1-[4-(Prop-2-en-1-yl­oxy)benz­yl]-2-[4-(prop-2-en-1-yl­oxy)phen­yl]-1H-benzimidazole

Md Lutfor Rahman; Huey Chong Kwong; Mashitah Mohd Yusoff; Gurumurthy Hegde; Mohamed Ibrahim Mohamed Tahir

doi:10.1107/S160053681204559X

. 2012 Nov 10;68(Pt 12):o3311–o3312. doi: 10.1107/S160053681204559X

1-[4-(Prop-2-en-1-yloxy)benzyl]-2-[4-(prop-2-en-1-yloxy)phenyl]-1H-benzimidazole

Md Lutfor Rahman ^a,^*, Huey Chong Kwong ^b, Mashitah Mohd Yusoff ^a, Gurumurthy Hegde ^a, Mohamed Ibrahim Mohamed Tahir ^b

PMCID: PMC3588921 PMID: 23476157

Abstract

In the title compound, C₂₆H₂₄N₂O₂, the benzimidazole ring system is almost planar [maximum displacement = 0.025 (1) Å] and makes dihedral angles of 80.48 (5) and 41.57 (5)° with the benzene rings, which are inclined to one another by 65.33 (6)°. In the crystal, molecules are linked via C—H⋯π and weak π–π interactions [centroid–centroid distance = 3.8070 (7) Å and interplanar distance = 3.6160 (5) Å].

Related literature

For the activity of benzimidazole derivatives against viruses, see: Tamm & Sehgal (1978 ▶); Porcari et al. (1998 ▶); Migawa et al. (1998 ▶). For their other biological activity, see: Spasov et al. (1999 ▶); Nakano et al. (2000 ▶); Zhao et al. (2000 ▶); White et al. (2000 ▶); Xiangming et al. (2007 ▶). For related structures, see: Kia et al. (2009 ▶); Zhou et al. (2009 ▶). For synthetic details, see: Lutfor et al. (2008 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₆H₂₄N₂O₂
M _r = 396.49
Monoclinic,
a = 12.5455 (1) Å
b = 10.1989 (1) Å
c = 15.9340 (2) Å
β = 99.5027 (11)°
V = 2010.78 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 100 K
0.35 × 0.23 × 0.08 mm

Data collection

Agilent Technologies Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.80, T _max = 0.95
38976 measured reflections
3908 independent reflections
3563 reflections with I > 2.0σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.100
S = 0.99
3891 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: CRYSTALS.

Supplementary Material

Click here for additional data file.^{(23.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204559X/su2508sup1.cif

e-68-o3311-sup1.cif^{(23.3KB, cif)}

Click here for additional data file.^{(245.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204559X/su2508Isup2.hkl

e-68-o3311-Isup2.hkl^{(245.1KB, hkl)}

Click here for additional data file.^{(8KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681204559X/su2508Isup3.cml

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

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

Cg2 is the centroid of the C2–C5/C26/C27 ring; Cg3 is the centroid of the C10–C15 ring and Cg4 is the centroid of the C16–C19/C24/25 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H121⋯Cg4ⁱ	0.97	2.62	3.5064 (13)	153
C23—H231⋯Cg3ⁱⁱ	0.96	2.73	3.6859 (15)	175
C30—H301⋯Cg2ⁱⁱⁱ	0.95	2.72	3.6202 (14)	159

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This research was supported by a UMP research grant (No. RDU100338).

supplementary crystallographic information

Comment

The importance of the benzimidazole nucleus is due to the fact that it is found in many biologically active compounds (Xiangming et al., 2007). Benzimidazole derivatives have been shown to have significant activity against several viruses such as, HIV (Porcari et al., 1998), herpes (Migawa et al., 1998), influenza (Tamm and Sehgal, 1978) and human cytomegalovirus (Porcari et al., 1998). Many benzimidazole containing compounds exhibited significant biological activities, such as novel anti-allergic agents (Nakano et al., 2000), factor Xa inhibitors (Zhao et al., 2000), poly (ADP-ribose) polymerase (PARP) inhibitors (White et al., 2000). Some substituted benzimidazole derivatives have been recently commercialized for applications in veterinarian medicine, and in diverse human therapeutic areas such as, the treatment of ulcers and as antihistamines (Spasov et al., 1999).

In the titled compound (Fig. 1) the bond lengths (Allen et al., 1987) and bond angles are normal. The benzimidazole ring system (N7/C8/N9/C10-C15) is almost planar, with a maximum displacement of 0.025 (1) Å for atom C8. The dihedral angle formed by the mean plane of the benzimidazole ring system and the two adjacent benzene rings (C2-C5/C26/C27 and C16-C19/C24/C25) are 80.48 (5)° and 41.57 (5)°, respectively. The benzene rings themselves are inclined to one another by 65.33 (6)°, rather than ca. 90° as observed elsewhere, for example in the related compounds, 4-[1-(4-Cyanobenzyl)-1H-benzimidazol-2-yl]benzonitrile (Kia et al., 2009) and 1-(4-tert-Butylbenzyl)-2-(4-tert-butylphenyl)-1H-benzimidazole (Zhou et al., 2009). The torsion angles of the allyloxy chains (O1-C28-C29-C30 and O20-C21-C22-C23) are 133.16 (13)° and 120.11 (14)°, respectively.

In the crystal, molecules are linked via C-H···π interactions (Table 1) and weak π-π interactions. The centroid to centroid distance, Cg1···Cg2ⁱ, is 3.8070 (7)Å with an interplanar distance of 3.6160 (5) Å [Cg1 and Cg2 are the centroids of the N7/C8/N9/C10/C11 and C2-C5/C26/C27 rings; symmetry code: (i) -x + 1/2, y + 1/2, -z + 3/2].

Experimental

4-Hydroxybenzaldehyde (10.0 g, 83.25 mmol) was dissolved in dry acetone (150 mL). Then allyl bromide (12.097 g, 100 mmol), potassium carbonate (13.80 g, 100 mmol) and a catalytic amount of potassium iodide (20 mg) were added and the mixture was refluxed for 24 h under argon atmosphere. Afterwards, it was poured into ice-cold water and acidified with dilute hydrochloric acid (pH<5). The precipitate was filtered off and was crystallized from methanol/chloroform to yield the 4-(prop-2-en-1-yloxy)benzaldehyde. A solution of 4-(prop-2-en-1-yloxy)benzaldehyde (5.00 g, 30.82 mmol) in ethanol was added to a solution of o-phenylenediamine (1.66 g, 15.41 mmol) in ethanol. The mixture was refluxed with a few drops of acetic acid as catalyst for 12 h to yield the title compound as a slightly grey solid. The product was filtered off and recrystallized from absolute ethanol to give pale-brown block-like crystals of the title compound, suitable for X-ray diffraction analysis (Lutfor et al., 2008).