Ethyl 2-(4-hy­droxy-3-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate

Yeong Keng Yoon; Mohamed Ashraf Ali; Tan Soo Choon; Safra Izuani Jama Asik; Ibrahim Abdul Razak

doi:10.1107/S1600536811052391

. 2011 Dec 10;68(Pt 1):o87–o88. doi: 10.1107/S1600536811052391

Ethyl 2-(4-hydroxy-3-methoxyphenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazole-5-carboxylate monohydrate

Yeong Keng Yoon ^a, Mohamed Ashraf Ali ^a, Tan Soo Choon ^a, Safra Izuani Jama Asik ^b, Ibrahim Abdul Razak ^b,^*,^‡

PMCID: PMC3254439 PMID: 22259586

Abstract

In the title compound, C₂₄H₂₇N₃O₅·H₂O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intramolecular C—H⋯π interaction is observed. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π–π stacking [centroid–centroid distance = 3.6632 (9) Å] and C—H⋯O interactions.

Related literature

For the biological activity of benzimidazole derivatives, see: Rao et al. (2002 ▶); Thakurdesai et al. (2007 ▶); Dubey & Sanyal (2010 ▶). For related structures, see: Yoon et al. (2011 ▶). For the ring conformation, see: Cremer & Pople (1975) ▶.

Experimental

Crystal data

C₂₄H₂₇N₃O₅·H₂O
M _r = 455.50
Triclinic,
a = 9.7460 (8) Å
b = 10.0436 (8) Å
c = 12.6072 (10) Å
α = 85.737 (1)°
β = 89.684 (2)°
γ = 70.238 (1)°
V = 1157.91 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.43 × 0.32 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.960, T _max = 0.985
18195 measured reflections
6686 independent reflections
4485 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.185
S = 1.07
6686 reflections
312 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 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/S1600536811052391/is5022sup1.cif

e-68-00o87-sup1.cif^{(24.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052391/is5022Isup2.hkl

e-68-00o87-Isup2.hkl^{(327.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811052391/is5022Isup3.cml

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

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

Cg4 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O2ⁱ	0.85 (3)	2.06 (3)	2.879 (2)	164 (2)
O1W—H1W1⋯N1ⁱⁱ	0.95 (3)	1.90 (3)	2.8416 (19)	176 (2)
O4—H1O4⋯O1W	0.88 (3)	1.80 (3)	2.675 (2)	169 (3)
C16—H16A⋯O5ⁱⁱⁱ	0.96	2.44	3.380 (3)	166
C20—H20B⋯Cg4	0.97	2.86	3.750 (3)	153

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia 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 of Sains Malaysia.

supplementary crystallographic information

Comment

Benzimidazole derivatives are of wide interest because of their diverse biological activities and various clinical applications. This ring system is present in numerous anti-HIV (Rao et al., 2002), anti-inflammatory (Thakurdesai et al., 2007) and anthelmintics (Dubey and Sanyal, 2010) drugs. 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 title compound, Fig. 1, the benzimidazole (N1/N2/C1–C7) ring system is essentially planar with a maximum deviation of 0.020 (1) Å for atom N2. Dihedral angles of benzimidazole, (N1/N2/C1–C7) ring with the mean plane of pyrrolidin-2-one ring (N3/C20–C23) and the 2-methoxyphenol (C8–C13) ring are 54.10 (11) and 67.79 (6)°, respectively. The pyrrolidin-2-one ring adopts an envelope conformation with puckering parameters of Q = 0.148 (3) Å and φ = 78.5 (10)° (Cremer & Pople, 1975) with atom C21 at the flap, deviating by 0.095 (3) Å. In the crystal packing (Fig. 2), intermolecular O1W—H2W1···O2, O4—H1O4···O1W and O1W—H1W1···N1 hydrogen bonds link the molecules into a double-tape structure running along the a axis. There is a π–π stacking interaction between the benzene (C1–C6; centroid Cg3) rings with a Cg3···Cg3^iv distance of 3.6632 (9) Å [symmetry code: (iv) -x, -y, -z + 1]. The crystal packing is further stabilized by a C16—H16A···O5 hydrogen bond and a weak C20—H20B···Cg4 interaction (Table 1), where Cg4 is the centroid of the benzene (C8–C13) ring.

Experimental

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-hydroxy-3-metoxybenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 hrs. 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.