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Acta Cryst. (2009). E65, o1256    [ doi:10.1107/S1600536809016523 ]

2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol

H.-Q. Xiao, M.-Z. Zhang and W. Wang

Abstract top

The molecule of the title compound, C15H14N2O2 is almost planar, the dihedral angle between the 6-methyl-1H-benzimidazole plane and the 2-methoxyphenol plane being 6.9 (2)°. An intramolecular O-H...N hydrogen bond is present. Adjacent molecules 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.

Comment top

Imidazole and its derivatives are an important class of heterocycle with N-donor atoms, therefore they can be excellent organic ligands to generate various complexes (Huang et al., 2004). Benzimidazoles are privileged structural units not only in the pharmaceutical industry but also in several other fields such as agricultural, electronic, and polymer chemistry (Perry et al., 1993). We report here the synthesis and crystal structure of the title compound.

The molecular structure is shown in Fig. 1. The values of the geometric parameters in the compound are normal (Savall et al., 2008) (Table 1). The benzimidazole and phenol groups are nearly coplanar, the dihedral angle between 6-methyl-1H-benzimidazole plane and 2-methoxyphenol plane is 6.9 (2)°. The compounds are linked by N—H···O hydrogen bonds [N1—H1A··· O1, N1—H1A···O2, O1—H1···N2] into a three-dimensional network structure.

Related literature top

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

Experimental top

A mixture of 4-methylbenzene-1,2-diamine (1 mmol) and 2-hydroxy-3-methoxybenzaldehyde (1 mmol) in ethanol (15 ml) was stirred for 8 h and then filtered. The resulting clear orange solution was vapor at room temperature for 7 d, after which orange block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained, yield 45%.

Refinement top

The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with C—H distances in the range of 0.93–0.96 Å and with Uiso(H) = 1.2Ueq(parent atom), or Uiso(H) = 1.5Ueq(Cmethyl). The coordinates of the H atoms of the N—H and O—H groups were found from difference Fourier maps and were allowed for as riding atoms with O—H 0.82 Å and N—H 0.92 Å and with Uiso(H) = 1.2Ueq(O).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol top
Crystal data top
C15H14N2O2F000 = 1072
Mr = 254.28Dx = 1.262 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2318 reflections
a = 17.986 (3) Åθ = 2.4–23.9º
b = 11.4452 (16) ŵ = 0.09 mm−1
c = 13.4105 (19) ÅT = 293 K
β = 104.216 (2)ºBlock, yellow
V = 2676.1 (7) Å30.21 × 0.17 × 0.13 mm
Z = 8
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2531 independent reflections
Radiation source: fine-focus sealed tube1441 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
T = 293 Kθmax = 25.7º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −21→11
Tmin = 0.982, Tmax = 0.989k = −13→13
6836 measured reflectionsl = −15→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.169  w = 1/[σ2(Fo2) + (0.0769P)2 + 0.8329P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2531 reflectionsΔρmax = 0.20 e Å−3
176 parametersΔρmin = −0.23 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C15H14N2O2V = 2676.1 (7) Å3
Mr = 254.28Z = 8
Monoclinic, C2/cMo Kα
a = 17.986 (3) ŵ = 0.09 mm−1
b = 11.4452 (16) ÅT = 293 K
c = 13.4105 (19) Å0.21 × 0.17 × 0.13 mm
β = 104.216 (2)º
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2531 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		1441 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.989Rint = 0.031
6836 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0563 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.05Δρmax = 0.20 e Å−3
2531 reflectionsΔρmin = −0.23 e Å−3
176 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.34998 (10)0.96117 (16)0.14576 (12)0.0718 (6)
H10.38090.92220.18790.086*
O20.23740 (12)1.0753 (2)0.03072 (14)0.0942 (7)
N10.39603 (12)0.94335 (19)0.46813 (14)0.0644 (6)
H1A0.36890.98060.50870.077*
N20.42667 (11)0.89053 (17)0.32288 (14)0.0568 (5)
C10.31924 (14)1.0273 (2)0.30233 (18)0.0568 (6)
C20.30615 (14)1.0242 (2)0.19534 (18)0.0574 (6)
C30.24529 (16)1.0877 (2)0.1342 (2)0.0691 (8)
C40.20037 (17)1.1559 (3)0.1795 (2)0.0839 (9)
H40.16051.19920.13890.101*
C50.21404 (19)1.1607 (3)0.2856 (3)0.0928 (10)
H50.18341.20750.31580.111*
C60.27225 (17)1.0974 (3)0.3463 (2)0.0797 (9)
H60.28071.10090.41750.096*
C70.38041 (14)0.9559 (2)0.36368 (17)0.0554 (6)
C80.1738 (2)1.1332 (4)−0.0374 (3)0.1217 (14)
H8A0.17481.1176−0.10740.183*
H8B0.17761.2158−0.02510.183*
H8C0.12661.1047−0.02520.183*
C90.45596 (15)0.8650 (2)0.49645 (19)0.0659 (7)
C100.47445 (14)0.8322 (2)0.40546 (19)0.0618 (7)
C110.53215 (16)0.7501 (3)0.4079 (2)0.0806 (9)
H110.54540.72700.34800.097*
C140.49349 (18)0.8175 (3)0.5915 (2)0.0865 (10)
H140.48070.83980.65190.104*
C12A0.56835 (19)0.7052 (3)0.5008 (3)0.1024 (16)0.724 (4)
H12A0.60720.65090.50330.123*0.724 (4)
C13A0.55061 (19)0.7359 (3)0.5920 (3)0.0988 (17)0.724 (4)
C15A0.5957 (3)0.6706 (5)0.6876 (3)0.1041 (15)0.724 (4)
H15A0.57970.69740.74690.156*0.724 (4)
H15B0.64950.68540.69690.156*0.724 (4)
H15C0.58610.58830.67880.156*0.724 (4)
C13B0.56835 (19)0.7052 (3)0.5008 (3)0.0988 (17)0.276 (4)
C12B0.55061 (19)0.7359 (3)0.5920 (3)0.1024 (16)0.276 (4)
H12B0.57690.70180.65360.123*0.276 (4)
C15B0.6306 (6)0.6287 (11)0.5397 (9)0.1041 (15)0.276 (4)
H15G0.64980.59920.48380.156*0.276 (4)
H15D0.61360.56480.57480.156*0.276 (4)
H15E0.67070.67030.58680.156*0.276 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0768 (12)0.0922 (13)0.0482 (10)0.0351 (10)0.0186 (9)0.0116 (9)
O20.0935 (15)0.1259 (18)0.0566 (12)0.0478 (13)0.0059 (10)0.0170 (11)
N10.0690 (14)0.0807 (15)0.0447 (12)−0.0114 (12)0.0164 (10)0.0033 (11)
N20.0514 (12)0.0654 (13)0.0528 (12)0.0031 (10)0.0112 (10)0.0091 (10)
C10.0562 (15)0.0652 (15)0.0518 (14)0.0051 (13)0.0186 (12)0.0053 (12)
C20.0553 (14)0.0654 (15)0.0550 (15)0.0130 (13)0.0205 (12)0.0091 (12)
C30.0693 (17)0.0807 (19)0.0588 (16)0.0191 (15)0.0185 (14)0.0146 (14)
C40.0738 (19)0.094 (2)0.088 (2)0.0316 (17)0.0277 (17)0.0206 (17)
C50.097 (2)0.103 (2)0.091 (2)0.038 (2)0.046 (2)0.0105 (19)
C60.090 (2)0.094 (2)0.0645 (17)0.0202 (18)0.0352 (16)0.0058 (15)
C70.0560 (14)0.0641 (15)0.0473 (14)−0.0055 (13)0.0147 (12)0.0061 (11)
C80.116 (3)0.151 (3)0.080 (2)0.059 (3)−0.010 (2)0.031 (2)
C90.0529 (15)0.0782 (18)0.0590 (16)−0.0160 (14)−0.0009 (13)0.0180 (13)
C100.0528 (15)0.0712 (17)0.0565 (16)−0.0081 (13)0.0042 (12)0.0166 (13)
C110.0611 (17)0.086 (2)0.087 (2)0.0102 (16)0.0036 (15)0.0235 (16)
C140.079 (2)0.112 (2)0.0576 (17)−0.0321 (19)−0.0033 (15)0.0269 (16)
C12A0.080 (4)0.103 (4)0.116 (3)0.015 (3)0.006 (3)0.042 (3)
C13A0.070 (3)0.129 (5)0.077 (2)−0.016 (4)−0.020 (2)0.055 (3)
C15A0.101 (3)0.131 (4)0.072 (3)0.028 (3)0.005 (2)0.034 (2)
C13B0.070 (3)0.129 (5)0.077 (2)−0.016 (4)−0.020 (2)0.055 (3)
C12B0.080 (4)0.103 (4)0.116 (3)0.015 (3)0.006 (3)0.042 (3)
C15B0.101 (3)0.131 (4)0.072 (3)0.028 (3)0.005 (2)0.034 (2)
Geometric parameters (Å, °) top
O1—C21.357 (3)C8—H8A0.9600
O1—H10.8200C8—H8B0.9600
O2—C31.367 (3)C8—H8C0.9600
O2—C81.438 (3)C9—C101.393 (4)
N1—C71.367 (3)C9—C141.397 (3)
N1—C91.382 (3)C10—C111.394 (4)
N1—H1A0.9194C11—C12A1.357 (4)
N2—C71.332 (3)C11—H110.9300
N2—C101.394 (3)C14—C13A1.388 (5)
C1—C21.396 (3)C14—H140.9300
C1—C61.397 (4)C12A—C13A1.383 (5)
C1—C71.453 (3)C12A—H12A0.9300
C2—C31.399 (3)C13A—C15A1.531 (4)
C3—C41.368 (4)C15A—H15A0.9600
C4—C51.384 (4)C15A—H15B0.9600
C4—H40.9300C15A—H15C0.9600
C5—C61.366 (4)C15B—H15G0.9600
C5—H50.9300C15B—H15D0.9600
C6—H60.9300C15B—H15E0.9600
C2—O1—H1109.2O2—C8—H8C109.5
C3—O2—C8117.7 (2)H8A—C8—H8C109.5
C7—N1—C9107.4 (2)H8B—C8—H8C109.5
C7—N1—H1A123.5N1—C9—C10105.8 (2)
C9—N1—H1A129.0N1—C9—C14132.3 (3)
C7—N2—C10105.6 (2)C10—C9—C14121.9 (3)
C2—C1—C6118.8 (2)C9—C10—C11119.8 (2)
C2—C1—C7118.8 (2)C9—C10—N2109.5 (2)
C6—C1—C7122.5 (2)C11—C10—N2130.7 (3)
O1—C2—C1123.0 (2)C12A—C11—C10117.6 (3)
O1—C2—C3117.0 (2)C12A—C11—H11121.2
C1—C2—C3120.0 (2)C10—C11—H11121.2
O2—C3—C4125.8 (2)C13A—C14—C9117.3 (3)
O2—C3—C2114.3 (2)C13A—C14—H14121.4
C4—C3—C2119.9 (2)C9—C14—H14121.4
C3—C4—C5120.3 (3)C11—C12A—C13A123.6 (3)
C3—C4—H4119.9C11—C12A—H12A118.2
C5—C4—H4119.9C13A—C12A—H12A118.2
C6—C5—C4120.5 (3)C12A—C13A—C14119.8 (3)
C6—C5—H5119.7C12A—C13A—C15A115.3 (4)
C4—C5—H5119.7C14—C13A—C15A124.9 (4)
C5—C6—C1120.6 (3)C13A—C15A—H15A109.5
C5—C6—H6119.7C13A—C15A—H15B109.5
C1—C6—H6119.7H15A—C15A—H15B109.5
N2—C7—N1111.7 (2)C13A—C15A—H15C109.5
N2—C7—C1123.1 (2)H15A—C15A—H15C109.5
N1—C7—C1125.2 (2)H15B—C15A—H15C109.5
O2—C8—H8A109.5H15G—C15B—H15D109.5
O2—C8—H8B109.5H15G—C15B—H15E109.5
H8A—C8—H8B109.5H15D—C15B—H15E109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.832.567 (2)148
N1—H1A···O2i0.922.543.173 (3)127
N1—H1A···O1i0.922.062.920 (3)155
Symmetry codes: (i) x, −y+2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.832.567 (2)148
N1—H1A···O2i0.922.543.173 (3)127
N1—H1A···O1i0.922.062.920 (3)155
Symmetry codes: (i) x, −y+2, z+1/2.
Acknowledgements top

This work was supported by the Zhejiang Provincial Natural Science Foundation (grant No. Y4080395).

references
References top

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Huang, X.-C., Zhang, J.-P. & Chen, X.-M. (2004). J. Am. Chem. Soc. 126, 13218–13219.

Perry, R. J. & Wilson, B. D. (1993). J. Org. Chem. 58, 7016–7021.

Savall, B. M. & Fontimayor, J. R. (2008). Tetrahedron Lett. 49, 6667–6669.

Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.