[Journal logo]

Volume 67 
Part 7 
Page o1818  
July 2011  

Received 20 June 2011
Accepted 22 June 2011
Online 25 June 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.142
Data-to-parameter ratio = 14.0
Details
Open access

(Z)-4-(2-Naphthylamino)pent-3-en-2-one

aLaboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia, BP 2390, 40001 Marrakech, Morocco,bUniversité Blaise Pascal, Laboratoire des Matèriaux Inorganiques, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubiére, France, and cDipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Universitá degli Studi di Parma, Viale G. P. Usberti 17/A, I-43124 Parma, Italy
Correspondence e-mail: corrado.rizzoli@unipr.it

The title compound, C15H15NO, which was synthesized under solvent-free conditions by the reaction of acetoacetone and 2-naphthylamine, adopts a Z conformation about the C=C bond. The enamine-ketone fragment is approximately planar [maximum deviation = 0.026 (3) Å] and forms a dihedral angle of 39.78 (3)° with the naphthalene ring system. An intramolecular N-H...O hydrogen bond is observed.

Related literature

For our studies on the synthesis of [beta]-enaminones and [beta]-enamino esters, see: Harrad et al. (2010[Harrad, M. A., Outtouch, R., Ait Ali, M., El Firdoussi, L., Karim, A. & Roucoux, A. (2010). Catal. Commun. 11, 442-446.], 2011[Harrad, M. A., Boualy, B., Ali, M. A., Firdoussi, L. E. & Rizzoli, C. (2011). Acta Cryst. E67, o1269-o1270.]). For related structures, see: Shaheen et al. (2006[Shaheen, F., Marchio, L., Badshah, A. & Khosa, M. K. (2006). Acta Cryst. E62, o873-o874.]); Arici et al. (1999[Arici, C., Tahir, M. N., Ülkü, D. & Atakol, O. (1999). Acta Cryst. C55, 1691-1692.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15NO

  • Mr = 225.28

  • Orthorhombic, P b c a

  • a = 11.2417 (18) Å

  • b = 8.2532 (10) Å

  • c = 26.570 (4) Å

  • V = 2465.2 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.48 × 0.34 × 0.12 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS, Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.660, Tmax = 0.746

  • 9535 measured reflections

  • 2221 independent reflections

  • 1179 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.142

  • S = 0.94

  • 2221 reflections

  • 159 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1 0.92 (2) 1.85 (2) 2.657 (2) 144 (2)

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and SCHAKAL97 (Keller, 1997[Keller, E. (1997). SCHAKAL97. University of Freiburg, Germany.]); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5187 ).


Acknowledgements

Financial support from the Universitá degli Studi di Parma is gratefully acknowledged.

References

Arici, C., Tahir, M. N., Ülkü, D. & Atakol, O. (1999). Acta Cryst. C55, 1691-1692.  [CrossRef] [details]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Harrad, M. A., Boualy, B., Ali, M. A., Firdoussi, L. E. & Rizzoli, C. (2011). Acta Cryst. E67, o1269-o1270.  [CrossRef] [details]
Harrad, M. A., Outtouch, R., Ait Ali, M., El Firdoussi, L., Karim, A. & Roucoux, A. (2010). Catal. Commun. 11, 442-446.  [CrossRef] [ChemPort]
Keller, E. (1997). SCHAKAL97. University of Freiburg, Germany.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Shaheen, F., Marchio, L., Badshah, A. & Khosa, M. K. (2006). Acta Cryst. E62, o873-o874.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2011). E67, o1818  [ doi:10.1107/S1600536811024494 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.