Ethyl 1-(2-hy-droxy-eth-yl)-2-[2-(methyl-sulfan-yl)eth-yl]-1H-benzimidazole-5-carboxyl-ate.

In the crystal structure of the title compound, C(15)H(20)N(2)O(3)S, the hy-droxy group is involved in the formation of O-H⋯N hydrogen bonds, which link two mol-ecules into a centrosymmetric dimer. Weak C-H⋯O hydrogen bonds further link these dimers into chains propagating along the a axis. The crystal packing exhibits π-π inter-actions between the five- and six-membered rings of neighbouring mol-ecules [centroid-centroid distance = 3.819 (2) Å] and short inter-molecular S⋯S contacts of 3.495 (1) Å.

Related literature

For details of the synthesis and related structures, see: Wright (1951 ▶); Preston (1974 ▶); Hamzah et al. (2010 ▶); Arumugam et al. 2011 ▶); Ruiz et al. (2010 ▶); Chou et al. (2011 ▶). For the therapeutic properties of benzimidazole derivatives, see: Li et al. (2006 ▶); Hwu et al. (2008 ▶); Cui et al. (2010 ▶); Sasmal et al. (2011 ▶); Demirayak et al. (2011 ▶). For bond lengths in organic compounds, see: Allen et al. (1987 ▶). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H20N2O3S

M = 308.39

Triclinic,

a = 8.3909 (1) Å

b = 8.8277 (2) Å

c = 11.5025 (2) Å

α = 110.218 (1)°

β = 102.529 (1)°

γ = 99.101 (1)°

V = 754.78 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.27 × 0.24 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.941, T max = 0.985

6027 measured reflections

2627 independent reflections

2243 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.086

S = 1.04

2627 reflections

196 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105389X/cv5217sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105389X/cv5217Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105389X/cv5217Isup3.cml

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

C15H20N2O3S	Z = 2
Mr = 308.39	F(000) = 328
Triclinic, P1	Dx = 1.357 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3909 (1) Å	Cell parameters from 2401 reflections
b = 8.8277 (2) Å	θ = 1.9–25.0°
c = 11.5025 (2) Å	µ = 0.23 mm−1
α = 110.218 (1)°	T = 100 K
β = 102.529 (1)°	Plate, colourless
γ = 99.101 (1)°	0.27 × 0.24 × 0.07 mm
V = 754.78 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2627 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 1.9°
φ and ω scan	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→10
Tmin = 0.941, Tmax = 0.985	l = −13→13
6027 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0307P)2 + 0.5234P] where P = (Fo2 + 2Fc2)/3
2627 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open=flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	1.33465 (6)	0.81922 (6)	0.91756 (5)	0.02048 (15)
O1	0.36330 (17)	−0.07772 (17)	0.28863 (14)	0.0244 (3)
O2	0.46252 (16)	−0.29862 (16)	0.19992 (13)	0.0195 (3)
O3	1.32576 (17)	0.48466 (17)	0.39325 (14)	0.0213 (3)
H3	1.2305 (18)	0.505 (3)	0.391 (2)	0.035 (7)*
N1	0.94054 (19)	0.36073 (19)	0.58614 (15)	0.0151 (3)
N2	1.14023 (19)	0.26662 (19)	0.50164 (15)	0.0140 (3)
C1	0.8668 (2)	0.2070 (2)	0.48209 (18)	0.0140 (4)
C2	0.6994 (2)	0.1144 (2)	0.43009 (18)	0.0158 (4)
H2	0.6138	0.1549	0.4640	0.019*
C3	0.6610 (2)	−0.0396 (2)	0.32689 (18)	0.0153 (4)
C4	0.7890 (2)	−0.0998 (2)	0.27731 (18)	0.0166 (4)
H4	0.7597	−0.2063	0.2081	0.020*
C5	0.9553 (2)	−0.0084 (2)	0.32637 (18)	0.0164 (4)
H5	1.0408	−0.0485	0.2921	0.020*
C6	0.9912 (2)	0.1465 (2)	0.42935 (18)	0.0141 (4)
C7	1.1022 (2)	0.3904 (2)	0.59415 (18)	0.0145 (4)
C8	0.4814 (2)	−0.1364 (2)	0.27111 (18)	0.0169 (4)
C9	0.2882 (3)	−0.3974 (2)	0.1397 (2)	0.0231 (5)
H9A	0.2271	−0.3537	0.0798	0.028*
H9B	0.2301	−0.3927	0.2067	0.028*
C10	0.2919 (3)	−0.5719 (3)	0.0675 (2)	0.0391 (6)
H10A	0.3534	−0.5743	0.0038	0.059*
H10B	0.1762	−0.6412	0.0227	0.059*
H10C	0.3486	−0.6153	0.1282	0.059*
C11	1.3032 (2)	0.2629 (2)	0.47536 (19)	0.0165 (4)
H11A	1.3195	0.1490	0.4552	0.020*
H11B	1.3949	0.3403	0.5538	0.020*
C12	1.3139 (2)	0.3126 (2)	0.36286 (19)	0.0181 (4)
H12A	1.4139	0.2852	0.3363	0.022*
H12B	1.2125	0.2463	0.2884	0.022*
C13	1.2355 (2)	0.5380 (2)	0.69567 (18)	0.0171 (4)
H13A	1.2923	0.6013	0.6533	0.021*
H13B	1.3214	0.4989	0.7436	0.021*
C14	1.1634 (2)	0.6532 (2)	0.79092 (18)	0.0179 (4)
H14A	1.0995	0.5893	0.8293	0.022*
H14B	1.0850	0.7012	0.7452	0.022*
C15	1.2132 (3)	0.9482 (3)	0.9979 (2)	0.0253 (5)
H15A	1.1466	0.9862	0.9373	0.038*
H15B	1.2896	1.0452	1.0725	0.038*
H15C	1.1373	0.8836	1.0275	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0191 (3)	0.0174 (3)	0.0193 (3)	0.0018 (2)	0.0047 (2)	0.0024 (2)
O1	0.0171 (8)	0.0243 (8)	0.0270 (8)	0.0040 (6)	0.0062 (6)	0.0053 (7)
O2	0.0192 (7)	0.0149 (7)	0.0191 (7)	0.0003 (6)	0.0016 (6)	0.0046 (6)
O3	0.0165 (8)	0.0198 (7)	0.0332 (9)	0.0064 (6)	0.0106 (7)	0.0144 (7)
N1	0.0152 (8)	0.0137 (8)	0.0161 (8)	0.0033 (6)	0.0047 (7)	0.0054 (7)
N2	0.0126 (8)	0.0142 (8)	0.0167 (8)	0.0043 (6)	0.0057 (7)	0.0065 (7)
C1	0.0168 (10)	0.0131 (9)	0.0135 (10)	0.0056 (8)	0.0046 (8)	0.0062 (8)
C2	0.0161 (10)	0.0172 (10)	0.0160 (10)	0.0059 (8)	0.0058 (8)	0.0075 (8)
C3	0.0174 (10)	0.0162 (10)	0.0144 (10)	0.0040 (8)	0.0038 (8)	0.0090 (8)
C4	0.0224 (11)	0.0129 (9)	0.0141 (10)	0.0039 (8)	0.0054 (8)	0.0049 (8)
C5	0.0189 (10)	0.0167 (10)	0.0175 (10)	0.0070 (8)	0.0095 (8)	0.0077 (8)
C6	0.0143 (10)	0.0146 (9)	0.0153 (10)	0.0037 (8)	0.0043 (8)	0.0083 (8)
C7	0.0176 (10)	0.0132 (9)	0.0153 (10)	0.0057 (8)	0.0059 (8)	0.0074 (8)
C8	0.0208 (11)	0.0174 (10)	0.0136 (10)	0.0040 (8)	0.0049 (8)	0.0079 (8)
C9	0.0184 (11)	0.0230 (11)	0.0224 (11)	−0.0025 (8)	0.0015 (9)	0.0085 (9)
C10	0.0296 (13)	0.0301 (13)	0.0410 (15)	−0.0038 (10)	0.0105 (12)	−0.0004 (11)
C11	0.0140 (10)	0.0162 (10)	0.0213 (11)	0.0070 (8)	0.0075 (8)	0.0070 (8)
C12	0.0170 (10)	0.0185 (10)	0.0219 (11)	0.0072 (8)	0.0094 (9)	0.0082 (9)
C13	0.0161 (10)	0.0169 (10)	0.0183 (11)	0.0038 (8)	0.0056 (8)	0.0065 (8)
C14	0.0161 (10)	0.0187 (10)	0.0161 (10)	0.0032 (8)	0.0034 (8)	0.0047 (8)
C15	0.0294 (12)	0.0214 (11)	0.0222 (11)	0.0087 (9)	0.0075 (10)	0.0043 (9)

S1—C15	1.799 (2)	C5—H5	0.9500
S1—C14	1.812 (2)	C7—C13	1.495 (3)
O1—C8	1.212 (2)	C9—C10	1.485 (3)
O2—C8	1.345 (2)	C9—H9A	0.9900
O2—C9	1.456 (2)	C9—H9B	0.9900
O3—C12	1.417 (2)	C10—H10A	0.9800
O3—H3	0.843 (10)	C10—H10B	0.9800
N1—C7	1.317 (2)	C10—H10C	0.9800
N1—C1	1.395 (2)	C11—C12	1.518 (3)
N2—C7	1.372 (2)	C11—H11A	0.9900
N2—C6	1.379 (2)	C11—H11B	0.9900
N2—C11	1.466 (2)	C12—H12A	0.9900
C1—C2	1.391 (3)	C12—H12B	0.9900
C1—C6	1.403 (2)	C13—C14	1.521 (3)
C2—C3	1.393 (3)	C13—H13A	0.9900
C2—H2	0.9500	C13—H13B	0.9900
C3—C4	1.414 (3)	C14—H14A	0.9900
C3—C8	1.485 (3)	C14—H14B	0.9900
C4—C5	1.379 (3)	C15—H15A	0.9800
C4—H4	0.9500	C15—H15B	0.9800
C5—C6	1.400 (3)	C15—H15C	0.9800
C15—S1—C14	99.19 (10)	C9—C10—H10A	109.5
C8—O2—C9	114.83 (15)	C9—C10—H10B	109.5
C12—O3—H3	110.8 (17)	H10A—C10—H10B	109.5
C7—N1—C1	104.86 (15)	C9—C10—H10C	109.5
C7—N2—C6	106.81 (14)	H10A—C10—H10C	109.5
C7—N2—C11	128.13 (16)	H10B—C10—H10C	109.5
C6—N2—C11	124.94 (15)	N2—C11—C12	111.81 (15)
C2—C1—N1	130.07 (17)	N2—C11—H11A	109.3
C2—C1—C6	120.17 (17)	C12—C11—H11A	109.3
N1—C1—C6	109.76 (16)	N2—C11—H11B	109.3
C1—C2—C3	118.05 (17)	C12—C11—H11B	109.3
C1—C2—H2	121.0	H11A—C11—H11B	107.9
C3—C2—H2	121.0	O3—C12—C11	113.02 (16)
C2—C3—C4	120.76 (17)	O3—C12—H12A	109.0
C2—C3—C8	117.54 (17)	C11—C12—H12A	109.0
C4—C3—C8	121.69 (17)	O3—C12—H12B	109.0
C5—C4—C3	121.96 (18)	C11—C12—H12B	109.0
C5—C4—H4	119.0	H12A—C12—H12B	107.8
C3—C4—H4	119.0	C7—C13—C14	112.12 (15)
C4—C5—C6	116.42 (17)	C7—C13—H13A	109.2
C4—C5—H5	121.8	C14—C13—H13A	109.2
C6—C5—H5	121.8	C7—C13—H13B	109.2
N2—C6—C5	131.88 (17)	C14—C13—H13B	109.2
N2—C6—C1	105.50 (16)	H13A—C13—H13B	107.9
C5—C6—C1	122.61 (17)	C13—C14—S1	109.23 (13)
N1—C7—N2	113.06 (17)	C13—C14—H14A	109.8
N1—C7—C13	124.93 (16)	S1—C14—H14A	109.8
N2—C7—C13	121.95 (16)	C13—C14—H14B	109.8
O1—C8—O2	122.83 (18)	S1—C14—H14B	109.8
O1—C8—C3	124.28 (18)	H14A—C14—H14B	108.3
O2—C8—C3	112.88 (16)	S1—C15—H15A	109.5
O2—C9—C10	107.31 (17)	S1—C15—H15B	109.5
O2—C9—H9A	110.3	H15A—C15—H15B	109.5
C10—C9—H9A	110.3	S1—C15—H15C	109.5
O2—C9—H9B	110.3	H15A—C15—H15C	109.5
C10—C9—H9B	110.3	H15B—C15—H15C	109.5
H9A—C9—H9B	108.5
C7—N1—C1—C2	179.65 (19)	C1—N1—C7—C13	−177.00 (17)
C7—N1—C1—C6	0.33 (19)	C6—N2—C7—N1	−0.9 (2)
N1—C1—C2—C3	−178.17 (17)	C11—N2—C7—N1	175.16 (16)
C6—C1—C2—C3	1.1 (3)	C6—N2—C7—C13	176.55 (16)
C1—C2—C3—C4	0.4 (3)	C11—N2—C7—C13	−7.4 (3)
C1—C2—C3—C8	−179.23 (16)	C9—O2—C8—O1	3.0 (3)
C2—C3—C4—C5	−1.4 (3)	C9—O2—C8—C3	−178.05 (15)
C8—C3—C4—C5	178.19 (17)	C2—C3—C8—O1	16.9 (3)
C3—C4—C5—C6	0.8 (3)	C4—C3—C8—O1	−162.71 (18)
C7—N2—C6—C5	−177.37 (19)	C2—C3—C8—O2	−162.02 (16)
C11—N2—C6—C5	6.4 (3)	C4—C3—C8—O2	18.4 (2)
C7—N2—C6—C1	1.00 (19)	C8—O2—C9—C10	−179.17 (17)
C11—N2—C6—C1	−175.20 (16)	C7—N2—C11—C12	−98.5 (2)
C4—C5—C6—N2	178.81 (18)	C6—N2—C11—C12	76.8 (2)
C4—C5—C6—C1	0.7 (3)	N2—C11—C12—O3	70.8 (2)
C2—C1—C6—N2	179.76 (16)	N1—C7—C13—C14	0.0 (3)
N1—C1—C6—N2	−0.84 (19)	N2—C7—C13—C14	−177.14 (16)
C2—C1—C6—C5	−1.7 (3)	C7—C13—C14—S1	175.48 (13)
N1—C1—C6—C5	177.72 (16)	C15—S1—C14—C13	171.67 (14)
C1—N1—C7—N2	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1i	0.84 (2)	2.01 (2)	2.808 (2)	159 (2)
C11—H11A···O1ii	0.99	2.39	3.224 (2)	142
C11—H11B···O3iii	0.99	2.42	3.222 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1i	0.84 (2)	2.01 (2)	2.808 (2)	159 (2)
C11—H11A⋯O1ii	0.99	2.39	3.224 (2)	142
C11—H11B⋯O3iii	0.99	2.42	3.222 (2)	138

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