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Volume 68 
Part 11 
Page o3176  
November 2012  

Received 5 October 2012
Accepted 16 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.065
wR = 0.211
Data-to-parameter ratio = 16.3
Details
Open access

(E)-N-[(2-Ethoxynaphthalen-1-yl)methylidene]-2-ethylaniline

aDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayis University, TR-55139 Kurupelit-Samsun, Turkey,bDepartment of Chemistry, Faculty of Arts & 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

In the title compound, C21H21NO, the dihedral angle between the naphthalene ring system and the benzene ring is 64.61 (6)°. The molecular structure is stabilized by an intramolecular C-H...N hydrogen bond.

Related literature

For 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 hydrogen-bonding motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a related structure, see: Vesek et al. (2012[Vesek, H., Kazak, C., Alaman Agar, A., Macit, M. & Soylu, M. S. (2012). Acta Cryst. E68, o2518.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21NO

  • Mr = 303.39

  • Monoclinic, P 21 /c

  • a = 11.6011 (11) Å

  • b = 20.457 (3) Å

  • c = 7.4335 (7) Å

  • [beta] = 101.303 (8)°

  • V = 1730.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.71 × 0.55 × 0.36 mm

Data collection
  • Stoe IPDS-II diffractometer

  • 14212 measured reflections

  • 3403 independent reflections

  • 1769 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.211

  • S = 0.94

  • 3403 reflections

  • 209 parameters

  • 16 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...N1 0.93 2.32 2.961 (4) 126

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: FJ2600 ).


Acknowledgements

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

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Vesek, H., Kazak, C., Alaman Agar, A., Macit, M. & Soylu, M. S. (2012). Acta Cryst. E68, o2518.  [CSD] [CrossRef] [details]
Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3176  [ doi:10.1107/S1600536812043097 ]

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