1-{(Z)-[2-Meth­oxy-5-(trifluoro­meth­yl)anilino]methyl­idene}naphthalen-2(1H)-one

Kargılı, H.; Alaman Ağar, A.; Alpaslan, G.; Büyükgüngör, O.; Erdönmez, A.

doi:10.1107/S1600536812051410

Volume 69
Part 2
Page o163
February 2013

Received 4 December 2012
Accepted 20 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.048
wR = 0.097
Data-to-parameter ratio = 12.1
Details

1-{(Z)-[2-Methoxy-5-(trifluoromethyl)anilino]methylidene}naphthalen-2(1H)-one

Hakan Kargili,^a Aysen Alaman Agar,^b Gökhan Alpaslan,^c ^* Orhan Büyükgüngör ^a and Ahmet Erdönmez ^a

^aDepartment of Physics, Faculty of Arts and Science, Ondokuz Mayis University, TR-55139 Kurupelit-Samsun, Turkey,^bDepartment of Chemistry, Faculty of Arts and Science, Ondokuz Mayis University, TR-55139 Kurupelit-Samsun, Turkey, and ^cDepartment of Medical Services and Techniques, Vocational School of Health Services, Giresun University, TR-28200 Giresun, Turkey
Correspondence e-mail: gokhan.alpaslan@giresun.edu.tr

The title compound, C₁₉H₁₄F₃NO₂, crystallizes in the keto-amine tautomeric form, with a strong intramolecular N-HO hydrogen bond. The molecule is almost planar; the dihedral angle between the naphthalene ring system and the benzene ring is 4.60 (7)°. In the crystal, molecules are linked into chains along the c axis by C-HO hydrogen bonds. The F atoms of the trifluoromethyl group are disordered over two positions with refined site occupancies of 0.668 (9) and 0.332 (9).

Related literature

For the biological properties of Schiff bases, see: Lozier et al. (1975). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009); Yeap et al. (2009). For Schiff base tautomerism, see: Hökelek et al. (2000); Odabasoglu et al. (2005). For related strucures, see: Özek et al. (2004); Temel et al. (2010).

Experimental

Crystal data

C₁₉H₁₄F₃NO₂
M_r = 345.31
Monoclinic, P 2₁ /c
a = 16.3922 (10) Å
b = 5.7201 (2) Å
c = 17.7632 (10) Å
= 106.284 (5)°
V = 1598.75 (14) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 296 K
0.58 × 0.35 × 0.13 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.949, T_max = 0.984
19794 measured reflections
3129 independent reflections
1722 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.097
S = 0.95
3129 reflections
258 parameters
72 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.15 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8O1ⁱ	0.93	2.51	3.423 (3)	166
N1-H1O1	1.00 (3)	1.70 (3)	2.554 (3)	140 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2084 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Science, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS-II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Hökelek, T., Kiliç, Z., Isiklan, M. & Toy, M. (2000). J. Mol. Struct. 523, 61-69.
Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403-m404.
Lozier, R. H., Bogomolni, R. A. & Stoeckenius, W. (1975). Biophys. J. 15, 955-962.
Odabasoglu, M., Albayrak, C. & Büyükgüngör, O. (2005). Acta Cryst. E61, o425-o426.
Özek, A., Yüce, S., Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2004). Acta Cryst. E60, o828-o830.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Temel, E., Agar, E. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1131.
Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.

organic compounds