Ethyl 2-[4-(dimethylamino)phenyl]-1-phenyl-1<i>H</i>-benzimidazole-5-carboxylate

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

doi:10.1107/s1600536813012440

Acta Cryst E

2013

DOI: 10.1107/s1600536813012440

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

Yeong Keng Yoon

Mohamed Ashraf Ali

Tan Soo Choon

et al.

Abstract: 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. Ainteracti… Show more

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Cited by 2 publications

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Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H...π interaction energies

Geiger

Deck

2014

Acta Crystallogr C

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The synthesis and structural characterization of 2-(furan-2-yl)-1-(furan-2-ylmethyl)-1H-benzimidazole [C16H12N2O2, (I)], 2-(furan-2-yl)-1-(furan-2-ylmethyl)-1H-benzimidazol-3-ium chloride monohydrate [C16H13N2O2(+)·Cl(-)·H2O, (II)] and the hydrobromide salt 5,6-dimethyl-2-(furan-2-yl)-1-(furan-2-ylmethyl)-1H-benzimidazol-3-ium bromide [C18H17N2O2(+)·Br(-), (III)] are described. Benzimidazole (I) displays two sets of aromatic interactions, each of which involves pairs of molecules in a head-to-tail arrangement. The first, denoted set (Ia), exhibits both intermolecular C-H···π interactions between the 2-(furan-2-yl) (abbreviated as Fn) and 1-(furan-2-ylmethyl) (abbreviated as MeFn) substituents, and π-π interactions involving the Fn substituents between inversion-center-related molecules. The second, denoted set (Ib), involves π-π interactions involving both the benzene ring (Bz) and the imidazole ring (Im) of benzimidazole. Hydrated salt (II) exhibits N-H···OH2···Cl hydrogen bonding that results in chains of molecules parallel to the a axis. There is also a head-to-head aromatic stacking of the protonated benzimidazole cations in which the Bz and Im rings of one molecule interact with the Im and Fn rings of adjacent molecules in the chain. Salt (III) displays N-H···Br hydrogen bonding and π-π interactions involving inversion-center-related benzimidazole rings in a head-to-tail arrangement. In all of the π-π interactions observed, the interacting moieties are shifted with respect to each other along the major molecular axis. Basis set superposition energy-corrected (counterpoise method) interaction energies were calculated for each interaction [DFT, M06-2X/6-31+G(d)] employing atomic coordinates obtained in the crystallographic analyses for heavy atoms and optimized H-atom coordinates. The calculated interaction energies are -43.0, -39.8, -48.5, and -55.0 kJ mol(-1) for (Ia), (Ib), (II), and (III), respectively. For (Ia), the analysis was used to partition the interaction energies into the C-H···π and π-π components, which are 9.4 and 24.1 kJ mol(-1), respectively. Energy-minimized structures were used to determine the optimal interplanar spacing, the slip distance along the major molecular axis, and the slip distance along the minor molecular axis for 2-(furan-2-yl)-1H-benzimidazole.

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Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H...π interaction energies

Geiger

Deck

2014

Acta Crystallogr C

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Synthesis and characterization of a novel long-alkyl-chain ester-substituted benzimidazole gelator and its octan-1-ol solvate

et al. 2017

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The synthesis of a novel benzimidazole derivative with a long-chain-ester substituent, namely methyl 8-[4-(1H-benzimidazol-2-yl)phenoxy]octanoate, (3), is reported. Ester (3) shows evidence of aggregation in solution and weak gelation ability with toluene. The octan-1-ol solvate, methyl 8-[4-(1H-benzimidazol-2-yl)phenoxy]octanoate octan-1-ol monosolvate, CHNO·CHO, (4), exhibits a four-molecule hydrogen-bonded motif in the solid state, with N-H...O hydrogen bonds between benzimidazole molecules and O-H...N hydrogen bonds between the octan-1-ol solvent molecules and the benzimidazole unit. The alkyl chains of the ester and the octan-1-ol molecules are in unfolded conformations. The phenylene ring is canted by 10.27 (6)° from the plane of the benzimidazole ring system. H...C contacts make up 20.7% of the Hirshfeld surface coverage. Weak C-H...π interactions involving the benzimidazole alkyl chain and three aromatic rings are observed.

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

Cited by 2 publications

References 6 publications

Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H...π interaction energies

Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H...π interaction energies

Synthesis and characterization of a novel long-alkyl-chain ester-substituted benzimidazole gelator and its octan-1-ol solvate

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