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

Zhi Li; Rui Li; Zhen-Yu Ding

doi:10.1107/S1600536809033984

. 2009 Aug 29;65(Pt 9):o2289. doi: 10.1107/S1600536809033984

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

Zhi Li ^a, Rui Li ^a,^*, Zhen-Yu Ding ^a

PMCID: PMC2969915 PMID: 21577681

Abstract

The benzyl ring of the title compound, C₁₇H₁₅NO₄, is twisted away from the plane defined by five atoms of the dioxane ring by 34.83 (4)°. The dioxane ring exhibits a half-boat conformation, with the C atom between the dioxane O atoms 0.571 (8) Å out of the plane through the remainder of the ring. An intramolecular N—H⋯O hydrogen bond may contribute to the stabilization of the planar conformation of the molecule. In the crystal, inversion dimers linked by pairs of C—H⋯O bonds occur.

Related literature

For the synthesis of related compounds, see: Cassis et al. (1985 ▶). For the pharmacological activity of 4(1H)-quinolone structures, see: Ruchelman et al. (2003 ▶).

Experimental

Crystal data

C₁₇H₁₅NO₄
M _r = 297.30
Triclinic,
a = 7.4696 (11) Å
b = 8.0805 (12) Å
c = 12.1240 (18) Å
α = 98.601 (2)°
β = 96.428 (2)°
γ = 92.198 (2)°
V = 717.87 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 153 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
4513 measured reflections
3194 independent reflections
2571 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.110
S = 1.03
3194 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033984/ez2178sup1.cif

e-65-o2289-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033984/ez2178Isup2.hkl

e-65-o2289-Isup2.hkl^{(156.7KB, 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—H1⋯O3	0.920 (18)	1.982 (18)	2.7130 (16)	135.2 (15)
C1—H1C⋯O4ⁱ	0.98	2.60	3.3709 (19)	136

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

4(1H)-Quinolone structures have long attracted pharmacological interest as anticancer agents, anti-malarial agents and reversible (H+/K+) ATPase inhibitors (Ruchelman et al., 2003). Thermolysis of 5-arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones is an effective method to synthesize 4(1H)quinolone derivatives (Cassis et al., 1985).

The benzyl ring is twisted away from the plane defined by the dioxane ring by 34.83 (4)°. In turn, the dioxane ring of the title compound exhibits an envelope conformation, in which the flap atom, the C atom between the dioxane oxygen atoms, is -0.571 (8) Å out of the plane. An intramolecular N—H···O hydrogen bond (Table 1) could lead to the dioxane ring and the aminomethylene group taking up their planar conformation.

Experimental

An ethanol solution (50 ml) of 2,2-dimethyl-1,3-dioxane-4,6-dione (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 naphthalen-1-amine (1.43 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 days.