[Journal logo]

Volume 66 
Part 10 
Page o2523  
October 2010  

Received 29 August 2010
Accepted 6 September 2010
Online 11 September 2010

[rz2483sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.047
wR = 0.107
Data-to-parameter ratio = 14.5
Details
Open access

4-Chloro-N-[(E)-2,4-dichlorobenzylidene]aniline

Umar Hayat,a Waseeq Ahmad Siddiqui,a M. Nawaz Tahirb* and Ghulam Hussaina

aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the molecule of the title compound, C13H8Cl3N, the 4-chloroaniline and 2,4-dichlorobenzaldehyde moieties are planar with r.m.s. deviation of 0.0115 and 0.0116 Å, respectively, and are oriented at a dihedral angle of 13.94 (8)°.

Related literature

For related structures, see: Bernstein (1972[Bernstein, J. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 946-950.]), Yin et al. (2007[Yin, Z.-G., Qian, H.-Y., Chen, Y.-Z. & Feng, Y.-L. (2007). Acta Cryst. E63, o4119.]). For graph-set notation, 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

  • C13H8Cl3N

  • Mr = 284.55

  • Monoclinic, P 21 /n

  • a = 3.9665 (3) Å

  • b = 27.639 (2) Å

  • c = 11.4287 (9) Å

  • [beta] = 99.165 (3)°

  • V = 1236.93 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.71 mm-1

  • T = 296 K

  • 0.32 × 0.12 × 0.08 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.903, Tmax = 0.946

  • 9236 measured reflections

  • 2239 independent reflections

  • 1372 reflections with I > 2[sigma](I)

  • Rint = 0.047
Refinement

  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.107

  • S = 1.02

  • 2239 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2483 ).

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. They also acknowledge the technical support provided by Bana International, Karachi, Pakistan.

References

Bernstein, J. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 946-950.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yin, Z.-G., Qian, H.-Y., Chen, Y.-Z. & Feng, Y.-L. (2007). Acta Cryst. E63, o4119.  [CSD] [CrossRef] [details]

Acta Cryst (2010). E66, o2523  [ doi:10.1107/S1600536810035774 ]

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.