 5 May 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.046
wR = 0.098
Data-to-parameter ratio = 18.1
Details
Open access

3,3'-[1,2-Phenylenebis(methylene)]bis(1-ethyl-1H-benzimidazol-1-ium) bis(hexaflourophosphate)

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C26H28N42+·2PF6-, the complete cation is generated by a crystallographic twofold axis. The benzimidazole ring is almost planar (r.m.s. deviation = 0.0207 Å) and makes dihedral angles of 50.12 (2)° with its symmetry-related component and 65.81 (2)° with the central benzene ring. In the crystal, molecules are linked into a three-dimensional network by C-H...F interactions. A [pi]-[pi] interaction with a centroid-centroid distance of 3.530 (1) Å is observed. Four F atoms of the hexafluorophosphate anion are disordered over two sets of sites in a 0.889 (6):0.111 (6) ratio.

Related literature

For the biological applications of benzimidazoles, see: Narasimhan et al. (2012[Narasimhan, B., Sharma, D. & Kumar, P. (2012). Med. Chem. Res. 21, 269-283.]). For a related structure, see: Haque et al. (2012[Haque, R. A., Iqbal, M. A., Fun, H.-K. & Arshad, S. (2012). Acta Cryst. E68, o924-o925.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28N42+·2PF6-

  • Mr = 686.46

  • Monoclinic, C 2/c

  • a = 23.2016 (5) Å

  • b = 8.1526 (2) Å

  • c = 16.9992 (4) Å

  • [beta] = 121.274 (1)°

  • V = 2748.23 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 100 K

  • 0.26 × 0.26 × 0.14 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.933, Tmax = 0.963

  • 14787 measured reflections

  • 3921 independent reflections

  • 3156 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.098

  • S = 1.05

  • 3921 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1A...F6i 0.95 2.42 3.142 (3) 133
C3-H3A...F5ii 0.95 2.45 3.374 (2) 166
C5-H5A...F5iii 0.95 2.52 3.420 (3) 159
C6-H6A...F4iv 0.95 2.53 3.392 (2) 151
C8-H8B...F1i 0.99 2.39 3.350 (3) 164
C13-H13C...F1v 0.98 2.55 3.523 (2) 174
C13-H13C...F5v 0.98 2.50 3.166 (2) 125
Symmetry codes: (i) x-1, y, z; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iv) [-x+1, y, -z+{\script{3\over 2}}]; (v) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6760 ).


Acknowledgements

RAH thanks Universiti Sains Malaysia (USM) for the Research University (RU) grants (1001/PKIMIA/811157 and 304/PKIMIA/6511123). MAI is grateful to (IPS) USM for financial support [fellowship: USM·IPS/JWT/1/19 (JLD 6)] and the research attachment fund [P-KM0018/10(R) - 308/AIPS/415401]. HKF thanks USM for the Research University Grant No. 1001/PFIZIK/811160.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Haque, R. A., Iqbal, M. A., Fun, H.-K. & Arshad, S. (2012). Acta Cryst. E68, o924-o925.  [CSD] [CrossRef] [details]
Narasimhan, B., Sharma, D. & Kumar, P. (2012). Med. Chem. Res. 21, 269-283.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o1635  [ doi:10.1107/S1600536812019344 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.