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

The mol-ecule of the title compound, C(15)H(14)N(2)O(2) is almost planar, the dihedral angle between the 6-methyl-1H-benz-imidazole plane and the 2-methoxy-phenol plane being 6.9 (2)°. An intra-molecular O-H⋯N hydrogen bond is present. Adjacent mol-ecules are linked by N-H⋯O hydrogen bonds into a three-dimensional network structure. The benzoimidazole methyl group and its attached C atom are positionally disordered in a 0.724 (4):0.276 (4) ratio.

Related literature

For background to imidazole and its derivatives, see: Huang et al. (2004 ▶) and to benzimidazoles, see: Perry & Wilson (1993 ▶). For related structures, see: Savall & Fontimayor (2008 ▶).

Experimental

Crystal data

C15H14N2O2

M = 254.28

Monoclinic,

a = 17.986 (3) Å

b = 11.4452 (16) Å

c = 13.4105 (19) Å

β = 104.216 (2)°

V = 2676.1 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.21 × 0.17 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.982, T max = 0.989

6836 measured reflections

2531 independent reflections

1441 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.169

S = 1.05

2531 reflections

176 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016523/hg2503sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016523/hg2503Isup2.hkl

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

C15H14N2O2	F(000) = 1072
Mr = 254.28	Dx = 1.262 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2318 reflections
a = 17.986 (3) Å	θ = 2.4–23.9°
b = 11.4452 (16) Å	µ = 0.09 mm−1
c = 13.4105 (19) Å	T = 293 K
β = 104.216 (2)°	Block, yellow
V = 2676.1 (7) Å3	0.21 × 0.17 × 0.13 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	2531 independent reflections
Radiation source: fine-focus sealed tube	1441 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −21→11
Tmin = 0.982, Tmax = 0.989	k = −13→13
6836 measured reflections	l = −15→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0769P)2 + 0.8329P] where P = (Fo2 + 2Fc2)/3
2531 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.20 e Å−3
3 restraints	Δρmin = −0.23 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	Occ. (<1)
O1	0.34998 (10)	0.96117 (16)	0.14576 (12)	0.0718 (6)
H1	0.3809	0.9222	0.1879	0.086*
O2	0.23740 (12)	1.0753 (2)	0.03072 (14)	0.0942 (7)
N1	0.39603 (12)	0.94335 (19)	0.46813 (14)	0.0644 (6)
H1A	0.3689	0.9806	0.5087	0.077*
N2	0.42667 (11)	0.89053 (17)	0.32288 (14)	0.0568 (5)
C1	0.31924 (14)	1.0273 (2)	0.30233 (18)	0.0568 (6)
C2	0.30615 (14)	1.0242 (2)	0.19534 (18)	0.0574 (6)
C3	0.24529 (16)	1.0877 (2)	0.1342 (2)	0.0691 (8)
C4	0.20037 (17)	1.1559 (3)	0.1795 (2)	0.0839 (9)
H4	0.1605	1.1992	0.1389	0.101*
C5	0.21404 (19)	1.1607 (3)	0.2856 (3)	0.0928 (10)
H5	0.1834	1.2075	0.3158	0.111*
C6	0.27225 (17)	1.0974 (3)	0.3463 (2)	0.0797 (9)
H6	0.2807	1.1009	0.4175	0.096*
C7	0.38041 (14)	0.9559 (2)	0.36368 (17)	0.0554 (6)
C8	0.1738 (2)	1.1332 (4)	−0.0374 (3)	0.1217 (14)
H8A	0.1748	1.1176	−0.1074	0.183*
H8B	0.1776	1.2158	−0.0251	0.183*
H8C	0.1266	1.1047	−0.0252	0.183*
C9	0.45596 (15)	0.8650 (2)	0.49645 (19)	0.0659 (7)
C10	0.47445 (14)	0.8322 (2)	0.40546 (19)	0.0618 (7)
C11	0.53215 (16)	0.7501 (3)	0.4079 (2)	0.0806 (9)
H11	0.5454	0.7270	0.3480	0.097*
C14	0.49349 (18)	0.8175 (3)	0.5915 (2)	0.0865 (10)
H14	0.4807	0.8398	0.6519	0.104*
C12A	0.56835 (19)	0.7052 (3)	0.5008 (3)	0.1024 (16)	0.724 (4)
H12A	0.6072	0.6509	0.5033	0.123*	0.724 (4)
C13A	0.55061 (19)	0.7359 (3)	0.5920 (3)	0.0988 (17)	0.724 (4)
C15A	0.5957 (3)	0.6706 (5)	0.6876 (3)	0.1041 (15)	0.724 (4)
H15A	0.5797	0.6974	0.7469	0.156*	0.724 (4)
H15B	0.6495	0.6854	0.6969	0.156*	0.724 (4)
H15C	0.5861	0.5883	0.6788	0.156*	0.724 (4)
C13B	0.56835 (19)	0.7052 (3)	0.5008 (3)	0.0988 (17)	0.276 (4)
C12B	0.55061 (19)	0.7359 (3)	0.5920 (3)	0.1024 (16)	0.276 (4)
H12B	0.5769	0.7018	0.6536	0.123*	0.276 (4)
C15B	0.6306 (6)	0.6287 (11)	0.5397 (9)	0.1041 (15)	0.276 (4)
H15G	0.6498	0.5992	0.4838	0.156*	0.276 (4)
H15D	0.6136	0.5648	0.5748	0.156*	0.276 (4)
H15E	0.6707	0.6703	0.5868	0.156*	0.276 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0768 (12)	0.0922 (13)	0.0482 (10)	0.0351 (10)	0.0186 (9)	0.0116 (9)
O2	0.0935 (15)	0.1259 (18)	0.0566 (12)	0.0478 (13)	0.0059 (10)	0.0170 (11)
N1	0.0690 (14)	0.0807 (15)	0.0447 (12)	−0.0114 (12)	0.0164 (10)	0.0033 (11)
N2	0.0514 (12)	0.0654 (13)	0.0528 (12)	0.0031 (10)	0.0112 (10)	0.0091 (10)
C1	0.0562 (15)	0.0652 (15)	0.0518 (14)	0.0051 (13)	0.0186 (12)	0.0053 (12)
C2	0.0553 (14)	0.0654 (15)	0.0550 (15)	0.0130 (13)	0.0205 (12)	0.0091 (12)
C3	0.0693 (17)	0.0807 (19)	0.0588 (16)	0.0191 (15)	0.0185 (14)	0.0146 (14)
C4	0.0738 (19)	0.094 (2)	0.088 (2)	0.0316 (17)	0.0277 (17)	0.0206 (17)
C5	0.097 (2)	0.103 (2)	0.091 (2)	0.038 (2)	0.046 (2)	0.0105 (19)
C6	0.090 (2)	0.094 (2)	0.0645 (17)	0.0202 (18)	0.0352 (16)	0.0058 (15)
C7	0.0560 (14)	0.0641 (15)	0.0473 (14)	−0.0055 (13)	0.0147 (12)	0.0061 (11)
C8	0.116 (3)	0.151 (3)	0.080 (2)	0.059 (3)	−0.010 (2)	0.031 (2)
C9	0.0529 (15)	0.0782 (18)	0.0590 (16)	−0.0160 (14)	−0.0009 (13)	0.0180 (13)
C10	0.0528 (15)	0.0712 (17)	0.0565 (16)	−0.0081 (13)	0.0042 (12)	0.0166 (13)
C11	0.0611 (17)	0.086 (2)	0.087 (2)	0.0102 (16)	0.0036 (15)	0.0235 (16)
C14	0.079 (2)	0.112 (2)	0.0576 (17)	−0.0321 (19)	−0.0033 (15)	0.0269 (16)
C12A	0.080 (4)	0.103 (4)	0.116 (3)	0.015 (3)	0.006 (3)	0.042 (3)
C13A	0.070 (3)	0.129 (5)	0.077 (2)	−0.016 (4)	−0.020 (2)	0.055 (3)
C15A	0.101 (3)	0.131 (4)	0.072 (3)	0.028 (3)	0.005 (2)	0.034 (2)
C13B	0.070 (3)	0.129 (5)	0.077 (2)	−0.016 (4)	−0.020 (2)	0.055 (3)
C12B	0.080 (4)	0.103 (4)	0.116 (3)	0.015 (3)	0.006 (3)	0.042 (3)
C15B	0.101 (3)	0.131 (4)	0.072 (3)	0.028 (3)	0.005 (2)	0.034 (2)

O1—C2	1.357 (3)	C8—H8A	0.9600
O1—H1	0.8200	C8—H8B	0.9600
O2—C3	1.367 (3)	C8—H8C	0.9600
O2—C8	1.438 (3)	C9—C10	1.393 (4)
N1—C7	1.367 (3)	C9—C14	1.397 (3)
N1—C9	1.382 (3)	C10—C11	1.394 (4)
N1—H1A	0.9194	C11—C12A	1.357 (4)
N2—C7	1.332 (3)	C11—H11	0.9300
N2—C10	1.394 (3)	C14—C13A	1.388 (5)
C1—C2	1.396 (3)	C14—H14	0.9300
C1—C6	1.397 (4)	C12A—C13A	1.383 (5)
C1—C7	1.453 (3)	C12A—H12A	0.9300
C2—C3	1.399 (3)	C13A—C15A	1.531 (4)
C3—C4	1.368 (4)	C15A—H15A	0.9600
C4—C5	1.384 (4)	C15A—H15B	0.9600
C4—H4	0.9300	C15A—H15C	0.9600
C5—C6	1.366 (4)	C15B—H15G	0.9600
C5—H5	0.9300	C15B—H15D	0.9600
C6—H6	0.9300	C15B—H15E	0.9600
C2—O1—H1	109.2	O2—C8—H8C	109.5
C3—O2—C8	117.7 (2)	H8A—C8—H8C	109.5
C7—N1—C9	107.4 (2)	H8B—C8—H8C	109.5
C7—N1—H1A	123.5	N1—C9—C10	105.8 (2)
C9—N1—H1A	129.0	N1—C9—C14	132.3 (3)
C7—N2—C10	105.6 (2)	C10—C9—C14	121.9 (3)
C2—C1—C6	118.8 (2)	C9—C10—C11	119.8 (2)
C2—C1—C7	118.8 (2)	C9—C10—N2	109.5 (2)
C6—C1—C7	122.5 (2)	C11—C10—N2	130.7 (3)
O1—C2—C1	123.0 (2)	C12A—C11—C10	117.6 (3)
O1—C2—C3	117.0 (2)	C12A—C11—H11	121.2
C1—C2—C3	120.0 (2)	C10—C11—H11	121.2
O2—C3—C4	125.8 (2)	C13A—C14—C9	117.3 (3)
O2—C3—C2	114.3 (2)	C13A—C14—H14	121.4
C4—C3—C2	119.9 (2)	C9—C14—H14	121.4
C3—C4—C5	120.3 (3)	C11—C12A—C13A	123.6 (3)
C3—C4—H4	119.9	C11—C12A—H12A	118.2
C5—C4—H4	119.9	C13A—C12A—H12A	118.2
C6—C5—C4	120.5 (3)	C12A—C13A—C14	119.8 (3)
C6—C5—H5	119.7	C12A—C13A—C15A	115.3 (4)
C4—C5—H5	119.7	C14—C13A—C15A	124.9 (4)
C5—C6—C1	120.6 (3)	C13A—C15A—H15A	109.5
C5—C6—H6	119.7	C13A—C15A—H15B	109.5
C1—C6—H6	119.7	H15A—C15A—H15B	109.5
N2—C7—N1	111.7 (2)	C13A—C15A—H15C	109.5
N2—C7—C1	123.1 (2)	H15A—C15A—H15C	109.5
N1—C7—C1	125.2 (2)	H15B—C15A—H15C	109.5
O2—C8—H8A	109.5	H15G—C15B—H15D	109.5
O2—C8—H8B	109.5	H15G—C15B—H15E	109.5
H8A—C8—H8B	109.5	H15D—C15B—H15E	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.83	2.567 (2)	148
N1—H1A···O2i	0.92	2.54	3.173 (3)	127
N1—H1A···O1i	0.92	2.06	2.920 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.83	2.567 (2)	148
N1—H1A⋯O2i	0.92	2.54	3.173 (3)	127
N1—H1A⋯O1i	0.92	2.06	2.920 (3)	155

Symmetry code: (i) .