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

Wu-Lan Zeng; Hua-Xiang Zhang; Fang-Fang Jian

doi:10.1107/S1600536809038781

. 2009 Sep 30;65(Pt 10):o2586. doi: 10.1107/S1600536809038781

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

Wu-Lan Zeng ^a, Hua-Xiang Zhang ^a, Fang-Fang Jian ^b,^*

PMCID: PMC2970375 PMID: 21578022

Abstract

In the title compound, C₁₈H₁₈O₄, the 1,3-dioxane ring adopts a distorted envelope conformation with the C atom common to the cyclohexane ring forming the flap. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur.

Related literature

For background information on spiro-compounds, see: Jiang et al. (1998 ▶); Lian et al. (2008 ▶); Wei et al. (2008 ▶).

Experimental

Crystal data

C₁₈H₁₈O₄
M _r = 298.32
Triclinic,
a = 7.1177 (14) Å
b = 9.5506 (19) Å
c = 11.734 (2) Å
α = 106.82 (3)°
β = 100.14 (3)°
γ = 93.35 (3)°
V = 746.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
7448 measured reflections
3401 independent reflections
2309 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.130
S = 1.17
3401 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 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/S1600536809038781/hb5108sup1.cif

e-65-o2586-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038781/hb5108Isup2.hkl

e-65-o2586-Isup2.hkl^{(166.8KB, 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
C10—H10A⋯O2ⁱ	0.97	2.52	3.440 (2)	158

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Spiro compounds are widely used in medicine, catalysis and optical materials (Lian et al., 2008; Jiang et al., 1998; Wei et al., 2008) owing to their interesting conformational features. We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new spiro compounds with potentially higher bioactivity.

The 1,3-dioxane ring is in a distored envelope conformation with atom C11 atom common to the cyclohexane forming the flap. The crystal structure is stabilized by weak 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 303K, 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 (Z)-3-phenylacrylaldehyde (7.92g, 0.06 mol) was added. The solution was then filtered and concentrated. Yellow blocks of (I) were obtained by evaporation of a petroleum ether–ethylacetate (3:1 v/v) solution at room temperature over a period of one week.