Ethyl 2-(4-chloro­phen­yl)-1-phenyl-1H-benzimidazole-5-carboxyl­ate

Yeong Keng Yoon; Elumalai Manogaran; Tan Soo Choon; Suhana Arshad; Ibrahim Abdul Razak

doi:10.1107/S1600536812022192

. 2012 May 23;68(Pt 6):o1863. doi: 10.1107/S1600536812022192

Ethyl 2-(4-chlorophenyl)-1-phenyl-1H-benzimidazole-5-carboxylate

Yeong Keng Yoon ^a, Elumalai Manogaran ^b, Tan Soo Choon ^a, Suhana Arshad ^c, Ibrahim Abdul Razak ^c,^*,^‡

PMCID: PMC3379429 PMID: 22719627

Abstract

In the title compound, C₂₂H₁₇ClN₂O₂, the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, molecules are linked into a zigzag chain along the a axis by intermolecular C—H⋯O hydrogen bonds. C—H⋯π interactions are also present.

Related literature

For applications of benzimidazoles, see: Tanious et al. (2004 ▶); Townsend & Revankar (1970 ▶). For related structures, see: Yoon et al. (2011 ▶, 2012 ▶); Kassim et al. (2012 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). graphic file with name e-68-o1863-scheme1.jpg

Experimental

Crystal data

C₂₂H₁₇ClN₂O₂
M _r = 376.83
Triclinic,
a = 9.3357 (2) Å
b = 9.7982 (2) Å
c = 11.7718 (4) Å
α = 107.502 (2)°
β = 102.106 (2)°
γ = 109.539 (1)°
V = 908.31 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.38 × 0.29 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.917, T _max = 0.946
18472 measured reflections
5326 independent reflections
4233 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.127
S = 1.04
5326 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812022192/is5137sup1.cif

e-68-o1863-sup1.cif^{(27.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022192/is5137Isup2.hkl

e-68-o1863-Isup2.hkl^{(260.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022192/is5137Isup3.cml

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

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

Cg1, Cg2 and Cg3 are the centroids of the N1/C7/N2/C1/C6, C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2ⁱ	0.95	2.39	3.324 (2)	166
C21—H21A⋯Cg1ⁱⁱ	0.99	2.63	3.5183 (16)	149
C12—H12A⋯Cg2ⁱⁱⁱ	0.95	2.96	3.5940 (16)	125
C19—H19A⋯Cg3ⁱⁱⁱ	0.95	2.60	3.4770 (18)	153

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant Nos.1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia. SA also thanks the Malaysian Government and USM for an Academic Staff Training Scheme (ASTS) fellowship.

supplementary crystallographic information

Comment

Substituted benzimidazoles are proven important drug leads. Substituted benzimidazole is the key building block for numerous compounds which plays crucial roles in the function of biologically important molecules (Tanious et al., 2004). In particular, 2-substituted benzimidazoles are recognized as potential anticancer agents (Townsend & Revankar, 1970). As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2011), we now report the structure of the title compound.

In the molecular structure (Fig. 1), The benzimidazole ring system (N1/N2/C1—C7) is essentially planar with a maximum deviation of 0.012 (2) Å at atom C1 and forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl (C8–C13) and chloro-substituted benzene (C14–C19) ring. The dihedral angle between the phenyl ring and the chloro-substituted benzene ring is 64.23 (8)°. Bond lengths and angles are within normal ranges and are comparable to related structures (Yoon et al., 2011; Kassim et al., 2012; Yoon et al., 2012).

The crystal packing is shown in Fig. 2. The molecules are linked into a zigzag chain along the a-axis via intermolecular C15—H15A···O2 (Table 1) hydrogen bonds. The crystal structure is further stabilized by intermolecular C21—H21A···Cg1, C1—H12A···Cg2 and C19—H19A···Cg3 (Table 1) interactions (Cg1, Cg2 and Cg3 are the centroids of N1/N2/C1/C6/C7, C1–C6 and C8–C13 rings, respectively).

Experimental

Ethyl 3-amino-4-(phenyl amino) benzoate (0.84 mmol) and sodium metabisulfite adduct of chlorobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na₂SO₄ and the evaporated in-vacuo to yield the product. The product was recrystallized from ethyl acetate.