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

Naser Eltaher Eltayeb; Siang Guan Teoh; Hoong-Kun Fun; Samuel Robinson Jebas; Rohana Adnan

doi:10.1107/S1600536809018698

. 2009 May 23;65(Pt 6):o1374–o1375. doi: 10.1107/S1600536809018698

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

Naser Eltaher Eltayeb ^a,^‡, Siang Guan Teoh ^a, Hoong-Kun Fun ^b,^*,^§, Samuel Robinson Jebas ^b,^¶, Rohana Adnan ^a

PMCID: PMC2969736 PMID: 21583223

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

Experimental

Crystal data

C₂₀H₁₆N₂O₂
M _r = 316.35
Monoclinic,
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 ▶) 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
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.29 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 ▶).

Supplementary Material

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

e-65-o1374-sup1.cif^{(20.5KB, cif)}

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

e-65-o1374-Isup2.hkl^{(356KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2ⁱ	0.931 (19)	1.712 (19)	2.6406 (9)	175.4 (17)
O2—H1O2⋯N2ⁱⁱ	0.994 (19)	1.646 (19)	2.6297 (10)	169.7 (16)
C3—H3A⋯O1ⁱⁱⁱ	0.93	2.57	3.2987 (10)	136
C9—H9A⋯O1^iv	0.93	2.59	3.4287 (10)	150
C12—H12A⋯Cg1ⁱⁱ	0.93	2.67	3.4521 (9)	142

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the ring C1–C6.

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.