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

Wu-Lan Zeng; Jin-Long Suo; Fang-fang Jian

doi:10.1107/S1600536810040675

. 2010 Oct 20;66(Pt 11):o2837. doi: 10.1107/S1600536810040675

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

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

PMCID: PMC3009085 PMID: 21589023

Abstract

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—H⋯O 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,
a = 15.723 (3) Å
b = 10.531 (2) Å
c = 9.2029 (18) Å
β = 90.00 (3)°
V = 1523.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.185
S = 1.11
3493 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040675/hb5678sup1.cif

e-66-o2837-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040675/hb5678Isup2.hkl

e-66-o2837-Isup2.hkl^{(171.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O3ⁱ	0.93	2.58	3.405 (3)	149 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Spiro compounds are widely used in medicine, catalysis and optical material (Lian et al., 2008; Jiang et al., 1998; Wei et al., 2008) owing to their interesting conformational features. We have recently reported the crystal structure of (Z)-3-(3-phenylallylidene)-1,5-dioxaspiro[5.5]undecane-2,4-dione (Zeng et al. 2009). As part of our ongoing studies on new spiro compounds with potentially higher bioactivity, the title compound, (I) (Fig. 1), has been synthesized and its structure is reported here.

The 1,3-dioxane ring is in a distored envelope conformation with atom C11 atom common to the cyclohexane forming the flap. The cyclohexane exists in a distorted chair comformation, with the puckering parameters Q=0.552Å, theta=175.1°, Phi=39.2°; The crystal structure is stabilized by weak intra and intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

A mixture of malonic acid (6.24 g, 0.06 mol) and acetic anhydride(9 ml) in strong sulfuric acid (0.25 ml) was stirred with water at 303 K. After dissolving, cyclohexanone (5.88 g, 0.06 mol) was added dropwise into solution for 1 h. The reaction was allowed to proceed for 4 h. The mixture was cooled and filtered, and then an ethanol solution of 4-methoxybenzaldehyde (8.16 g, 0.06 mol) was added. The solution was then filtered and concentrated. Colourless blocks of (I) were obtained by evaporation of an petroleum ether-ethylacetate (3:1 v/v) solution at room temperature over a period of one week.