1-Cyclo­hexyl­methyl-3-methyl-2-[(phenyl­imino)(sulfido)meth­yl]benzimidazolium

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

doi:10.1107/S1600536808008842

Volume 64
Part 5
Page o809
May 2008

Received 1 April 2008
Accepted 1 April 2008
Online 10 April 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 16.9
Details

1-Cyclohexylmethyl-3-methyl-2-[(phenylimino)(sulfido)methyl]benzimidazolium

Mehmet Akkurt,^a ^* Selvi Karaca,^a Hasan Küçükbay,^b Nihat Sireci ^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, Ínönü University, 44280 Malatya, Turkey,^cDepartment of Chemistry, Faculty of Arts and Sciences, Adiyaman University, 02040 Adiyaman, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the zwitterionic title compound, C₂₂H₂₅N₃S, the benzimidazole ring system makes a dihedral angle of 55.69 (11)° with the phenyl ring. In the crystal structure, inter- and intramolecular C-HS interactions occur.

Related literature

For related structures, see: Öztürk et al. (2004); Akkurt et al. (2005). For background, see: Allen et al. (1987); Cremer & Pople (1975); Küçükbay et al. (1995); Winberg & Coffman (1965).

Experimental

Crystal data

C₂₂H₂₅N₃S
M_r = 363.52
Monoclinic, P 2₁ /c
a = 11.0999 (8) Å
b = 12.4601 (7) Å
c = 15.0143 (14) Å
= 99.007 (7)°
V = 2051.0 (3) Å³
Z = 4
Mo K radiation
= 0.17 mm^-1
T = 296 K
0.62 × 0.56 × 0.51 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.903, T_max = 0.919
11769 measured reflections
3997 independent reflections
2727 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.127
S = 1.02
3997 reflections
236 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C16-H16AS1ⁱ	0.97	2.73	3.683 (2)	167
C16-H16BS1	0.97	2.78	3.451 (2)	127
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: HB2714 ).

Acknowledgements

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

References

Akkurt, M., Karaca, S., Küçükbay, H., Yilmaz, U. & Büyükgüngör, O. (2005). Acta Cryst. E61, o2875-o2877.
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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Küçükbay, H., Çetinkaya, E. & Durmaz, R. (1995). Arzneim.-Forsch. Drug. Res. 45, 1331-1334.
Öztürk, S., Akkurt, M., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o936-o938.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Winberg, H. E. & Coffman, D. D. (1965). J. Am. Chem. Soc. 87, 2776-2777.

organic compounds