2-(1-Phenyl-1H-benzimidazol-2-yl)phenol.

In the title mol-ecule, C19H14N2O, the benzimidazole unit is close to being planar [maximum deviation = 0.0253 (11) Å] and forms dihedral angles of 68.98 (6) and 20.38 (7)° with the adjacent phenyl and benzene rings; the dihedral angle between the latter two planes is 64.30 (7)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯N and C-H⋯O hydrogen bonds, and consolidated into a three-dimensional architecture by π-π stacking inter-actions, with a centroid-centroid distance of 3.8428 (12) Å.

Related literature

For the range of pharmacological activities and toxicological properties of benzimidazole derivatives, see: Spasov et al. (1999 ▶). For closely related crystal structures, see: Jayamoorthy et al. (2012 ▶); Rosepriya et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H14N2O

M = 286.32

Triclinic,

a = 8.1941 (6) Å

b = 9.5983 (14) Å

c = 10.3193 (18) Å

α = 64.637 (16)°

β = 80.356 (10)°

γ = 83.610 (9)°

V = 722.3 (2) Å3

Z = 2

Cu Kα radiation

μ = 0.66 mm−1

T = 123 K

0.76 × 0.46 × 0.32 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), using a multi-faceted crystal model (Clark & Reid, 1995 ▶)] T min = 0.731, T max = 0.811

4335 measured reflections

2826 independent reflections

2420 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.171

S = 1.04

2826 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049859/tk5179sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049859/tk5179Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049859/tk5179Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049859/tk5179Isup4.cml

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

C19H14N2O	Z = 2
Mr = 286.32	F(000) = 300
Triclinic, P1	Dx = 1.316 Mg m−3
Hall symbol: -P 1	Melting point: 387 K
a = 8.1941 (6) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.5983 (14) Å	Cell parameters from 772 reflections
c = 10.3193 (18) Å	θ = 4.8–75.4°
α = 64.637 (16)°	µ = 0.66 mm−1
β = 80.356 (10)°	T = 123 K
γ = 83.610 (9)°	Block, colourless
V = 722.3 (2) Å3	0.76 × 0.46 × 0.32 mm

Agilent Xcalibur Ruby Gemini diffractometer	2826 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2420 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 10.5081 pixels mm-1	θmax = 75.8°, θmin = 5.5°
ω scans	h = −10→10
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), using a multi-faceted crystal model (Clark & Reid, 1995)]	k = −9→12
Tmin = 0.731, Tmax = 0.811	l = −12→12
4335 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.1182P)2 + 0.1646P] where P = (Fo2 + 2Fc2)/3
2826 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.31 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

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 > 2σ(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
O26	0.61570 (15)	−0.11111 (15)	−0.08352 (15)	0.0336 (4)
N1	0.78361 (16)	0.03924 (16)	0.19436 (15)	0.0249 (4)
N3	0.70983 (17)	−0.15812 (16)	0.15919 (16)	0.0262 (4)
C2	0.75812 (18)	−0.01378 (18)	0.09515 (18)	0.0238 (4)
C4	0.6537 (2)	−0.3401 (2)	0.4242 (2)	0.0331 (5)
C5	0.6508 (2)	−0.3488 (2)	0.5613 (2)	0.0384 (5)
C6	0.6940 (3)	−0.2238 (2)	0.5834 (2)	0.0386 (6)
C7	0.7442 (2)	−0.0876 (2)	0.4680 (2)	0.0340 (5)
C8	0.7465 (2)	−0.07982 (18)	0.33084 (19)	0.0272 (5)
C9	0.70108 (19)	−0.20226 (19)	0.30605 (19)	0.0269 (5)
C11	0.8035 (2)	0.19445 (18)	0.17495 (18)	0.0250 (5)
C12	0.9424 (2)	0.2276 (2)	0.2142 (2)	0.0301 (5)
C13	0.9554 (2)	0.3752 (2)	0.2042 (2)	0.0344 (5)
C14	0.8320 (2)	0.4876 (2)	0.1542 (2)	0.0331 (5)
C15	0.6936 (2)	0.4524 (2)	0.1156 (2)	0.0345 (5)
C16	0.6775 (2)	0.30484 (19)	0.1263 (2)	0.0306 (5)
C21	0.77729 (18)	0.07290 (18)	−0.06192 (18)	0.0245 (5)
C22	0.8703 (2)	0.2056 (2)	−0.13605 (19)	0.0286 (5)
C23	0.8821 (2)	0.2863 (2)	−0.2849 (2)	0.0343 (5)
C24	0.7977 (2)	0.2376 (2)	−0.3632 (2)	0.0359 (5)
C25	0.7070 (2)	0.1065 (2)	−0.2933 (2)	0.0330 (5)
C26	0.69972 (19)	0.0214 (2)	−0.14465 (19)	0.0272 (5)
H4	0.62439	−0.42523	0.41012	0.0397*
H5	0.61885	−0.44136	0.64270	0.0460*
H6	0.68856	−0.23287	0.67934	0.0463*
H7	0.77567	−0.00349	0.48246	0.0408*
H12	1.02792	0.15069	0.24756	0.0361*
H13	1.04993	0.39890	0.23189	0.0413*
H14	0.84218	0.58863	0.14649	0.0397*
H15	0.60863	0.52966	0.08129	0.0414*
H16	0.58178	0.28037	0.10080	0.0367*
H22	0.92633	0.24072	−0.08287	0.0343*
H23	0.94752	0.37448	−0.33327	0.0411*
H24	0.80249	0.29466	−0.46494	0.0431*
H25	0.64902	0.07421	−0.34740	0.0395*
H26	0.629 (4)	−0.158 (3)	0.018 (3)	0.057 (7)*

	U11	U22	U33	U12	U13	U23
O26	0.0296 (6)	0.0337 (7)	0.0436 (8)	−0.0070 (5)	−0.0042 (5)	−0.0208 (6)
N1	0.0230 (7)	0.0213 (7)	0.0301 (7)	−0.0004 (5)	−0.0039 (5)	−0.0105 (6)
N3	0.0218 (6)	0.0218 (7)	0.0342 (8)	−0.0001 (5)	−0.0030 (5)	−0.0113 (6)
C2	0.0175 (7)	0.0225 (7)	0.0316 (8)	0.0013 (5)	−0.0026 (6)	−0.0123 (6)
C4	0.0269 (8)	0.0230 (8)	0.0422 (10)	−0.0008 (6)	−0.0021 (7)	−0.0078 (7)
C5	0.0349 (9)	0.0295 (9)	0.0374 (10)	−0.0012 (7)	0.0001 (8)	−0.0032 (8)
C6	0.0390 (10)	0.0397 (10)	0.0310 (9)	0.0025 (8)	−0.0034 (8)	−0.0106 (8)
C7	0.0360 (9)	0.0297 (9)	0.0360 (9)	0.0011 (7)	−0.0065 (7)	−0.0135 (8)
C8	0.0222 (7)	0.0231 (8)	0.0335 (9)	0.0006 (6)	−0.0020 (6)	−0.0103 (7)
C9	0.0209 (7)	0.0236 (8)	0.0342 (9)	0.0019 (6)	−0.0034 (6)	−0.0111 (7)
C11	0.0252 (8)	0.0201 (8)	0.0287 (8)	−0.0022 (6)	−0.0007 (6)	−0.0100 (6)
C12	0.0244 (8)	0.0262 (8)	0.0401 (10)	0.0016 (6)	−0.0068 (7)	−0.0140 (7)
C13	0.0265 (8)	0.0341 (10)	0.0474 (10)	−0.0045 (7)	−0.0055 (7)	−0.0206 (8)
C14	0.0331 (9)	0.0237 (8)	0.0422 (10)	−0.0041 (7)	0.0008 (7)	−0.0149 (7)
C15	0.0289 (9)	0.0243 (8)	0.0481 (11)	0.0034 (6)	−0.0053 (7)	−0.0141 (8)
C16	0.0234 (8)	0.0251 (8)	0.0433 (10)	−0.0007 (6)	−0.0068 (7)	−0.0135 (7)
C21	0.0170 (7)	0.0243 (8)	0.0322 (9)	0.0023 (6)	−0.0018 (6)	−0.0130 (7)
C22	0.0208 (7)	0.0293 (9)	0.0347 (9)	−0.0009 (6)	−0.0013 (6)	−0.0134 (7)
C23	0.0285 (9)	0.0318 (9)	0.0357 (10)	−0.0009 (7)	0.0019 (7)	−0.0100 (8)
C24	0.0316 (9)	0.0406 (10)	0.0300 (9)	0.0077 (7)	−0.0027 (7)	−0.0122 (8)
C25	0.0259 (8)	0.0399 (10)	0.0368 (10)	0.0059 (7)	−0.0054 (7)	−0.0208 (8)
C26	0.0189 (7)	0.0295 (8)	0.0352 (9)	0.0029 (6)	−0.0018 (6)	−0.0170 (7)

O26—C26	1.361 (2)	C21—C26	1.411 (3)
O26—H26	0.97 (3)	C21—C22	1.405 (3)
N1—C2	1.376 (2)	C22—C23	1.384 (3)
N1—C8	1.392 (2)	C23—C24	1.390 (3)
N1—C11	1.440 (2)	C24—C25	1.381 (3)
N3—C9	1.379 (2)	C25—C26	1.389 (3)
N3—C2	1.328 (2)	C4—H4	0.9500
C2—C21	1.460 (2)	C5—H5	0.9500
C4—C9	1.401 (3)	C6—H6	0.9500
C4—C5	1.377 (3)	C7—H7	0.9500
C5—C6	1.405 (3)	C12—H12	0.9500
C6—C7	1.385 (3)	C13—H13	0.9500
C7—C8	1.382 (3)	C14—H14	0.9500
C8—C9	1.404 (3)	C15—H15	0.9500
C11—C12	1.381 (2)	C16—H16	0.9500
C11—C16	1.384 (3)	C22—H22	0.9500
C12—C13	1.391 (3)	C23—H23	0.9500
C13—C14	1.381 (3)	C24—H24	0.9500
C14—C15	1.382 (2)	C25—H25	0.9500
C15—C16	1.392 (3)
C26—O26—H26	106.6 (19)	C23—C24—C25	120.11 (17)
C2—N1—C8	106.88 (15)	C24—C25—C26	120.62 (17)
C8—N1—C11	121.93 (15)	O26—C26—C25	117.70 (16)
C2—N1—C11	129.56 (15)	C21—C26—C25	120.26 (17)
C2—N3—C9	106.46 (15)	O26—C26—C21	122.04 (16)
N1—C2—C21	126.44 (16)	C5—C4—H4	121.00
N3—C2—C21	121.90 (16)	C9—C4—H4	121.00
N1—C2—N3	111.66 (15)	C4—C5—H5	119.00
C5—C4—C9	118.13 (18)	C6—C5—H5	119.00
C4—C5—C6	121.46 (18)	C5—C6—H6	119.00
C5—C6—C7	121.27 (18)	C7—C6—H6	119.00
C6—C7—C8	116.87 (18)	C6—C7—H7	122.00
N1—C8—C7	131.52 (18)	C8—C7—H7	122.00
N1—C8—C9	105.57 (15)	C11—C12—H12	120.00
C7—C8—C9	122.88 (17)	C13—C12—H12	120.00
N3—C9—C8	109.43 (16)	C12—C13—H13	120.00
C4—C9—C8	119.38 (17)	C14—C13—H13	120.00
N3—C9—C4	131.18 (18)	C13—C14—H14	120.00
N1—C11—C16	119.08 (15)	C15—C14—H14	120.00
C12—C11—C16	121.35 (18)	C14—C15—H15	120.00
N1—C11—C12	119.43 (16)	C16—C15—H15	120.00
C11—C12—C13	119.07 (17)	C11—C16—H16	121.00
C12—C13—C14	120.50 (17)	C15—C16—H16	121.00
C13—C14—C15	119.69 (19)	C21—C22—H22	119.00
C14—C15—C16	120.66 (17)	C23—C22—H22	119.00
C11—C16—C15	118.73 (16)	C22—C23—H23	120.00
C2—C21—C26	118.85 (16)	C24—C23—H23	120.00
C22—C21—C26	117.79 (16)	C23—C24—H24	120.00
C2—C21—C22	123.35 (16)	C25—C24—H24	120.00
C21—C22—C23	121.43 (17)	C24—C25—H25	120.00
C22—C23—C24	119.65 (18)	C26—C25—H25	120.00
C8—N1—C2—N3	−0.83 (19)	C6—C7—C8—N1	177.26 (19)
C8—N1—C2—C21	178.31 (15)	C6—C7—C8—C9	−0.1 (3)
C11—N1—C2—N3	−166.19 (16)	N1—C8—C9—N3	−0.26 (19)
C11—N1—C2—C21	13.0 (3)	N1—C8—C9—C4	−179.06 (15)
C2—N1—C8—C7	−177.06 (18)	C7—C8—C9—N3	177.69 (16)
C2—N1—C8—C9	0.64 (18)	C7—C8—C9—C4	−1.1 (3)
C11—N1—C8—C7	−10.3 (3)	N1—C11—C12—C13	−175.74 (16)
C11—N1—C8—C9	167.36 (15)	C16—C11—C12—C13	−0.1 (3)
C2—N1—C11—C12	−124.86 (19)	N1—C11—C16—C15	176.42 (16)
C2—N1—C11—C16	59.4 (2)	C12—C11—C16—C15	0.8 (3)
C8—N1—C11—C12	71.7 (2)	C11—C12—C13—C14	−0.7 (3)
C8—N1—C11—C16	−104.04 (19)	C12—C13—C14—C15	0.8 (3)
C9—N3—C2—N1	0.66 (19)	C13—C14—C15—C16	−0.2 (3)
C9—N3—C2—C21	−178.53 (15)	C14—C15—C16—C11	−0.6 (3)
C2—N3—C9—C4	178.37 (18)	C2—C21—C22—C23	−178.51 (17)
C2—N3—C9—C8	−0.23 (19)	C26—C21—C22—C23	1.8 (3)
N1—C2—C21—C22	19.6 (3)	C2—C21—C26—O26	−3.8 (3)
N1—C2—C21—C26	−160.78 (16)	C2—C21—C26—C25	176.02 (16)
N3—C2—C21—C22	−161.38 (17)	C22—C21—C26—O26	175.86 (16)
N3—C2—C21—C26	18.3 (2)	C22—C21—C26—C25	−4.3 (3)
C9—C4—C5—C6	−0.1 (3)	C21—C22—C23—C24	1.4 (3)
C5—C4—C9—N3	−177.34 (17)	C22—C23—C24—C25	−2.1 (3)
C5—C4—C9—C8	1.2 (3)	C23—C24—C25—C26	−0.4 (3)
C4—C5—C6—C7	−1.2 (3)	C24—C25—C26—O26	−176.50 (17)
C5—C6—C7—C8	1.2 (3)	C24—C25—C26—C21	3.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O26—H26···N3	0.97 (3)	1.70 (3)	2.583 (2)	150 (3)
C14—H14···N3i	0.95	2.60	3.456 (3)	151
C16—H16···O26ii	0.95	2.49	3.388 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O26—H26⋯N3	0.97 (3)	1.70 (3)	2.583 (2)	150 (3)
C14—H14⋯N3i	0.95	2.60	3.456 (3)	151
C16—H16⋯O26ii	0.95	2.49	3.388 (2)	157

Symmetry codes: (i) ; (ii) .