1,2;5,6-Di-O-isopropyl­idene-3-C-nitro­methyl-α-d-allofuran­ose

Zhang, Q.; Ke, Y.; Cheng, W.; Li, P.; Liu, H.

doi:10.1107/S1600536811017314

Volume 67
Part 6
Page o1402
June 2011

Received 4 May 2011
Accepted 7 May 2011
Online 14 May 2011

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.008 Å
R = 0.061
wR = 0.164
Data-to-parameter ratio = 7.9
Details

1,2;5,6-Di-O-isopropylidene-3-C-nitromethyl--D-allofuranose

Qiurong Zhang,^a Yu Ke,^a Weiyan Cheng,^a Pengyun Li ^a and Hongmin Liu ^a ^*

^aNew Drug Reseach & Development Center, Zhengzhou University, Zhengzhou 450001, People's Republic of China
Correspondence e-mail: zqr409@126.com

The molecule of the title compound, C₁₃H₂₁NO₈, consists of two methylenedioxy rings and one tetrahydrofuran ring. In the crystal, intermolecular O-HO hydrogen bonds link the molecules into helical chains running along the 6₁ screw axis. Weak intermolecular C-HO hydrogen bonds help to stabilize the crystal packing. Voids of 245 Å³ per unit cell occur.

Related literature

For details of the synthesis, see: Saito et al. (2002). For recent studies of the biological activity of azasugars, see: Loiseleur et al. (2007); Rahman et al. (2008).

Experimental

Crystal data

C₁₃H₂₁NO₈
M_r = 319.31
Hexagonal, P 6₁
a = 13.2581 (19) Å
c = 16.462 (3) Å
V = 2506.0 (7) Å³
Z = 6
Mo K radiation
= 0.11 mm^-1
T = 291 K
0.24 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS-IV diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.975, T_max = 0.979
8380 measured reflections
1612 independent reflections
1534 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.164
S = 1.08
1612 reflections
205 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.43 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3EO6ⁱ	0.90 (8)	1.95 (8)	2.814 (5)	161 (7)
C1-H1AO3ⁱⁱ	0.98	2.37	3.258 (4)	151
C5-H5AO1ⁱⁱⁱ	0.98	2.50	3.320 (4)	141
Symmetry codes: (i) $[x-y, x, z+{\script{1\over 6}}]$ ; (ii) $[x-y+1, x+1, z+{\script{1\over 6}}]$ ; (iii) $[-x+y, -x+1, z-{\script{1\over 3}}]$ .

Data collection: R-AXIS-IV Software (Rigaku, 1997); cell refinement: R-AXIS-IV Software; data reduction: R-AXIS-IV Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: TEXSAN (Molecular Structure Corporation, 1992); software used to prepare material for publication: TEXSAN.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5090 ).

Acknowledgements

We gratefully acknowledge financial support by the National Natural Science Foundation of China (grant No. 20572103).

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Loiseleur, O., Ritson, D., Mafalda, N., Crowley, P., Wagner, T. & Hanessian, S. (2007). J. Org. Chem. 72, 6353-6363.
Molecular Structure Corporation (1992). TEXSAN. MSC, The Woodlands, Texas, USA.
Rahman, S. M. A., Seki, S., Obika, S., Yoshikawa, H., Miyashita, K. & Imanishi, T. (2008). J. Am. Chem. Soc. 130, 4886-4896.
Rigaku (1997). R-AXIS IV Software. Rigaku Corporation, Tokyo, Japan.
Saito, Y., Zevaco, T. A. & Agrofoglio, L. A. (2002). Tetrahedron, 58, 9593-9603.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds