[Journal logo]

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 [sigma](C-C) = 0.004 Å
R = 0.058
wR = 0.151
Data-to-parameter ratio = 13.6
Details
Open access

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

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-H...N hydrogen bond occurs. In the crystal, weak C-H...F 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[Gül, Z. S., Ersahin, F., Agar, E. & Isik, S. (2007). Acta Cryst. E63, o2902.]); Kantar et al. (2012[Kantar, E. N., Köysal, Y., Gümüs, S., Agar, E. & Soylu, M. S. (2012). Acta Cryst. E68, o1587.]); Kargili et al. (2012[Kargili, H., Macit, M., Alpaslan, G., Kazak, C. & Erdönmez, A. (2012). Acta Cryst. E68, o3176.]); Pekdemir et al. (2012[Pekdemir, M., Isik, S. & Alaman Agar, A. (2012). Acta Cryst. E68, o2148.]); Vesek et al. (2012[Vesek, H., Kazak, C., Alaman Agar, A., Macit, M. & Soylu, M. S. (2012). Acta Cryst. E68, o2518.]). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17F2NO

  • Mr = 325.35

  • Monoclinic, P 21 /c

  • a = 12.5963 (8) Å

  • b = 14.3010 (8) Å

  • c = 9.8693 (8) Å

  • [beta] = 108.672 (8)°

  • V = 1684.3 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.703, Tmax = 1.000

  • 5942 measured reflections

  • 2958 independent reflections

  • 1997 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.151

  • S = 1.06

  • 2958 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...N1 0.93 2.32 2.955 (3) 125
C6-H6...F1i 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[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: CV5376 ).


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


Acta Cryst (2013). E69, o361  [ doi:10.1107/S1600536813001967 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.