2-(1H-Benzimidazol-2-yl)phenol.

The title mol-ecule, C13H10N2O, is essentially planar, the maximum deviation from the plane of the non-H atoms being 0.016 (2) Å. The imidazole ring makes a dihedral angle of 0.37 (13)° with the attached benzene ring. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds, forming chains propagating in [001]. The crystal packing also features four π-π stacking inter-actions involving the imidazole ring, fused benzene ring and attached benzene ring system [centroid-centroid distances = 3.6106 (17), 3.6108 (17), 3.6666 (17) and 3.6668 (17) Å].

Related literature

For applications and general background to substituted benzimidazole derivatives, see: Nakamura et al. (2004 ▶); Su Han & Kim (2001 ▶); Roman et al. 2007 ▶; Congiu et al. 2008 ▶. For related crystal structures, see: Han (2010 ▶); Zhan et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). Note added in proof: a low temperature determination of the same structure has been reported [Konoshima, H., Nagao, S., Kiyota, I., Amimoto, K., Yamamoto, N., Sekine, M., Nakata, M., Furukawa, K. & Sekiya, H. (2012). Phys. Chem. Chem. Phys. 14, 16448–16457].

Experimental

Crystal data

C13H10N2O

M = 210.23

Monoclinic,

a = 16.864 (4) Å

b = 4.7431 (8) Å

c = 12.952 (2) Å

β = 102.34 (2)°

V = 1012.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.30 × 0.25 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.829, T max = 1.000

4073 measured reflections

2338 independent reflections

1184 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.131

S = 1.03

2338 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2011 (Burla et al., 2012 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814001366/hg5377sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001366/hg5377Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001366/hg5377Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001366/hg5377Isup4.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H10N2O	F(000) = 440
Mr = 210.23	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Melting point: 386 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.864 (4) Å	Cell parameters from 612 reflections
b = 4.7431 (8) Å	θ = 4.8–23.8°
c = 12.952 (2) Å	µ = 0.09 mm−1
β = 102.34 (2)°	T = 293 K
V = 1012.1 (3) Å3	Block, colourless
Z = 4	0.30 × 0.30 × 0.25 mm

Agilent Xcalibur Eos Gemini diffractometer	2338 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1184 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 16.3291 pixels mm-1	θmax = 29.2°, θmin = 3.2°
ω scans	h = −23→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −3→6
Tmin = 0.829, Tmax = 1.000	l = −15→17
4073 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)] = 0.067	Hydrogen site location: mixed
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0339P)2] where P = (Fo2 + 2Fc2)/3
2338 reflections	(Δ/σ)max < 0.001
150 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

	x	y	z	Uiso*/Ueq
O26	0.20929 (12)	0.7018 (4)	0.54707 (12)	0.0640 (8)
N1	0.25872 (13)	0.5474 (4)	0.25071 (16)	0.0459 (8)
N3	0.28328 (12)	0.4482 (4)	0.42170 (14)	0.0448 (7)
C2	0.24046 (15)	0.6055 (5)	0.34606 (18)	0.0420 (8)
C4	0.38923 (16)	0.0807 (5)	0.4149 (2)	0.0561 (10)
C5	0.42862 (16)	−0.0543 (5)	0.3475 (2)	0.0603 (11)
C6	0.41275 (17)	0.0093 (6)	0.2410 (2)	0.0621 (11)
C7	0.35740 (17)	0.2089 (5)	0.1985 (2)	0.0554 (10)
C8	0.31718 (15)	0.3444 (5)	0.26679 (19)	0.0438 (9)
C9	0.33257 (15)	0.2825 (5)	0.37415 (18)	0.0434 (9)
C21	0.18120 (15)	0.8077 (4)	0.36215 (19)	0.0424 (8)
C22	0.13653 (15)	0.9671 (5)	0.28084 (19)	0.0512 (9)
C23	0.08097 (17)	1.1585 (5)	0.2980 (2)	0.0614 (11)
C24	0.06758 (18)	1.1945 (5)	0.3980 (3)	0.0640 (11)
C25	0.11064 (18)	1.0406 (5)	0.4800 (2)	0.0617 (11)
C26	0.16741 (16)	0.8493 (5)	0.4634 (2)	0.0485 (9)
H1	0.2390 (15)	0.643 (5)	0.190 (2)	0.068 (9)*
H4	0.40039	0.03737	0.48660	0.0673*
H5	0.46693	−0.19179	0.37380	0.0722*
H6	0.44063	−0.08687	0.19714	0.0748*
H7	0.34708	0.25216	0.12684	0.0666*
H22	0.14474	0.94254	0.21266	0.0613*
H23	0.05206	1.26504	0.24222	0.0737*
H24	0.02909	1.32393	0.40988	0.0768*
H25	0.10138	1.06568	0.54762	0.0741*
H26	0.23899	0.58738	0.52659	0.0960*

	U11	U22	U33	U12	U13	U23
O26	0.0835 (16)	0.0762 (13)	0.0334 (11)	0.0152 (10)	0.0147 (10)	−0.0050 (9)
N1	0.0540 (15)	0.0546 (13)	0.0295 (12)	−0.0037 (11)	0.0100 (10)	0.0028 (11)
N3	0.0511 (14)	0.0521 (12)	0.0304 (11)	0.0005 (11)	0.0070 (10)	−0.0010 (10)
C2	0.0486 (16)	0.0465 (14)	0.0314 (14)	−0.0094 (12)	0.0095 (12)	−0.0032 (12)
C4	0.0567 (19)	0.0620 (17)	0.0475 (17)	0.0017 (14)	0.0068 (14)	−0.0017 (14)
C5	0.0532 (18)	0.0608 (17)	0.067 (2)	0.0028 (14)	0.0129 (15)	−0.0089 (16)
C6	0.062 (2)	0.0648 (17)	0.067 (2)	−0.0066 (16)	0.0304 (16)	−0.0132 (16)
C7	0.067 (2)	0.0610 (17)	0.0436 (17)	−0.0111 (16)	0.0241 (15)	−0.0073 (14)
C8	0.0454 (16)	0.0462 (14)	0.0410 (15)	−0.0080 (13)	0.0122 (12)	−0.0022 (12)
C9	0.0443 (16)	0.0488 (14)	0.0370 (15)	−0.0055 (13)	0.0087 (12)	−0.0015 (12)
C21	0.0454 (16)	0.0424 (13)	0.0391 (15)	−0.0070 (12)	0.0087 (12)	−0.0033 (12)
C22	0.0537 (17)	0.0547 (15)	0.0440 (17)	−0.0030 (14)	0.0081 (13)	0.0020 (13)
C23	0.0558 (19)	0.0583 (17)	0.067 (2)	0.0025 (15)	0.0062 (16)	0.0056 (15)
C24	0.0547 (19)	0.0539 (16)	0.085 (2)	0.0048 (14)	0.0187 (17)	−0.0042 (17)
C25	0.067 (2)	0.0645 (18)	0.059 (2)	0.0004 (16)	0.0255 (16)	−0.0112 (15)
C26	0.0534 (18)	0.0508 (15)	0.0410 (16)	−0.0033 (13)	0.0092 (13)	−0.0051 (13)

O26—C26	1.355 (3)	C21—C26	1.394 (4)
O26—H26	0.8200	C21—C22	1.382 (3)
N1—C2	1.363 (3)	C22—C23	1.357 (4)
N1—C8	1.362 (3)	C23—C24	1.372 (5)
N3—C9	1.381 (3)	C24—C25	1.363 (4)
N3—C2	1.317 (3)	C25—C26	1.369 (4)
N1—H1	0.91 (2)	C4—H4	0.9300
C2—C21	1.432 (3)	C5—H5	0.9300
C4—C9	1.376 (4)	C6—H6	0.9300
C4—C5	1.364 (4)	C7—H7	0.9300
C5—C6	1.381 (4)	C22—H22	0.9300
C6—C7	1.361 (4)	C23—H23	0.9300
C7—C8	1.383 (4)	C24—H24	0.9300
C8—C9	1.390 (3)	C25—H25	0.9300
C26—O26—H26	109.00	C22—C23—C24	119.8 (2)
C2—N1—C8	107.5 (2)	C23—C24—C25	120.1 (3)
C2—N3—C9	106.09 (19)	C24—C25—C26	120.4 (3)
C8—N1—H1	127.3 (16)	O26—C26—C21	121.1 (2)
C2—N1—H1	124.9 (16)	O26—C26—C25	118.6 (2)
N1—C2—N3	111.4 (2)	C21—C26—C25	120.3 (2)
N1—C2—C21	124.5 (2)	C5—C4—H4	121.00
N3—C2—C21	124.0 (2)	C9—C4—H4	121.00
C5—C4—C9	118.3 (2)	C4—C5—H5	119.00
C4—C5—C6	121.3 (2)	C6—C5—H5	119.00
C5—C6—C7	121.7 (3)	C5—C6—H6	119.00
C6—C7—C8	116.9 (2)	C7—C6—H6	119.00
N1—C8—C7	132.0 (2)	C6—C7—H7	122.00
C7—C8—C9	122.0 (2)	C8—C7—H7	122.00
N1—C8—C9	106.1 (2)	C21—C22—H22	119.00
C4—C9—C8	119.8 (2)	C23—C22—H22	119.00
N3—C9—C8	108.9 (2)	C22—C23—H23	120.00
N3—C9—C4	131.3 (2)	C24—C23—H23	120.00
C2—C21—C22	122.6 (2)	C23—C24—H24	120.00
C2—C21—C26	119.6 (2)	C25—C24—H24	120.00
C22—C21—C26	117.8 (2)	C24—C25—H25	120.00
C21—C22—C23	121.6 (2)	C26—C25—H25	120.00
C8—N1—C2—N3	−0.8 (3)	C6—C7—C8—N1	−179.1 (3)
C8—N1—C2—C21	−179.7 (2)	C6—C7—C8—C9	0.5 (4)
C2—N1—C8—C7	180.0 (3)	N1—C8—C9—N3	0.1 (3)
C2—N1—C8—C9	0.4 (3)	N1—C8—C9—C4	179.5 (2)
C9—N3—C2—N1	0.8 (3)	C7—C8—C9—N3	−179.6 (2)
C9—N3—C2—C21	179.7 (2)	C7—C8—C9—C4	−0.1 (4)
C2—N3—C9—C4	−179.9 (3)	C2—C21—C22—C23	−179.7 (2)
C2—N3—C9—C8	−0.6 (3)	C26—C21—C22—C23	0.1 (4)
N1—C2—C21—C22	−0.4 (4)	C2—C21—C26—O26	0.1 (4)
N1—C2—C21—C26	179.9 (2)	C2—C21—C26—C25	−179.6 (2)
N3—C2—C21—C22	−179.2 (2)	C22—C21—C26—O26	−179.6 (2)
N3—C2—C21—C26	1.1 (4)	C22—C21—C26—C25	0.7 (4)
C9—C4—C5—C6	0.3 (4)	C21—C22—C23—C24	−0.7 (4)
C5—C4—C9—N3	179.0 (3)	C22—C23—C24—C25	0.7 (4)
C5—C4—C9—C8	−0.3 (4)	C23—C24—C25—C26	0.0 (4)
C4—C5—C6—C7	0.1 (4)	C24—C25—C26—O26	179.6 (2)
C5—C6—C7—C8	−0.4 (4)	C24—C25—C26—C21	−0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O26i	0.91 (2)	1.96 (3)	2.851 (3)	169 (2)
O26—H26···N3	0.82	1.81	2.551 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O26i	0.91 (2)	1.96 (3)	2.851 (3)	169 (2)
O26—H26⋯N3	0.82	1.81	2.551 (3)	150

Symmetry code: (i) .