2-{[2-(Pyridin-4-yl)-1H-benzimidazol-1-yl]meth-yl}phenol.

In the title compound, C19H15N3O, the benzimidazole ring system makes dihedral angles of 44.36 (7) and 75.67 (7)° with the pyridine and benzene rings, respectively. In the crystal, phenolic O-H⋯N hydrogen bonds to benzimidazole N-atom acceptors give rise to a chain extending along [011].

Related literature

For applications of benzimidazole derivatives as ligands, see: Janiak (2000 ▶); Kühler et al. (2002 ▶); Li et al. (2007 ▶); Carcanague et al. (2002 ▶); Yang et al. (2006 ▶). For the synthesis of the title compound, see: Fellah et al. (2010 ▶). For the structure of a similar compound, see: Kitazume & Ishikawa (1974 ▶).

Experimental

Crystal data

C19H15N3O

M = 301.34

Monoclinic,

a = 16.1886 (7) Å

b = 8.4863 (4) Å

c = 21.4316 (10) Å

β = 93.756 (4)°

V = 2938.0 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.36 × 0.28 × 0.25 mm

Data collection

Agilent SuperNova CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.982, T max = 1.000

6104 measured reflections

3010 independent reflections

2398 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.06

3010 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) globalk, I. DOI: 10.1107/S1600536813009458/zs2254sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009458/zs2254Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009458/zs2254Isup3.cml

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

C19H15N3O	F(000) = 1264
Mr = 301.34	Dx = 1.362 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 16.1886 (7) Å	Cell parameters from 2313 reflections
b = 8.4863 (4) Å	θ = 3.1–28.4°
c = 21.4316 (10) Å	µ = 0.09 mm−1
β = 93.756 (4)°	T = 291 K
V = 2938.0 (2) Å3	Block, colourless
Z = 8	0.36 × 0.28 × 0.25 mm

Agilent SuperNova CCD diffractometer	3010 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2398 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.026
Detector resolution: 16.0733 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −19→20
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→8
Tmin = 0.982, Tmax = 1.000	l = −26→12
6104 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0458P)2 + 1.9069P] where P = (Fo2 + 2Fc2)/3
3010 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
O1	0.14368 (7)	0.81061 (16)	0.41079 (6)	0.0423 (3)
H1	0.0999	0.8588	0.4055	0.063*
N1	0.38187 (8)	0.62034 (16)	0.40429 (6)	0.0283 (3)
N2	0.49801 (8)	0.48060 (17)	0.39527 (7)	0.0336 (4)
N3	0.32187 (10)	0.05156 (18)	0.48316 (8)	0.0428 (4)
C1	0.43786 (10)	0.7203 (2)	0.37809 (8)	0.0295 (4)
C2	0.43205 (11)	0.8769 (2)	0.35956 (9)	0.0389 (4)
H2	0.3843	0.9358	0.3640	0.047*
C3	0.50055 (12)	0.9406 (3)	0.33434 (10)	0.0478 (5)
H3	0.4992	1.0456	0.3219	0.057*
C4	0.57225 (12)	0.8523 (3)	0.32683 (10)	0.0475 (5)
H4	0.6170	0.8993	0.3091	0.057*
C5	0.57749 (11)	0.6972 (2)	0.34522 (9)	0.0417 (5)
H5	0.6248	0.6381	0.3398	0.050*
C6	0.50936 (10)	0.6314 (2)	0.37236 (8)	0.0318 (4)
C7	0.42090 (9)	0.47799 (19)	0.41279 (8)	0.0281 (4)
C8	0.38405 (10)	0.33423 (19)	0.43756 (7)	0.0283 (4)
C9	0.30488 (10)	0.2814 (2)	0.41897 (8)	0.0325 (4)
H9	0.2709	0.3400	0.3910	0.039*
C10	0.27757 (12)	0.1415 (2)	0.44250 (9)	0.0381 (4)
H10	0.2247	0.1075	0.4292	0.046*
C11	0.39780 (12)	0.1031 (2)	0.50078 (9)	0.0433 (5)
H11	0.4299	0.0425	0.5293	0.052*
C12	0.43145 (11)	0.2401 (2)	0.47940 (8)	0.0378 (4)
H12	0.4851	0.2695	0.4927	0.045*
C13	0.29647 (9)	0.6653 (2)	0.41536 (8)	0.0289 (4)
H13A	0.2968	0.7650	0.4375	0.035*
H13B	0.2725	0.5864	0.4415	0.035*
C14	0.24385 (10)	0.68048 (19)	0.35455 (8)	0.0274 (4)
C15	0.16757 (10)	0.75871 (19)	0.35461 (8)	0.0296 (4)
C16	0.12004 (11)	0.7808 (2)	0.29896 (9)	0.0365 (4)
H16	0.0702	0.8353	0.2991	0.044*
C17	0.14634 (11)	0.7224 (2)	0.24338 (9)	0.0413 (5)
H17	0.1144	0.7380	0.2062	0.050*
C18	0.21993 (12)	0.6410 (3)	0.24306 (9)	0.0437 (5)
H18	0.2370	0.5990	0.2060	0.052*
C19	0.26815 (10)	0.6220 (2)	0.29809 (8)	0.0355 (4)
H19	0.3183	0.5687	0.2973	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0284 (7)	0.0537 (9)	0.0450 (7)	0.0191 (6)	0.0052 (5)	−0.0023 (6)
N1	0.0204 (6)	0.0291 (8)	0.0358 (8)	0.0049 (5)	0.0060 (6)	0.0042 (6)
N2	0.0233 (7)	0.0334 (8)	0.0449 (9)	0.0074 (6)	0.0073 (6)	0.0041 (7)
N3	0.0508 (10)	0.0338 (9)	0.0452 (9)	0.0011 (8)	0.0126 (8)	0.0048 (7)
C1	0.0226 (8)	0.0337 (9)	0.0324 (8)	0.0011 (7)	0.0037 (7)	0.0031 (7)
C2	0.0303 (9)	0.0353 (10)	0.0516 (11)	0.0054 (8)	0.0064 (8)	0.0087 (9)
C3	0.0403 (11)	0.0404 (11)	0.0630 (13)	−0.0016 (9)	0.0064 (10)	0.0189 (10)
C4	0.0314 (10)	0.0546 (13)	0.0571 (12)	−0.0072 (9)	0.0088 (9)	0.0173 (10)
C5	0.0225 (8)	0.0515 (12)	0.0519 (11)	0.0033 (8)	0.0086 (8)	0.0079 (10)
C6	0.0231 (8)	0.0346 (10)	0.0378 (9)	0.0022 (7)	0.0026 (7)	0.0050 (8)
C7	0.0222 (8)	0.0306 (9)	0.0313 (8)	0.0056 (7)	0.0017 (6)	0.0004 (7)
C8	0.0297 (8)	0.0273 (9)	0.0286 (8)	0.0056 (7)	0.0078 (7)	−0.0009 (7)
C9	0.0300 (9)	0.0347 (10)	0.0330 (9)	0.0033 (7)	0.0026 (7)	0.0020 (7)
C10	0.0384 (10)	0.0356 (10)	0.0411 (10)	−0.0040 (8)	0.0078 (8)	−0.0014 (8)
C11	0.0453 (11)	0.0409 (11)	0.0438 (11)	0.0093 (9)	0.0028 (9)	0.0131 (9)
C12	0.0332 (9)	0.0403 (11)	0.0394 (10)	0.0055 (8)	−0.0010 (8)	0.0048 (8)
C13	0.0217 (8)	0.0292 (9)	0.0366 (9)	0.0064 (7)	0.0082 (7)	0.0014 (7)
C14	0.0220 (7)	0.0244 (8)	0.0363 (9)	0.0016 (6)	0.0061 (7)	0.0025 (7)
C15	0.0226 (8)	0.0261 (9)	0.0405 (9)	0.0022 (7)	0.0052 (7)	0.0027 (7)
C16	0.0240 (8)	0.0363 (10)	0.0489 (11)	0.0016 (7)	0.0001 (8)	0.0074 (8)
C17	0.0342 (10)	0.0499 (12)	0.0391 (10)	−0.0072 (8)	−0.0037 (8)	0.0058 (9)
C18	0.0381 (10)	0.0574 (13)	0.0363 (10)	−0.0058 (9)	0.0077 (8)	−0.0041 (9)
C19	0.0257 (8)	0.0407 (11)	0.0410 (10)	0.0024 (8)	0.0079 (7)	−0.0019 (8)

O1—H1	0.8200	C8—C12	1.393 (2)
O1—C15	1.362 (2)	C9—H9	0.9300
N1—C1	1.387 (2)	C9—C10	1.374 (2)
N1—C7	1.370 (2)	C10—H10	0.9300
N1—C13	1.4684 (19)	C11—H11	0.9300
N2—C6	1.387 (2)	C11—C12	1.376 (3)
N2—C7	1.327 (2)	C12—H12	0.9300
N3—C10	1.332 (2)	C13—H13A	0.9700
N3—C11	1.336 (3)	C13—H13B	0.9700
C1—C2	1.389 (2)	C13—C14	1.515 (2)
C1—C6	1.394 (2)	C14—C15	1.402 (2)
C2—H2	0.9300	C14—C19	1.388 (2)
C2—C3	1.376 (3)	C15—C16	1.389 (2)
C3—H3	0.9300	C16—H16	0.9300
C3—C4	1.399 (3)	C16—C17	1.383 (3)
C4—H4	0.9300	C17—H17	0.9300
C4—C5	1.375 (3)	C17—C18	1.378 (3)
C5—H5	0.9300	C18—H18	0.9300
C5—C6	1.397 (2)	C18—C19	1.380 (3)
C7—C8	1.472 (2)	C19—H19	0.9300
C8—C9	1.391 (2)
C15—O1—H1	109.5	N3—C10—C9	124.25 (18)
C1—N1—C13	123.64 (13)	N3—C10—H10	117.9
C7—N1—C1	106.57 (13)	C9—C10—H10	117.9
C7—N1—C13	129.68 (14)	N3—C11—H11	118.0
C7—N2—C6	105.34 (14)	N3—C11—C12	124.03 (17)
C10—N3—C11	116.32 (16)	C12—C11—H11	118.0
N1—C1—C2	131.86 (15)	C8—C12—H12	120.5
N1—C1—C6	105.87 (14)	C11—C12—C8	119.07 (17)
C2—C1—C6	122.27 (15)	C11—C12—H12	120.5
C1—C2—H2	121.7	N1—C13—H13A	109.3
C3—C2—C1	116.55 (17)	N1—C13—H13B	109.3
C3—C2—H2	121.7	N1—C13—C14	111.43 (13)
C2—C3—H3	119.0	H13A—C13—H13B	108.0
C2—C3—C4	122.08 (18)	C14—C13—H13A	109.3
C4—C3—H3	119.0	C14—C13—H13B	109.3
C3—C4—H4	119.5	C15—C14—C13	119.01 (14)
C5—C4—C3	121.03 (17)	C19—C14—C13	122.95 (14)
C5—C4—H4	119.5	C19—C14—C15	118.03 (16)
C4—C5—H5	121.1	O1—C15—C14	117.08 (15)
C4—C5—C6	117.82 (17)	O1—C15—C16	122.82 (15)
C6—C5—H5	121.1	C16—C15—C14	120.10 (16)
N2—C6—C1	109.76 (14)	C15—C16—H16	119.8
N2—C6—C5	130.01 (16)	C17—C16—C15	120.43 (16)
C1—C6—C5	120.21 (16)	C17—C16—H16	119.8
N1—C7—C8	125.77 (14)	C16—C17—H17	120.0
N2—C7—N1	112.44 (15)	C18—C17—C16	119.96 (17)
N2—C7—C8	121.79 (14)	C18—C17—H17	120.0
C9—C8—C7	123.44 (15)	C17—C18—H18	120.2
C9—C8—C12	117.26 (16)	C17—C18—C19	119.66 (18)
C12—C8—C7	119.21 (15)	C19—C18—H18	120.2
C8—C9—H9	120.5	C14—C19—H19	119.1
C10—C9—C8	119.06 (16)	C18—C19—C14	121.77 (17)
C10—C9—H9	120.5	C18—C19—H19	119.1
O1—C15—C16—C17	−178.45 (17)	C7—N1—C1—C6	−0.32 (18)
N1—C1—C2—C3	−179.45 (18)	C7—N1—C13—C14	−104.93 (19)
N1—C1—C6—N2	−0.75 (19)	C7—N2—C6—C1	1.54 (19)
N1—C1—C6—C5	177.82 (16)	C7—N2—C6—C5	−176.85 (19)
N1—C7—C8—C9	44.3 (2)	C7—C8—C9—C10	176.76 (15)
N1—C7—C8—C12	−139.15 (18)	C7—C8—C12—C11	−177.78 (16)
N1—C13—C14—C15	−164.53 (14)	C8—C9—C10—N3	0.7 (3)
N1—C13—C14—C19	14.6 (2)	C9—C8—C12—C11	−1.0 (3)
N2—C7—C8—C9	−134.83 (18)	C10—N3—C11—C12	−0.2 (3)
N2—C7—C8—C12	41.7 (2)	C11—N3—C10—C9	−0.7 (3)
N3—C11—C12—C8	1.1 (3)	C12—C8—C9—C10	0.2 (2)
C1—N1—C7—N2	1.36 (19)	C13—N1—C1—C2	3.4 (3)
C1—N1—C7—C8	−177.87 (15)	C13—N1—C1—C6	−176.74 (14)
C1—N1—C13—C14	70.6 (2)	C13—N1—C7—N2	177.48 (15)
C1—C2—C3—C4	0.8 (3)	C13—N1—C7—C8	−1.7 (3)
C2—C1—C6—N2	179.12 (17)	C13—C14—C15—O1	−2.9 (2)
C2—C1—C6—C5	−2.3 (3)	C13—C14—C15—C16	176.89 (15)
C2—C3—C4—C5	−0.8 (3)	C13—C14—C19—C18	−178.34 (16)
C3—C4—C5—C6	−0.8 (3)	C14—C15—C16—C17	1.8 (3)
C4—C5—C6—N2	−179.47 (19)	C15—C14—C19—C18	0.8 (3)
C4—C5—C6—C1	2.3 (3)	C15—C16—C17—C18	0.3 (3)
C6—N2—C7—N1	−1.79 (19)	C16—C17—C18—C19	−1.8 (3)
C6—N2—C7—C8	177.48 (15)	C17—C18—C19—C14	1.2 (3)
C6—C1—C2—C3	0.7 (3)	C19—C14—C15—O1	177.92 (16)
C7—N1—C1—C2	179.83 (19)	C19—C14—C15—C16	−2.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.82	1.95	2.7659 (18)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.82	1.95	2.7659 (18)	177

Symmetry code: (i) .