2-[2-(Methyl­sulfan­yl)benzimidazol-1-yl]ethanol

Ludovic Akonan; Kouassi Yves Guillaume Molou; Adjo Adohi-Krou; Akoun Abou; Abodou Jules Tenon

doi:10.1107/S1600536810001960

. 2010 Jan 23;66(Pt 2):o442. doi: 10.1107/S1600536810001960

2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol

Ludovic Akonan ^a,^*, Kouassi Yves Guillaume Molou ^b, Adjo Adohi-Krou ^a, Akoun Abou ^a, Abodou Jules Tenon ^a

PMCID: PMC2979779 PMID: 21579857

Abstract

In the title compound, C₁₀H₁₂N₂OS, the asymmetric unit consists of two independent molecules. In the crystal structure, molecules form R ₄ ⁴(28) centrosymmetric tetramers via O—H⋯N hydrogen bonds. These tetramers are stacked along the c axis via C—H⋯O hydrogen bonds. C—H⋯π and π–π interactions are also present; in the latter, the centroid–centroid distances are 4.075 (1) and 3.719 (1) Å.

Related literature

For the biological activity of compounds having benzimidazole ring systems, and a related structure, see: Akkurt et al. (2006 ▶). For other studies of the biological activity of benzimidazoles, see: Küçükbay et al. (2003 ▶), (2004 ▶); Puratchikody et al. (2008 ▶). For hydrogen-bond graph sets, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₀H₁₂N₂OS
M _r = 208.28
Triclinic,
a = 9.3235 (2) Å
b = 9.7659 (2) Å
c = 11.4588 (3) Å
α = 78.0849 (9)°
β = 88.9066 (8)°
γ = 88.1399 (9)°
V = 1020.25 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 223 K
0.20 × 0.20 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer
13769 measured reflections
5257 independent reflections
3996 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.102
S = 0.96
5242 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: CRYSTALS.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001960/wn2372sup1.cif

e-66-0o442-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001960/wn2372Isup2.hkl

e-66-0o442-Isup2.hkl^{(262.5KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the N1A-C3A-N2A-C6A-C5A and C5A—C10A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1B—H1B⋯N2Aⁱ	0.95 (3)	1.88 (3)	2.825 (3)	174 (3)
O1A—H1A⋯N2B	1.01 (3)	1.80 (3)	2.808 (3)	175 (3)
C4A—H41A⋯O1Aⁱⁱ	0.95	2.42	3.366 (3)	174
C4A—H43A⋯Cg2ⁱⁱⁱ	0.95	2.86	3.627 (2)	139
C4B—H43B⋯Cg1	0.95	2.86	3.486 (2)	125
C10B—H10B⋯Cg2^iv	0.95	2.74	3.631 (2)	157

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

We thank the Laboratoire de Physique des Interactions Ioniques et Spectropôle, Université de Provence, et Université Paul Cézanne, Faculté des Sciences et Techniques de Saint Jérôme, Marseilles, France, for the use of their diffractometer.

supplementary crystallographic information

Comment

Numerous compounds having benzimidazole ring systems possess versatile pharmacological activities such as antiviral, anthelmintic, spasmolytic, antihypertensive and vasodilator (Akkurt et al., 2006). It has also been reported that many benzimidazole derivatives have antimicrobial and antifungal activities (Küçükbay et al., 2003, 2004, Puratchikody et al., 2008). Therefore, the synthesis of new benzimidazole derivatives is of considerable interest. In order to explore new benzimidazole properties, the title compound has been synthesized and its crystal structure determined.

The two independent molecules in the asymmetric unit of the title compound and the atomic labeling scheme are shown in Fig.1. In this structure, the nine-membered benzimidazole ring systems (N1A/C3A/N2A/C6A/C7A/C8A/C9A/C10A/C5A, N1B/C3B/N2B/C6B/C7B/C8B/C9B/C10B/C5B) of both independent molecules are essentially planar, the maximum deviation from planarity being, respectively, 0.016 (2) Å for atom C8A and 0.078 (16) Å for atom C3B. These two ring systems make a dihedral angle of 73.95 (6)°.

In the crystal structure, we observe the formation of R₄⁴(28) centrosymmetric tetramers (Bernstein et al., 1995) via O—H···N hydrogen bonds. The tetramers are linked by two symmetric C—H···O hydrogen bonds to form a zigzag infinite chain along the c axis. The supramolecular aggregation is completed by the presence of C—H···π interactions (Table 1) and π–π stacking between two parallel imidazole rings. The centroid···centroid distance of those rings, Cg1···Cg1(1 - x,1 - y,1 - z) and Cg4···Cg4(-x,2 - y,-z) are 4.075 (1) Å and 3.719 (1) Å, respectively (Fig.3).

Experimental

2-Chloroethanol (1.6 ml, 24.4 mmol) and potasium carbonate (1.68 g, 12.2 mmol) were added to 2-methylsulfanyl-1H-benzimidazole (1 g, 6.1 mmol) in dimethyl sulfoxide (DMSO) (5 ml). The reaction mixture was successively agitated for 30 min at room temperature and at 323 K for 24 h. 50 ml of water was then added to the reaction mixture, and the products were extracted with dichloromethane (3 × 50 ml). The combined organic extracts were washed with brine (10 g of sodium chloride in 100 ml of water), dried (Na₂SO₄) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (elution: hexane/ethyl acetate (70:30, v/v)) and the title compound resulted as a brown powder (0.77 g, 61%) with a melting point of 409 K. The brown powder was dissolved in ethanol/hexane (3:1, v/v) and, after four days, brown crystals suitable for single-crystal X-ray diffraction analysis were obtained.