(IUCr) (11R)-13-[2-(4-Hydroxyphenyl)ethylamino]-4,5-epoxy-11,13-dihydrocostunolide monohydrate

Volume 64
Part 3
Page o644
March 2008

Received 25 January 2008
Accepted 5 February 2008
Online 29 February 2008

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.041
wR = 0.113
Data-to-parameter ratio = 12.8
Details

(11R)-13-[2-(4-Hydroxyphenyl)ethylamino]-4,5-epoxy-11,13-dihydrocostunolide monohydrate

Shama. Nasim,^a Sean Parkin ^b and Peter A. Crooks ^a ^*

^aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA, and ^bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA
Correspondence e-mail: pcrooks@email.uky.edu

The title compound (systematic name: 12-{[2-(4-hydroxyphenyl)ethyl]aminomethyl}-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0^2,4]tetradec-7-en-13-one monohydrate), C₂₃H₃₁NO₄·H₂O, was obtained by the reaction of tyramine with parthenolide. The configuration of the new chiral center in the title compound is R, establishing the stereospecificity of the amination reaction. The water molecule is disordered over three positions; the site occupancy factors are 0.45, 0.40 and 0.15.

Related literature

For related literature, see: Allen et al. (1987); Crooks et al. (2005); Desiraju & Steiner (1999); Hewlett et al. (1996); Nasim et al. (2007a,b).

Experimental

Crystal data

C₂₃H₃₁NO₄·H₂O
M_r = 403.50
Monoclinic, P 2₁
a = 10.8307 (7) Å
b = 6.9478 (5) Å
c = 14.4835 (9) Å
= 94.631 (3)°
V = 1086.32 (12) Å³
Z = 2
Cu K radiation
= 0.70 mm^-1
T = 90.0 (2) K
0.25 × 0.10 × 0.03 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS in APEX2; Bruker-Nonius, 2004) T_min = 0.763, T_max = 0.979
13335 measured reflections
3532 independent reflections
3420 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.113
S = 1.07
3532 reflections
276 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.40 e Å^-3
_min = -0.20 e Å^-3
Absolute structure: Flack (1983), 1365 Friedel pairs
Flack parameter: 0.12 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3	0.94 (3)	2.22 (3)	2.979 (3)	137 (2)
O1'-H1'O1W1ⁱ	0.84	1.75	2.568 (4)	164
O1'-H1'O1W2ⁱ	0.84	2.01	2.832 (6)	166
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker-Nonius, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and local procedures.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2375 ).

Acknowledgements

Financial support from the Kentucky Lung Cancer Research Program is gratefully acknowleged.

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.
Bruker-Nonius (2004). APEX2. Bruker-Nonius AXS Inc., Madison, Wisconsin, USA.
Crooks, P. A., Jordan, C. T. & Wei, X. (2005). US Patent Appl. Publ. Cont.-Part. US Ser. No. 888 274.
Desiraju, G. R. & Steiner, T. D. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, p. 13. Oxford University Press.
Hewlett, M. J., Begley, M. J., Groenewegen, W. A., Heptinstall, S., Knight, D. W., May, J., Salan, U. & Toplis, D. (1996). J. Chem. Soc. Perkin Trans. 1, pp. 1979-1986..
Nasim, S., Parkin, S. & Crooks, P. A. (2007a). Acta Cryst. E63, o3922.
Nasim, S., Parkin, S. & Crooks, P. A. (2007b). Acta Cryst. E63, o4274.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds