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Volume 69 
Part 6 
Page o889  
June 2013  

Received 6 March 2013
Accepted 7 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.009 Å
R = 0.068
wR = 0.186
Data-to-parameter ratio = 14.0
Details
Open access

2-{[3-Chloro-4-(4-chlorophenoxy)phenyl]iminomethyl}-4-nitrophenol

aYesilyurt Demir Celik Higher Vocational School, Ondokuz Mayis University, TR-55300 Samsun, Turkey,bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Samsun, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Samsun, Turkey
Correspondence e-mail: nevzatk@omu.edu.tr

In the title compound, C19H12Cl2N2O4, the imine bond length of 1.257 (6) Å is typical of a double bond. The dihedral angle between the para-nitro benzene ring and the central benzene ring is 12.06 (3)° and that between the central benzene and the para-chloro benzene ring is 73.81 (2)°. An intramolecular O-H...N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked together by two pairs of C-H...O interactions (to the same O atom acceptor), forming inversion dimers. A short Cl...Cl contact [3.232 (4) Å] is observed.

Related literature

For applications of related Schiff base compounds, see: Santos et al. (2001[Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.]); Cohen et al. (1964[Cohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2041-2051.]). For related structures, see: Aygün et al. (1998[Aygün, M., Isik, S., Öcal, N., Tahir, M. N., Kaban, S. & Büyükgüngör, O. (1998). Acta Cryst. C54, 527-529.]); Karadayi et al. (2003[Karadayi, N., Gözüyesil, S., Güzel, B., Kazak, C. & Büyükgüngör, O. (2003). Acta Cryst. E59, o851-o853.], 2005[Karadayi, N., Aydemir, E., Kazak, C., Kirpi, E., Tugcu, F. T., Gümüs, M. K. & Kaban, S. (2005). Acta Cryst. E61, o2671-o2673.], 2006[Karadayi, N., Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1699-o1701.]); Faridbod et al. (2008[Faridbod, F., Ganjali, M. R., Dinarvand, R., Norouzi, P. & Riahi, S. (2008). Sensors, 8, 1645-1703.]); Raja et al. (2008[Raja, K. K., Bilal, I. M., Thambidurai, S., Rajagopal, G. & SubbiahPandi, A. (2008). Acta Cryst. E64, o2265.]); Li & Zhang (2004[Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, m1017-m1019.]); Köysal et al. (2012[Köysal, Y., Öztürk Yildirim, S., Butcher, R. J. & Dügdü, E. (2012). Acta Cryst. E68, o2993-o2994.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H12Cl2N2O4

  • Mr = 403.21

  • Triclinic, [P \overline 1]

  • a = 5.5649 (8) Å

  • b = 7.929 (1) Å

  • c = 21.778 (4) Å

  • [alpha] = 86.260 (12)°

  • [beta] = 83.596 (12)°

  • [gamma] = 70.739 (10)°

  • V = 901.1 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.39 mm-1

  • T = 296 K

  • 0.76 × 0.39 × 0.03 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.849, Tmax = 0.985

  • 10061 measured reflections

  • 3475 independent reflections

  • 1473 reflections with I > 2[sigma](I)

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.186

  • S = 1.05

  • 3475 reflections

  • 248 parameters

  • 52 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 1.85 2.564 (5) 145
C7-H7...O3i 0.93 2.51 3.321 (6) 146
C6-H6...O3i 0.93 2.49 3.319 (4) 148
Symmetry code: (i) -x, -y+2, -z.

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: RN2114 ).


Acknowledgements

The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Aygün, M., Isik, S., Öcal, N., Tahir, M. N., Kaban, S. & Büyükgüngör, O. (1998). Acta Cryst. C54, 527-529.  [CSD] [CrossRef] [details]
Cohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2041-2051.  [CrossRef]
Faridbod, F., Ganjali, M. R., Dinarvand, R., Norouzi, P. & Riahi, S. (2008). Sensors, 8, 1645-1703.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Karadayi, N., Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1699-o1701.  [CSD] [CrossRef] [details]
Karadayi, N., Aydemir, E., Kazak, C., Kirpi, E., Tugcu, F. T., Gümüs, M. K. & Kaban, S. (2005). Acta Cryst. E61, o2671-o2673.  [CSD] [CrossRef] [details]
Karadayi, N., Gözüyesil, S., Güzel, B., Kazak, C. & Büyükgüngör, O. (2003). Acta Cryst. E59, o851-o853.  [CSD] [CrossRef] [details]
Köysal, Y., Öztürk Yildirim, S., Butcher, R. J. & Dügdü, E. (2012). Acta Cryst. E68, o2993-o2994.  [CSD] [CrossRef] [details]
Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, m1017-m1019.  [CSD] [CrossRef] [ChemPort] [details]
Raja, K. K., Bilal, I. M., Thambidurai, S., Rajagopal, G. & SubbiahPandi, A. (2008). Acta Cryst. E64, o2265.  [CSD] [CrossRef] [details]
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2013). E69, o889  [ doi:10.1107/S1600536813012518 ]

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