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Volume 69 
Part 5 
Page o757  
May 2013  

Received 27 March 2013
Accepted 15 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.051
wR = 0.158
Data-to-parameter ratio = 16.7
Details
Open access

(E)-N-(3,3-Diphenylallylidene)-2-(trifluoromethyl)aniline

aAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and bCenter for Neuro-Medicine, Brain Science Institute, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
Correspondence e-mail: j9601@kist.re.kr

In the title compound, C22H16F3N, the C=N bond of the central imine group adopts an E conformation. The dihedral angles between the 2-(trifluoromethyl)phenyl ring and the benzene rings are 9.34 (1) and 68.8 (1)°. The imine group displays a C-C-N=C torsion angle of 41.6 (3)°. In the crystal, weak C-H...F hydrogen bonds link the molecules into chains parallel to the b-axis direction.

Related literature

For the crystal structures of 2-phenylcinnamaldehyde derivatives studied recently our group, see: Cha et al. (2012[Cha, J. H., Kang, Y. K., Cho, Y. S., Lee, J. K. & Woo, J. C. (2012). Acta Cryst. E68, o3030.]); Kang et al. (2012[Kang, Y. K., Cho, Y. S., Lee, J. K., Yu, B.-Y. & Cha, J. H. (2012). Acta Cryst. E68, o3031.]).

[Scheme 1]

Experimental

Crystal data
  • C22H16F3N

  • Mr = 351.37

  • Monoclinic, P 21 /n

  • a = 8.6733 (8) Å

  • b = 11.8116 (9) Å

  • c = 17.6227 (15) Å

  • [beta] = 95.661 (3)°

  • V = 1796.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.725, Tmax = 0.990

  • 16660 measured reflections

  • 4059 independent reflections

  • 1842 reflections with F2 > 2[sigma](F2)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.158

  • S = 1.02

  • 4059 reflections

  • 243 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15...F1i 0.93 2.52 3.392 (3) 157
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2102 ).


Acknowledgements

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.  [ISI] [CrossRef] [ChemPort] [details]
Cha, J. H., Kang, Y. K., Cho, Y. S., Lee, J. K. & Woo, J. C. (2012). Acta Cryst. E68, o3030.  [CSD] [CrossRef] [details]
Kang, Y. K., Cho, Y. S., Lee, J. K., Yu, B.-Y. & Cha, J. H. (2012). Acta Cryst. E68, o3031.  [CSD] [CrossRef] [details]
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o757  [ doi:10.1107/S1600536813010283 ]

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