5-(1-Cyclo­hexen-1-yl)-3-(4-methoxy­phen­yl)isoxazole

Vallejos, G.; Gutierrez, M.; Astudillo, L.; Brito, I.; Cárdenas, A.

doi:10.1107/S1600536809010903

Volume 65
Part 4
Page o920
April 2009

Received 20 March 2009
Accepted 24 March 2009
Online 28 March 2009

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.055
wR = 0.135
Data-to-parameter ratio = 12.8
Details

5-(1-Cyclohexen-1-yl)-3-(4-methoxyphenyl)isoxazole

Gabriel Vallejos,^a Margarita Gutierrez,^b Luis Astudillo,^b Iván Brito ^c ^* and Alejandro Cárdenas ^d

^aLaboratorio de Biorgánica, Instituto de Química, Facultad de Ciencias, Universidad Austral de Chile, Casilla 567, Isla Teja S/N, Valdivia, Chile,^bLaboratorio de Síntesis Orgánica, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile,^cDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, and ^dDepartamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile
Correspondence e-mail: ivanbritob@yahoo.com

In the title compound, C₁₆H₁₇NO₂, the isoxazole ring makes a dihedral angle of 14.81 (13)° with the 4-methoxyphenyl ring. Two atoms of the cyclohexene ring are disordered over two almost equally occupied positions [0.526 (13)/0.474 (13)]. The molecular structure features a short intramolecular C-HO contact.

Related literature

For background to isoxazoles, see: Melo (2005). For their biological activities, see: Narlawar et al. (2008); Patrick et al. (2007); Taldone et al. (2008); Rizzi et al. (2008); Velaparthi et al. (2008). For synthetic details, see: Hansen et al. (2005).

Experimental

Crystal data

C₁₆H₁₇NO₂
M_r = 255.31
Triclinic, $[P \overline 1]$
a = 5.8690 (11) Å
b = 10.9646 (19) Å
c = 11.481 (5) Å
= 77.889 (2)°
= 75.728 (5)°
= 80.262 (9)°
V = 694.7 (4) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 295 K
0.20 × 0.16 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: none
4217 measured reflections
2467 independent reflections
2023 reflections with I > 2(I)
R_int = 0.076

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.135
S = 1.14
2467 reflections
192 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1	0.93	2.48	2.811 (3)	101

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2910 ).

Acknowledgements

We thank the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the CSD system.

References

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organic compounds