(IUCr) 1-Methyl-1H-benzimidazole-2(3H)-thione

Volume 64
Part 6
Page o1141
June 2008

Received 21 April 2008
Accepted 18 May 2008
Online 24 May 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.029
wR = 0.078
Data-to-parameter ratio = 9.5
Details

1-Methyl-1H-benzimidazole-2(3H)-thione

Hizbullah Khan,^a Amin Badshah,^a ^* Farkhanda Shaheen,^a Christine Gieck ^b and Rizwana Aleem Qureshi ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan,^bDISTA, Universita del Piemonte Orientale, Alessandria I-15100, Italy, and ^cDepartment of Plant Sciences, Faculty of Biological Sciences, Quaid-I-Azam University, Islamabad 45320, Pakistan
Correspondence e-mail: aminbadshah@yahoo.com

The title compound, C₈H₈N₂S, was prepared by the condensation of N-methyl-1,2-phenylenediamine and carbon disulfide. The crystal structure is stabilized by a C-H [pi] interaction between a benzene H atom and the benzene ring of a neighbouring molecule, and by intermolecular N-HS interactions.

Related literature

For related literature, see: Baily et al. (1996); Koch (2001); Namgun et al. (2001); Schuster et al. (1990); Patel & Chedekel (1984).

Experimental

Crystal data

C₈H₈N₂S
M_r = 164.22
Monoclinic, P 2₁ /n
a = 9.997 (4) Å
b = 5.8140 (7) Å
c = 13.703 (4) Å
= 94.05 (3)°
V = 794.5 (4) Å³
Z = 4
Mo K radiation
= 0.34 mm^-1
T = 293 (2) K
0.20 × 0.10 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur2 CCD diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction; 2004 $[Oxford Diffraction (2004). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ; Clark & Reid, 1995) T_min = 0.929, T_max = 0.967
7237 measured reflections
962 independent reflections
855 reflections with I > 2(I)
R_int = 0.023
_max = 23.1°

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.077
S = 1.09
962 reflections
101 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2Sⁱ	0.86	2.57	3.408 (2)	166
C3-H3Cgⁱⁱ	0.93	2.74	3.464 (3)	136
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg is the centroid of the C2-C7 ring.

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2055 ).

Acknowledgements

The authors acknowledge the Higher Education Commission, Pakistan, for financial support.

References

Baily, N., Dean, A. W., Judd, D. B., Middlemiss, D., Storer, R. & Watson, S. P. (1996). Bioorg. Med. Chem. Lett. 6, 1409-1413.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Koch, K. R. (2001). Coord. Chem. Rev. 216, 473-482.
Namgun, L., Mi-Hyun, C. & Tack, H. K. (2001). J. Korean Chem. Soc. 45, 96-99.
Oxford Diffraction (2004). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Patel, D. G. & Chedekel, M. R. (1984). J. Org. Chem. 49, 997-1000.
Schuster, M., Kugler, B. & Konig, K. H. (1990). J. Anal. Chem. 338, 717-720.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds