(±)-1-(1H-Benzimidazol-2-yl)ethanol

Xia, R.; Xu, H.-J.

doi:10.1107/S1600536808013871

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1223

doi:10.1107/S1600536808013871

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(±)-1-(1H-Benzimidazol-2-yl)ethanol

Rong Xia ^a and Hai-Jun Xu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: xuhj@seu.edu.cn

(Received 18 April 2008; accepted 9 May 2008; online 7 June 2008)

The asymmetric unit of the title molecule, C₉H₁₀N₂O, contains two molecules. The fused benzene and imidazole rings are nearly coplanar, the largest deviations from the mean plane being 0.025 (3) Å at the non-bridgehead imidazole C atom of one molecule and 0.018 (3) Å at one of the bridgehead C atoms in the other molecule. Intermolecular O—H⋯N and N—H⋯O hydrogen bonds result in the formation of a sheet parallel to the (010) plane.

Related literature

For related literature, see: Allen et al. (1987 ); Chen & Ruan (2007 ); Garuti et al. (1999 ); Matsuno et al. (2000 ); Tlahuext et al. (2007 ).

Experimental

Crystal data

C₉H₁₀N₂O
M_r = 162.19
Orthorhombic, P 2₁ 2₁ 2
a = 13.734 (3) Å
b = 15.376 (3) Å
c = 7.9163 (16) Å
V = 1671.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.20 × 0.18 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.912, T_max = 1.00 (expected range = 0.908–0.996)
17487 measured reflections
2199 independent reflections
1380 reflections with I > 2σ(I)
R_int = 0.115

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.123
S = 1.07
2199 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3	0.82	1.91	2.713 (4)	165
N4—H4⋯O1ⁱ	0.86	1.97	2.828 (4)	178
O2—H2⋯N2ⁱⁱ	0.82	1.93	2.743 (4)	170
N1—H1A⋯O2ⁱⁱⁱ	0.86	1.93	2.751 (4)	160
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) x, y, z-1; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013871/dn2341sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013871/dn2341Isup2.hkl

checkCIF report

Comment top

Imidazole and benzimidazole derivatives are important heteroaromatic compounds and have attracted considerable attention because of good biological and pharmaceutical activities (Matsuno et al., 2000; Garuti et al., 1999). These compounds also play an important role in the development of coordination chemistry. Many derivatives of benzimidazole have been prepared and their complexes have been studied (Tlahuext et al., 2007; Chen & Ruan, 2007). In this paper, we report the crystal structure of the title compound.

There are two crystallographically independent molecules, A and B, linked by a O-H···N hydrogen bond in the asymmetric unit . The bond lengths and angles in A and B are within normal ranges (Allen et al., 1987). The two fused benzene and imidazole rings are nearly planar with the largest deviations from the mean plane being 0.025 (3) Å at C7 and 0.018 (3) Å at C10 . These two fused rings make a dihedral angle of 35.01 (9)°.

The molecules are further connected through O-H···N and N-H···O hydrogen bond buiding up a two dimmensional network which is parallel to the (0 1 0) plane (Table 1, Fig. 2).

Only the relative absolute configuration could be determined, the C8 and C17 have the same absolute configuration (S,S) or (R,R). The (S,S) configuration is represented in Fig. 1.

Related literature top

For related literature, see: Allen et al. (1987); Chen & Ruan (2007); Garuti et al. (1999); Matsuno et al. (2000); Tlahuext et al. (2007).

Experimental top

All chemicals were obtained from commercial sources and used directly without further purification. Benzene-1, 2-diamine (2.16 g, 20 mmol) was dissolved in hydrochloric acid (25 mL, 4 M) at 100°C, and ethyl 2-hydroxypropanoate (2.48 g, 21 mmol) was added to the solution. The mixture were then heated to reflux for 7 h at 115°C. After cooling to room temperature, the product was divided by neutralizing the mixture solution using NaOH to make the pH 7–9. Solid product was collected by filtration and the yield was 80%. ¹H-NMR(CDCl₃, 300 MHz): δ1.72 (d, 3 H), 5.22 (q, 1 H), 7.47(m, 1 H), 7.58 (m, 2 H), 7.81 (m, 1 H). Esi-MS: calcd for C₁₄H₉N₂O–H m/z 161.19, found 161.18. Deep-red single crystals of the title compound suitable for X-ray diffraction analysis were obtained from methanol solution by slow evaporation after a week.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dashed line. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the hydrogen bonds network. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry codes: (i) x-1/2, -y+1/2, -z+1; (ii) x, y, z-1; (iii) x+1/2, -y+1/2, -z+1 ]

(±)-1-(1H-Benzimidazol-2-yl)ethanol top

Crystal data top

C₉H₁₀N₂O	F(000) = 688
M_r = 162.19	D_x = 1.289 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 10749 reflections
a = 13.734 (3) Å	θ = 2.4–28.0°
b = 15.376 (3) Å	µ = 0.09 mm⁻¹
c = 7.9163 (16) Å	T = 293 K
V = 1671.7 (6) Å³	Block, red
Z = 8	0.20 × 0.18 × 0.05 mm

Data collection top

Rigaku Mercury2 diffractometer	2199 independent reflections
Radiation source: fine-focus sealed tube	1380 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.115
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −19→19
T_min = 0.912, T_max = 1.00	l = −10→10
17487 measured reflections

Refinement top

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0395P)² + 0.22P] where P = (F_o² + 2F_c²)/3
2199 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₉H₁₀N₂O	V = 1671.7 (6) Å³
M_r = 162.19	Z = 8
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 13.734 (3) Å	µ = 0.09 mm⁻¹
b = 15.376 (3) Å	T = 293 K
c = 7.9163 (16) Å	0.20 × 0.18 × 0.05 mm

Data collection top

Rigaku Mercury2 diffractometer	2199 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1380 reflections with I > 2σ(I)
T_min = 0.912, T_max = 1.00	R_int = 0.115
17487 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.07	Δρ_max = 0.17 e Å⁻³
2199 reflections	Δρ_min = −0.18 e Å⁻³
221 parameters

Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6823 (3)	0.3355 (2)	1.1332 (4)	0.0383 (9)
C2	0.7541 (3)	0.3880 (2)	1.1995 (5)	0.0496 (10)
H2A	0.8168	0.3885	1.1551	0.060*
C3	0.7292 (3)	0.4388 (3)	1.3323 (5)	0.0605 (12)
H3	0.7760	0.4750	1.3801	0.073*
C4	0.6362 (4)	0.4384 (3)	1.3984 (6)	0.0652 (13)
H4A	0.6219	0.4740	1.4900	0.078*
C5	0.5647 (3)	0.3868 (3)	1.3328 (6)	0.0622 (12)
H5	0.5021	0.3872	1.3774	0.075*
C6	0.5887 (3)	0.3340 (2)	1.1975 (5)	0.0427 (9)
C7	0.5899 (3)	0.2474 (2)	0.9864 (5)	0.0428 (9)
C8	0.5593 (3)	0.1874 (3)	0.8498 (5)	0.0520 (11)
H8	0.4882	0.1823	0.8527	0.062*
C9	0.6018 (4)	0.0985 (3)	0.8690 (6)	0.0919 (18)
H9A	0.5832	0.0632	0.7743	0.138*
H9B	0.5781	0.0725	0.9713	0.138*
H9C	0.6715	0.1027	0.8737	0.138*
C10	0.3684 (3)	0.3451 (2)	0.6778 (5)	0.0423 (9)
C11	0.4085 (3)	0.3972 (3)	0.8015 (5)	0.0563 (11)
H11	0.4721	0.3888	0.8385	0.068*
C12	0.3517 (3)	0.4614 (3)	0.8676 (5)	0.0614 (12)
H12	0.3768	0.4974	0.9514	0.074*
C13	0.2571 (3)	0.4740 (3)	0.8120 (5)	0.0576 (11)
H13	0.2203	0.5186	0.8591	0.069*
C14	0.2166 (3)	0.4234 (2)	0.6914 (5)	0.0511 (10)
H14	0.1527	0.4317	0.6561	0.061*
C15	0.2740 (3)	0.3592 (2)	0.6231 (4)	0.0401 (9)
C16	0.3419 (2)	0.2520 (2)	0.4833 (4)	0.0380 (8)
C17	0.3509 (3)	0.1825 (2)	0.3527 (4)	0.0463 (10)
H17	0.2934	0.1450	0.3628	0.056*
C18	0.4389 (3)	0.1262 (3)	0.3790 (6)	0.0581 (11)
H18A	0.4414	0.0826	0.2924	0.087*
H18B	0.4349	0.0986	0.4876	0.087*
H18C	0.4965	0.1614	0.3739	0.087*
N1	0.68087 (19)	0.27939 (19)	0.9990 (3)	0.0451 (8)
H1A	0.7292	0.2669	0.9345	0.054*
N2	0.5316 (2)	0.2773 (2)	1.1042 (4)	0.0486 (8)
N3	0.4093 (2)	0.27755 (19)	0.5867 (4)	0.0443 (8)
N4	0.25902 (19)	0.29851 (18)	0.4998 (4)	0.0425 (7)
H4	0.2063	0.2912	0.4429	0.051*
O1	0.58658 (16)	0.2215 (2)	0.6915 (3)	0.0532 (7)
H1	0.5385	0.2415	0.6440	0.080*
O2	0.34919 (16)	0.21938 (19)	0.1892 (3)	0.0546 (7)
H2	0.4018	0.2426	0.1697	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.041 (2)	0.046 (2)	0.0280 (19)	−0.0019 (17)	0.0020 (17)	0.0067 (17)
C2	0.042 (2)	0.060 (3)	0.047 (2)	−0.0057 (19)	0.000 (2)	0.008 (2)
C3	0.065 (3)	0.065 (3)	0.052 (3)	−0.006 (2)	−0.009 (3)	−0.005 (2)
C4	0.086 (4)	0.060 (3)	0.050 (3)	0.001 (3)	0.002 (3)	−0.009 (2)
C5	0.059 (3)	0.073 (3)	0.055 (3)	0.000 (2)	0.018 (2)	−0.008 (3)
C6	0.041 (2)	0.051 (2)	0.036 (2)	−0.0025 (18)	0.0054 (19)	0.0037 (19)
C7	0.039 (2)	0.052 (2)	0.037 (2)	−0.0042 (19)	−0.0017 (19)	0.0043 (18)
C8	0.047 (2)	0.063 (3)	0.046 (2)	−0.0012 (19)	−0.002 (2)	0.000 (2)
C9	0.135 (5)	0.062 (3)	0.078 (4)	0.008 (3)	−0.040 (4)	−0.005 (3)
C10	0.042 (2)	0.044 (2)	0.040 (2)	−0.0017 (17)	−0.007 (2)	0.0045 (18)
C11	0.057 (3)	0.057 (3)	0.055 (3)	0.005 (2)	−0.015 (2)	−0.003 (2)
C12	0.076 (3)	0.057 (3)	0.051 (3)	−0.002 (2)	−0.009 (3)	−0.003 (2)
C13	0.064 (3)	0.056 (3)	0.053 (3)	0.003 (2)	0.006 (3)	−0.006 (2)
C14	0.043 (2)	0.054 (3)	0.057 (3)	0.0029 (19)	0.005 (2)	0.003 (2)
C15	0.040 (2)	0.048 (2)	0.0323 (19)	0.0002 (18)	−0.0009 (18)	0.0053 (18)
C16	0.0317 (19)	0.042 (2)	0.040 (2)	−0.0067 (16)	−0.0017 (18)	0.0069 (17)
C17	0.041 (2)	0.055 (2)	0.042 (2)	−0.0082 (18)	−0.0007 (19)	−0.0018 (19)
C18	0.053 (2)	0.056 (3)	0.065 (3)	0.009 (2)	−0.005 (2)	−0.005 (2)
N1	0.0335 (16)	0.066 (2)	0.0355 (16)	0.0029 (15)	0.0070 (15)	−0.0025 (17)
N2	0.0388 (17)	0.063 (2)	0.0443 (17)	−0.0022 (16)	0.0071 (15)	0.0033 (17)
N3	0.0394 (17)	0.048 (2)	0.0453 (17)	0.0020 (16)	−0.0106 (16)	−0.0019 (16)
N4	0.0292 (15)	0.0576 (19)	0.0407 (16)	0.0002 (15)	−0.0056 (15)	0.0033 (17)
O1	0.0353 (14)	0.088 (2)	0.0368 (14)	0.0083 (14)	−0.0012 (13)	0.0011 (16)
O2	0.0335 (14)	0.089 (2)	0.0413 (14)	−0.0056 (14)	−0.0032 (13)	−0.0031 (15)

Geometric parameters (Å, º) top

C1—N1	1.368 (4)	C10—C15	1.385 (5)
C1—C2	1.379 (5)	C11—C12	1.364 (5)
C1—C6	1.383 (5)	C11—H11	0.9300
C2—C3	1.354 (5)	C12—C13	1.385 (5)
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.381 (6)	C13—C14	1.352 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.364 (6)	C14—C15	1.374 (5)
C4—H4A	0.9300	C14—H14	0.9300
C5—C6	1.384 (5)	C15—N4	1.366 (4)
C5—H5	0.9300	C16—N3	1.297 (4)
C6—N2	1.386 (5)	C16—N4	1.350 (4)
C7—N2	1.312 (4)	C16—C17	1.492 (5)
C7—N1	1.347 (4)	C17—O2	1.413 (4)
C7—C8	1.482 (5)	C17—C18	1.501 (5)
C8—O1	1.410 (4)	C17—H17	0.9800
C8—C9	1.494 (6)	C18—H18A	0.9600
C8—H8	0.9800	C18—H18B	0.9600
C9—H9A	0.9600	C18—H18C	0.9600
C9—H9B	0.9600	N1—H1A	0.8600
C9—H9C	0.9600	N4—H4	0.8600
C10—C11	1.379 (5)	O1—H1	0.8200
C10—N3	1.384 (4)	O2—H2	0.8200

N1—C1—C2	132.5 (3)	C10—C11—H11	121.2
N1—C1—C6	105.2 (3)	C11—C12—C13	121.1 (4)
C2—C1—C6	122.3 (3)	C11—C12—H12	119.5
C3—C2—C1	116.9 (4)	C13—C12—H12	119.5
C3—C2—H2A	121.5	C14—C13—C12	122.0 (4)
C1—C2—H2A	121.5	C14—C13—H13	119.0
C2—C3—C4	121.7 (4)	C12—C13—H13	119.0
C2—C3—H3	119.1	C13—C14—C15	117.1 (4)
C4—C3—H3	119.1	C13—C14—H14	121.5
C5—C4—C3	121.6 (4)	C15—C14—H14	121.5
C5—C4—H4A	119.2	N4—C15—C14	133.3 (4)
C3—C4—H4A	119.2	N4—C15—C10	105.0 (3)
C4—C5—C6	117.6 (4)	C14—C15—C10	121.8 (4)
C4—C5—H5	121.2	N3—C16—N4	112.4 (3)
C6—C5—H5	121.2	N3—C16—C17	126.5 (3)
C1—C6—C5	119.8 (4)	N4—C16—C17	121.1 (3)
C1—C6—N2	109.9 (3)	O2—C17—C16	110.2 (3)
C5—C6—N2	130.3 (4)	O2—C17—C18	111.8 (3)
N2—C7—N1	112.6 (3)	C16—C17—C18	112.6 (3)
N2—C7—C8	124.3 (3)	O2—C17—H17	107.3
N1—C7—C8	123.0 (3)	C16—C17—H17	107.3
O1—C8—C7	110.0 (3)	C18—C17—H17	107.3
O1—C8—C9	109.1 (4)	C17—C18—H18A	109.5
C7—C8—C9	112.6 (3)	C17—C18—H18B	109.5
O1—C8—H8	108.4	H18A—C18—H18B	109.5
C7—C8—H8	108.4	C17—C18—H18C	109.5
C9—C8—H8	108.4	H18A—C18—H18C	109.5
C8—C9—H9A	109.5	H18B—C18—H18C	109.5
C8—C9—H9B	109.5	C7—N1—C1	107.5 (3)
H9A—C9—H9B	109.5	C7—N1—H1A	126.2
C8—C9—H9C	109.5	C1—N1—H1A	126.2
H9A—C9—H9C	109.5	C7—N2—C6	104.7 (3)
H9B—C9—H9C	109.5	C16—N3—C10	105.4 (3)
C11—C10—N3	130.1 (3)	C16—N4—C15	107.7 (3)
C11—C10—C15	120.4 (4)	C16—N4—H4	126.2
N3—C10—C15	109.5 (3)	C15—N4—H4	126.2
C12—C11—C10	117.6 (4)	C8—O1—H1	109.5
C12—C11—H11	121.2	C17—O2—H2	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.82	1.91	2.713 (4)	165
N4—H4···O1ⁱ	0.86	1.97	2.828 (4)	178
O2—H2···N2ⁱⁱ	0.82	1.93	2.743 (4)	170
N1—H1A···O2ⁱⁱⁱ	0.86	1.93	2.751 (4)	160

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, y, z−1; (iii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₂O
M_r	162.19
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	13.734 (3), 15.376 (3), 7.9163 (16)
V (Å³)	1671.7 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.18 × 0.05

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.912, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	17487, 2199, 1380
R_int	0.115
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.123, 1.07
No. of reflections	2199
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.82	1.91	2.713 (4)	164.6
N4—H4···O1ⁱ	0.86	1.97	2.828 (4)	178.0
O2—H2···N2ⁱⁱ	0.82	1.93	2.743 (4)	169.6
N1—H1A···O2ⁱⁱⁱ	0.86	1.93	2.751 (4)	159.6

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, y, z−1; (iii) x+1/2, −y+1/2, −z+1.

Acknowledgements

HJX acknowledges a Start-up Grant from Southeast University, P. R. China

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