(E)-1,1′-Bis[(E)-but-2-en­yl]-3,3′-(propane-1,3-di­yl)bis­(1H-benzimidazol-3-ium) dibromide monohydrate

Akkurt, M.; Yıldırım, S.Ö.; Şireci, N.; Küçükbay, H.; Büyükgüngör, O.

doi:10.1107/S160053680803095X

Volume 64
Part 11
Pages o2136-o2137
November 2008

Received 15 September 2008
Accepted 25 September 2008
Online 18 October 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.009 Å
R = 0.054
wR = 0.124
Data-to-parameter ratio = 20.8
Details

(E)-1,1'-Bis[(E)-but-2-enyl]-3,3'-(propane-1,3-diyl)bis(1H-benzimidazol-3-ium) dibromide monohydrate

Mehmet Akkurt,^a ^* Sema Öztürk Yildirim,^a Nihat Sireci,^b Hasan Küçükbay ^c and Orhan Büyükgüngör ^d

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

The title compound, C₂₅H₃₀N₄²⁺·2Br^-·H₂O, was synthesized from 1,1'-propylenedibenzimidazole and (E)-1-bromobut-2-ene in dimethylformamide solution. The two benzimidazole ring systems are essentially planar, with maximum deviations of 0.011 (4) and 0.023 (3) Å. The dihedral angle between these two ring systems is 25.87 (15)°. The crystal structure is stabilized by intermolecular O-HBr and C-HBr hydrogen-bonding interactions. Atmospheric water was incorporated into the crystal structure.

Related literature

For bond-length data, see: Allen et al. (1987). For general background, see: Sakai et al. (1989); Tidwell et al. (1993); Küçükbay et al. (1995, 2001); Turner & Denny (1996); Hall et al. (1998). For related structures, see, for example: Öztürk et al. (2003); Akkurt et al. (2003, 2006).

Experimental

Crystal data

C₂₅H₃₀N₄²⁺·2Br^-·H₂O
M_r = 564.35
Triclinic, $[P \overline 1]$
a = 8.7989 (9) Å
b = 11.1878 (13) Å
c = 14.8813 (14) Å
= 106.381 (8)°
= 96.490 (8)°
= 106.227 (8)°
V = 1319.9 (3) Å³
Z = 2
Mo K radiation
= 3.09 mm^-1
T = 296 K
0.53 × 0.45 × 0.31 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.291, T_max = 0.447
16109 measured reflections
6181 independent reflections
4101 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.124
S = 1.05
6181 reflections
297 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.56 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-HW1Br1	0.81 (8)	2.54 (8)	3.342 (6)	171 (8)
O1-HW2Br2ⁱ	0.89 (9)	2.45 (8)	3.333 (5)	171 (7)
C4-H4ABr2ⁱⁱ	0.97	2.81	3.773 (4)	172
C4-H4BBr2ⁱ	0.97	2.86	3.802 (6)	164
C11-H11Br1	0.93	2.76	3.536 (4)	142
C12-H12ABr2	0.97	2.89	3.822 (5)	161
C19-H19Br2ⁱⁱⁱ	0.93	2.92	3.816 (5)	162
C21-H21Br1	0.93	2.65	3.550 (5)	162
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x, -y, -z.

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: SJ2540 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the diffractometer (purchased under grant F.279 of the University Research Fund). HK and NS thank Inönü University Research Fund (directed project BAPB-2007-46) for financial support for this study.

References

Akkurt, M., Öztürk, S., Küçükbay, H., Okuyucu, N. & Fun, H.-K. (2003). Acta Cryst. E59, o786-o788.
Akkurt, M., Yildirim, S. Ö., Küçükbay, H., Sireci, N. & Büyükgüngör, O. (2006). Acta Cryst. E62, o3184-o3186.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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.
Hall, J. E., Kerrigan, J. E., Ramachandran, K., Bender, B. C., Stanko, J. P., Jones, S. K., Patric, D. A. & Tidwell, R. R. (1998). Antimicrob. Agents Chemother. 42, 666-674.
Küçükbay, H., Çetinkaya, E. & Durmaz, R. (1995). Arzneim. Forsch. 45, 1331-1334.
Küçükbay, H., Durmaz, R., Güven, M. & Günal, S. (2001). Arzneim. Forsch. 51, 420-424.
Öztürk, S., Akkurt, M., Küçükbay, H., Okuyucu, N. & Fun, H.-K. (2003). Acta Cryst. E59, o1014-o1016.
Sakai, T., Hamada, T., Awata, N. & Watanabe, J. (1989). J. Pharmacobiodyn. 12, 530-536.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Tidwell, R. R., Jones, S. K., Naiman, N. A., Berger, L. C., Brake, W. B., Dykstra, C. C. & Hall, J. E. (1993). Antimicrob. Agents Chemother. 37, 1713-1716.
Turner, P. R. & Denny, W. A. (1996). Mutat. Res. 335, 141-169.

organic compounds