3-(4-Meth­oxy­benzyl­idene)-1,5-dioxa­spiro­[5.5]undecane-2,4-dione

Zeng, W.-L.; Suo, J.-L.; Jian, F.

doi:10.1107/S1600536810040675

Volume 66
Part 11
Page o2837
November 2010

Received 9 October 2010
Accepted 11 October 2010
Online 20 October 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.060
wR = 0.185
Data-to-parameter ratio = 17.6
Details

3-(4-Methoxybenzylidene)-1,5-dioxaspiro[5.5]undecane-2,4-dione

Wu-Lan Zeng,^a Jin-Long Suo ^a and Fang-fang Jian ^b ^*

^aMicroScale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroScale Science Institute, Weifang University, Weifang 261061, People's Republic of China
Correspondence e-mail: wulanzeng@163.com

In the title molecule, C₁₇H₁₈O₅, which was prepared by the reaction of (R)-1,5-dioxaspiro[5.5]undecane-2,4-dione and 4-methoxybenzaldehyde with ethanol, the 1,3-dioxane ring is in a distorted envelope conformation with the spiro C atom forming the flap. The crystal structure is stabilized by weak intermolecular C-HO hydrogen bonds.

Related literature

For background information on spiro-compounds, see: Jiang et al. (1998); Lian et al. (2008); Wei et al. (2008). For a related structure, see: Zeng et al. (2009). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₇H₁₈O₅
M_r = 302.31
Monoclinic, P 2₁ /c
a = 15.723 (3) Å
b = 10.531 (2) Å
c = 9.2029 (18) Å
= 90.00 (3)°
V = 1523.8 (5) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.25 × 0.16 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
14509 measured reflections
3493 independent reflections
2450 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.185
S = 1.11
3493 reflections
199 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8AO3ⁱ	0.93	2.58	3.405 (3)	149 (3)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5678 ).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 6, 1354-1358.
Jiang, Y. Z., Xue, S., Li, Z., Deng, J. G., Mi, A. Q. & Albert, S. C. C. (1998). Tetrahedron, 9, 3185-3189.
Lian, Y., Guo, J. J., Liu, X. M. & Wei, R. B. (2008). Chem. Res. Chin. Univ. 24, 441-444.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wei, R. B., Liu, B., Liu, Y., Guo, J. J. & Zhang, D. W. (2008). Chin. J. Org. Chem. 28, 1501-1514.
Zeng, W.-L., Zhang, H.-X. & Jian, F.-F. (2009). Acta Cryst. E65, o2586.

organic compounds