(4R*,5R*)-Diethyl 2-(4-nitro­phen­yl)-1,3-dioxolane-4,5-dicarboxyl­ate

Chun-Lei Lv; Jian-Hui Chen; Yu-Zhe Zhang; Ding-Qiang Lu; Ping-Kai OuYang

doi:10.1107/S160053681201118X

. 2012 Mar 21;68(Pt 4):o1128. doi: 10.1107/S160053681201118X

(4R,5R)-Diethyl 2-(4-nitrophenyl)-1,3-dioxolane-4,5-dicarboxylate

Chun-Lei Lv ^a,^b, Jian-Hui Chen ^a,^b, Yu-Zhe Zhang ^c, Ding-Qiang Lu ^a,^*, Ping-Kai OuYang ^a

PMCID: PMC3344074 PMID: 22589983

Abstract

In the title compound, C₁₅H₁₇NO₈, the nitro group is essentially coplanar with the aromatic ring [dihedral angle = 6.4 (3) Å]. The five-membered ring has a twist conformation. In the crystal, C—H⋯O interactions link the molecules into a helical chain propagating along [010].

Related literature

For the synthesis of the title compound, see: Kim et al. (1994 ▶). For the use of (2S,3S)-diethyl 2,3-O-alkyltartrate analogues as intermediates in organic synthesis, see: Pandey et al. (1997 ▶). For typical bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₇NO₈
M _r = 339.30
Monoclinic,
a = 12.261 (3) Å
b = 4.5200 (9) Å
c = 15.656 (3) Å
β = 112.27 (3)°
V = 802.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.966, T _max = 0.989
3062 measured reflections
1660 independent reflections
1364 reflections with I > 2σ(I)
R _int = 0.017
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.142
S = 1.01
1660 reflections
218 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.16 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: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201118X/su2384sup1.cif

e-68-o1128-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201118X/su2384Isup2.hkl

e-68-o1128-Isup2.hkl^{(81.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201118X/su2384Isup3.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
C12—H12A⋯O8ⁱ	0.96	2.50	3.356 (7)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Liu Bo Nian from Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for their support.

supplementary crystallographic information

Comment

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

The molecular structure of the title compound is shown in Fig. 1. The bond lengths are within normal ranges (Allen et al., 1987). The nitro group (N1/O1/O2) is essentially coplanar with the aromatic ring (C1-C6) being inclined to it by 6.4 (3)°. The five-membered ring (O3/O4/C7-C9) has a twist conformation on bond O4-C8.

In the crystal, a C—H···O interaction (Table 1) links the molecules to form a a helical chain propagating along the b axis direction (Fig. 2).

Experimental

4-Nitrobenzaldehyde (299 mg, 1.98 mmol), (2S,3S)-diethyltartrate (378 mg, 1.84 mmol) and cyclohexane (10 ml) were placed in a round-bottomed flask, and 30 mg of 4-methylbenzenesulfonic acid was added. The flask was fitted with a water distributor. The mixture was heated under reflux for 4 h. The reaction mixture was then added dropwise to water (600 ml) with vigorous stirring. A pale yellow precipitate was obtained, filtered off and dried in vacuo. Colourless block-like crystals, suitable for X-ray analysis, were obtained by slow evaporation of a methanol solution after 4 weeks.