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Title: Redetermination of the structure of anthracen-9-yl-methanol, C 15H12O
Authors: Isloor, A.M.
Somashekara, B.
Garudachari, B.
Gerber, T.
Hosten, E.
Betz, R.
Issue Date: 2013
Citation: Zeitschrift fur Kristallographie - New Crystal Structures, 2013, Vol.228, 3, pp.303-304
Abstract: (Equation presentation) (Table presentation) Source of material The title compound was synthesized according to the literature [4]. Experimental details Carbon-bound hydrogen atoms were placed in calculated positions (C-H 0.95 for aromatic carbon atoms and C-H 0.99 for methylene groups) and were included in the refinement in the ridingmodel approximation, withU iso(H) set to 1.2Ueq(C). TheHatoms of the hydroxyl groups were allowed to rotate with a fixed angle around the C-O bond to best fit the experimental electron density (HFIX 147 in the SHELXprogram suite [5]), withUiso(H) set to 1.5Ueq(C). Due to the absence of a strong anomalous scatterer, the Flack-X parameter is meaningless. Thus, Friedel opposites (1703 pairs) have been merged and the item was removed from the CIF. Discussion Anthracene is a key substance in the production of anthraquinone as well a various dyes, pigments, insecticides, wood preservatives and coatingmaterials. As several anthracene derivatives exhibit light and temperature sensitivity, heat resistance, conductivity, emittability, and corrosion resistance, they have been a focus of chemical research. Due to ?-electron cloud overlaps, anthracene itself exhibits semiconductor properties [1]. Organic semiconductors are interesting due to their abilities of self radiation next to their flexibility, light weight, easy fabrication and low cost. They have been investigated as organic electroluminescence materials for application in organic solar cells, biosensitizers and display devices such as organic light-emitting diodes (OLEDs) [2]. The structure of the title compound at room temperature has been determined earlier during an investigation about triboluminescence effects and the discussion of structural features in this manuscript is scant [3]. The asymmetric unit features two crystallographic independant molecules of the title compound. The aromatic scaffold of both molecules is essentailly flat (r.m.s. of all fitted non-hydrogen atoms = 0.0167 and 0.0175 , respectively). The least-squares planes defined by the carbon atoms of the "outer" phenyl rings intersect at angles of 1.7(1) and 1.8(1) , respectively, in both molecules. The two molecules are not stacked parallel or perpendicular with respect to each other, the aromatic moieties of both molecules enclose an angle of 54.48(5) . In bothmolecules, the hydroxy-methyl group is orientated approximately perpendicular to the aromatic system, the respective O-C-C-C dihedral angles are measured at -77.8(2) and 77.9(2) . The crystal structure is characterized by hydrogen bonds by the hydroxyl groups. These connect the two molecules present in the asymmetric unit intermittently to chains along the crystallographic b axis. (Table presentation).
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