N-[4-(β-d-Allopyranos­yloxy)benzyl­idene]methyl­amine

Lv, S.-M.; Zheng, L.; Zhao, H.; Li, Y.; Yin, S.-F.

doi:10.1107/S1600536809000944

Volume 65
Part 2
Page o290
February 2009

Received 23 December 2008
Accepted 8 January 2009
Online 10 January 2009

Key indicators
Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.004 Å
R = 0.034
wR = 0.093
Data-to-parameter ratio = 7.5
Details

N-[4-(-D-Allopyranosyloxy)benzylidene]methylamine

Shi-Ming Lv,^a Lei Zheng,^a Hui Zhao,^a Ying Li ^a and Shu-Fan Yin ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
Correspondence e-mail: chuandayouji217@163.com

The title compound, C₁₄H₁₉NO₆, was synthesized by the condensation reaction between hecilid (4-formylphenl- [beta] -D-allopyranoside) and methylamine in methanol. In the crystal structure, the pyran ring adopts a chair conformation and adjacent molecules are linked by intermolecular O-HO and O-HN hydrogen bonds, forming a three-dimensional network.

Related literature

For the pharmaceutical and biological properties of hecilid and its derivatives, see: Chen et al. (1981); Sha & Mao (1987); Zhu et al. (2006); Yang et al. (2008).

Experimental

Crystal data

C₁₄H₁₉NO₆
M_r = 297.30
Monoclinic, P 2₁
a = 6.721 (4) Å
b = 7.751 (3) Å
c = 14.119 (4) Å
= 91.46 (3)°
V = 735.3 (6) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 292 (2) K
0.48 × 0.46 × 0.44 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
1479 measured reflections
1469 independent reflections
1325 reflections with I > 2(I)
R_int = 0.004
3 standard reflections every 120 reflections intensity decay: 0.8%

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.093
S = 1.09
1469 reflections
195 parameters
1 restraint
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2OO5ⁱ	0.82	2.02	2.742 (3)	147
O3-H3OO2ⁱⁱ	0.82	2.14	2.942 (3)	165
O4-H4OO2ⁱⁱⁱ	0.82	2.02	2.824 (3)	167
O5-H5ON1^iv	0.82	1.91	2.723 (3)	170
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) x, y+1, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: DIFRAC (Gabe et al., 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2284 ).

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

Chen, W. S., Lu, S. D. & Eberhard, B. (1981). Liebigs Ann. Chem. 10, 1893-1897.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.
Gabe, E. J., White, P. S. & Enright, G. D. (1993). DIFRAC. Pittsburgh Meeting Abstract, PA 104. American Crystallographic Association, Buffalo, New York, USA.
Sha, J. Z. & Mao, H. K. (1987). Chin. Pharm. Bull. 22, 21-27.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, H. J., Hu, C., Li, Y. & Yin, S. F. (2008). Chin. J. Org. Chem. 28, 899-902.
Zhu, Q. L., Tang, Q., Li, Y. & Yin, S. F. (2006). Chin. J. Org. Chem. 26, 1264-1267.

organic compounds