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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1256.
Published online 2009 May 14. doi:  10.1107/S1600536809016523
PMCID: PMC2969644

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

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o1256-scheme1.jpg

Experimental

Crystal data

  • C15H14N2O2
  • M r = 254.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1256-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
The independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C15H14N2O2F(000) = 1072
Mr = 254.28Dx = 1.262 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2318 reflections
a = 17.986 (3) Åθ = 2.4–23.9°
b = 11.4452 (16) ŵ = 0.09 mm1
c = 13.4105 (19) ÅT = 293 K
β = 104.216 (2)°Block, yellow
V = 2676.1 (7) Å30.21 × 0.17 × 0.13 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer2531 independent reflections
Radiation source: fine-focus sealed tube1441 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 25.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −21→11
Tmin = 0.982, Tmax = 0.989k = −13→13
6836 measured reflectionsl = −15→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0769P)2 + 0.8329P] where P = (Fo2 + 2Fc2)/3
2531 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.20 e Å3
3 restraintsΔρmin = −0.23 e Å3

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2503).

References

  • 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. [PubMed]
  • 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. [PubMed]

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