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Volume 69 
Part 4 
Page o548  
April 2013  

Received 28 February 2013
Accepted 6 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.125
Data-to-parameter ratio = 15.6
Details
Open access

(E)-N-[(E)-3-(4-Nitrophenyl)allylidene]naphthalen-1-amine

aChemical Kinomics Research Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea,bAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and cCenter 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, C19H14N2O2, the dihedral angle between the mean planes of the 4-nitrophenyl ring and the naphthalene ring system is 12.79 (2)°. The imine group displays a C-C-N=C torsion angle of 41.0 (2)° and the C=N group has an E conformation. In the crystal, weak C-H...O hydrogen bonds link molecules into layers parallel to the b axis.

Related literature

For the synthesis and biological activity of naphthalene compounds, see: Upadhayaya et al. (2010[Upadhayaya, R. S., Vandavasi, J. K., Kardile, R. A., Lahore, S. V., Dixit, S. S., Deokar, H. S., Shinde, P. D., Sarmah, M. P. & Chattopadhyaya, J. (2010). Eur. J. Med. Chem. 2, 1854-1867.]); Rokade & Sayyed (2009[Rokade, Y. B. & Sayyed, R. Z. (2009). RASAYAN J. Chem. 2, 972-980.]). For a related structure, see: Yang et al. (2012[Yang, P., Ding, B. & Du, G.-X. (2012). Acta Cryst. E68, o2966.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14N2O2

  • Mr = 302.33

  • Monoclinic, P 21 /c

  • a = 7.7021 (5) Å

  • b = 13.8713 (12) Å

  • c = 14.2554 (10) Å

  • [beta] = 98.096 (2)°

  • V = 1507.8 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.20 × 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 = 0.714, Tmax = 0.991

  • 14376 measured reflections

  • 3426 independent reflections

  • 1824 reflections with F2 > 2[sigma](F2)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.125

  • S = 1.00

  • 3426 reflections

  • 220 parameters

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O1i 0.93 2.66 3.422 (3) 139
C15-H15...O2ii 0.93 2.46 3.326 (3) 155
Symmetry codes: (i) x-1, y, z+1; (ii) x-1, y, z.

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: FF2100 ).


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]
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Rokade, Y. B. & Sayyed, R. Z. (2009). RASAYAN J. Chem. 2, 972-980.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Upadhayaya, R. S., Vandavasi, J. K., Kardile, R. A., Lahore, S. V., Dixit, S. S., Deokar, H. S., Shinde, P. D., Sarmah, M. P. & Chattopadhyaya, J. (2010). Eur. J. Med. Chem. 2, 1854-1867.  [ISI] [CrossRef]
Yang, P., Ding, B. & Du, G.-X. (2012). Acta Cryst. E68, o2966.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o548  [ doi:10.1107/S1600536813006417 ]

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