Natarajan Arumugam

Ethyl 1-sec-butyl-2-(4-chloro­phen­yl)-1H-benzimidazole-5-carboxyl­ate

In the title compound, C20H21ClN2O2, the ethyl 1H-benzimidazole-5-carboxylate ring system, excluding the methylene and methyl H atoms, is almost planar, with a maximum deviation of 0.055 (1) Å, and makes a dihedral angle of 40.63 (4)° with the benzene ring. The sec-butyl group is disordered over two positions, with refined site occupancies of 0.855 (4) and 0.145 (4). In the crystal, molecules are linked into chains along [010] via intermolecular C—H⋯O hydrogen bonds and are further interconnected by C—H⋯Cl interactions into two-dimensional networks parallel to (001). The crystal structure is further consolidated by C—H⋯π interactions.

Ethyl 1-tert-butyl-2-(4-methoxy-phen-yl)-1H-benzimidazole-5-carboxyl-ate.

In the title molecule, C21H24N2O3, the imidazole ring is essentially planar, with a maxium deviation of 0.015 (1) Å. The dihedral angle between the benzene and imidazole rings is 65.47 (6)°. The crystal packing is stabilized by weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds, forming zigzag chains along the c axis. The crystal structure is further stabilized by C—H⋯π interactions.

Ethyl 1-sec-butyl-2-phenyl-1H-benzimidazole-5-carboxyl­ate

In the title molecule, C20H22N2O2, the benzimidazole ring system is essentially planar, with a maximum deviation of 0.024 (1) Å. The dihedral angle between the phenyl and benzimidazole ring system is 43.71 (5)°. The atoms of the butyl group are disordered over two sets of sites with occupancies of 0.900 (4) and 0.100 (4). In the crystal structure, molecules are connected by weak intermolecular C—H⋯O hydrogen bonds, forming chains along the b axis. The crystal structure is further stabilized by C—H⋯π interactions.

Ethyl 1-sec-butyl-2-(4-methoxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate

In the title molecule, C21H24N2O3, the dihedral angle between the benzene and imidazole rings is 66.33 (13)°. The imidazole ring is essentially planar, with a maximum deviation of 0.004 (2) Å. In the crystal structure, molecules are connected by weak C—H⋯O hydrogen bonds, forming chains along the b axis

Ethyl 3-amino-4-[(2-hy­droxy­ethyl)­amino]benzoate

In the crystal structure of the title compound, C11H16N2O3, molecules are linked by one O—H⋯N and two N—H⋯O intermolecular hydrogen bonds into a three-dimensional network, which incorporates R 2 2(14) and R 2 2(16) graph-set motifs.

Ethyl 1-tert-butyl-2-(4-hydr­oxy-3-methoxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate

In the title compound, C21H24N2O4, the benzimidazole ring system is almost planar, with a maximum deviation of 0.047 (1) Å and makes a dihedral angle of 88.44 (5)° with the attached benzene ring. In the crystal, molecules form infinite chains along the b axis by way of intermolecular O—H⋯N and C—H⋯O interactions. Weak C—H⋯π also contribute to the stabilization of the crystal structure.

Ethyl 1-(2-hy­droxy­eth­yl)-2-(4-meth­oxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate monohydrate

In the title molecule, C19H20N2O4·H2O, the benzimidazole ring system is essentially planar [maximum deviation = 0.013 (11) Å] and is inclined to the 4-methoxyphenyl ring by 30.98 (5)°. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds involving the water molecule link neighbouring molecules, forming a two-dimensional network lying parallel to the bc plane. There are also C—H⋯π and π–π interactions present. The latter involve inversion-related benzimidazole rings with centroid–centroid distances of 3.5552 (8) and 3.7466 (8) Å.

Ethyl 1-(butan-2-yl)-2-(2-meth­oxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate

In the title compound, C21H24N2O3, the mean planes of the benzene ring and the benzimidazole ring system form a dihedral angle of 69.94 (7)°. The ethyl group atoms of the ethanoate fragment are disordered over two sets of sites, with refined occupancies of 0.742 (6) and 0.258 (6). In the crystal, there are weak C—H⋯N hydrogen bonds which connect molecules into chains along the b axis. A weak intermolecular C—H⋯π interaction is also observed.

Ethyl 2-(4-bromo­phen­yl)-1-sec-butyl-1H-benzimidazole-5-carboxyl­ate

In the title compound, C20H21BrN2O2, the bromophenyl ring is twisted by 40.13 (8)° from the benzimidazole mean plane and the Br atom deviates by 0.753 (1) Å from that plane. The sec-butyl group is disordered over two conformations in a 0.898 (5):0.102 (5) ratio. In the crystal, molecules related by translation along [10] are linked into chains via weak C—H⋯Br hydrogen bonds.

Ethyl 1-sec-butyl-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate

In the title compound, C21H24N2O2, the butyl group is disordered over two orientations with refined site occupancies of 0.883 (3) and 0.117 (3). The dihedral angle between the mean plane of benzimidazole ring system and the benzene ring is 39.32 (4)° and the dihedral angle between the mean plane of carboxylate group and the benzimidazole ring system is 6.87 (5)°. A weak intramolecular C—H⋯π interaction may have some influence on the conformation of the molecule. In the crystal structure, molecules are linked into infinite chains along the b axis by weak intermolecular C—H⋯O hydrogen bonds.