Ethyl 1-(2-hy-droxy-eth-yl)-2-propyl-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(15)H(20)N(2)O(3), the benzimidazole ring is essentially planar, with a maximum deviation from the mean plane of 0.012 (1) Å. The crystal structure is stabilized by inter-molecular O-H⋯N hydrogen bonds, forming centrosymmetric dimers, which are connected in the [100] direction through weak C-H⋯O contacts.

Related literature

For the synthesis of the title compound, see: Arumugam et al. (2010 ▶); Kappe (2004 ▶). For general background and therapeutic properties of benzimidazole derivatives, see: Rao et al. (2002 ▶); Khalafi-Nezhad et al. (2005 ▶); Tonelli et al. (2010 ▶); Chen et al. (2007 ▶). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H20N2O3

M = 276.33

Triclinic,

a = 8.5081 (3) Å

b = 8.5573 (3) Å

c = 10.0117 (4) Å

α = 94.671 (3)°

β = 106.903 (2)°

γ = 98.334 (3)°

V = 684.16 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.60 × 0.20 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.946, T max = 0.994

10526 measured reflections

2401 independent reflections

2075 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.087

S = 1.08

2401 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.25 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/S1600536811037421/bh2376sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037421/bh2376Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037421/bh2376Isup3.cml

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

C15H20N2O3	Z = 2
Mr = 276.33	F(000) = 296
Triclinic, P1	Dx = 1.341 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5081 (3) Å	Cell parameters from 5332 reflections
b = 8.5573 (3) Å	θ = 2.1–25.0°
c = 10.0117 (4) Å	µ = 0.09 mm−1
α = 94.671 (3)°	T = 100 K
β = 106.903 (2)°	Plate, colourless
γ = 98.334 (3)°	0.60 × 0.20 × 0.07 mm
V = 684.16 (4) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2401 independent reflections
Radiation source: fine-focus sealed tube	2075 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.946, Tmax = 0.994	l = −11→11
10526 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0378P)2 + 0.2619P] where P = (Fo2 + 2Fc2)/3
2401 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 e Å−3
0 constraints

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.

	x	y	z	Uiso*/Ueq
O1	0.27470 (12)	0.59246 (12)	0.65294 (11)	0.0183 (3)
O2	0.45117 (13)	0.43517 (13)	0.75699 (12)	0.0241 (3)
O3	−0.40580 (13)	−0.06135 (12)	0.88681 (11)	0.0184 (3)
H3A	−0.315 (3)	−0.088 (2)	0.879 (2)	0.045 (6)*
N1	−0.14250 (14)	0.23821 (13)	0.99931 (12)	0.0132 (3)
N2	0.12077 (14)	0.19893 (14)	1.09005 (12)	0.0138 (3)
C1	0.11012 (17)	0.28238 (16)	0.97476 (15)	0.0134 (3)
C2	0.23274 (18)	0.33848 (16)	0.91519 (15)	0.0145 (3)
H2A	0.3441	0.3213	0.9524	0.017*
C3	0.18718 (18)	0.42060 (16)	0.79936 (15)	0.0146 (3)
C4	0.02190 (18)	0.44787 (17)	0.74524 (15)	0.0152 (3)
H4A	−0.0053	0.5061	0.6673	0.018*
C5	−0.10116 (18)	0.39202 (16)	0.80289 (15)	0.0149 (3)
H5A	−0.2123	0.4100	0.7663	0.018*
C6	−0.05419 (17)	0.30799 (16)	0.91746 (14)	0.0130 (3)
C7	−0.03154 (17)	0.17548 (16)	1.10106 (15)	0.0134 (3)
C8	0.31874 (18)	0.48006 (17)	0.73628 (15)	0.0160 (3)
C9	0.39782 (19)	0.65961 (18)	0.58856 (17)	0.0207 (4)
H9A	0.3987	0.5840	0.5086	0.025*
H9B	0.5106	0.6813	0.6582	0.025*
C10	0.3502 (2)	0.81088 (19)	0.53830 (17)	0.0239 (4)
H10A	0.4265	0.8557	0.4888	0.036*
H10B	0.3571	0.8873	0.6191	0.036*
H10C	0.2357	0.7889	0.4741	0.036*
C11	−0.32301 (17)	0.22441 (17)	0.97243 (15)	0.0147 (3)
H11A	−0.3564	0.3274	0.9492	0.018*
H11B	−0.3508	0.2007	1.0589	0.018*
C12	−0.42069 (18)	0.09446 (17)	0.85251 (15)	0.0162 (3)
H12A	−0.5400	0.1044	0.8252	0.019*
H12B	−0.3809	0.1103	0.7701	0.019*
C13	−0.08488 (18)	0.09237 (17)	1.21037 (15)	0.0158 (3)
H13A	−0.1637	−0.0071	1.1638	0.019*
H13B	−0.1456	0.1610	1.2540	0.019*
C14	0.05897 (19)	0.05117 (18)	1.32650 (16)	0.0184 (3)
H14A	0.0130	−0.0277	1.3786	0.022*
H14B	0.1328	0.0009	1.2827	0.022*
C15	0.1621 (2)	0.19530 (19)	1.43011 (16)	0.0238 (4)
H15A	0.2517	0.1615	1.5019	0.036*
H15B	0.0904	0.2445	1.4754	0.036*
H15C	0.2107	0.2727	1.3797	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0174 (5)	0.0194 (5)	0.0219 (6)	0.0049 (4)	0.0097 (5)	0.0088 (5)
O2	0.0174 (6)	0.0319 (6)	0.0297 (6)	0.0102 (5)	0.0117 (5)	0.0145 (5)
O3	0.0151 (6)	0.0148 (5)	0.0271 (6)	0.0033 (4)	0.0089 (5)	0.0033 (5)
N1	0.0115 (6)	0.0135 (6)	0.0149 (6)	0.0026 (5)	0.0045 (5)	0.0019 (5)
N2	0.0145 (6)	0.0139 (6)	0.0138 (6)	0.0036 (5)	0.0051 (5)	0.0023 (5)
C1	0.0146 (7)	0.0111 (7)	0.0142 (7)	0.0036 (6)	0.0039 (6)	0.0002 (6)
C2	0.0116 (7)	0.0139 (7)	0.0170 (7)	0.0035 (6)	0.0029 (6)	−0.0004 (6)
C3	0.0154 (7)	0.0111 (7)	0.0169 (8)	0.0016 (6)	0.0054 (6)	−0.0002 (6)
C4	0.0182 (8)	0.0123 (7)	0.0141 (7)	0.0034 (6)	0.0031 (6)	0.0014 (6)
C5	0.0123 (7)	0.0142 (7)	0.0165 (7)	0.0037 (6)	0.0019 (6)	0.0001 (6)
C6	0.0141 (7)	0.0110 (7)	0.0133 (7)	0.0012 (6)	0.0046 (6)	−0.0018 (6)
C7	0.0159 (7)	0.0107 (7)	0.0137 (7)	0.0033 (6)	0.0048 (6)	−0.0008 (6)
C8	0.0176 (8)	0.0160 (7)	0.0136 (7)	0.0026 (6)	0.0037 (6)	0.0009 (6)
C9	0.0197 (8)	0.0239 (8)	0.0236 (8)	0.0036 (7)	0.0132 (7)	0.0080 (7)
C10	0.0257 (9)	0.0245 (9)	0.0221 (8)	0.0019 (7)	0.0091 (7)	0.0047 (7)
C11	0.0112 (7)	0.0164 (7)	0.0181 (8)	0.0047 (6)	0.0054 (6)	0.0034 (6)
C12	0.0127 (7)	0.0172 (8)	0.0185 (8)	0.0029 (6)	0.0040 (6)	0.0030 (6)
C13	0.0169 (8)	0.0148 (7)	0.0175 (8)	0.0027 (6)	0.0077 (6)	0.0025 (6)
C14	0.0215 (8)	0.0202 (8)	0.0176 (8)	0.0074 (6)	0.0093 (7)	0.0065 (6)
C15	0.0210 (8)	0.0295 (9)	0.0200 (8)	0.0041 (7)	0.0046 (7)	0.0048 (7)

O1—C8	1.3471 (17)	C9—C10	1.494 (2)
O1—C9	1.4565 (18)	C9—H9A	0.9900
O2—C8	1.2094 (18)	C9—H9B	0.9900
O3—C12	1.4177 (17)	C10—H10A	0.9800
O3—H3A	0.86 (2)	C10—H10B	0.9800
N1—C7	1.3762 (18)	C10—H10C	0.9800
N1—C6	1.3785 (19)	C11—C12	1.518 (2)
N1—C11	1.4653 (18)	C11—H11A	0.9900
N2—C7	1.3202 (18)	C11—H11B	0.9900
N2—C1	1.3937 (18)	C12—H12A	0.9900
C1—C2	1.392 (2)	C12—H12B	0.9900
C1—C6	1.405 (2)	C13—C14	1.529 (2)
C2—C3	1.393 (2)	C13—H13A	0.9900
C2—H2A	0.9500	C13—H13B	0.9900
C3—C4	1.414 (2)	C14—C15	1.522 (2)
C3—C8	1.486 (2)	C14—H14A	0.9900
C4—C5	1.382 (2)	C14—H14B	0.9900
C4—H4A	0.9500	C15—H15A	0.9800
C5—C6	1.394 (2)	C15—H15B	0.9800
C5—H5A	0.9500	C15—H15C	0.9800
C7—C13	1.494 (2)
C8—O1—C9	115.89 (11)	C9—C10—H10A	109.5
C12—O3—H3A	111.6 (14)	C9—C10—H10B	109.5
C7—N1—C6	106.93 (11)	H10A—C10—H10B	109.5
C7—N1—C11	127.84 (12)	C9—C10—H10C	109.5
C6—N1—C11	125.05 (12)	H10A—C10—H10C	109.5
C7—N2—C1	105.09 (11)	H10B—C10—H10C	109.5
C2—C1—N2	130.08 (13)	N1—C11—C12	111.97 (11)
C2—C1—C6	120.14 (13)	N1—C11—H11A	109.2
N2—C1—C6	109.77 (12)	C12—C11—H11A	109.2
C1—C2—C3	117.98 (13)	N1—C11—H11B	109.2
C1—C2—H2A	121.0	C12—C11—H11B	109.2
C3—C2—H2A	121.0	H11A—C11—H11B	107.9
C2—C3—C4	120.92 (13)	O3—C12—C11	113.35 (12)
C2—C3—C8	117.67 (13)	O3—C12—H12A	108.9
C4—C3—C8	121.40 (13)	C11—C12—H12A	108.9
C5—C4—C3	121.66 (13)	O3—C12—H12B	108.9
C5—C4—H4A	119.2	C11—C12—H12B	108.9
C3—C4—H4A	119.2	H12A—C12—H12B	107.7
C4—C5—C6	116.73 (13)	C7—C13—C14	114.12 (12)
C4—C5—H5A	121.6	C7—C13—H13A	108.7
C6—C5—H5A	121.6	C14—C13—H13A	108.7
N1—C6—C5	131.94 (13)	C7—C13—H13B	108.7
N1—C6—C1	105.49 (12)	C14—C13—H13B	108.7
C5—C6—C1	122.55 (13)	H13A—C13—H13B	107.6
N2—C7—N1	112.72 (12)	C15—C14—C13	113.25 (12)
N2—C7—C13	125.88 (13)	C15—C14—H14A	108.9
N1—C7—C13	121.40 (12)	C13—C14—H14A	108.9
O2—C8—O1	123.07 (13)	C15—C14—H14B	108.9
O2—C8—C3	124.77 (13)	C13—C14—H14B	108.9
O1—C8—C3	112.16 (12)	H14A—C14—H14B	107.7
O1—C9—C10	107.38 (12)	C14—C15—H15A	109.5
O1—C9—H9A	110.2	C14—C15—H15B	109.5
C10—C9—H9A	110.2	H15A—C15—H15B	109.5
O1—C9—H9B	110.2	C14—C15—H15C	109.5
C10—C9—H9B	110.2	H15A—C15—H15C	109.5
H9A—C9—H9B	108.5	H15B—C15—H15C	109.5
C7—N2—C1—C2	179.98 (14)	C1—N2—C7—N1	0.20 (15)
C7—N2—C1—C6	0.06 (15)	C1—N2—C7—C13	−179.22 (13)
N2—C1—C2—C3	−179.43 (14)	C6—N1—C7—N2	−0.39 (15)
C6—C1—C2—C3	0.5 (2)	C11—N1—C7—N2	174.91 (12)
C1—C2—C3—C4	0.8 (2)	C6—N1—C7—C13	179.07 (12)
C1—C2—C3—C8	−179.97 (12)	C11—N1—C7—C13	−5.6 (2)
C2—C3—C4—C5	−1.2 (2)	C9—O1—C8—O2	−0.5 (2)
C8—C3—C4—C5	179.59 (13)	C9—O1—C8—C3	178.95 (12)
C3—C4—C5—C6	0.3 (2)	C2—C3—C8—O2	16.6 (2)
C7—N1—C6—C5	−178.15 (14)	C4—C3—C8—O2	−164.22 (14)
C11—N1—C6—C5	6.4 (2)	C2—C3—C8—O1	−162.86 (12)
C7—N1—C6—C1	0.39 (14)	C4—C3—C8—O1	16.34 (19)
C11—N1—C6—C1	−175.07 (12)	C8—O1—C9—C10	−163.28 (12)
C4—C5—C6—N1	179.43 (13)	C7—N1—C11—C12	−98.59 (16)
C4—C5—C6—C1	1.1 (2)	C6—N1—C11—C12	75.92 (16)
C2—C1—C6—N1	179.78 (12)	N1—C11—C12—O3	70.35 (16)
N2—C1—C6—N1	−0.28 (15)	N2—C7—C13—C14	7.5 (2)
C2—C1—C6—C5	−1.5 (2)	N1—C7—C13—C14	−171.87 (12)
N2—C1—C6—C5	178.43 (12)	C7—C13—C14—C15	73.93 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2i	0.86 (3)	1.98 (2)	2.8047 (17)	159.6 (17)
C11—H11A···O2ii	0.99	2.48	3.2901 (19)	139
C11—H11B···O3iii	0.99	2.46	3.2457 (19)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2i	0.86 (3)	1.98 (2)	2.8047 (17)	159.6 (17)
C11—H11A⋯O2ii	0.99	2.48	3.2901 (19)	139

Symmetry codes: (i) ; (ii) .