title: Synthesis and characterization of a novel long-alkyl-chain ester-substituted benzimidazole gelator and its octan-1-ol solvate.
abstract: 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, C22H26N2O3·C8H18O, (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.
authors.affiliation: Department of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USA.
authors.forename: H Cristina
authors.initials: HC
authors.lastname: Geiger
authors.affiliation: Department of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USA.
authors.forename: Patricia L
authors.initials: PL
authors.lastname: Zick
authors.affiliation: Department of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USA.
authors.forename: William R
authors.initials: WR
authors.lastname: Roberts
authors.affiliation: Department of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USA.
authors.forename: David K
authors.initials: DK
authors.lastname: Geiger
keywords: C—H...π interaction; Hirshfeld surface analysis; aggregation; benzimidazole; crystal structure; gelation; hydrogen bonding; octan-1-ol