title: Octyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate: complex sheets built from N-H···N, C-H···N and C-H···O hydrogen bonds.
abstract: In the title compound, C29H35ClN4O2, the bond lengths provide evidence for aromatic delocalization in the pyrazole ring but bond fixation in the fused imidazole ring, and the octyl chain is folded, rather than adopting an all-trans chain-extended conformation. A combination of N-H···N, C-H···N and C-H···O hydrogen bonds links the molecules into sheets, in which the hydrogen bonds occupy the central layer with the tert-butyl and octyl groups arranged on either side, such that the closest contacts between adjacent sheets involve only the octyl groups. Comparisons are made with the supramolecular assembly in some simpler analogues.
authors.affiliation: Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.
authors.forename: Edwar
authors.initials: E
authors.lastname: Cortés
authors.affiliation: Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.
authors.forename: Rodrigo
authors.initials: R
authors.lastname: Abonía
authors.affiliation: Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain.
authors.forename: Justo
authors.initials: J
authors.lastname: Cobo
authors.affiliation: School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D001562:Benzimidazoles / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*
chemical_list: D001562:Benzimidazoles; D007093:Imidazoles; C000590247:Octyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate; D011720:Pyrazoles
keywords: antitumour activity; benzimidazole carboxylic acid ester; crystal structure; hydrogen bonding; supramolecular assembly