3-{5-Eth­oxy­carbonyl-1-[3-(2-oxopyrrol­idin-1-yl)prop­yl]-1H-benzimidazol-2-yl}benzoic acid

Yeong Keng Yoon; Mohamed Ashraf Ali; Soo Choon Tan; Mohd Mustaqim Rosli; Ibrahim Abdul Razak

doi:10.1107/S1600536813001116

. 2013 Jan 31;69(Pt 2):o304. doi: 10.1107/S1600536813001116

3-{5-Ethoxycarbonyl-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazol-2-yl}benzoic acid

Yeong Keng Yoon ^a, Mohamed Ashraf Ali ^a, Soo Choon Tan ^a, Mohd Mustaqim Rosli ^b, Ibrahim Abdul Razak ^b,^*

PMCID: PMC3569823 PMID: 23424569

Abstract

In the title compound, C₂₄H₂₅N₃O₅, the ethoxy group is disordered over two orientations in a 0.853 (14):0.147 (14) ratio. The benzimadazole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 35.47 (7)° with the attached benzene ring. The pyrrolidine ring adopts an envelope conformation with a methylene C atom as the flap. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R ₂ ²(16) loops. C—H⋯O interactions link the dimers into a three-dimensional network.

Related literature

For a related structure and background to benzimidazoles, see: Yoon et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₄H₂₅N₃O₅
M _r = 435.47
Monoclinic,
a = 9.3097 (3) Å
b = 24.8252 (7) Å
c = 9.6761 (3) Å
β = 112.322 (1)°
V = 2068.71 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.39 × 0.23 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.963, T _max = 0.992
23636 measured reflections
6010 independent reflections
3706 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.134
S = 1.03
6010 reflections
317 parameters
69 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 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

Click here for additional data file.^{(25.3KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001116/hb7017sup1.cif

e-69-0o304-sup1.cif^{(25.3KB, cif)}

Click here for additional data file.^{(294.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001116/hb7017Isup2.hkl

e-69-0o304-Isup2.hkl^{(294.2KB, hkl)}

Click here for additional data file.^{(8.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813001116/hb7017Isup3.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
O2—H1O2⋯N2ⁱ	1.04 (4)	1.66 (4)	2.675 (2)	166 (3)
C5—H5A⋯O3ⁱ	0.95	2.57	3.367 (2)	141
C9—H9A⋯O2ⁱ	0.95	2.46	3.177 (2)	132
C15—H15A⋯O3ⁱⁱ	0.99	2.34	3.314 (3)	167
C17—H17B⋯O5ⁱⁱⁱ	0.99	2.51	3.429 (3)	154
C20—H20B⋯O4^iv	0.99	2.55	3.340 (3)	137

Open in a new tab

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

Acknowledgments

The authors thank the Pharmacogenetics and Novel Therapeutics Research Cluster, Institute for Research in Molecular Medicine, Universiti Sains Malaysia (USM), Penang, for supporting this work. This work was funded through Research Grant (RUC) No. 1001/PSK/8620012 and HiCoE Research Grant No. 311.CIPPM.4401005. IAR also thanks USM for the Research University Grant No. 1001/PFIZIK/811151.

supplementary crystallographic information

Comment

As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2012), we now report the structure of the title compound.

The ethoxy group is disordered over two position with the final refined occupancies of 0.853 (14):0.147 (14). The benzimidazole (N1—N2/C—C7) ring in the title compound, Fig. 1, is almost planar with maximum deviation of 0.02 Å for atom N2 and makes a dihedral angle of 35.63° with the attached benzene ring (C8—C13). The pyrrolidine ring (N3/C18—C21) adopts an envelope conformation with C19 as the flap and puckering parameters Q = 0.262 (3) Å and φ = 64.0 (5)°.

In the crystal (Fig. 2), O—H···N and C—H···O interactions (Table 1) link the molecules into a three-dimensional network.

Experimental

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-carboxy benzaldehyde (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 as brown plates.