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Volume 69 
Part 4 
Page o469  
April 2013  

Received 26 January 2013
Accepted 26 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.093
Data-to-parameter ratio = 13.9
Details
Open access

(E)-N-(2,4-Dichlorobenzylidene)-2,5-dimethoxyaniline

aCollege of Chemical Engineering, Inner Mongolia University of Technology, Inner Mongolia 010051, People's Republic of China, and bSchool of Chemistry and Chemical Engineering, Zhaoqing University, Zhaoqing 526061, People's Republic of China
Correspondence e-mail: guohaifu@zqu.edu.cn

In the title compound, C15H13Cl2NO2, which was obtained by a condensation reaction of 2,5-dimethoxyaniline and 2,4-dichlorobenzaldehyde, the dihedral angle between the benzene rings is 51.94 (2)°. The 2,5-dimethoxyphenyl and 2,4-dichlorophenyl groups are attached to the ends of the N=C group in an E conformation. Intramolecular C-H...Cl and C-H...N contacts are observed. In the crystal, molecules are linked by C-H...O hydrogen bonds, forming chains parallel to the b axis.

Related literature

For the synthesis and applications of Schiff base-metal complexes, see: Jin et al. (2011[Jin, X.-D., Jin, Y.-H., Zou, Z.-Y., Cui, Z.-G., Wang, H.-B., Kang, P.-L., Ge, C.-H. & Li, K. (2011). J. Coord. Chem. 64, 1533-1543.]). For the preparation of Schiff base compounds by the condensation reaction between 2,4-dichlorobenzaldehyde with organic amines, see: Guo et al. (2012[Guo, H.-F., Pan, Y., Ma, D.-Y., Lu, K. & Qin, L. (2012). Transition Met. Chem. 37, 661-669.]). 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
  • C15H13Cl2NO2

  • Mr = 310.16

  • Monoclinic, P 21 /n

  • a = 13.2879 (12) Å

  • b = 5.1329 (5) Å

  • c = 21.1490 (18) Å

  • [beta] = 96.622 (2)°

  • V = 1432.9 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.45 mm-1

  • T = 296 K

  • 0.33 × 0.27 × 0.22 mm

Data collection
  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.875, Tmax = 0.917

  • 7646 measured reflections

  • 2545 independent reflections

  • 2166 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.093

  • S = 1.04

  • 2545 reflections

  • 183 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
C13-H13...O1i 0.93 2.62 3.357 (2) 137
C7-H7...Cl1 0.93 2.72 3.100 (1) 106
C13-H13...N1 0.93 2.52 2.826 (6) 100
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Burker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Burker 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CQ2001 ).


Acknowledgements

This work was supported financially by the Science and Technology Planning Project of Zhaoqing City (2012 G030), the Science and Technology Innovation Planning Project of Zhaoqing City (2012 G013) and the Distinguished Young Talents in Higher Education of Guangdong Province (2012LYM_0134).

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.
Bruker (2004). APEX2 and SAINT. Burker AXS Inc., Madison, Wisconsin, USA.
Guo, H.-F., Pan, Y., Ma, D.-Y., Lu, K. & Qin, L. (2012). Transition Met. Chem. 37, 661-669.  [ISI] [CrossRef] [ChemPort]
Jin, X.-D., Jin, Y.-H., Zou, Z.-Y., Cui, Z.-G., Wang, H.-B., Kang, P.-L., Ge, C.-H. & Li, K. (2011). J. Coord. Chem. 64, 1533-1543.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o469  [ doi:10.1107/S1600536813005552 ]

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