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Volume 69 
Part 5 
Page o630  
May 2013  

Received 22 March 2013
Accepted 24 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.042
wR = 0.112
Data-to-parameter ratio = 16.0
Details
Open access

N-[(E)-4-Bromobenzylidene]-2,3-dimethylaniline

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

The title compound, C15H14BrN, has an E conformation about the C=N bond and the dihedral angle between the benzene rings is 50.7 (2)°. In the crystal, molecules are linked via C-H...[pi] interactions, forming columns propagating along [010].

Related literature

Schiff base derivativies have many pharmaceutical activities. For their antifungal effects, 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

  • Monoclinic, P 21 /n

  • a = 12.945 (9) Å

  • b = 7.857 (5) Å

  • c = 14.497 (10) Å

  • [beta] = 113.384 (8)°

  • V = 1353.3 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.02 mm-1

  • T = 296 K

  • 0.25 × 0.20 × 0.19 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.]) Tmin = 0.519, Tmax = 0.598

  • 5865 measured reflections

  • 2525 independent reflections

  • 1154 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.112

  • S = 0.94

  • 2525 reflections

  • 157 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg2i 0.93 2.99 3.830 (6) 151
C15-H15B...Cg1ii 0.96 2.99 3.781 (6) 140
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+1, -z+1.

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: SU2578 ).


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 Gottingen, 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, o630  [ doi:10.1107/S1600536813008088 ]

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