(±)-1-(1H-Benzimidazol-2-yl)ethanol.

The asymmetric unit of the title mol-ecule, C(9)H(10)N(2)O, contains two mol-ecules. 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 mol-ecule and 0.018 (3) Å at one of the bridgehead C atoms in the other mol-ecule. 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 = 162.19

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.123

S = 1.07

2199 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

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.

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

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

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

C9H10N2O	F000 = 688
Mr = 162.19	Dx = 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 = 2.4–28.0º
b = 15.376 (3) Å	µ = 0.09 mm−1
c = 7.9163 (16) Å	T = 293 (2) K
V = 1671.7 (6) Å3	Block, red
Z = 8	0.20 × 0.18 × 0.05 mm

Rigaku Mercury2 diffractometer	2199 independent reflections
Radiation source: fine-focus sealed tube	1380 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.115
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.0º
ω scans	h = −17→17
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −19→19
Tmin = 0.912, Tmax = 1.00	l = −10→10
17487 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0395P)2 + 0.22P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2199 reflections	Δρmax = 0.17 e Å−3
221 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) ; (iii) .