2-(Naphthalen-1-yl)-4-(thio­phen-2-yl­methyl­idene)-1,3-oxazol-5(4H)-one

Gündoğdu, C.; Alp, S.; Ergün, Y.; Tercan, B.; Hökelek, T.

doi:10.1107/S1600536811016151

Volume 67
Part 6
Pages o1321-o1322
June 2011

Received 27 April 2011
Accepted 28 April 2011
Online 7 May 2011

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.054
wR = 0.133
Data-to-parameter ratio = 17.0
Details

2-(Naphthalen-1-yl)-4-(thiophen-2-ylmethylidene)-1,3-oxazol-5(4H)-one

Cevher Gündogdu,^a Serap Alp,^a Yavuz Ergün,^a Baris Tercan ^b and Tuncer Hökelek ^c ^*

^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: merzifon@hacettepe.edu.tr

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. [pi] - [pi] 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.

Related literature

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).

Experimental

Crystal data

C₁₈H₁₁NO₂S
M_r = 305.35
Monoclinic, P 2₁ /c
a = 11.1509 (3) Å
b = 7.0871 (2) Å
c = 35.2592 (5) Å
= 97.914 (4)°
V = 2759.91 (12) Å³
Z = 8
Mo K radiation
= 0.24 mm^-1
T = 294 K
0.35 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.921, T_max = 0.953
25128 measured reflections
6899 independent reflections
3925 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.133
S = 1.01
6899 reflections
405 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N1	0.93	2.27	2.924 (3)	127
C3'-H3'N1'	0.93	2.29	2.946 (3)	127
C6-H6O2ⁱ	0.93	2.59	3.483 (3)	160
C9'-H9'O2ⁱⁱ	0.93	2.46	3.310 (3)	152
C16'-H16'O2'ⁱⁱⁱ	0.93	2.50	3.329 (3)	149
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+2.

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 ).

Acknowledgements

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).

References

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organic compounds