title: Structures of six industrial benzimidazolone pigments from laboratory powder diffraction data.
abstract: The crystal structures of six industrially produced benzimidazolone pigments [Pigment Orange 36 (beta phase), Pigment Orange 62, Pigment Yellow 151, Pigment Yellow 154 (alpha phase), Pigment Yellow 181 (beta phase) and Pigment Yellow 194] were determined from laboratory X-ray powder diffraction data by means of real-space methods using the programs DASH and MRIA, respectively. Subsequent Rietveld refinements were carried out with TOPAS. The crystal phases correspond to those produced industrially. Additionally, the crystal structures of the non-commercial compound 'BIRZIL' (a chloro derivative of Pigment Yellow 194) and of a dimethylsulfoxide solvate of Pigment Yellow 154 were determined by single-crystal structure analyses. All eight crystal structures are different; the six industrial pigments even exhibit five different hydrogen-bond topologies. Apparently, the good application properties of the benzimidazolone pigments are not the result of one specific hydrogen-bonding pattern, but are the result of a combination of efficient molecular packing and strong intermolecular hydrogen bonds.
authors.affiliation: Institute of Inorganic and Analytical Chemistry, Goethe University, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany.
authors.forename: Jacco
authors.initials: J
authors.lastname: van de Streek
authors.forename: Jürgen
authors.initials: J
authors.lastname: Brüning
authors.forename: Svetlana N
authors.initials: SN
authors.lastname: Ivashevskaya
authors.forename: Martin
authors.initials: M
authors.lastname: Ermrich
authors.forename: Erich F
authors.initials: EF
authors.lastname: Paulus
authors.forename: Michael
authors.initials: M
authors.lastname: Bolte
authors.forename: Martin U
authors.initials: MU
authors.lastname: Schmidt
mesh_terms: D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D004396:Coloring Agents / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D033362:Powder Diffraction; D013237:Stereoisomerism
chemical_list: D001562:Benzimidazoles; D004396:Coloring Agents; C014353:benzimidazolone