2-[2-(Methyl-sulfan-yl)benzimidazol-1-yl]ethanol.

In the title compound, C(10)H(12)N(2)OS, the asymmetric unit consists of two independent mol-ecules. In the crystal structure, mol-ecules form R(4) (4)(28) centrosymmetric tetra-mers via O-H⋯N hydrogen bonds. These tetra-mers are stacked along the c axis via C-H⋯O hydrogen bonds. C-H⋯π and π-π inter-actions 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 = 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

Δρmax = 0.51 e Å−3

Δρmin = −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.

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

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

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

C10H12N2OS	Z = 4
Mr = 208.28	F(000) = 440
Triclinic, P1	Dx = 1.356 Mg m−3
Hall symbol: -P 1	Melting point: 409 K
a = 9.3235 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7659 (2) Å	Cell parameters from 13769 reflections
c = 11.4588 (3) Å	θ = 2–29°
α = 78.0849 (9)°	µ = 0.28 mm−1
β = 88.9066 (8)°	T = 223 K
γ = 88.1399 (9)°	Prism, brown
V = 1020.25 (4) Å3	0.20 × 0.20 × 0.15 mm

Nonius KappaCCD diffractometer	3996 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 29.1°, θmin = 1.8°
φ and ω scans	h = −12→12
13769 measured reflections	k = −12→12
5257 independent reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.04P)2 + 0.62P], where P = [max(Fo2,0) + 2Fc2]/3
5242 reflections	(Δ/σ)max = 0.001
261 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.32 e Å−3
88 constraints

Experimental. 1H NMR (DMSO-d6, 300 MHz, p.p.m.) δ: 2.71 (s, 3H, CH3); 3.68–3.74 (m 2H, CH2O, JCH2—CH2 = 5.7 Hz and JCH2—OH = 5.4 Hz); 4.17 (t, 2H, CH2N, JCH2—CH2 = 5.7 Hz); 5.00 (t, 1H, OH, JCH2—OH = 5.4 Hz); 7.13–7.17 and 7.46–7.55 (m, 4H, C6H4). 13C NMR (DMSO-d6, 300 MHz, p.p.m.) δ: 14.35 (CH3); 46.25 (CH2N); 59.14 (CH2O); 109.75, 117.31, 121.14, 121.21, 136.75, 142.92 (C6H5); 152.48 (C═N).

Refinement. The 15 reflections 1 0 0; -1 1 0; 0 1 0; 1 1 0; -1 - 1 1; 0 - 1 1; 1 - 1 1; -1 0 1; 0 0 1; 1 0 1; -1 1 1; 0 1 1; 1 1 1; 0 0 2; 0 1 2 have been measured with too low intensities. It might be caused by some systematical error, probably by shielding by a beam stop of these diffractions. They were not used in the refinement.

	x	y	z	Uiso*/Ueq
S1A	0.49131 (5)	0.82212 (5)	0.49825 (4)	0.0390
C3A	0.42886 (16)	0.69994 (15)	0.42198 (14)	0.0286
N1A	0.28691 (13)	0.66663 (13)	0.43140 (12)	0.0286
C5A	0.26838 (17)	0.57367 (15)	0.35708 (15)	0.0298
C6A	0.40349 (17)	0.55494 (15)	0.30706 (15)	0.0309
N2A	0.50366 (14)	0.63619 (13)	0.34868 (12)	0.0309
C7A	0.4221 (2)	0.46382 (18)	0.22858 (18)	0.0430
C8A	0.3031 (2)	0.39422 (19)	0.20412 (19)	0.0507
C9A	0.1686 (2)	0.41504 (19)	0.25355 (19)	0.0481
C10A	0.14723 (19)	0.50586 (17)	0.33090 (17)	0.0386
C2A	0.17826 (17)	0.70834 (17)	0.51181 (15)	0.0336
C1A	0.07853 (17)	0.82574 (17)	0.45194 (16)	0.0354
O1A	0.15279 (14)	0.95034 (13)	0.41601 (12)	0.0405
C4A	0.67938 (19)	0.8087 (2)	0.4688 (2)	0.0463
S1B	0.34070 (5)	1.07040 (5)	0.04701 (4)	0.0402
C3B	0.16057 (17)	1.10450 (15)	0.07442 (14)	0.0299
N2B	0.09036 (15)	1.06622 (14)	0.17658 (12)	0.0325
C6B	−0.04765 (17)	1.12427 (16)	0.15371 (14)	0.0307
C5B	−0.05673 (17)	1.19801 (16)	0.03565 (14)	0.0306
N1B	0.07856 (14)	1.18307 (13)	−0.01412 (12)	0.0313
C2B	0.12112 (19)	1.23474 (17)	−0.13814 (14)	0.0357
C1B	0.1892 (2)	1.37598 (19)	−0.15947 (16)	0.0419
O1B	0.21179 (14)	1.42576 (15)	−0.28301 (12)	0.0521
C10B	−0.18151 (19)	1.26805 (18)	−0.01093 (16)	0.0395
C9B	−0.2986 (2)	1.2612 (2)	0.06571 (18)	0.0458
C8B	−0.2918 (2)	1.1879 (2)	0.18335 (18)	0.0449
C7B	−0.16712 (19)	1.11853 (18)	0.22973 (16)	0.0381
C4B	0.3871 (2)	0.9554 (2)	0.18458 (19)	0.0578
H1B	0.305 (3)	1.398 (3)	−0.306 (3)	0.091 (9)*
H1A	0.136 (3)	0.992 (3)	0.329 (3)	0.094 (9)*
H10A	0.0555	0.5211	0.3642	0.0468*
H9A	0.0895	0.3657	0.2337	0.0576*
H8A	0.3134	0.3303	0.1520	0.0612*
H7A	0.5130	0.4501	0.1934	0.0516*
H10B	−0.1862	1.3181	−0.0913	0.0468*
H9B	−0.3860	1.3078	0.0373	0.0552*
H8B	−0.3748	1.1855	0.2331	0.0540*
H7B	−0.1630	1.0688	0.3102	0.0456*
H41A	0.7284	0.8715	0.5062	0.0552*
H42A	0.6966	0.8319	0.3851	0.0552*
H43A	0.7132	0.7157	0.4993	0.0552*
H41B	0.4855	0.9276	0.1822	0.0696*
H42B	0.3707	1.0025	0.2486	0.0681*
H43B	0.3296	0.8751	0.1961	0.0681*
H11A	0.0039	0.8396	0.5063	0.0420*
H12A	0.0383	0.8011	0.3838	0.0420*
H21A	0.2257	0.7382	0.5744	0.0408*
H22A	0.1226	0.6293	0.5442	0.0408*
H21B	0.0383	1.2421	−0.1863	0.0432*
H22B	0.1881	1.1693	−0.1609	0.0432*
H11B	0.1277	1.4401	−0.1289	0.0504*
H12B	0.2787	1.3675	−0.1200	0.0504*

	U11	U22	U33	U12	U13	U23
S1A	0.0358 (2)	0.0417 (2)	0.0440 (3)	−0.00593 (17)	−0.00121 (18)	−0.01874 (19)
C3A	0.0264 (7)	0.0263 (7)	0.0320 (8)	−0.0010 (5)	−0.0012 (6)	−0.0030 (6)
N1A	0.0250 (6)	0.0282 (6)	0.0324 (7)	−0.0025 (5)	0.0027 (5)	−0.0059 (5)
C5A	0.0301 (8)	0.0237 (7)	0.0345 (8)	−0.0019 (6)	−0.0017 (6)	−0.0030 (6)
C6A	0.0304 (8)	0.0254 (7)	0.0370 (9)	0.0010 (6)	−0.0024 (6)	−0.0067 (6)
N2A	0.0258 (6)	0.0304 (7)	0.0371 (7)	0.0003 (5)	0.0009 (5)	−0.0085 (5)
C7A	0.0469 (10)	0.0357 (9)	0.0496 (11)	0.0062 (7)	−0.0007 (8)	−0.0174 (8)
C8A	0.0676 (14)	0.0342 (9)	0.0557 (12)	0.0016 (9)	−0.0119 (10)	−0.0213 (8)
C9A	0.0518 (11)	0.0344 (9)	0.0596 (12)	−0.0108 (8)	−0.0156 (10)	−0.0107 (8)
C10A	0.0331 (8)	0.0319 (8)	0.0487 (10)	−0.0086 (6)	−0.0055 (7)	−0.0017 (7)
C2A	0.0312 (8)	0.0368 (8)	0.0311 (8)	−0.0020 (6)	0.0077 (7)	−0.0034 (6)
C1A	0.0288 (8)	0.0419 (9)	0.0362 (9)	0.0013 (6)	0.0049 (7)	−0.0107 (7)
O1A	0.0449 (7)	0.0375 (6)	0.0389 (7)	−0.0012 (5)	−0.0030 (6)	−0.0068 (5)
C4A	0.0330 (9)	0.0471 (10)	0.0608 (13)	−0.0082 (7)	−0.0080 (8)	−0.0140 (9)
S1B	0.0384 (2)	0.0427 (2)	0.0365 (2)	0.00559 (17)	0.00863 (18)	−0.00300 (17)
C3B	0.0355 (8)	0.0259 (7)	0.0286 (8)	−0.0031 (6)	0.0039 (6)	−0.0065 (6)
N2B	0.0381 (7)	0.0304 (7)	0.0284 (7)	−0.0011 (5)	0.0044 (6)	−0.0051 (5)
C6B	0.0365 (8)	0.0270 (7)	0.0296 (8)	−0.0048 (6)	0.0043 (6)	−0.0079 (6)
C5B	0.0341 (8)	0.0292 (7)	0.0292 (8)	−0.0060 (6)	0.0040 (6)	−0.0072 (6)
N1B	0.0349 (7)	0.0315 (7)	0.0263 (7)	−0.0031 (5)	0.0037 (5)	−0.0036 (5)
C2B	0.0414 (9)	0.0400 (9)	0.0245 (8)	−0.0014 (7)	0.0047 (7)	−0.0041 (6)
C1B	0.0409 (10)	0.0404 (9)	0.0397 (10)	−0.0038 (7)	0.0071 (8)	0.0021 (7)
O1B	0.0349 (7)	0.0628 (9)	0.0443 (8)	0.0089 (6)	0.0116 (6)	0.0195 (6)
C10B	0.0398 (9)	0.0407 (9)	0.0367 (9)	−0.0002 (7)	−0.0023 (7)	−0.0052 (7)
C9B	0.0358 (9)	0.0508 (11)	0.0519 (12)	0.0036 (8)	0.0000 (8)	−0.0137 (9)
C8B	0.0390 (10)	0.0491 (10)	0.0491 (11)	−0.0024 (8)	0.0116 (8)	−0.0170 (8)
C7B	0.0433 (10)	0.0378 (9)	0.0336 (9)	−0.0055 (7)	0.0104 (7)	−0.0088 (7)
C4B	0.0442 (11)	0.0745 (14)	0.0448 (12)	0.0157 (10)	0.0037 (9)	0.0072 (10)

S1A—C3A	1.7383 (16)	S1B—C3B	1.7369 (16)
S1A—C4A	1.7851 (19)	S1B—C4B	1.788 (2)
C3A—N1A	1.3700 (19)	C3B—N2B	1.321 (2)
C3A—N2A	1.321 (2)	C3B—N1B	1.368 (2)
N1A—C5A	1.384 (2)	N2B—C6B	1.396 (2)
N1A—C2A	1.461 (2)	C6B—C5B	1.398 (2)
C5A—C6A	1.396 (2)	C6B—C7B	1.396 (2)
C5A—C10A	1.396 (2)	C5B—N1B	1.390 (2)
C6A—N2A	1.397 (2)	C5B—C10B	1.388 (2)
C6A—C7A	1.395 (2)	N1B—C2B	1.458 (2)
C7A—C8A	1.382 (3)	C2B—C1B	1.509 (2)
C7A—H7A	0.950	C2B—H21B	0.950
C8A—C9A	1.392 (3)	C2B—H22B	0.950
C8A—H8A	0.950	C1B—O1B	1.413 (2)
C9A—C10A	1.385 (3)	C1B—H11B	0.950
C9A—H9A	0.950	C1B—H12B	0.950
C10A—H10A	0.950	O1B—H1B	0.95 (3)
C2A—C1A	1.510 (2)	C10B—C9B	1.382 (3)
C2A—H21A	0.950	C10B—H10B	0.950
C2A—H22A	0.950	C9B—C8B	1.391 (3)
C1A—O1A	1.402 (2)	C9B—H9B	0.950
C1A—H11A	0.950	C8B—C7B	1.385 (3)
C1A—H12A	0.950	C8B—H8B	0.950
O1A—H1A	1.01 (3)	C7B—H7B	0.950
C4A—H41A	0.950	C4B—H41B	0.950
C4A—H42A	0.950	C4B—H42B	0.950
C4A—H43A	0.950	C4B—H43B	0.950
C3A—S1A—C4A	100.28 (8)	C3B—S1B—C4B	100.22 (9)
S1A—C3A—N1A	119.56 (12)	S1B—C3B—N2B	126.69 (13)
S1A—C3A—N2A	126.71 (12)	S1B—C3B—N1B	119.73 (12)
N1A—C3A—N2A	113.67 (14)	N2B—C3B—N1B	113.53 (14)
C3A—N1A—C5A	106.27 (13)	C3B—N2B—C6B	104.41 (13)
C3A—N1A—C2A	127.66 (14)	N2B—C6B—C5B	110.28 (14)
C5A—N1A—C2A	125.82 (13)	N2B—C6B—C7B	129.65 (15)
N1A—C5A—C6A	105.66 (13)	C5B—C6B—C7B	120.07 (16)
N1A—C5A—C10A	131.55 (15)	C6B—C5B—N1B	105.33 (14)
C6A—C5A—C10A	122.79 (15)	C6B—C5B—C10B	122.56 (15)
C5A—C6A—N2A	110.23 (13)	N1B—C5B—C10B	132.10 (15)
C5A—C6A—C7A	120.05 (15)	C5B—N1B—C3B	106.45 (13)
N2A—C6A—C7A	129.72 (15)	C5B—N1B—C2B	126.32 (14)
C6A—N2A—C3A	104.17 (13)	C3B—N1B—C2B	127.15 (14)
C6A—C7A—C8A	117.44 (17)	N1B—C2B—C1B	113.41 (14)
C6A—C7A—H7A	120.6	N1B—C2B—H21B	108.5
C8A—C7A—H7A	122.0	C1B—C2B—H21B	108.4
C7A—C8A—C9A	121.94 (17)	N1B—C2B—H22B	108.5
C7A—C8A—H8A	119.0	C1B—C2B—H22B	108.5
C9A—C8A—H8A	119.0	H21B—C2B—H22B	109.5
C8A—C9A—C10A	121.66 (17)	C2B—C1B—O1B	109.85 (15)
C8A—C9A—H9A	119.2	C2B—C1B—H11B	109.4
C10A—C9A—H9A	119.2	O1B—C1B—H11B	109.5
C5A—C10A—C9A	116.10 (17)	C2B—C1B—H12B	109.4
C5A—C10A—H10A	122.0	O1B—C1B—H12B	109.3
C9A—C10A—H10A	121.9	H11B—C1B—H12B	109.5
N1A—C2A—C1A	113.63 (13)	C1B—O1B—H1B	110.3 (18)
N1A—C2A—H21A	108.4	C5B—C10B—C9B	116.51 (17)
C1A—C2A—H21A	108.3	C5B—C10B—H10B	121.8
N1A—C2A—H22A	108.5	C9B—C10B—H10B	121.7
C1A—C2A—H22A	108.5	C10B—C9B—C8B	121.79 (18)
H21A—C2A—H22A	109.5	C10B—C9B—H9B	119.1
C2A—C1A—O1A	110.78 (13)	C8B—C9B—H9B	119.1
C2A—C1A—H11A	109.2	C9B—C8B—C7B	121.60 (17)
O1A—C1A—H11A	109.2	C9B—C8B—H8B	119.2
C2A—C1A—H12A	109.1	C7B—C8B—H8B	119.2
O1A—C1A—H12A	109.0	C6B—C7B—C8B	117.47 (17)
H11A—C1A—H12A	109.5	C6B—C7B—H7B	121.3
C1A—O1A—H1A	110.8 (16)	C8B—C7B—H7B	121.3
S1A—C4A—H41A	109.5	S1B—C4B—H41B	109.5
S1A—C4A—H42A	109.5	S1B—C4B—H42B	109.5
H41A—C4A—H42A	109.5	H41B—C4B—H42B	109.5
S1A—C4A—H43A	109.5	S1B—C4B—H43B	109.4
H41A—C4A—H43A	109.5	H41B—C4B—H43B	109.5
H42A—C4A—H43A	109.5	H42B—C4B—H43B	109.5

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···Cg2iv	0.95	2.74	3.631 (2)	157

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⋯Cg2iv	0.95	2.74	3.631 (2)	157

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