2-Meth-oxy-6-(6-methyl-1H-benzimid-azol-2-yl)phenol.

In the title mol-ecule, C(15)H(14)N(2)O(2), the substituted benzene ring forms a dihedral angle of 4.15 (1)° with the benzimidazole ring system. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the solid state, mol-ecules are linked into chains along the [001] via inter-molecular bifurcated N-H⋯(O,O) hydrogen bonds, which generate R(1) (2)(5) ring motifs. The crystal packing is also consolidated by C-H⋯π inter-actions, and π-π stacking inter-actions between the imidazole and substituted benzene rings [centroid-centroid distance = 3.5746 (13) Å]. The methyl group attached to the benzimidazole ring system is disordered over two positions with occupancies of 0.587 (6) and 0.413 (6), suggesting 180° rotational disorder for the benzimidazole group.

Related literature

For the biological activity of benzimidazole derivatives, see: Minoura et al. (2004 ▶); Pawar et al. (2004 ▶); Tomei et al. (2003 ▶); Rao et al. (2003 ▶); Demirayak et al. (2002 ▶). For related structures, see: Eltayeb et al. (2007a ▶,b ▶,c ▶); Yeap et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H14N2O2

M = 254.28

Tetragonal,

a = 14.4118 (2) Å

c = 12.0995 (2) Å

V = 2513.07 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.27 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.969, T max = 0.978

28200 measured reflections

2215 independent reflections

1725 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.156

S = 1.08

2215 reflections

193 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022478/ci2825sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022478/ci2825Isup2.hkl

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

C15H14N2O2	Dx = 1.344 Mg m−3
Mr = 254.28	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42/n	Cell parameters from 9054 reflections
Hall symbol: -P 4bc	θ = 2.2–29.6°
a = 14.4118 (2) Å	µ = 0.09 mm−1
c = 12.0995 (2) Å	T = 100 K
V = 2513.07 (6) Å3	Block, yellow
Z = 8	0.35 × 0.27 × 0.24 mm
F(000) = 1072

Bruker SMART APEXII CCD area-detector diffractometer	2215 independent reflections
Radiation source: fine-focus sealed tube	1725 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→16
Tmin = 0.969, Tmax = 0.978	k = −17→17
28200 measured reflections	l = −14→13

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0696P)2 + 1.1514P] where P = (Fo2 + 2Fc2)/3
2215 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.29 e Å−3
6 restraints	Δρmin = −0.17 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
O1	0.63382 (12)	0.20396 (13)	−0.12954 (12)	0.0575 (5)
H1O	0.632 (2)	0.268 (2)	−0.104 (3)	0.094 (10)*
O2	0.63393 (12)	0.02461 (12)	−0.12218 (13)	0.0641 (5)
N1	0.62805 (13)	0.37806 (15)	0.14723 (17)	0.0556 (5)
H1N	0.6438 (18)	0.3647 (18)	0.219 (3)	0.077 (8)*
N2	0.62434 (13)	0.36357 (13)	−0.03521 (15)	0.0506 (5)
C1	0.62626 (15)	0.46707 (17)	0.1047 (2)	0.0579 (6)
C2	0.62707 (18)	0.5541 (2)	0.1545 (3)	0.0726 (8)
H2	0.6299	0.5608	0.2309	0.087*
C3	0.62340 (18)	0.63115 (19)	0.0839 (3)	0.0753 (8)
H3	0.6235	0.6906	0.1139	0.090*	0.413 (6)
C4	0.6197 (2)	0.6204 (2)	−0.0292 (3)	0.0787 (9)
H4	0.6168	0.6729	−0.0738	0.094*	0.587 (6)
C5	0.62015 (19)	0.53499 (19)	−0.0773 (3)	0.0730 (8)
H5	0.6182	0.5289	−0.1538	0.088*
C6	0.62354 (15)	0.45686 (17)	−0.0092 (2)	0.0540 (6)
C7	0.62715 (14)	0.31865 (16)	0.06068 (17)	0.0469 (6)
C8	0.62766 (14)	0.21826 (16)	0.06973 (17)	0.0456 (5)
C9	0.63060 (14)	0.16508 (16)	−0.02796 (16)	0.0456 (5)
C10	0.63048 (15)	0.06902 (17)	−0.02064 (18)	0.0511 (6)
C11	0.62696 (16)	0.02486 (17)	0.0801 (2)	0.0559 (6)
H11	0.6263	−0.0396	0.0838	0.067*
C12	0.62437 (16)	0.07732 (17)	0.17613 (19)	0.0572 (6)
H12	0.6227	0.0478	0.2444	0.069*
C13	0.62424 (15)	0.17223 (16)	0.17120 (18)	0.0513 (6)
H13	0.6218	0.2065	0.2363	0.062*
C14	0.6320 (2)	−0.07360 (18)	−0.1201 (2)	0.0739 (8)
H14A	0.6353	−0.0970	−0.1942	0.111*
H14B	0.5754	−0.0942	−0.0862	0.111*
H14C	0.6840	−0.0962	−0.0784	0.111*
C15	0.6189 (3)	0.7303 (3)	0.1250 (4)	0.0672 (15)	0.587 (6)
H15A	0.6664	0.7664	0.0896	0.101*	0.587 (6)
H15B	0.6282	0.7314	0.2035	0.101*	0.587 (6)
H15C	0.5592	0.7561	0.1078	0.101*	0.587 (6)
C15A	0.6243 (6)	0.7101 (5)	−0.0739 (9)	0.106 (3)	0.413 (6)
H15D	0.5763	0.7175	−0.1282	0.160*	0.413 (6)
H15E	0.6837	0.7191	−0.1080	0.160*	0.413 (6)
H15F	0.6159	0.7549	−0.0161	0.160*	0.413 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0754 (11)	0.0642 (11)	0.0329 (9)	0.0026 (8)	0.0016 (7)	0.0016 (7)
O2	0.0800 (12)	0.0649 (11)	0.0474 (10)	0.0083 (9)	−0.0050 (8)	−0.0113 (8)
N1	0.0574 (12)	0.0687 (14)	0.0407 (11)	0.0040 (10)	−0.0037 (9)	−0.0075 (10)
N2	0.0537 (12)	0.0567 (12)	0.0415 (11)	0.0009 (9)	0.0024 (8)	0.0063 (9)
C1	0.0444 (13)	0.0568 (15)	0.0725 (17)	0.0022 (10)	0.0038 (11)	−0.0055 (12)
C2	0.0608 (16)	0.079 (2)	0.0781 (18)	0.0009 (13)	0.0067 (14)	−0.0209 (16)
C3	0.0564 (15)	0.0563 (16)	0.113 (2)	−0.0023 (12)	0.0144 (15)	−0.0108 (15)
C4	0.0736 (19)	0.071 (2)	0.092 (2)	−0.0012 (14)	0.0211 (16)	0.0047 (16)
C5	0.0750 (18)	0.0601 (17)	0.0837 (19)	0.0024 (13)	0.0163 (15)	0.0105 (15)
C6	0.0490 (13)	0.0562 (15)	0.0568 (15)	−0.0009 (10)	0.0053 (11)	0.0012 (11)
C7	0.0393 (12)	0.0602 (14)	0.0413 (13)	−0.0005 (10)	−0.0004 (9)	−0.0022 (10)
C8	0.0388 (11)	0.0593 (14)	0.0387 (12)	0.0020 (9)	−0.0018 (9)	0.0024 (10)
C9	0.0405 (12)	0.0641 (15)	0.0323 (11)	0.0027 (10)	0.0007 (9)	0.0040 (10)
C10	0.0476 (13)	0.0619 (15)	0.0438 (13)	0.0049 (10)	−0.0056 (10)	−0.0051 (10)
C11	0.0579 (14)	0.0548 (14)	0.0549 (15)	0.0010 (11)	−0.0065 (11)	0.0047 (11)
C12	0.0632 (15)	0.0655 (16)	0.0429 (13)	0.0008 (12)	−0.0042 (11)	0.0075 (11)
C13	0.0563 (14)	0.0637 (15)	0.0338 (12)	0.0018 (11)	−0.0030 (10)	0.0008 (10)
C14	0.085 (2)	0.0676 (18)	0.0689 (18)	0.0108 (14)	−0.0186 (15)	−0.0187 (14)
C15	0.066 (3)	0.061 (3)	0.074 (3)	0.001 (2)	0.005 (2)	−0.009 (2)
C15A	0.102 (6)	0.056 (5)	0.162 (9)	0.003 (4)	0.001 (6)	0.031 (5)

O1—C9	1.352 (2)	C5—H5	0.93
O1—H1O	0.97 (3)	C7—C8	1.451 (3)
O2—C10	1.386 (3)	C8—C13	1.396 (3)
O2—C14	1.416 (3)	C8—C9	1.409 (3)
N1—C7	1.353 (3)	C9—C10	1.387 (3)
N1—C1	1.382 (3)	C10—C11	1.376 (3)
N1—H1N	0.92 (3)	C11—C12	1.387 (3)
N2—C7	1.329 (3)	C11—H11	0.93
N2—C6	1.381 (3)	C12—C13	1.369 (3)
C1—C6	1.387 (4)	C12—H12	0.93
C1—C2	1.392 (4)	C13—H13	0.93
C2—C3	1.402 (4)	C14—H14A	0.96
C2—H2	0.93	C14—H14B	0.96
C3—C4	1.378 (5)	C14—H14C	0.96
C3—C15	1.515 (5)	C15—H15A	0.96
C3—H3	0.93	C15—H15B	0.96
C4—C5	1.362 (4)	C15—H15C	0.96
C4—C15A	1.403 (8)	C15A—H15D	0.96
C4—H4	0.93	C15A—H15E	0.96
C5—C6	1.396 (4)	C15A—H15F	0.96
C9—O1—H1O	95.9 (19)	C13—C8—C7	122.7 (2)
C10—O2—C14	116.42 (19)	C9—C8—C7	118.62 (19)
C7—N1—C1	107.4 (2)	O1—C9—C10	118.15 (19)
C7—N1—H1N	127.0 (17)	O1—C9—C8	122.6 (2)
C1—N1—H1N	123.5 (16)	C10—C9—C8	119.28 (19)
C7—N2—C6	106.02 (19)	C11—C10—O2	125.0 (2)
N1—C1—C6	105.8 (2)	C11—C10—C9	121.2 (2)
N1—C1—C2	132.5 (3)	O2—C10—C9	113.8 (2)
C6—C1—C2	121.8 (3)	C10—C11—C12	119.4 (2)
C1—C2—C3	116.7 (3)	C10—C11—H11	120.3
C1—C2—H2	121.6	C12—C11—H11	120.3
C3—C2—H2	121.6	C13—C12—C11	120.5 (2)
C4—C3—C2	121.2 (3)	C13—C12—H12	119.7
C4—C3—C15	115.5 (3)	C11—C12—H12	119.7
C2—C3—C15	123.3 (3)	C12—C13—C8	120.8 (2)
C4—C3—H3	119.4	C12—C13—H13	119.6
C2—C3—H3	119.4	C8—C13—H13	119.6
C5—C4—C3	121.7 (3)	O2—C14—H14A	109.5
C5—C4—C15A	131.9 (5)	O2—C14—H14B	109.5
C3—C4—C15A	106.1 (5)	H14A—C14—H14B	109.5
C5—C4—H4	119.1	O2—C14—H14C	109.5
C3—C4—H4	119.1	H14A—C14—H14C	109.5
C4—C5—C6	118.5 (3)	H14B—C14—H14C	109.5
C4—C5—H5	120.8	C3—C15—H15A	109.5
C6—C5—H5	120.8	C3—C15—H15B	109.5
N2—C6—C1	109.2 (2)	C3—C15—H15C	109.5
N2—C6—C5	130.7 (2)	C4—C15A—H15D	109.5
C1—C6—C5	120.1 (2)	C4—C15A—H15E	109.5
N2—C7—N1	111.6 (2)	H15D—C15A—H15E	109.5
N2—C7—C8	123.48 (19)	C4—C15A—H15F	109.5
N1—C7—C8	124.9 (2)	H15D—C15A—H15F	109.5
C13—C8—C9	118.7 (2)	H15E—C15A—H15F	109.5
C7—N1—C1—C6	0.5 (2)	C1—N1—C7—N2	−0.4 (2)
C7—N1—C1—C2	−179.3 (2)	C1—N1—C7—C8	−179.45 (19)
N1—C1—C2—C3	−179.2 (2)	N2—C7—C8—C13	−175.5 (2)
C6—C1—C2—C3	1.1 (4)	N1—C7—C8—C13	3.5 (3)
C1—C2—C3—C4	−0.4 (4)	N2—C7—C8—C9	3.7 (3)
C1—C2—C3—C15	176.8 (3)	N1—C7—C8—C9	−177.3 (2)
C2—C3—C4—C5	−0.5 (4)	C13—C8—C9—O1	179.87 (19)
C15—C3—C4—C5	−177.9 (3)	C7—C8—C9—O1	0.6 (3)
C2—C3—C4—C15A	−175.4 (4)	C13—C8—C9—C10	−0.3 (3)
C15—C3—C4—C15A	7.2 (5)	C7—C8—C9—C10	−179.56 (19)
C3—C4—C5—C6	0.6 (4)	C14—O2—C10—C11	1.1 (3)
C15A—C4—C5—C6	174.0 (5)	C14—O2—C10—C9	−178.7 (2)
C7—N2—C6—C1	0.2 (2)	O1—C9—C10—C11	−179.8 (2)
C7—N2—C6—C5	−179.4 (2)	C8—C9—C10—C11	0.4 (3)
N1—C1—C6—N2	−0.4 (3)	O1—C9—C10—O2	0.1 (3)
C2—C1—C6—N2	179.4 (2)	C8—C9—C10—O2	−179.74 (18)
N1—C1—C6—C5	179.3 (2)	O2—C10—C11—C12	179.6 (2)
C2—C1—C6—C5	−0.9 (4)	C9—C10—C11—C12	−0.6 (3)
C4—C5—C6—N2	179.7 (2)	C10—C11—C12—C13	0.7 (3)
C4—C5—C6—C1	0.1 (4)	C11—C12—C13—C8	−0.7 (3)
C6—N2—C7—N1	0.1 (2)	C9—C8—C13—C12	0.4 (3)
C6—N2—C7—C8	179.20 (19)	C7—C8—C13—C12	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.92 (4)	2.03 (3)	2.919 (3)	164 (2)
N1—H1N···O2i	0.92 (4)	2.58 (3)	3.168 (3)	123 (2)
O1—H1O···N2	0.97 (3)	1.61 (3)	2.572 (3)	167 (3)
C14—H14B···Cg1ii	0.96	2.95	3.840 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.92 (4)	2.03 (3)	2.919 (3)	164 (2)
N1—H1N⋯O2i	0.92 (4)	2.58 (3)	3.168 (3)	123 (2)
O1—H1O⋯N2	0.97 (3)	1.61 (3)	2.572 (3)	167 (3)
C14—H14B⋯Cg1ii	0.96	2.95	3.840 (3)	154

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C8–C13 benzene ring.