2,2-Dimethyl-5-(2,3,4-trimeth­oxy­benzyl­idene)-1,3-dioxane-4,6-dione

Wu-Lan Zeng

doi:10.1107/S1600536811026201

. 2011 Jul 6;67(Pt 8):o1937. doi: 10.1107/S1600536811026201

2,2-Dimethyl-5-(2,3,4-trimethoxybenzylidene)-1,3-dioxane-4,6-dione

Wu-Lan Zeng ^a,^*

PMCID: PMC3212324 PMID: 22090981

Abstract

The title compound, C₁₆H₁₈O₇, was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and 2,3,4-trimethoxybenzaldehyde. The 1,3-dioxane ring is in a slightly distorted boat conformation. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Zeng (2011a ▶,b ▶).

Experimental

Crystal data

C₁₆H₁₈O₇
M _r = 322.30
Monoclinic,
a = 12.722 (3) Å
b = 9.2669 (19) Å
c = 13.537 (3) Å
β = 98.83 (3)°
V = 1577.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
14870 measured reflections
3613 independent reflections
3073 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.131
S = 1.03
3613 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 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 datablock(s) global, I. DOI: 10.1107/S1600536811026201/lh5270sup1.cif

e-67-o1937-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026201/lh5270Isup2.hkl

e-67-o1937-Isup2.hkl^{(177.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026201/lh5270Isup3.cml

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
C3—H3A⋯O4ⁱ	0.96	2.46	3.392 (2)	163
C16—H16B⋯O5ⁱⁱ	0.96	2.58	3.397 (2)	143

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

In previous papers the crystal structures of 2,2-Dimethyl-5-[(5-methylfuran-2-yl)methylidene]-1,3- dioxane-4,6-dione and (5-(3,4-Dimethylbenzylidene)-2,2- dimethyl-1,3-dioxane-4,6-dione are reported (Zeng. 2011a,b). As part of the search for new Meldrum's acids, the molecular structure of title compound (I) has been synthesized and its crystal structure is reported herein. The crystal structure of the title compound is shown in Fig. 1. The 1,3-dioxane ring exhibits a slightly distorted boat conformation. 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, propan-2-one (3.48 g, 0.06 mol) was added dropwise into the solution for 1 h. The reaction was allowed to proceed for 2 h. The mixture was cooled and filtered, and then an ethanol solution of 2,3,4-trimethoxybenzaldehyde (11.76g,0.06 mol) was added. The solution was then filtered and concentrated. Single crystals were obtained by evaporation of an petroleum ether-ethylacetate (3:1 v/v) solution of (I) at room temperature over a period of several days.