(4S,5S)-2-(3-Methoxy­phen­yl)-1,3-dioxolane-4,5-dicarboxamide

De-Cai Wang; Tao Ge; Wen-Yuan Wu; Wei Xu; Zheng Yang

doi:10.1107/S1600536809032991

. 2009 Aug 26;65(Pt 9):o2230. doi: 10.1107/S1600536809032991

(4S,5S)-2-(3-Methoxyphenyl)-1,3-dioxolane-4,5-dicarboxamide

De-Cai Wang ^a,^*, Tao Ge ^a, Wen-Yuan Wu ^b, Wei Xu ^a, Zheng Yang ^a

PMCID: PMC2970133 PMID: 21577629

Abstract

In the title compound, C₁₂H₁₄N₂O₅, the five-membered ring adopts an envelope conformation. In the crystal structure, intermolecular N—H⋯O interactions link the molecules into a three-dimensional network. A weak C—H⋯π interaction is also found.

Related literature

For general background, see: Kim et al. (1994 ▶); Pandey et al. (1997 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₂H₁₄N₂O₅
M _r = 266.25
Orthorhombic,
a = 9.2340 (18) Å
b = 9.852 (2) Å
c = 14.266 (3) Å
V = 1297.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.971, T _max = 0.979
2599 measured reflections
1378 independent reflections
1157 reflections with I > 2σ(I)
R _int = 0.027
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.132
S = 1.33
1378 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032991/hk2731sup1.cif

e-65-o2230-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032991/hk2731Isup2.hkl

e-65-o2230-Isup2.hkl^{(68.1KB, 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
N2—H2B⋯O5ⁱ	0.86	2.33	3.076 (4)	145
N2—H2A⋯O4ⁱ	0.86	2.13	2.926 (4)	153
N1—H1B⋯O2ⁱⁱ	0.86	2.31	3.045 (4)	143
N1—H1A⋯O5ⁱⁱⁱ	0.86	2.20	2.952 (4)	146
C9—H9A⋯Cg1^iv	0.98	2.82	3.640 (4)	141

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C2–C7 ring.

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University for support.

supplementary crystallographic information

Comment

Antitumor platinum drug is one kind of the most effective anticancer agents currently available. (2S,3S)-Diethyl 2,3-O-alkyltartrate analogues are the starting materials for the syntheses of platinum complexes with antitumor activity (Kim et al., 1994) and are also important intermediates in organic syntheses (Pandey et al., 1997). As part of our studies on the syntheses and characterizations of these compounds, we report herein the crystal structure of the title compound.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C2-C7) is, of course, planar, while ring B (O2/O3/C8-C10) adopts envelope conformation with atom O2 displaced by 0.456 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular N-H···O interactions (Table 1) link the molecules into a three-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. A weak C—H···π interaction (Table 1) is also found.

Experimental

For the preparation of the title compound, a mixture of (2S,3S)-diethyl- tartrate (500 mg, 2.43 mmol), 3-methoxybenzaldehyde (331 mg, 2.43 mmol), anhydrous copper(II) sulfate (776 mg, 2.86 mmol) and one drop of methanesulfonic acid in anhydrous toluene (8 ml) was stirred at room temperature for 8 h. Anhydrous magnesium sulfate (30 mg) was added to the reaction mixture, which was then stirred for 20 min. Then, the resulting colorless precipitate was obtained by evaporation and dried in the vacuo (yield; 83%). The obtained colorless product (654 mg, 2 mmol) was dissolved in anhydrous ethanol (40 ml), and a current of dry ammonia, dried by calcium cholride was passed into the reaction mixture at room temperature for 4 h. Then, the reaction mixture was filtered and the resulting product was evaporated to dryness. Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution after four weeks.