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

Kargılı, H.; Macit, M.; Alpaslan, G.; Kazak, C.; Erdönmez, A.

doi:10.1107/S1600536812043097

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 (C-C) = 0.005 Å
R = 0.065
wR = 0.211
Data-to-parameter ratio = 16.3
Details

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

Hakan Kargili,^a Mustafa Macit,^b Gökhan Alpaslan,^c ^* Canan Kazak ^a and Ahmet Erdönmez ^a

^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-HN hydrogen bond.

Related literature

For 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 hydrogen-bonding motifs, see: Bernstein et al. (1995). For a related structure, see: Vesek et al. (2012).

Experimental

Crystal data

C₂₁H₂₁NO
M_r = 303.39
Monoclinic, P 2₁ /c
a = 11.6011 (11) Å
b = 20.457 (3) Å
c = 7.4335 (7) Å
= 101.303 (8)°
V = 1730.0 (3) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.211
S = 0.94
3403 reflections
209 parameters
16 restraints
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9N1	0.93	2.32	2.961 (4)	126

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: 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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.

organic compounds