(E)-(2,5-Difluoro­benz­yl)[(2-eth­oxy­naphthalen-1-yl)methyl­idene]amine

Pekdemir, M.; Işık, Ş.; Macit, M.; Alaman Ağar, A.; Soylu, M.S.

doi:10.1107/S1600536813001967

Volume 69
Part 3
Page o361
March 2013

Received 20 December 2012
Accepted 19 January 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.058
wR = 0.151
Data-to-parameter ratio = 13.6
Details

(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine

Merve Pekdemir,^a ^* Samil Isik,^a Mustafa Macit,^b Aysen Alaman Agar ^b and Mustafa Serkan Soylu ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, Kurupelit, TR-55139 Samsun, Turkey,^bDepartment of Chemistry, Art and Science Faculty, Ondokuz Mayis University, Kurupelit, TR-55139 Samsun, Turkey, and ^cGiresun University, Arts and Science Faculty, Department of Physics, Giresun, Turkey
Correspondence e-mail: merve.pekdemir@oposta.omu.edu.tr

In the title molecule, C₂₀H₁₇F₂NO, which adopts an E conformation with respect to the imine C=N double bond, the mean planes of the naphthalene ring system and the difluorophenyl ring form a dihedral angle of 85.82 (7)°. An intramolecular C-HN hydrogen bond occurs. In the crystal, weak C-HF hydrogen bonds link the molecules into zigzag chains along [010].

Related literature

For structural studies of Schiff bases by our group, see: Gül et al. (2007); Kantar et al. (2012); Kargili et al. (2012); Pekdemir et al. (2012); Vesek et al. (2012). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₀H₁₇F₂NO
M_r = 325.35
Monoclinic, P 2₁ /c
a = 12.5963 (8) Å
b = 14.3010 (8) Å
c = 9.8693 (8) Å
= 108.672 (8)°
V = 1684.3 (2) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.30 × 0.25 × 0.25 mm

Data collection

Oxford Diffraction SuperNova Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.703, T_max = 1.000
5942 measured reflections
2958 independent reflections
1997 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.151
S = 1.06
2958 reflections
217 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N1	0.93	2.32	2.955 (3)	125
C6-H6F1ⁱ	0.93	2.61	3.505 (4)	162
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: CV5376 ).

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.
Gül, Z. S., Ersahin, F., Agar, E. & Isik, S. (2007). Acta Cryst. E63, o2902.
Kantar, E. N., Köysal, Y., Gümüs, S., Agar, E. & Soylu, M. S. (2012). Acta Cryst. E68, o1587.
Kargili, H., Macit, M., Alpaslan, G., Kazak, C. & Erdönmez, A. (2012). Acta Cryst. E68, o3176.
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Pekdemir, M., Isik, S. & Alaman Agar, A. (2012). Acta Cryst. E68, o2148.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vesek, H., Kazak, C., Alaman Agar, A., Macit, M. & Soylu, M. S. (2012). Acta Cryst. E68, o2518.

organic compounds