Received 27 April 2011
aDepartment of Chemistry, Faculty of Arts and Sciences, Dokuz Eylül University, Tinaztepe, 35160 Buca, Izmir, Turkey,bDepartment of Physics, Karabük University, 78050, Karabük, Turkey, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: email@example.com
The asymmetric unit of the title compound, C18H11NO2S, contains two crystallographically independent molecules. In one molecule, the oxazole and thiophene rings are oriented at dihedral angles of 17.40 (9) and 18.18 (7)° with respect to the naphthalene ring system, while the oxazole and thiophene rings are oriented to each other at a dihedral angle of 0.86 (9)°. In the other molecule, the corresponding angles are 3.05 (8), 9.62 (6) and 7.02 (8)°, respectively. In each molecule, a weak intramolecular C-HN hydrogen bond links the oxazole N atom to the naphthalene group. Weak intermolecular C-HO hydrogen bonding is present in the crystal structure. - stacking between the oxazole and thiophene rings, between the thiophene and naphthalene rings, and between the oxaozole and naphthalene rings, [centroid-centroid distances = 3.811 (2), 3.889 (2), 3.697 (2) and 3.525 (2) Å] may further stabilize the crystal structure.
For potential applications of the title compound, such as organic light-emitting diodes (OLEDs), organic thin-film transistors (OTFTs), and organic photovoltaics (OPVs) of various aromatic ring-based conjugated polymers, see: Liu et al. (2007); Allard et al. (2008); Woudenbergh et al. (2004); Zhang et al. (2007); Günes et al. (2007); Soci et al. (2007). For the roles of thiophene-based molecules widely used in the syntheses of the charge-transporting molecules used in organic field effect transistors, organic solar cells and organic light emitting diodes, see: Mas-Torrent & Rovira (2008); Shirota & Kageyama (2007); Varis et al. (2006). For bond-length data, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5202 ).
The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of X-ray diffractometer. This study was supported by TUBITAK (grant No. 107T817).
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