2-Methyl­benzimidazolium thio­cyanate–2-methyl­benzimidazole (1/1)

Shayma A Shaker; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536810031181

. 2010 Aug 11;66(Pt 9):o2291. doi: 10.1107/S1600536810031181

2-Methylbenzimidazolium thiocyanate–2-methylbenzimidazole (1/1)

Shayma A Shaker ^a, Hamid Khaledi ^a,^*, Hapipah Mohd Ali ^a

PMCID: PMC3008113 PMID: 21588643

Abstract

In the crystal structure of the title compound, C₈H₉N₂ ⁺·SCN⁻·C₈H₈N₂, the three components are linked by intermolecular N—H⋯N and N—H⋯S hydrogen bonds into infinite chains along the c axis.

Related literature

For related structures, see: Bhattacharya et al. (2004 ▶); Ding et al. (2004 ▶); Huang et al. (2006 ▶). For applications of benzimidazole derivatives in crystal engineering, see: Cai et al. (2002 ▶). For the biological properties of benzimidazole derivatives, see: Refaat (2010 ▶); Ansari & Lal (2009 ▶).

Experimental

Crystal data

C₈H₉N₂ ⁺·SCN⁻·C₈H₈N₂
M _r = 323.42
Monoclinic,
a = 11.0952 (7) Å
b = 6.9664 (4) Å
c = 21.4195 (13) Å
β = 100.745 (1)°
V = 1626.56 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.950, T _max = 0.988
8812 measured reflections
3193 independent reflections
2427 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.093
S = 1.03
3193 reflections
222 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031181/pv2314sup1.cif

e-66-o2291-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031181/pv2314Isup2.hkl

e-66-o2291-Isup2.hkl^{(156.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N5	0.90 (2)	1.90 (2)	2.799 (2)	176 (2)
N2—H2N⋯N4ⁱ	0.90 (2)	1.88 (2)	2.781 (2)	179 (2)
N3—H3N⋯S1	0.86 (2)	2.47 (2)	3.317 (2)	168 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the University of Malaya for funding this study (FRGS grant FP009/2008 C).

supplementary crystallographic information

Comment

Benzimidazole derivatives are biologically active compounds (Refaat, 2010; Ansari & Lal, 2009). Their applications in crystal-engineering have been reported (Cai et al., 2002). The crystal structures of several compounds similar to the title compound have been publsihed (Bhattacharya et al., 2004; Ding et al., 2004; Huang et al., 2006. In this article, the preparation and crystal structure of the title compound is presented.

The asymmetric unit of the title compound contains a 2-methylbenzimidazolium cation, a thiocyante anion and a molecule of 2-methylbenzimidazole (Fig. 1). In the crystal structure, the three moieties are linked by intramolecular N—H···N and N—H···S hydrogen bondings into infinite one-dimensional chains (Tab. 1 & Fig. 2).

Experimental

An ethanolic solution (12 ml) of 2-methylbenzimidazole (9 mmol, 1.2 g) was added to an aqueous solution (10 ml) of FeCl₃ (3 mmol) followed by addition of an aqueous solution (10 ml) of KSCN (9 mmol). The mixture was heated in a water bath for 15 min. The resulting precipitates were filtered off, washed with ethanol (50%) and recrystallized from ethanol whereupon the pale yellow crystals of the title compound were obtained unexpectedly.