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Volume 70 
Part 5 
Page o603  
May 2014  

Received 11 April 2014
Accepted 18 April 2014
Online 26 April 2014

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.102
Data-to-parameter ratio = 13.6
Details
Open access

(E)-4-Chloro-2-{[4-(di­methyl­amino)­benzyl­idene]amino}­phenol

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, Algeria
Correspondence e-mail: king.ali@hotmail.fr

In the title aromatic Schiff base compound, C15H15ClN2O, the mol­ecule exists in a trans conformation with respect to the C=N bond. The dihedral angle between the benzene rings is 14.49 (6)°. In the crystal, weak C-H...[pi] inter­actions link mol­ecules into supra­molecular chains propagated along the a-axis direction.

Related literature

For the use of Schiff bases in synthesis, see: Arora et al. (2002[Arora, K., Gupta, A. & Agarwal, D. D. (2002). Asian J. Chem. 14, 1611-1615.]). For their use as biological, analytical, polymer and liquid crystalline materials, see: Tanaka & Shiraishi (2000[Tanaka, K. & Shiraishi, R. (2000). Green Chem. 2, 272-273.]). Schiff bases have been reported to show anti­bacterial (Jarrahpour & Khalili, 2006[Jarrahpour, A. A. & Khalili, D. (2006). Molecules, 11, 59-63.]; Jarrahpour et al., 2004[Jarrahpour, A. A., Motamedifar, M., Pakshir, K., Hadi, N. & Zarei, M. (2004). Molecules, 9, 815-824.]; El-masry et al., 2000[El-masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429-1438.]), anti­fungal (More et al., 2001[More, P. G., Bhalvankar, R. B. & Pattar, S. C. (2001). J. Indian Chem. Soc. 78, 474-475.]; Singh & Dash, 1988[Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.]), anti­cancer (Desai et al., 2001[Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.]; Phatak et al., 2000[Phatak, P., Jolly, V. S. & Sharma, K. P. (2000). Orient. J. Chem. 16, 493-494.]) and herbicidal activity (Samadhiya & Halve, 2001[Samadhiya, S. & Halve, A. (2001). Orient. J. Chem. 17, 119-122.]). For related structures, see: Akkurt et al. (2005[Akkurt, M., Karaca, S., Jarrahpour, A. A., Zarei, M. & Büyükgüngör, O. (2005). Acta Cryst. E61, o776-o778.], 2008[Akkurt, M., Jarrahpour, A., Aye, M., Gençaslan, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o2087.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15ClN2O

  • Mr = 274.74

  • Orthorhombic, P b c a

  • a = 7.411 (5) Å

  • b = 12.314 (5) Å

  • c = 29.684 (5) Å

  • V = 2709 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.03 × 0.02 × 0.01 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 14319 measured reflections

  • 2346 independent reflections

  • 1895 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.102

  • S = 1.10

  • 2346 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C9-H9...Cg2i 0.93 2.70 3.533 (3) 150
C15-H15B...Cg1ii 0.96 2.76 3.581 (4) 142
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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, 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.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: XU5785 ).


Acknowledgements

We thank all researchers of the CHEMS Research Unit, University of Constantine 1, Algeria, for their valuable assistance. The authors thank the MESRS (Algeria) for financial support.

References

Akkurt, M., Jarrahpour, A., Aye, M., Gençaslan, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o2087.  [CSD] [CrossRef] [IUCr Journals]
Akkurt, M., Karaca, S., Jarrahpour, A. A., Zarei, M. & Büyükgüngör, O. (2005). Acta Cryst. E61, o776-o778.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Arora, K., Gupta, A. & Agarwal, D. D. (2002). Asian J. Chem. 14, 1611-1615.  [ChemPort]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.  [CrossRef] [ChemPort]
El-masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429-1438.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jarrahpour, A. A. & Khalili, D. (2006). Molecules, 11, 59-63.  [CrossRef] [PubMed] [ChemPort]
Jarrahpour, A. A., Motamedifar, M., Pakshir, K., Hadi, N. & Zarei, M. (2004). Molecules, 9, 815-824.  [CrossRef] [PubMed] [ChemPort]
More, P. G., Bhalvankar, R. B. & Pattar, S. C. (2001). J. Indian Chem. Soc. 78, 474-475.  [ChemPort]
Phatak, P., Jolly, V. S. & Sharma, K. P. (2000). Orient. J. Chem. 16, 493-494.  [ChemPort]
Samadhiya, S. & Halve, A. (2001). Orient. J. Chem. 17, 119-122.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.
Tanaka, K. & Shiraishi, R. (2000). Green Chem. 2, 272-273.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o603  [ doi:10.1107/S1600536814008873 ]

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