5-[(4-Acetyl­phenyl)­aminomethyl­ene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Rui Li; Zhen-Yu Ding; Yu-Quan Wei; Jian Ding

doi:10.1107/S1600536809017425

. 2009 May 14;65(Pt 6):o1297. doi: 10.1107/S1600536809017425

5-[(4-Acetylphenyl)aminomethylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Rui Li ^a,^*, Zhen-Yu Ding ^a, Yu-Quan Wei ^a, Jian Ding ^b

PMCID: PMC2969769 PMID: 21583156

Abstract

In the title compound, C₁₅H₁₅NO₅, the six-membered dioxane ring assumes an envelope conformation with the dimethyl substituted C atom as the flap atom. An intramolecular N—H⋯O interaction is also present. In the crystal structure the molecules are linked via C—H⋯O hydrogen bonds into supramolecular chains along the b axis.

Related literature

For the biological activity of 4(1H)-quinolone structures, see: Ruchelman et al. (2003 ▶). 5-Arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones are key intermediates in the synthesis of 4(1H)quinolone derivatives by thermolysis (Cassis et al., 1985 ▶).

Experimental

Crystal data

C₁₅H₁₅NO₅
M _r = 289.28
Triclinic,
a = 7.102 (3) Å
b = 7.356 (4) Å
c = 13.856 (4) Å
α = 82.79 (4)°
β = 83.19 (4)°
γ = 86.03 (4)°
V = 712.0 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 292 K
0.44 × 0.36 × 0.32 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2894 measured reflections
2621 independent reflections
1399 reflections with I > 2σ(I)
R _int = 0.008
3 standard reflections every 100 reflections intensity decay: 1.8%

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.179
S = 1.03
2621 reflections
197 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809017425/xu2521sup1.cif

e-65-o1297-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017425/xu2521Isup2.hkl

e-65-o1297-Isup2.hkl^{(128.7KB, 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
N1—H1N⋯O4	0.84 (4)	2.05 (3)	2.699 (3)	133 (2)
C1—H1B⋯O3ⁱ	0.96	2.57	3.480 (4)	158
C9—H9⋯O5ⁱ	0.93	2.59	3.429 (4)	150

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This research is financially supported by the State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences.

supplementary crystallographic information

Comment

The 4(1H)quinolone structure plays an extremely important role in the field of pharmaceutical chemistry. These compounds have been used as precursors for anticancer agents, anti-malarial agents and reversible (H+/K+) ATPase inhibitors (Ruchelman et al., 2003). 5-Arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones are the key intermediates which can be used to synthesize the 4(1H)quinolone derivatives by thermolysis (Cassis et al., 1985).

The molecular structure is shown in Fig. 1. The six membered dioxane ring assumes an envelope conformation. The imino group links with the adjacent O atom via O—H···O hydrogen bonding. In the crystal structure the molecules are linked via C—H···O hydrogen bonding into one dimensional supra-molecualr chain along the b axis (Table 1).

Experimental

A methanol solution (50 ml) of Meldrum's acid (1.44 g, 0.01 mol) and methylorthoformate (1.27 g, 0.012 mol) was heated to reflux for 2 h, then the arylamine (1.35 g, 0.01 mol) was added into the above solution. The mixture was heated under reflux for another 8 h and then filtered. Single crystals were obtained from the filtrate after 2 d.