2-sec-Butyl-1-(2-hy-droxy-eth-yl)-1H-benzimidazole-5-carboxylic acid.

In the title compound, C(14)H(18)N(2)O(3), the carb-oxy-lic group is tilted by 12.00 (4)° with respect to the mean plane throught the benzimidazole ring system. The alcohol and carboxyl hydroxy groups are involved in intermolecular O-H⋯O and O-H⋯N hydrogen bonds, forming a two-dimensional network extending parallel the ab plane. The network is further stabilized by weak C-H⋯O inter-actions. The sec-butyl group is disordered over two sets of sites with refined occupancies of 0.484 (4) and 0.516 (4).

Related literature

For related structures, see: Arumugam et al. (2011 ▶); Hamzah et al. (2012 ▶). For therapeutic properties of benzimidazole derivatives, see: Xue et al. (2011 ▶); Gellis et al. (2008 ▶); Boiani et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H18N2O3

M = 262.30

Monoclinic,

a = 8.9427 (2) Å

b = 8.2067 (2) Å

c = 18.3536 (3) Å

β = 94.415 (1)°

V = 1342.97 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.50 × 0.36 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.955, T max = 0.986

11481 measured reflections

2491 independent reflections

2190 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.03

2491 reflections

200 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 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/S1600536812023884/rz2764sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023884/rz2764Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023884/rz2764Isup3.cml

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

C14H18N2O3	F(000) = 560
Mr = 262.30	Dx = 1.297 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6388 reflections
a = 8.9427 (2) Å	θ = 2.4–25.5°
b = 8.2067 (2) Å	µ = 0.09 mm−1
c = 18.3536 (3) Å	T = 100 K
β = 94.415 (1)°	Block, colourless
V = 1342.97 (5) Å3	0.50 × 0.36 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2491 independent reflections
Radiation source: fine-focus sealed tube	2190 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 83.66 pixels mm-1	θmax = 25.5°, θmin = 2.4°
φ and ω scan	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→9
Tmin = 0.955, Tmax = 0.986	l = −22→22
11481 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.5356P] where P = (Fo2 + 2Fc2)/3
2491 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.20 e Å−3
6 restraints	Δρmin = −0.19 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	Occ. (<1)
O1	−0.34306 (10)	0.27634 (12)	0.46443 (5)	0.0256 (2)
O2	−0.18373 (11)	0.07220 (12)	0.49284 (5)	0.0287 (2)
O3	0.20151 (10)	0.42060 (11)	0.12007 (5)	0.0219 (2)
N1	0.12053 (11)	0.03383 (12)	0.26410 (5)	0.0190 (2)
N2	−0.00305 (11)	0.18127 (12)	0.17645 (5)	0.0180 (2)
C1	−0.00646 (13)	0.10204 (14)	0.29170 (6)	0.0170 (3)
C2	−0.05883 (13)	0.09255 (15)	0.36115 (6)	0.0180 (3)
H2A	−0.0087	0.0282	0.3985	0.022*
C3	−0.18717 (13)	0.18066 (15)	0.37392 (7)	0.0186 (3)
C4	−0.26332 (14)	0.27436 (16)	0.31848 (7)	0.0211 (3)
H4A	−0.3507	0.3330	0.3290	0.025*
C5	−0.21368 (14)	0.28282 (16)	0.24910 (7)	0.0214 (3)
H5A	−0.2653	0.3450	0.2114	0.026*
C6	−0.08397 (13)	0.19556 (15)	0.23719 (6)	0.0176 (3)
C7	0.11917 (13)	0.08457 (15)	0.19581 (6)	0.0181 (3)
C8	−0.24608 (13)	0.18323 (15)	0.44752 (7)	0.0194 (3)
C9	−0.03388 (14)	0.27534 (16)	0.10911 (6)	0.0205 (3)
H9A	−0.1435	0.2911	0.1000	0.025*
H9B	0.0017	0.2136	0.0674	0.025*
C10	0.04292 (14)	0.44020 (16)	0.11404 (7)	0.0217 (3)
H10A	0.0124	0.5050	0.0699	0.026*
H10B	0.0116	0.5000	0.1572	0.026*
C11	0.23294 (13)	0.03938 (15)	0.14321 (6)	0.0212 (3)
H11A	0.2217	0.1164	0.1009	0.025*	0.484 (4)
H11B	0.2149	0.1112	0.0994	0.025*	0.516 (4)
C12	0.3911 (9)	0.061 (4)	0.1808 (11)	0.0279 (10)	0.484 (4)
H12A	0.4656	0.0439	0.1451	0.042*	0.484 (4)
H12B	0.4070	−0.0189	0.2204	0.042*	0.484 (4)
H12C	0.4015	0.1712	0.2010	0.042*	0.484 (4)
C13	0.208 (3)	−0.135 (2)	0.1137 (10)	0.0288 (5)	0.484 (4)
H13A	0.2441	−0.2149	0.1513	0.035*	0.484 (4)
H13B	0.0998	−0.1539	0.1012	0.035*	0.484 (4)
C14	0.2951 (4)	−0.1541 (4)	0.04528 (15)	0.0302 (8)	0.484 (4)
H14A	0.2766	−0.2628	0.0244	0.045*	0.484 (4)
H14B	0.4026	−0.1406	0.0586	0.045*	0.484 (4)
H14C	0.2616	−0.0713	0.0092	0.045*	0.484 (4)
C12X	0.202 (2)	−0.1350 (18)	0.1179 (9)	0.0288 (5)	0.516 (4)
H12D	0.2770	−0.1682	0.0847	0.043*	0.516 (4)
H12E	0.1017	−0.1412	0.0924	0.043*	0.516 (4)
H12F	0.2071	−0.2077	0.1604	0.043*	0.516 (4)
C13X	0.3932 (8)	0.068 (4)	0.1744 (10)	0.0279 (10)	0.516 (4)
H13C	0.4247	−0.0221	0.2081	0.033*	0.516 (4)
H13D	0.3986	0.1709	0.2025	0.033*	0.516 (4)
C14X	0.4982 (3)	0.0770 (3)	0.11315 (15)	0.0282 (8)	0.516 (4)
H14D	0.6015	0.0908	0.1341	0.042*	0.516 (4)
H14E	0.4702	0.1698	0.0814	0.042*	0.516 (4)
H14F	0.4905	−0.0238	0.0845	0.042*	0.516 (4)
H3	0.248 (2)	0.459 (2)	0.1644 (11)	0.055 (5)*
H2	−0.224 (2)	0.080 (2)	0.5373 (11)	0.057 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0245 (5)	0.0349 (5)	0.0183 (5)	0.0060 (4)	0.0066 (4)	−0.0005 (4)
O2	0.0299 (5)	0.0407 (6)	0.0167 (5)	0.0106 (4)	0.0103 (4)	0.0073 (4)
O3	0.0202 (5)	0.0288 (5)	0.0172 (5)	−0.0024 (4)	0.0056 (4)	−0.0024 (4)
N1	0.0204 (5)	0.0202 (5)	0.0170 (5)	0.0017 (4)	0.0062 (4)	0.0013 (4)
N2	0.0179 (5)	0.0223 (5)	0.0143 (5)	0.0006 (4)	0.0046 (4)	0.0019 (4)
C1	0.0165 (6)	0.0178 (6)	0.0169 (6)	−0.0027 (5)	0.0034 (4)	−0.0007 (5)
C2	0.0187 (6)	0.0193 (6)	0.0162 (6)	−0.0019 (5)	0.0024 (5)	0.0008 (5)
C3	0.0179 (6)	0.0218 (6)	0.0166 (6)	−0.0036 (5)	0.0035 (5)	−0.0015 (5)
C4	0.0172 (6)	0.0264 (7)	0.0203 (6)	0.0016 (5)	0.0050 (5)	−0.0005 (5)
C5	0.0184 (6)	0.0273 (7)	0.0185 (6)	0.0016 (5)	0.0023 (5)	0.0030 (5)
C6	0.0177 (6)	0.0204 (6)	0.0150 (6)	−0.0034 (5)	0.0038 (5)	−0.0005 (5)
C7	0.0191 (6)	0.0186 (6)	0.0171 (6)	−0.0006 (5)	0.0043 (5)	0.0008 (5)
C8	0.0164 (6)	0.0249 (6)	0.0170 (6)	−0.0026 (5)	0.0019 (5)	−0.0012 (5)
C9	0.0184 (6)	0.0294 (7)	0.0139 (6)	0.0021 (5)	0.0026 (5)	0.0038 (5)
C10	0.0227 (6)	0.0254 (7)	0.0177 (6)	0.0047 (5)	0.0059 (5)	0.0042 (5)
C11	0.0235 (6)	0.0243 (6)	0.0168 (6)	0.0051 (5)	0.0077 (5)	0.0030 (5)
C12	0.0227 (7)	0.033 (2)	0.029 (2)	−0.0012 (6)	0.0104 (7)	−0.006 (2)
C13	0.0250 (15)	0.0337 (8)	0.0282 (15)	0.0024 (7)	0.0053 (10)	−0.0113 (9)
C14	0.0394 (17)	0.0299 (16)	0.0210 (15)	0.0092 (13)	0.0008 (12)	−0.0061 (12)
C12X	0.0250 (15)	0.0337 (8)	0.0282 (15)	0.0024 (7)	0.0053 (10)	−0.0113 (9)
C13X	0.0227 (7)	0.033 (2)	0.029 (2)	−0.0012 (6)	0.0104 (7)	−0.006 (2)
C14X	0.0217 (14)	0.0327 (15)	0.0313 (15)	0.0008 (11)	0.0089 (11)	0.0010 (12)

O1—C8	1.2140 (15)	C10—H10B	0.9900
O2—C8	1.3273 (16)	C11—C13X	1.520 (11)
O2—H2	0.92 (2)	C11—C12X	1.523 (11)
O3—C10	1.4231 (15)	C11—C12	1.535 (12)
O3—H3	0.94 (2)	C11—C13	1.537 (12)
N1—C7	1.3199 (16)	C11—H11A	1.0000
N1—C1	1.3958 (15)	C11—H11B	1.0000
N2—C7	1.3750 (16)	C12—H12A	0.9800
N2—C6	1.3799 (15)	C12—H12B	0.9800
N2—C9	1.4653 (15)	C12—H12C	0.9800
C1—C2	1.3936 (17)	C13—C14	1.536 (12)
C1—C6	1.4013 (17)	C13—H13A	0.9900
C2—C3	1.3916 (17)	C13—H13B	0.9900
C2—H2A	0.9500	C14—H14A	0.9800
C3—C4	1.4084 (18)	C14—H14B	0.9800
C3—C8	1.4873 (16)	C14—H14C	0.9800
C4—C5	1.3822 (17)	C12X—H12D	0.9800
C4—H4A	0.9500	C12X—H12E	0.9800
C5—C6	1.3947 (17)	C12X—H12F	0.9800
C5—H5A	0.9500	C13X—C14X	1.521 (11)
C7—C11	1.5019 (16)	C13X—H13C	0.9900
C9—C10	1.5169 (18)	C13X—H13D	0.9900
C9—H9A	0.9900	C14X—H14D	0.9800
C9—H9B	0.9900	C14X—H14E	0.9800
C10—H10A	0.9900	C14X—H14F	0.9800
C8—O2—H2	109.3 (12)	C13X—C11—C12X	113.8 (16)
C10—O3—H3	113.7 (12)	C7—C11—C12	109.2 (7)
C7—N1—C1	105.66 (10)	C12X—C11—C12	112.6 (16)
C7—N2—C6	107.23 (9)	C7—C11—C13	111.6 (6)
C7—N2—C9	128.04 (10)	C13X—C11—C13	112.5 (15)
C6—N2—C9	124.07 (10)	C12—C11—C13	111.6 (16)
C2—C1—N1	130.52 (11)	C7—C11—H11A	108.1
C2—C1—C6	120.07 (11)	C13X—C11—H11A	103.3
N1—C1—C6	109.39 (10)	C12X—C11—H11A	110.6
C3—C2—C1	117.68 (11)	C12—C11—H11A	108.1
C3—C2—H2A	121.2	C13—C11—H11A	108.1
C1—C2—H2A	121.2	C7—C11—H11B	107.2
C2—C3—C4	121.41 (11)	C13X—C11—H11B	107.5
C2—C3—C8	120.98 (11)	C12X—C11—H11B	107.1
C4—C3—C8	117.58 (11)	C12—C11—H11B	112.3
C5—C4—C3	121.42 (11)	C13—C11—H11B	104.7
C5—C4—H4A	119.3	C11—C12—H12A	109.5
C3—C4—H4A	119.3	C11—C12—H12B	109.5
C4—C5—C6	116.65 (11)	C11—C12—H12C	109.5
C4—C5—H5A	121.7	C14—C13—C11	108.4 (12)
C6—C5—H5A	121.7	C14—C13—H13A	110.0
N2—C6—C5	131.64 (11)	C11—C13—H13A	110.0
N2—C6—C1	105.60 (10)	C14—C13—H13B	110.0
C5—C6—C1	122.75 (11)	C11—C13—H13B	110.0
N1—C7—N2	112.11 (10)	H13A—C13—H13B	108.4
N1—C7—C11	125.12 (11)	C11—C12X—H12D	109.5
N2—C7—C11	122.74 (10)	C11—C12X—H12E	109.5
O1—C8—O2	123.08 (11)	H12D—C12X—H12E	109.5
O1—C8—C3	123.44 (11)	C11—C12X—H12F	109.5
O2—C8—C3	113.48 (10)	H12D—C12X—H12F	109.5
N2—C9—C10	111.39 (10)	H12E—C12X—H12F	109.5
N2—C9—H9A	109.3	C11—C13X—C14X	110.3 (11)
C10—C9—H9A	109.3	C11—C13X—H13C	109.6
N2—C9—H9B	109.3	C14X—C13X—H13C	109.6
C10—C9—H9B	109.3	C11—C13X—H13D	109.6
H9A—C9—H9B	108.0	C14X—C13X—H13D	109.6
O3—C10—C9	110.35 (10)	H13C—C13X—H13D	108.1
O3—C10—H10A	109.6	C13X—C14X—H14D	109.5
C9—C10—H10A	109.6	C13X—C14X—H14E	109.5
O3—C10—H10B	109.6	H14D—C14X—H14E	109.5
C9—C10—H10B	109.6	C13X—C14X—H14F	109.5
H10A—C10—H10B	108.1	H14D—C14X—H14F	109.5
C7—C11—C13X	112.7 (7)	H14E—C14X—H14F	109.5
C7—C11—C12X	108.1 (6)
C7—N1—C1—C2	−178.32 (12)	C9—N2—C7—C11	−10.00 (19)
C7—N1—C1—C6	0.04 (13)	C2—C3—C8—O1	168.54 (12)
N1—C1—C2—C3	177.08 (12)	C4—C3—C8—O1	−9.59 (18)
C6—C1—C2—C3	−1.13 (17)	C2—C3—C8—O2	−12.30 (16)
C1—C2—C3—C4	0.97 (18)	C4—C3—C8—O2	169.57 (11)
C1—C2—C3—C8	−177.09 (11)	C7—N2—C9—C10	−84.32 (15)
C2—C3—C4—C5	−0.06 (19)	C6—N2—C9—C10	85.16 (14)
C8—C3—C4—C5	178.06 (11)	N2—C9—C10—O3	64.65 (12)
C3—C4—C5—C6	−0.67 (18)	N1—C7—C11—C13X	−51.4 (13)
C7—N2—C6—C5	177.59 (13)	N2—C7—C11—C13X	130.8 (13)
C9—N2—C6—C5	6.3 (2)	N1—C7—C11—C12X	75.2 (10)
C7—N2—C6—C1	−1.03 (13)	N2—C7—C11—C12X	−102.5 (10)
C9—N2—C6—C1	−172.36 (11)	N1—C7—C11—C12	−47.6 (13)
C4—C5—C6—N2	−177.92 (12)	N2—C7—C11—C12	134.7 (13)
C4—C5—C6—C1	0.50 (18)	N1—C7—C11—C13	76.3 (11)
C2—C1—C6—N2	179.18 (11)	N2—C7—C11—C13	−101.4 (11)
N1—C1—C6—N2	0.62 (13)	C7—C11—C13—C14	163.5 (10)
C2—C1—C6—C5	0.41 (18)	C13X—C11—C13—C14	−68.6 (16)
N1—C1—C6—C5	−178.15 (11)	C12X—C11—C13—C14	179 (100)
C1—N1—C7—N2	−0.72 (14)	C12—C11—C13—C14	−73.9 (18)
C1—N1—C7—C11	−178.65 (11)	C7—C11—C13X—C14X	−160.6 (13)
C6—N2—C7—N1	1.13 (14)	C12X—C11—C13X—C14X	76 (2)
C9—N2—C7—N1	172.02 (11)	C12—C11—C13X—C14X	153 (29)
C6—N2—C7—C11	179.12 (11)	C13—C11—C13X—C14X	72 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.92 (2)	1.71 (2)	2.6227 (13)	175.8 (16)
O3—H3···N1ii	0.94 (2)	1.801 (19)	2.7193 (13)	165.1 (17)
C9—H9B···O1iii	0.99	2.43	3.2925 (15)	145
C12X—H12E···O1iv	0.98	2.55	3.517 (18)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.92 (2)	1.71 (2)	2.6227 (13)	175.8 (16)
O3—H3⋯N1ii	0.94 (2)	1.801 (19)	2.7193 (13)	165.1 (17)
C9—H9B⋯O1iii	0.99	2.43	3.2925 (15)	145
C12X—H12E⋯O1iv	0.98	2.55	3.517 (18)	167

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