4-(9-Anthryl)-2-methylbutyn-2-ol

There are two molecules in the asymmetric unit of the title compound, C19H16O. Neighbouring molecules are linked through O—H⋯O hydrogen bonds into an R 4 4(8) ring motif. There are also C—H⋯π hydrogen and π–π interactions. The molecules are either parallel to each other or are inclined at an angle of 12.5 (1)°.

There are two molecules in the asymmetric unit of the title compound, C 19 H 16 O. Neighbouring molecules are linked through O-HÁ Á ÁO hydrogen bonds into an R 4 4 (8) ring motif.
There are also C-HÁ Á Á hydrogen andinteractions. The molecules are either parallel to each other or are inclined at an angle of 12.5 (1) .

Crystal data
Cg3 is the centroid of the C25/30-C34 ring and Cg4 is the centroid of the C26-C29/C33/C34 ring. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is the perpendicular distance of ring I from ring J. Data collection: KM-4 Software (Oxford Diffraction, 1995-2003; cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Comment
Recently there is a need for molecules containing triple bond because of their electroconductive, magnetic and nonlinear optical properties. This class of the compounds are used as molecular wires (Bunz, 2000), molecular scale logic gates (De Silva et al., 1999), optical and microelectronic devices (Schumm et al., 1994), sensors (Krasovitski & Bolotin, 1988) and molecular photovoltaic cells (O'Regan & Grätzel, 1991)). Ethynylanthracene derivatives are substrates in many synthesis (Wen et al., 2004;Xiao et al., 2007). 2-Methyl-3-butyn-2-ol is an alternative protecting group for (trimethylsilyl)acetylene, more useful in reaction carried at higher temperature (because of its higher boiling point) as well as giving acetylene derivatives containing various substituents in homo-and heterocoupling. Because of that we use this protecting group to synthesize acetylene derivatives to study influence of the aromatic subtituent size on the photophysical properties of the compounds in search for organic material with extended π system, characterized by high fluorescence quantum yield. As an intermediate in the synthesis of anthracene derivative, 9-(3-hydroxy-3-methyl-1-butyne)anthracene was isolated and its crystal structure was determined.
In the crystal structure, neighbouring molecules are linked through O-H···O hydrogen bond forming R 4 4 (8) ring motif (Table 1 and Fig. 2). Molecules which forming this motif are linked by C-H···π hydrogen bonds (Table 2 and Fig. 2) or π-π interactions ( Table 3 and Fig. 2). In the packing, the anthracene moieties are either parallel or inclined at an angle of 12.5 (1)°.
supplementary materials sup-2 Refinement All H atoms were positioned geometrically and refined using a riding model, with C-H distances of 0.93 Å and with U iso (H) = 1.2U eq (C) (C-H = 0.96 Å and U iso (H) = 1.5U eq (C) for the methyl group) and O-H distances of 0.82 Å and with U iso (H) = 1.5U eq (C). Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 25% probability level and H atoms are shown as small spheres of arbitrary radii. Cg1, Cg2, Cg3 and Cg4 denote the ring centroids.