1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl 2,3,4-tri-O-acetyl-β-d-xyloside

Runan Tian; Haoriqinbatu; Hongchang Liu; Xiaoming Wang; Yonghua Yang

doi:10.1107/S1600536812004369

. 2012 Feb 10;68(Pt 3):o635. doi: 10.1107/S1600536812004369

1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl 2,3,4-tri-O-acetyl-β-d-xyloside

Runan Tian ^a,^b, Haoriqinbatu ^a, Hongchang Liu ^a, Xiaoming Wang ^a,^*, Yonghua Yang ^a,^*

PMCID: PMC3295429 PMID: 22412540

Abstract

The title compound, C₁₉H₁₉NO₁₀, was obtained from the reaction of α-d-1-bromo-2,3,4-tri-O-acetylxylose with N-hydroxyphthalimide in the presence of potassium carbonate. The asymmetric unit contains two independent molecules, in which the O—CH—O—N torsion angles are 73.0 (4) and 65.0 (4)°. The hexapyranosyl rings adopt chair conformations and the substituent groups are in equatorial positions. In the crystal, molecules are linked by nonclassical C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Yang et al. (2004 ▶); Wang et al. (2008 ▶); Bai et al. (2008 ▶).

Experimental

Crystal data

C₁₉H₁₉NO₁₀
M _r = 421.35
Monoclinic,
a = 11.722 (2) Å
b = 9.2270 (18) Å
c = 19.615 (4) Å
β = 104.52 (3)°
V = 2053.8 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.957, T _max = 0.978
4180 measured reflections
3977 independent reflections
2784 reflections with I > 2σ(I)
R _int = 0.058
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.131
S = 1.00
3977 reflections
541 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004369/rk2311sup1.cif

e-68-0o635-sup1.cif^{(33.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004369/rk2311Isup2.hkl

e-68-0o635-Isup2.hkl^{(194.9KB, 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
C11—H11A⋯O15ⁱ	0.98	2.42	3.339 (6)	157
C22—H22A⋯O1ⁱⁱ	0.96	2.39	3.329 (7)	165
C26—H26A⋯O3ⁱⁱⁱ	0.98	2.54	3.385 (6)	144
C30—H30B⋯O5	0.97	2.56	3.429 (6)	149
C35—H35⋯O5^iv	0.93	2.54	3.294 (8)	138

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

Acknowledgments

We are grateful to the National Natural Science Foundation of China (grant No. 30711041) and the Fundamental Research Funds for the Central Universities (grant No. 1106020824)

supplementary crystallographic information

Comment

In the present work, the structure of 2,3,4-tri-O-acetyl-β-D-xyloside-N-hydroxyphthalimide, I, has been determined (Fig. 1). The asymmetric unit of I contains two independent molecules. The molecules are twisted at the CH–O bonds with the O7–C8–O8–N1 and O17–C29–O18–N2 torsion angles of 73.0 (4)° (molecule 1) and 65.0 (4)° (molecule 2), respectively. The bond lengths and angles in the title molecules show normal values. The hexapyranosyl ring adopts chair conformation (Fig. 1) and the substituented groups are individually planar and occupy equatorial positions (Yang et al., 2004; Wang et al., 2008; Bai et al., 2008).

Experimental

The solution of α-D-1-bromo-2,3,4-tri-O-acetyl-xylose (0.1 mol) and N-hydroxyphthalimide (0.1 mol) in chloroform (100 ml) and water (100 ml) was treated with sodium carbonate (0.1 mol) with triethyl benzyl ammonium chloride in present at room temperature overnight. The chloroform layer was separated, washed with water and allowed to evaporate slowly. The residual 2,3,4-tri-O-acetyl-β-D-xyloside-N- hydroxyphthalimide was then recrystallized to constant melting point (m.p. 455.6-456 K) from ethyl acetate. The purity of the compound was checked and characterized by NMR spectra. Fine block colourless crystals for X-ray diffraction were obtained by slow evaporation of an ethyl acetate at room temperature. ¹H NMR, 500 MHz, CDCl₃, δ: 8.15 (d, J = 9.6 Hz, 1H, Ar–H), 7.85 (d, J = 9.3 Hz, 1H, Ar–H), 5.82(d, J = 8.2 Hz, 1H, G–H), 5.25 (t, J = 9.9 Hz, 1H, G–H), 4.87(t, J = 9.6 Hz, 1H, G–H), 4.62 (t, J = 9.0 Hz, 1H, G–H), 3.80 (m, 2H, G–H), 2.14, 2.12, 2.09 (3s, COCH₃).