(2E)-3-[4-(1H-Benzimidazol-2-ylmeth­oxy)phen­yl]-1-(4-meth­oxy­phen­yl)prop-2-en-1-one

Mehmet Akkurt; Zeliha Baktır; S Samshuddin; B Narayana; H S Yathirajan

doi:10.1107/S1600536811012645

. 2011 Apr 13;67(Pt 5):o1088–o1089. doi: 10.1107/S1600536811012645

(2E)-3-[4-(1H-Benzimidazol-2-ylmethoxy)phenyl]-1-(4-methoxyphenyl)prop-2-en-1-one

Mehmet Akkurt ^a,^*, Zeliha Baktır ^a, S Samshuddin ^b, B Narayana ^b, H S Yathirajan ^c

PMCID: PMC3089334 PMID: 21754409

Abstract

In the title compound, C₂₄H₂₀N₂O₃, the mean plane of the benzimidazole unit makes dihedral angles of 79.88 (11) and 85.44 (12)° with the benzene and 4-methoxybenzene rings, respectively. The benzene and 4-methoxybenzene rings maske a dihedral angle of 16.10 (14)°. A pair of intermolecular N—H⋯O hydrogen bonds connects adjacent molecules into an inversion dimer, generating an R ₂ ²(26) ring motif. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For the biological activity of benzimidazoles, see: Dhar (1981 ▶); Pujar et al. (1988 ▶); Bouwman et al. 1990 ▶); Dimmock et al. (1999 ▶); Satyanarayana et al. (2004 ▶); Madkour et al. (2006 ▶); Sarojini et al. (2006 ▶). For related structures, see: Jian et al. (2003 ▶); Jasinski et al. (2010 ▶); Odabaşoğlu et al. (2007 ▶). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₄H₂₀N₂O₃
M _r = 384.42
Triclinic,
a = 7.2244 (5) Å
b = 9.3201 (8) Å
c = 14.9422 (9) Å
α = 98.449 (2)°
β = 99.183 (4)°
γ = 99.478 (4)°
V = 964.01 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T _min = 0.983, T _max = 0.983
20466 measured reflections
3952 independent reflections
2206 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.162
S = 1.07
3952 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012645/xu5184sup1.cif

e-67-o1088-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012645/xu5184Isup2.hkl

e-67-o1088-Isup2.hkl^{(193.7KB, hkl)}

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

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

Cg1 and Cg4 are the centroids of the N1/N2/C1/C6/C7 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯O2ⁱ	0.86	2.12	2.927 (3)	157
C11—H11⋯Cg1ⁱⁱ	0.93	2.58	3.490 (3)	165
C24—H24A⋯Cg4ⁱⁱⁱ	0.96	2.61	3.467 (3)	149

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

Acknowledgments

ZB and MA thank the Unit of the Scientific Research Projects of Erciyes University, Turkey, for the research grant FBD-10–2949, and for support of the data collection at Atatürk University, Turkey. SS thanks Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave.

supplementary crystallographic information

Comment

The benzimidazole ring system and its related compounds play an important role in pharmaceutical and agricultural fields due to their broad spectrum of biological activities (Pujar et al., 1988, Bouwman et al., 1990). The synthesis of novel benzimidazole derivatives remains a main focus of medicinal research. Benzimidazoles are also useful as insecticides, acaricides, nematocides, herbicides and other plant-protective agents in the field of pest control (Madkour et al., 2006). In recent years, attention has increasingly been given to the synthesis of benzimidazole derivatives as a source of new antimicrobial agents. In addition, benzimidazole derivatives have played a crucial role in the theoretical development of heterocyclic chemistry and are also used extensively in organic synthesis. Chalcones constitute an important family of substances belonging to flavonoids, a large group of natural and synthetic products with interesting physicochemical properties, biological activity and structural characteristics. Chalcones are highly reactive substances of varied nature. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006).

The crystal structures of some benzimidazole derivatives viz., 2-chloromethyl-1H-benzimidazole nitrate (Jian et al., 2003) and 5-methoxy-1H-benzo[d]imidazole-2(3H)-thione (Odabaşoğlu et al., 2007) have been reported. In continuation of our work on the synthesis of benzimidazole derivatives (Jasinski et al., 2010) and in view of the importance of benzimidazoles, the title compound (I) is synthesized and its crystal structure is reported here.

In the title compound (I), (Fig. 1). the dihedral angles between the least squares planes of the benzimidazole (N1/N2/C1–C7) and the benzene (C9–C14) and 4-methoxybenzene (C18–C23) rings are79.88 (11)° and 85.44 (12)°, respectively. The benzene and 4-methoxybenzene rings form a dihedral angle of 16.10 (14)° with each other.

Molecule conformation of (I) is stabilized by one weak intramolecular C15—H15···O2 interaction (Table 1). Two molecules are connected by N—H···O hydrogen bonds into an inversion dimer, forming an R²₂(26) ring motif (Bernstein et al., 1995; Table 1, Fig. 2). Furthermore, crystal packing is stabilized by C—H···π interactions (Table 1), involving N1/N2/C1/C6/C7 (centroid Cg1) and C18–C23 (centroid Cg4) rings.

Experimental

A mixture of a 4-(1H-benzimidazol-2-ylmethoxy)benzaldehyde (2.52 g, 0.01 mole) and p-methoxy acetophenone (1.5 g, 0.01 mole) in 50 ml ethanolic sodium hydroxide was stirred at 278–283 K for 3 h, then maintained at room temperature for 24 h and poured into ice cold water. The precipitate that appeared after neutralization with dilute HCl was filtered off and recystallized from 1,4-dioxane. The single crystals were grown from DMF by slow evaporation method and yield of the compound was 75% (m.p.: 521 K).