Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate

Yeong Keng Yoon; Mohamed Ashraf Ali; Tan Soo Choon; Madhukar Hemamalini; Hoong-Kun Fun

doi:10.1107/S160053681104342X

. 2011 Oct 29;67(Pt 11):o3060. doi: 10.1107/S160053681104342X

Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)propyl]-1H-benzimidazole-5-carboxylate monohydrate

Yeong Keng Yoon ^a, Mohamed Ashraf Ali ^a, Tan Soo Choon ^a, Madhukar Hemamalini ^b, Hoong-Kun Fun ^b,^*,^‡

PMCID: PMC3247451 PMID: 22220069

Abstract

In the title compound, C₂₂H₂₁BrN₄O₂·H₂O, the two pyrazole rings are essentially planar [maximum deviations 0.002 (1) and 0.002 (1) Å], and form a dihedral angle of 73.46 (9)°. The dihedral angle between the benzene rings is 29.33 (7)°. In the crystal, molecules are connected via C—H⋯O and O—H⋯N hydrogen bonds, forming layers in the ab plane.

Related literature

For applications of benzimidazole derivatives, see: Garuti et al. (2000 ▶); Rao et al. (2002 ▶); Thakurdesai et al. (2007 ▶); Yoon et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₂H₂₁BrN₄O₂·H₂O
M _r = 471.35
Monoclinic,
a = 9.1854 (1) Å
b = 16.7389 (2) Å
c = 13.7379 (2) Å
β = 98.283 (1)°
V = 2090.22 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.00 mm⁻¹
T = 100 K
0.47 × 0.42 × 0.41 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.452, T _max = 0.494
28847 measured reflections
7482 independent reflections
5514 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.085
S = 1.03
7482 reflections
280 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.34 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/S160053681104342X/tk5002sup1.cif

e-67-o3060-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104342X/tk5002Isup2.hkl

e-67-o3060-Isup2.hkl^{(358.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104342X/tk5002Isup3.cml

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
O1W—H2W1⋯N4ⁱ	0.92 (3)	1.99 (3)	2.910 (2)	175 (3)
O1W—H1W1⋯N1ⁱⁱ	0.81 (3)	2.16 (3)	2.891 (2)	151 (2)
C17—H17B⋯O1Wⁱⁱⁱ	0.99	2.41	3.236 (2)	141
C19—H19B⋯O1Wⁱⁱⁱ	0.99	2.56	3.327 (2)	135
C20—H20A⋯O2^iv	0.95	2.58	3.301 (2)	133

Open in a new tab

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

Acknowledgments

YKY, MAA and TSC thank the Department of Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Penang. This work was funded through a Research Grant (No. RUC 1001/PSK/8620012). HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for a Research University grant (No. 1001/PFIZIK/811160). MH thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

supplementary crystallographic information

Comment

Benzimidazole derivatives are of wide interest because of their diverse biological activities and various clinical applications. Benzimidazoles are a class of bioactive heterocyclic compounds which exhibit a wide range of activities such as anti-proliferative (Garuti et al., 2000), anti-HIV (Rao et al., 2002), anti-inflammatory and anthelmintic (Thakurdesai et al., 2007) properties. As part of our on-going structural studies of benzimidazole derivatives (Yoon et al., 2011), we now report the structure of the title compound.

In the title compound (Fig. 1), the two pyrazole (N1,N2/C7,C8/C13 and N3,N4/C20–C22) rings are essentially planar, with a maximum deviation of 0.002 (1) Å for atom C8 and 0.002 (1) Å for atom N3. The dihedral angle between the two pyrazole (N1,N2/C7,C8/C13 : N3,N4/C20–C22) rings is 73.46 (9)° and between the two benzene (C8–C13 : C1–C6) rings is 29.33 (7)°.

In the crystal structure, molecules are connected via intermolecular C—H···O and O—H···N (Table 1) hydrogen bonds, forming layers in the ab plane.

Experimental

Ethyl-4-(3-(1H-imidazol-1-yl-propylamino)-3-aminobenzoate (0.84 mmol) and sodium metabisulfite adduct of bromobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was refluxed 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 then evaporated in vacuo to yield the product. The product was recrystallised from its ethyl acetate solution.