5'-Hydroxythalidomide (1)

Reagents:(a) Z-Cl, NaHCO3, water, (b) ammonia, methanol, (c) acetic anhydride, reflux, (d) H2/10% Pd/C, ethanol, (e) phthalic anhydride, acetic acid, reflux, (f) p-toluenesulfonic acid, methanol, reflux.
(Ortep drawing)    @Nov. 2003.

This structer was produced by RasMol,
and stucked by GifBuilder (Yves Piguet, 1997)

Paper Crystal Structure of 5'-Hydroxythalidomide In Vivo Metabolite of Thalidomide in Humans.
Doi, M., Ijiri, Y., Akagi, M., Uenishi, M. & Urata, H.
Anal. Sci. 19, x51-52 (2003).    (PDF articles are listed here)

X-Ray Data Summary

formula C13 H10 N2 O5
weight 274.23
space group C2/c
Cell Crystal
a (A) 21.724(2) description plate
b (A) 7.9633(6) colour Colorless
c (A) 13.607(1) size (mm) 0.38x0.30x0.10
a (deg) 90 Dx (g/ml) 1.556
b (deg) 95.924(1) F(000) 1136
g (deg) 90 m (mm^-1) 0.122
volume 2341.4(3) wavelength (A) 0.71073
Z 8
Diffrn measurementRefinementspace
device type Bruker AXS SMART APEX    Flack x parameter ---
Rint 0.0234 parameters 185
T (K) 90 restraints 0
q max (deg) 28.3 R_factor_gt 0.0639
reflections obs. 9927 wR_factor_gt 0.1432
reflections for ref. 2661 .gt. 2s(I) Dr max (e/A^3) 0.560
Dr min (e/A^3) -0.239
Structure D/s max lt.0.001
solutionSHELXS-97 Goodness of fit 1.248
refinementSHELXL-97 fraction for q max  0.954
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