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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1374–o1375.
Published online 2009 May 23. doi:  10.1107/S1600536809018698
PMCID: PMC2969736

3-[1-(3-Hydroxy­benz­yl)-1H-benz­imid­azol-2-yl]phenol

Abstract

In the title mol­ecule, C20H16N2O2, the benzimidazole mean plane forms dihedral angles of 56.55 (3) and 81.65 (4)° with the two benzene rings. In the crystal structure, inter­molecular O—H(...)O and O—H(...)N hydrogen bonds link the mol­ecules into layers parallel to the (101) plane. The crystal packing also exhibits weak inter­molecular C—H(...)O and C—H(...)π inter­actions.

Related literature

For the biological activity of benzimidazole derivatives, see: Demirayak et al. (2002 [triangle]); Minoura et al. (2004 [triangle]); Pawar et al. (2004 [triangle]); Tomei et al. (2003 [triangle]). For related structures, see: Eltayeb et al. (2007a [triangle],b [triangle],c [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1374-scheme1.jpg

Experimental

Crystal data

  • C20H16N2O2
  • M r = 316.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1374-efi1.jpg
  • a = 10.5128 (2) Å
  • b = 12.1096 (2) Å
  • c = 12.5235 (2) Å
  • β = 96.948 (1)°
  • V = 1582.61 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.55 × 0.34 × 0.15 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.954, T max = 0.987
  • 34106 measured reflections
  • 7426 independent reflections
  • 6004 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.136
  • S = 1.05
  • 7426 reflections
  • 225 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.29 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018698/cv2563sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018698/cv2563Isup2.hkl

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

Acknowledgments

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the E-Science Fund and RU research grants (Nos. PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120). The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for a Science Fund grant (No. 305/PFIZIK/613312). SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for a Research University Golden Goose grant (No. 1001/PFIZIK/811012).

supplementary crystallographic information

Comment

The synthesis of benzimidazoles has received much attention owing to the varied biological activities such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), and anticancer (Demirayak et al., 2002) properties exhibited by a number of derivatives of these compounds. In continuation of our structural study of benzimidazole derivatives (Eltayeb et al. 2007a,b,c), we describe in this paper the crystal structure of the title compound (I).

In (I) (Fig. 1), the bond lengths and bond angles are normal (Allen et al., 1987). The benzimidazole unit is planar with the maximum deviation from planarity of 0.0403 (9) Å for atom C3. The dihedral angle formed by the benzimidazole unit with the two benzene rings (C8–C13 and C15–C20) are 56.55 (3)° and 81.65 (4)° respectively. The two benzene rings (C8–C13 and C15–C20) are inclined to each other forming a dihedral angle of 72.54 (4)°.

In the crystal, intermolecular O—H···O, O—H···N hydrogen bonds (Table 1) link the molecules into layers parallel to the (101) plane. The crystal packing exhibits also weak C—H···O and C—H···π interactions (Table 1).

Experimental

To a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (30 ml) was added 3-hydroxybenzaldehyde (0.488 g, 4 mmol). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Crystals suitable for XRD were formed after several days of slow evaporation of solvent at room temperature.

Refinement

H atoms were positioned geometrically [C—H = 0.93–0.97 Å] and refined using a riding model with Uiso(H) = 1.2Ueq(C). The O-bound H atoms were located on a Fourier map and were refined isotropically.

Figures

Fig. 1.
The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom numbering scheme.

Crystal data

C20H16N2O2F(000) = 664
Mr = 316.35Dx = 1.328 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8327 reflections
a = 10.5128 (2) Åθ = 2.4–37.2°
b = 12.1096 (2) ŵ = 0.09 mm1
c = 12.5235 (2) ÅT = 100 K
β = 96.948 (1)°Plate, colourless
V = 1582.61 (5) Å30.55 × 0.34 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer7426 independent reflections
Radiation source: fine-focus sealed tube6004 reflections with I > 2σ(I)
graphiteRint = 0.040
[var phi] and ω scansθmax = 36.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −14→17
Tmin = 0.954, Tmax = 0.987k = −20→20
34106 measured reflectionsl = −19→20

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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0723P)2 + 0.2344P] where P = (Fo2 + 2Fc2)/3
7426 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = −0.29 e Å3

Special details

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 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*/Ueq
O10.60369 (7)0.60548 (5)0.04595 (5)0.01932 (13)
O20.21201 (7)0.70928 (6)0.49193 (6)0.02850 (16)
N10.36876 (7)0.35014 (5)0.31082 (5)0.01366 (12)
N20.55084 (7)0.30903 (6)0.41524 (5)0.01468 (12)
C10.34113 (8)0.26119 (6)0.37376 (6)0.01385 (13)
C20.22644 (8)0.20556 (7)0.38301 (6)0.01625 (14)
H2A0.15020.22470.34150.019*
C30.23254 (9)0.12006 (7)0.45759 (7)0.01787 (15)
H3A0.15810.08200.46760.021*
C40.34872 (9)0.08978 (7)0.51829 (7)0.01903 (16)
H4A0.34970.03080.56590.023*
C50.46206 (9)0.14602 (7)0.50872 (7)0.01765 (15)
H5A0.53880.12550.54860.021*
C60.45615 (8)0.23468 (6)0.43671 (6)0.01408 (13)
C70.49493 (8)0.37658 (6)0.34028 (6)0.01328 (13)
C80.55758 (8)0.47449 (6)0.29966 (6)0.01346 (13)
C90.55681 (8)0.49315 (6)0.18938 (6)0.01442 (13)
H9A0.52140.44110.13980.017*
C100.60956 (8)0.59058 (6)0.15413 (6)0.01466 (14)
C110.66423 (8)0.66833 (7)0.22849 (6)0.01679 (15)
H11A0.69880.73330.20490.020*
C120.66666 (9)0.64783 (7)0.33810 (7)0.01769 (15)
H12A0.70410.69900.38760.021*
C130.61356 (8)0.55155 (7)0.37433 (6)0.01600 (14)
H13A0.61530.53850.44770.019*
C140.27189 (8)0.40916 (7)0.23858 (6)0.01493 (14)
H14A0.21990.35600.19480.018*
H14B0.31440.45560.19070.018*
C150.18581 (8)0.47993 (7)0.29866 (6)0.01546 (14)
C160.05416 (9)0.46392 (8)0.28541 (7)0.02214 (17)
H16A0.01820.40780.24090.027*
C17−0.02425 (10)0.53232 (10)0.33909 (9)0.0298 (2)
H17A−0.11260.52260.32890.036*
C180.02893 (10)0.61473 (9)0.40753 (8)0.0276 (2)
H18A−0.02350.66010.44320.033*
C190.16150 (9)0.62907 (8)0.42254 (7)0.02011 (16)
C200.23951 (8)0.56315 (7)0.36681 (6)0.01647 (14)
H20A0.32760.57460.37500.020*
H1O10.6430 (17)0.6716 (15)0.0307 (14)0.053 (5)*
H1O20.3026 (18)0.6952 (15)0.5216 (14)0.055 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0266 (3)0.0181 (3)0.0133 (2)−0.0054 (2)0.0028 (2)0.00132 (19)
O20.0206 (3)0.0285 (3)0.0336 (4)0.0103 (3)−0.0083 (3)−0.0167 (3)
N10.0134 (3)0.0145 (3)0.0127 (3)0.0004 (2)0.0002 (2)0.0011 (2)
N20.0139 (3)0.0155 (3)0.0144 (3)0.0006 (2)0.0007 (2)0.0009 (2)
C10.0148 (3)0.0135 (3)0.0131 (3)−0.0001 (2)0.0012 (3)−0.0002 (2)
C20.0151 (3)0.0170 (3)0.0162 (3)−0.0022 (3)0.0003 (3)−0.0013 (2)
C30.0204 (4)0.0161 (3)0.0173 (3)−0.0041 (3)0.0029 (3)−0.0011 (2)
C40.0242 (4)0.0149 (3)0.0181 (3)−0.0023 (3)0.0027 (3)0.0015 (3)
C50.0197 (4)0.0158 (3)0.0169 (3)0.0008 (3)0.0001 (3)0.0024 (2)
C60.0147 (3)0.0136 (3)0.0137 (3)0.0002 (2)0.0008 (3)−0.0003 (2)
C70.0131 (3)0.0143 (3)0.0124 (3)0.0001 (2)0.0013 (2)−0.0007 (2)
C80.0122 (3)0.0142 (3)0.0140 (3)0.0001 (2)0.0018 (2)−0.0003 (2)
C90.0159 (3)0.0142 (3)0.0131 (3)−0.0019 (2)0.0018 (3)−0.0008 (2)
C100.0154 (3)0.0151 (3)0.0138 (3)−0.0006 (3)0.0026 (3)−0.0001 (2)
C110.0183 (4)0.0148 (3)0.0173 (3)−0.0026 (3)0.0023 (3)−0.0013 (2)
C120.0186 (4)0.0180 (3)0.0165 (3)−0.0035 (3)0.0021 (3)−0.0036 (2)
C130.0161 (4)0.0180 (3)0.0138 (3)−0.0011 (3)0.0016 (3)−0.0019 (2)
C140.0145 (3)0.0177 (3)0.0120 (3)0.0020 (3)−0.0010 (3)0.0002 (2)
C150.0148 (3)0.0176 (3)0.0136 (3)0.0022 (3)0.0000 (3)0.0002 (2)
C160.0145 (4)0.0283 (4)0.0229 (4)0.0005 (3)−0.0007 (3)−0.0069 (3)
C170.0133 (4)0.0409 (6)0.0349 (5)0.0020 (4)0.0017 (4)−0.0144 (4)
C180.0162 (4)0.0369 (5)0.0292 (5)0.0071 (4)0.0002 (3)−0.0126 (4)
C190.0174 (4)0.0217 (4)0.0200 (4)0.0057 (3)−0.0028 (3)−0.0053 (3)
C200.0137 (3)0.0178 (3)0.0172 (3)0.0026 (3)−0.0006 (3)−0.0017 (3)

Geometric parameters (Å, °)

O1—C101.3607 (10)C9—C101.3977 (11)
O1—H1O10.931 (19)C9—H9A0.9300
O2—C191.3671 (11)C10—C111.3980 (11)
O2—H1O20.994 (19)C11—C121.3922 (11)
N1—C71.3709 (10)C11—H11A0.9300
N1—C11.3861 (10)C12—C131.3922 (11)
N1—C141.4641 (11)C12—H12A0.9300
N2—C71.3275 (10)C13—H13A0.9300
N2—C61.3923 (10)C14—C151.5114 (11)
C1—C21.3981 (11)C14—H14A0.9700
C1—C61.3986 (12)C14—H14B0.9700
C2—C31.3906 (11)C15—C161.3874 (13)
C2—H2A0.9300C15—C201.3951 (11)
C3—C41.4070 (13)C16—C171.3970 (13)
C3—H3A0.9300C16—H16A0.9300
C4—C51.3901 (12)C17—C181.3882 (14)
C4—H4A0.9300C17—H17A0.9300
C5—C61.3987 (11)C18—C191.3944 (14)
C5—H5A0.9300C18—H18A0.9300
C7—C81.4763 (10)C19—C201.3911 (11)
C8—C91.3985 (10)C20—H20A0.9300
C8—C131.3995 (11)
C10—O1—H1O1110.5 (11)C9—C10—C11120.33 (7)
C19—O2—H1O2113.3 (10)C12—C11—C10119.59 (7)
C7—N1—C1106.91 (6)C12—C11—H11A120.2
C7—N1—C14129.07 (7)C10—C11—H11A120.2
C1—N1—C14123.56 (7)C11—C12—C13120.69 (8)
C7—N2—C6105.62 (7)C11—C12—H12A119.7
N1—C1—C2131.58 (8)C13—C12—H12A119.7
N1—C1—C6105.82 (7)C12—C13—C8119.56 (7)
C2—C1—C6122.56 (7)C12—C13—H13A120.2
C3—C2—C1116.37 (8)C8—C13—H13A120.2
C3—C2—H2A121.8N1—C14—C15112.50 (6)
C1—C2—H2A121.8N1—C14—H14A109.1
C2—C3—C4121.56 (8)C15—C14—H14A109.1
C2—C3—H3A119.2N1—C14—H14B109.1
C4—C3—H3A119.2C15—C14—H14B109.1
C5—C4—C3121.52 (8)H14A—C14—H14B107.8
C5—C4—H4A119.2C16—C15—C20119.87 (7)
C3—C4—H4A119.2C16—C15—C14120.66 (7)
C4—C5—C6117.39 (8)C20—C15—C14119.46 (7)
C4—C5—H5A121.3C15—C16—C17119.85 (9)
C6—C5—H5A121.3C15—C16—H16A120.1
N2—C6—C1109.41 (7)C17—C16—H16A120.1
N2—C6—C5130.08 (8)C18—C17—C16120.42 (9)
C1—C6—C5120.50 (7)C18—C17—H17A119.8
N2—C7—N1112.19 (7)C16—C17—H17A119.8
N2—C7—C8124.10 (7)C17—C18—C19119.60 (8)
N1—C7—C8123.52 (7)C17—C18—H18A120.2
C9—C8—C13120.26 (7)C19—C18—H18A120.2
C9—C8—C7121.37 (7)O2—C19—C20121.29 (8)
C13—C8—C7118.31 (7)O2—C19—C18118.63 (8)
C10—C9—C8119.55 (7)C20—C19—C18120.08 (8)
C10—C9—H9A120.2C19—C20—C15120.13 (8)
C8—C9—H9A120.2C19—C20—H20A119.9
O1—C10—C9117.03 (7)C15—C20—H20A119.9
O1—C10—C11122.64 (7)
C7—N1—C1—C2175.17 (8)N1—C7—C8—C13121.97 (8)
C14—N1—C1—C22.30 (12)C13—C8—C9—C10−1.55 (12)
C7—N1—C1—C6−2.40 (8)C7—C8—C9—C10175.65 (7)
C14—N1—C1—C6−175.27 (6)C8—C9—C10—O1−178.61 (7)
N1—C1—C2—C3−178.27 (8)C8—C9—C10—C110.81 (12)
C6—C1—C2—C3−1.05 (11)O1—C10—C11—C12179.82 (8)
C1—C2—C3—C4−1.54 (12)C9—C10—C11—C120.44 (13)
C2—C3—C4—C51.89 (13)C10—C11—C12—C13−0.95 (13)
C3—C4—C5—C60.40 (12)C11—C12—C13—C80.22 (13)
C7—N2—C6—C1−1.16 (8)C9—C8—C13—C121.04 (12)
C7—N2—C6—C5180.00 (8)C7—C8—C13—C12−176.24 (8)
N1—C1—C6—N22.23 (8)C7—N1—C14—C15−98.85 (9)
C2—C1—C6—N2−175.61 (7)C1—N1—C14—C1572.35 (9)
N1—C1—C6—C5−178.80 (7)N1—C14—C15—C16−121.88 (9)
C2—C1—C6—C53.37 (11)N1—C14—C15—C2059.08 (10)
C4—C5—C6—N2175.81 (8)C20—C15—C16—C170.98 (14)
C4—C5—C6—C1−2.93 (11)C14—C15—C16—C17−178.05 (9)
C6—N2—C7—N1−0.41 (8)C15—C16—C17—C18−1.43 (17)
C6—N2—C7—C8174.77 (7)C16—C17—C18—C190.02 (18)
C1—N1—C7—N21.81 (8)C17—C18—C19—O2−178.72 (10)
C14—N1—C7—N2174.16 (7)C17—C18—C19—C201.83 (16)
C1—N1—C7—C8−173.40 (7)O2—C19—C20—C15178.29 (8)
C14—N1—C7—C8−1.05 (11)C18—C19—C20—C15−2.28 (14)
N2—C7—C8—C9130.08 (8)C16—C15—C20—C190.86 (13)
N1—C7—C8—C9−55.28 (11)C14—C15—C20—C19179.91 (8)
N2—C7—C8—C13−52.67 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O1···O2i0.931 (19)1.712 (19)2.6406 (9)175.4 (17)
O2—H1O2···N2ii0.994 (19)1.646 (19)2.6297 (10)169.7 (16)
C3—H3A···O1iii0.932.573.2987 (10)136
C9—H9A···O1iv0.932.593.4287 (10)150
C12—H12A···Cg1ii0.932.673.4521 (9)142

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2563).

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