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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 [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.048
wR = 0.097
Data-to-parameter ratio = 12.1
Details
Open access

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

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-H...O 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-H...O 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[Lozier, R. H., Bogomolni, R. A. & Stoeckenius, W. (1975). Biophys. J. 15, 955-962.]). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009[Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403-m404.]); Yeap et al. (2009[Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.]). For Schiff base tautomerism, see: Hökelek et al. (2000[Hökelek, T., Kiliç, Z., Isiklan, M. & Toy, M. (2000). J. Mol. Struct. 523, 61-69.]); Odabasoglu et al. (2005[Odabasoglu, M., Albayrak, C. & Büyükgüngör, O. (2005). Acta Cryst. E61, o425-o426.]). For related strucures, see: Özek et al. (2004[Özek, A., Yüce, S., Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2004). Acta Cryst. E60, o828-o830.]); Temel et al. (2010[Temel, E., Agar, E. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1131.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14F3NO2

  • Mr = 345.31

  • Monoclinic, P 21 /c

  • a = 16.3922 (10) Å

  • b = 5.7201 (2) Å

  • c = 17.7632 (10) Å

  • [beta] = 106.284 (5)°

  • V = 1598.75 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.949, Tmax = 0.984

  • 19794 measured reflections

  • 3129 independent reflections

  • 1722 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O1i 0.93 2.51 3.423 (3) 166
N1-H1...O1 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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


Acta Cryst (2013). E69, o163  [ doi:10.1107/S1600536812051410 ]

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