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

Harrad, M.A.; Boualy, B.; Oudahmane, A.; Avignant, D.; Rizzoli, C.

doi:10.1107/S1600536811024494

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 (C-C) = 0.003 Å
R = 0.050
wR = 0.142
Data-to-parameter ratio = 14.0
Details

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

Mohamed Anoir Harrad,^a Brahim Boualy,^a Abdelghani Oudahmane,^b Daniel Avignant ^b and Corrado Rizzoli ^c ^*

^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-HO hydrogen bond is observed.

Related literature

For our studies on the synthesis of [beta] -enaminones and [beta] -enamino esters, see: Harrad et al. (2010, 2011). For related structures, see: Shaheen et al. (2006); Arici et al. (1999).

Experimental

Crystal data

C₁₅H₁₅NO
M_r = 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 radiation
= 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) T_min = 0.660, T_max = 0.746
9535 measured reflections
2221 independent reflections
1179 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(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
_max = 0.19 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1	0.92 (2)	1.85 (2)	2.657 (2)	144 (2)

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995).

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

organic compounds