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Volume 69 
Part 5 
Page o631  
May 2013  

Received 24 March 2013
Accepted 25 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.008 Å
R = 0.058
wR = 0.148
Data-to-parameter ratio = 15.7
Details
Open access

N-[(E)-4-Bromobenzylidene]-3,4-dimethylaniline

aCollege of Materials Science & Engineering, China Jiliang University, Hangzhou 310018, People's Republic of China
Correspondence e-mail: nanocrystal11@163.com

In the title compound, C15H14BrN, the dihedral angle between the benzene rings is 6.4 (2)° and the molecule has an E conformation about the C=N bond. In the crystal, molecules are linked by C-H...[pi] interactions, forming two-dimensional networks lying parallel to (001).

Related literature

Schiff bases derivatives have many pharmaceutical activities. For their antifungal properties, see: Aziz et al. (2010[Aziz, A. A. A., Salem, A. N. M., Sayed, M. A. & Aboaly, M. M. (2010). J. Mol. Struct. 1010, 130-138.]), for their radical scavenging activity, see: Lu et al. (2012[Lu, J., Li, C., Chai, Y.-F., Yang, D.-Y. & Sun, C.-R. (2012). Bioorg. Med. Chem. Lett. 22, 5744-5747.]), for their inhibition of enzyme activity, see: Schmidt et al. (2009[Schmidt, M. F., El-Dahshan, A., Keller, S. & Rademann, J. (2009). Angew. Chem. Int. Ed. 48, 6346-6349.]) and for their antibacterial activity, see: Shi et al. (2010[Shi, L., Fang, R.-Q., Zhu, Z.-W., Yang, Y., Cheng, K., Zhu, H.-L. & Zhong, W.-Q. (2010). Eur. J. Med. Chem. 45, 4358-4364.]). For related structures, see: Sun et al. (2011a[Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011a). Acta Cryst. E67, o1564.],b[Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011b). Acta Cryst. E67, o1578.]); Guo et al. (2011[Guo, Y., Pan, M.-X., Xiang, H., Liu, W.-H. & Song, Z.-C. (2011). Acta Cryst. E67, o1999.]). 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
  • C15H14BrN

  • Mr = 288.18

  • Orthorhombic, P b c n

  • a = 14.868 (7) Å

  • b = 6.161 (3) Å

  • c = 28.609 (13) Å

  • V = 2621 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.11 mm-1

  • T = 296 K

  • 0.22 × 0.19 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.547, Tmax = 0.670

  • 17312 measured reflections

  • 2445 independent reflections

  • 1438 reflections with I > 2[sigma](I)

  • Rint = 0.090

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

  • wR(F2) = 0.148

  • S = 1.03

  • 2445 reflections

  • 156 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.56 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...Cg1i 0.93 2.99 3.773 (5) 143
C12-H12...Cg2ii 0.93 2.77 3.507 (5) 137
Symmetry codes: (i) [-x, y, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

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


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2579 ).


Acknowledgements

This project was supported by the Natural Science Foundation of Zhejiang Province of China (grant No. LQ12E01007).

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.
Aziz, A. A. A., Salem, A. N. M., Sayed, M. A. & Aboaly, M. M. (2010). J. Mol. Struct. 1010, 130-138.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Guo, Y., Pan, M.-X., Xiang, H., Liu, W.-H. & Song, Z.-C. (2011). Acta Cryst. E67, o1999.  [CrossRef] [details]
Lu, J., Li, C., Chai, Y.-F., Yang, D.-Y. & Sun, C.-R. (2012). Bioorg. Med. Chem. Lett. 22, 5744-5747.  [CrossRef] [ChemPort] [PubMed]
Schmidt, M. F., El-Dahshan, A., Keller, S. & Rademann, J. (2009). Angew. Chem. Int. Ed. 48, 6346-6349.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shi, L., Fang, R.-Q., Zhu, Z.-W., Yang, Y., Cheng, K., Zhu, H.-L. & Zhong, W.-Q. (2010). Eur. J. Med. Chem. 45, 4358-4364.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011a). Acta Cryst. E67, o1564.  [CSD] [CrossRef] [details]
Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011b). Acta Cryst. E67, o1578.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o631  [ doi:10.1107/S1600536813008143 ]

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