2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol

Abstract

In the title mol­ecule, C15H14N2O2, the substituted benzene ring forms a dihedral angle of 4.15 (1)° with the benzimidazole ring system. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the solid state, mol­ecules are linked into chains along the [001] via inter­molecular bifurcated N—H⋯(O,O) hydrogen bonds, which generate R 1 2(5) ring motifs. The crystal packing is also consolidated by C—H⋯π inter­actions, and π–π stacking inter­actions between the imidazole and substituted benzene rings [centroid–centroid distance = 3.5746 (13) Å]. The methyl group attached to the benzimidazole ring system is disordered over two positions with occupancies of 0.587 (6) and 0.413 (6), suggesting 180° rotational disorder for the benzimidazole group.

2-Methyl-5-nitro-1H-benzimidazole monohydrate

“…The 2-methyl-5-nitro-1H-benzimidazole molecule (O1/O2/N1-N3/C1-C8), excluding methyl H atoms, is almost planar, with a maximum deviation of 0.137 (1) Å for atom O2. Bond lengths (Allen et al, 1987) and angles are within normal ranges and comparable to related structures (Eltayeb et al, 2009;Arumugam et al, 2010).…”

“…For standard bondlength data, see: Allen et al (1987). For related structures, see: Eltayeb et al (2009); Arumugam et al (2010).…”

Crystal structure of 2-(1H-imidazo-[4,5-c]-pyridine-2-yl)-6-methoxyphenol, C13H11N3O2

“…The dihedral angle between the 1H-imidazo-[4,5-c]-pyridine plane and the 2-methoxy-phenol plane is 7.9(2)°. All the bond parameters are comparable to the other two benzimidazole compounds [2][3]. Two intra-and intermolecular N×××H-O hydrogen bond interactions can be found, and depending on the intermolecular N×××H-O hydrogen bond interactions one-dimensional structure are formed.…”

(2-{[2-(1H-Benzimidazol-2-yl-κN3)phenyl]iminomethyl-κN}-5-methylphenolato-κO)chloridozinc(II)

“…For background to benzimidazoles and their applications, see: Chassaing et al (2008); Kucukbay et al (2003); Podunavac-Kuzmanovic & Cvetkovic (2010); Podunavac-Kuzmanovic et al (1999); Podunavac-Kuzmanovic & Markov (2006); Xue et al (2011). For related structures, see: Eltayeb et al (2007Eltayeb et al ( , 2009; Eltayeb, Teoh, Chantrapromma & Fun (2011); Eltayeb, Teoh, Yeap & Fun (2011); Maldonado-Rogado et al (2007); Tong & Ye (2004). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986).…”

“…Benzimidazole compounds and their complexes have been found to show diverse biological activity (Chassaing et al, 2008;Kucukbay et al, 2003;Podunavac-Kuzmanovic & Cvetkovic, 2010;Podunavac-Kuzmanovic et al, 1999;Podunavac-Kuzmanovic & Markov, 2006) including inhibition against enteroviruses (Xue et al, 2011). Our ongoing structural studies involves benzimidazoles (Eltayeb et al, 2007(Eltayeb et al, , 2009Eltayeb, Teoh, Yeap & Fun, 2011) and their complexes (Eltayeb, Teoh, Chantrapromma & Fun, 2011). In the preparation of the title complex (I), 2-(2-aminophenyl)-1H-benzimidazole undergoes a condensation reaction with 2-hydroxy-4-methylbenzaldehyde to give a Schiff base ligand and forming the zinc(II) complex.…”