4-Acetyl-3,3-diethyl-5-hydr­oxy-2-morpholino-2,3-dihydro-1-benzofuran

Vega, A.; Ramírez-Rodríguez, O.; Martínez-Cifuentes, M.; Ibañez, A.; Araya-Maturana, R.

doi:10.1107/S1600536808034065

Volume 64
Part 12
Page o2329
December 2008

Received 3 September 2008
Accepted 17 October 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.099
Data-to-parameter ratio = 13.9
Details

4-Acetyl-3,3-diethyl-5-hydroxy-2-morpholino-2,3-dihydro-1-benzofuran

Andrés Vega,^a Oney Ramírez-Rodríguez,^b Maximiliano Martínez-Cifuentes,^b Andrés Ibañez ^c and Ramiro Araya-Maturana ^b ^*

^aUniversidad Andres Bello, Facultad de Ecología y Recursos Naturales, Departamento de Química, Chile,^bDepartamento de Química Orgánica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Chile, and ^cCentro de Investigación Interdisciplinaria, Avanzada en Ciencia de los Materiales, Universidad de Chile, Chile
Correspondence e-mail: raraya@ciq.uchile.cl

In the title compound, C₁₈H₂₅NO₄, the benzofuran ring is almost planar and the morpholino ring displays a chair conformation. The packing of compound has a one-dimensional structure constructed through intermolecular O-HO hydrogen bonds. The conformation is stabilized by intramolecular C-HN and C-HO interactions.

Related literature

For biological activity, see: Araya-Maturana et al. (2002, 2006). For related structures, see: Dusausoy et al. (1973); Filarowski et al. (2005); Huang et al. (2004). For the synthesis, see: Castro et al. (1983). For hydrogen bonding, see: Desiraju (2002). For puckering parameters, see: Cremer & Pople, 1975).

Experimental

Crystal data

C₁₈H₂₅NO₄
M_r = 319.39
Orthorhombic, P b c a
a = 7.7769 (2) Å
b = 19.4256 (5) Å
c = 22.3875 (6) Å
V = 3382.10 (15) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 150 (2) K
0.43 × 0.30 × 0.30 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker 1999) T_min = 0.963, T_max = 0.974
19635 measured reflections
2988 independent reflections
2537 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.099
S = 1.04
2988 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O4ⁱ	0.90 (2)	1.86 (2)	2.7639 (14)	177 (2)
C11-H11AN1	0.98	2.61	3.205 (2)	119
C12-H12AO3	0.99	2.54	3.333 (2)	137
C15-H15CO2	0.98	2.46	3.037 (2)	118
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-NT (Bruker, 1999); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-NT (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-NT.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2104 ).

Acknowledgements

The authors gratefully acknowledge generous financial support from FONDECYT 1071077

References

Araya-Maturana, R., Cardona, W., Cassels, B. K., Delgado-Castro, T., Soto-Delgado, J., Pessoa-Mahana, H., Weiss-Lopez, B., Pavani, M. & Ferreira, J. (2006). Bioorg. Med. Chem. 14, 4664-4669.
Araya-Maturana, R., Delgado-Castro, T., Garate, M., Ferreira, J., Pavani, M., Pessoa-Mahana, H. & Cassels, B. K. (2002). Bioorg. Med. Chem. 10, 3057-3060.
Bruker (1999). SAINT-NT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SMART-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Castro, C. G., Santos, J. G., Valcarce, J. C. & Valderrama, J. A. (1983). J. Org. Chem. 48, 3026-3029.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.
Dusausoy, Y., Protas, J., Besancon, J. & Tirouflet, J. (1973). Acta Cryst. B29, 469-476.
Filarowski, A., Kochel, A., Cieslik, K. & Koll, A. (2005). J. Phys. Org. Chem. 18, 986-993.
Huang, H.-R., Xia, X.-K., She, Z.-G., Lin, Y.-C., Vrijmoed, L. L. P. & Jones, E. B. G. (2004). Acta Cryst. E60, o2509-o2510.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds