1,3-Bis(3-phenyl­prop­yl)benzimidazolium bromide monohydrate

Akkurt, M.; Karaca, S.; Yılmaz, Ü.; Küçükbay, H.; Büyükgüngör, O.

doi:10.1107/S1600536808030432

Volume 64
Part 10
Pages o2019-o2020
October 2008

Received 18 September 2008
Accepted 22 September 2008
Online 27 September 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.010 Å
R = 0.065
wR = 0.172
Data-to-parameter ratio = 19.7
Details

1,3-Bis(3-phenylpropyl)benzimidazolium bromide monohydrate

Mehmet Akkurt,^a ^* Selvi Karaca,^a Ülkü Yilmaz,^b Hasan Küçükbay ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey,^bDepartment of Chemistry, Faculty of Arts and Sciences, Ínönü University, 44280 Malatya, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C₂₅H₂₇N₂⁺·Br^-·H₂O, the benzimidazole unit is essentially planar, with a maximum deviation of 0.020 (6) Å. The benzimidazole unit makes dihedral angles of 83.6 (3) and 81.0 (3)° with the two terminal phenyl rings. The dihedral angle between the phenyl rings is 58.5 (4)°. In the crystal structure, there are C-HO hydrogen bonds, a C-H [pi] interaction between a phenyl H atom and the phenyl ring of a neighbouring molecule, and a [pi] - [pi] interaction [3.512 (3) Å] between the centroids of the five-membered ring and the benzene ring of the benzimidazole unit of an adjacent molecule.

Related literature

For general background, see: Sakai et al. (1989); Küçükbay et al. (2001, 2003, 2004). For a similar structure, see: Akkurt et al. (2005). For related structures, see: Akkurt et al. (2004, 2007); Karaca et al. (2005); Pinar et al. (2006); Yildirim et al. (2005).

Experimental

Crystal data

C₂₅H₂₇N₂⁺·Br^-·H₂O
M_r = 453.40
Monoclinic, P 2₁ /c
a = 14.1933 (8) Å
b = 11.4594 (3) Å
c = 18.3014 (10) Å
= 128.916 (3)°
V = 2316.1 (2) Å³
Z = 4
Mo K radiation
= 1.79 mm^-1
T = 295 (2) K
0.71 × 0.63 × 0.54 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.363, T_max = 0.444
18735 measured reflections
5283 independent reflections
2688 reflections with I > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.172
S = 0.99
5283 reflections
268 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.47 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7O1	0.93	2.50	3.257 (10)	139
C17-H17AO1	0.97	2.38	3.236 (13)	148
C24-H24Cg1ⁱ	0.93	2.84	3.771 (14)	176
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ . Cg1 is the centriod of the C11-C16 phenyl ring.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2337 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund). HK and ÜY thank Inönü University Research Fund (Directed project BAPB-2008/60) for financial support ofthis study.

References

Akkurt, M., Karaca, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2005). Acta Cryst. E61, o2452-o2454.
Akkurt, M., Öztürk, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o219-o221.
Akkurt, M., Pinar, S., Yilmaz, Ü., Küçükbay, H. & Büyükgüngör, O. (2007). Acta Cryst. E63, o379-o381.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Karaca, S., Akkurt, M., Yilmaz, U., Küçükbay, H. & Büyükgüngör, O. (2005). Acta Cryst. E61, o2128-o2130.
Küçükbay, H., Durmaz, R., Güven, M. & Günal, S. (2001). Arzneim. Forsch. Drug. Res. 51, 420-424.
Küçükbay, H., Durmaz, R., Okuyucu, N., Günal, S. & Kazaz, C. (2004). Arzneim. Forsch. Drug. Res. 54, 64-68.
Küçükbay, H., Durmaz, H., Orhan, E. & Günal, S. (2003). Farmaco, 58, 431-437.
Pinar, S., Akkurt, M., Küçükbay, H., Sireci, N. & Büyükgüngör, O. (2006). Acta Cryst. E62, o2223-o2225.
Sakai, T., Hamada, T., Awata, N. & Watanabe, J. (1989). Pharmacobiol. Dyn. 12, 530-536.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Yildirim, S. O., Akkurt, M., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2005). Acta Cryst. E61, o2038-o2039.

organic compounds