Carb­oxy­methyl ursolate monohydrate

Zhong, Y.; Dai, Z.H.; Teng, Y.B.; Wu, B.; Zhou, J.P.

doi:10.1107/S1600536811001619

Volume 67
Part 2
Page o428
February 2011

Received 1 January 2011
Accepted 11 January 2011
Online 15 January 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.048
wR = 0.134
Data-to-parameter ratio = 15.6
Details

Carboxymethyl ursolate monohydrate

Yan Zhong,^a,^b ZhaoHui Dai,^c YanBo Teng,^c Bin Wu ^c and JianPing Zhou ^a ^*

^aSchool of Pharmacy, China Pharmaceutical University, Tongjiaxiang No. 24 Nanjing, Nanjing 210009, People's Republic of China,^bSchool of Chemistry and Chemical Engineering, Southeast University, Sipailou No. 2 Nanjing, Nanjing 210096, People's Republic of China, and ^cSchool of Pharmacy, Nanjing Medical University, Hanzhong Road No.140 Nanjing, Nanjing 210029, People's Republic of China
Correspondence e-mail: wjy090202@yahoo.com.cn

In the title compound, C₂₈H₅₀O₅·H₂O, all of the six-membered rings of the pentacyclic triterpene skeleton adopt chair conformations. In the crystal, molecules are linked by O-HO and C-HO hydrogen bonds.

Related literature

For the synthesis, see: Wen et al. (2006). The crystal structure of ursolic acid is known from its ethanol solvate, see: Simon et al. (1992). For methyl uroslate-3-bromoacetate, see: Stout & Stevens (1963). For methyl ursolate-3-p-bromobenzoate, see: Paton & Paul (1979). For background to ursolic acid derivatives and their biological activity, see: Es-saady et al. (1996). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₃₂H₅₀O₅·H₂O
M_r = 532.74
Monoclinic, P 2₁
a = 13.338 (3) Å
b = 8.1010 (16) Å
c = 14.311 (3) Å
= 106.26 (3)°
V = 1484.5 (5) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.976, T_max = 0.992
5692 measured reflections
5446 independent reflections
4536 reflections with I > 2(I)
R_int = 0.025
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.134
S = 1.00
5446 reflections
350 parameters
1 restraint
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
OW-HWBO2ⁱ	0.85	2.41	2.839 (3)	112
OW-HWBO4ⁱ	0.85	2.58	3.365 (3)	154
O1-H1AO4ⁱⁱ	0.82	1.98	2.758 (3)	159
OW-HWAO1ⁱⁱⁱ	0.86	1.88	2.681 (3)	154
O5-H5BOW	0.85	1.74	2.575 (3)	165
C12-H12AOWⁱ	0.93	2.57	3.455 (3)	159
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (ii) x+1, y-1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5787 ).

Acknowledgements

The authors acknowledge support from the Natural Science Fundation of Jiangsu Province (No. BK2010538). The authors also thank Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for collecting the crystallographic data.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Es-saady, D., Simon, A., Ollier, M., Maurizis, J. C., Chulia, A. J. & Delage, C. (1996). Cancer Lett. 106, 193-197.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Paton, W. F. & Paul, I. C. (1979). Cryst. Struct. Commun. 8, 207-211.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Simon, A., Delage, C., Saux, M., Chulia, A. J., Najid, A. & Rigaud, M. (1992). Acta Cryst. C48, 726-728.
Stout, G. H. & Stevens, K. L. (1963). J. Org. Chem. 28, 1259-1262.
Wen, X.-A., Zhang, P., Liu, J., Zhang, L.-Y., Wu, X.-M., Ni, P.-Z. & Sun, H.-B. (2006). Bioorg. Med. Chem. Lett. 16, 722-726.

organic compounds