Ethyl 2-(4-nitrophenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1<i>H</i>-benzimidazole-5-carboxylate

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

doi:10.1107/s1600536811052408

Cited by 4 publications

(6 citation statements)

References 6 publications

(4 reference statements)

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“…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).…”

Section: Related Literaturementioning

confidence: 99%

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

et al. 2013

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Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.003 Å; disorder in main residue; R factor = 0.064; wR factor = 0.134; data-to-parameter ratio = 19.0.In the title compound, C 24 H 25 N 3 O 5 , 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-HÁ Á ÁN hydrogen bonds generate R 2 2 (16) loops. C-HÁ Á ÁO interactions link the dimers into a three-dimensional network. Related literature

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“…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).…”

Section: Related Literaturementioning

confidence: 99%

“…(2013). E69, o304 As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al, 2012), we now report the structure of the title compound.…”

Section: Sup-1mentioning

confidence: 99%

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

et al. 2013

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“…For applications of benzimidazole compounds, see: Rao et al (2002); Thakurdesai et al (2007); McKellar & Scott (1990). For a related structure, see: Yoon et al (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).…”

Section: Related Literaturementioning

confidence: 99%

“…Benzimidazoles are a class of bioactive heterocyclic compounds which exhibit a wide range of activities such as anti-HIV (Rao et al, 2002), anti-inflammatory (Thakurdesai et al, 2007) and anthelmintics (McKellar & Scott, 1990). As part of our ongoing structural studies on benzimidazole derivatives (Yoon et al, 2012), we now report the structure of the title compound.…”

Section: Data Collectionmentioning

confidence: 99%

Ethyl 2-[4-(dimethylamino)phenyl]-1-phenyl-1H-benzimidazole-5-carboxylate

et al. 2013

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Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.050; wR factor = 0.125; data-to-parameter ratio = 21.8.In the title compound, C 24 H 23 N 3 O 2 , the benzimidazole ring system makes dihedral angles of 7.28 (5) and 67.17 (5) , respectively, with the planes of the benzene and phenyl rings, which in turn make a dihedral angle of 69.77 (6) . In the crystal, molecules are connected by C-HÁ Á ÁN and C-HÁ Á ÁO interactions, forming a layer parallel to the bc plane. Ainteraction, with a centroid-centroid distance of 3.656 (1) Å , is observed in the layer. Related literature ExperimentalCrystal data

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“…For biological applications of benzimidazole derivatives, see: Tanious et al (2004); Coburn et al (1987); Rao et al (2002). For a related structure, see: Yoon et al (2012). Symmetry codes: (i) Àx þ 1; y À 1 2 ; Àz þ 1 2 ; (ii) x; y þ 1; z; (iii) x À 1; y; z; (iv) Àx þ 2; y þ 1 2 ; Àz þ 1 2 .…”

Section: Related Literaturementioning

confidence: 99%

Ethyl 2-[5-(4-fluorophenyl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazole-5-carboxylate

Yoon¹,

Ali²,

Choon³

et al. 2013

Acta Cryst E

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In the title compound, C28H27FN4O3·H2O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each other. The pyrrolidine ring shows an envelope conformation with one of the methylene C atoms as the flap. In the crystal, the components are connected into a tape along the b-axis direction through O—H⋯O and O—H⋯N hydrogen bonds and a π–π interaction between the pyridine and benzene rings [centroid–centroid distance of 3.685 (8) Å]. The tapes are further linked into layers parallel to the ab plane by C—H⋯O and C—H⋯F interactions.

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

Cited by 4 publications

References 6 publications

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

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

Ethyl 2-[4-(dimethylamino)phenyl]-1-phenyl-1H-benzimidazole-5-carboxylate

Ethyl 2-[5-(4-fluorophenyl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazole-5-carboxylate

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