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Volume 69 
Part 12 
Pages o1734-o1735  
December 2013  

Received 22 October 2013
Accepted 23 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.002 Å
R = 0.024
wR = 0.061
Data-to-parameter ratio = 10.4
Details
Open access

13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate

aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA, and bDepartment of Chemistry, University of Kentucky, Lexington KY 40506, USA
Correspondence e-mail: pacrooks@uams.edu

The title compound, C18H24N2O4·H2O {systematic name: (1aR,7aS,8R,10aS,10bS,E)-5-hy­droxy­methyl-8-[(1H-imidazol-1-yl)meth­yl]-1a-methyl-2,3,6,7,7a,8,10a,10b-octa­hydro­oxireno[2',3':9,10]cyclo­deca­[1,2-b]furan-9(1aH)-one monohydrate}, an imidazole derivative of melampomagnolide B was synthesized under Michael addition conditions. The mol­ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The inter­nal double bond of the ten-membered ring identifies it as the cis or E isomer. The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O-H...O, O-H...N and weak C-H...O hydrogen bonds link the mol­ecules (along with water) into sheets parallel to the bc plane.

Related literature

For the biological activity of similar compounds, see: El-Feraly (1984[El-Feraly, F. S. (1984). Phytochemistry, 23, 2372-2374.]); Macias et al. (1992[Macias, F. A., Galindo, J. C. G. & Massanet, G. M. (1992). Phytochemistry, 31, 1969-1977.]); Nasim et al. (2011[Nasim, S., Pei, S. S., Hagan, F. K., Jordan, C. T. & Crooks, P. A. (2011). Bioorg. Med. Chem. 19, 1515-1519.]); Nasim & Crooks (2008[Nasim, S. & Crooks, P. A. (2008). Bioorg. Med. Chem. Lett. 18, 3870-3873.]). For the structures of similar compounds, see; Neelakantan et al. (2009[Neelakantan, S., Nasim, S., Guzman, M. L., Jordan, C. T. & Crooks, P. A. (2009). Bioorg. Med. Chem. Lett. 19, 4346-4349.]); Woods et al. (2011[Woods, J. R., Mo, H., Bieberich, A. A., Alavanja, T. & Colby, D. A. (2011). J. Med. Chem. 54, 7934-7941.]); Neukirch et al. (2003[Neukirch, H., Guerriero, A. & Ambrosio, M. D. (2003). Eur. J. Org. Chem. pp. 3969-3975.]); Gonzalez et al. (1988[Gonzalez, A. G., Galindo, A., Mar Afonso, M., Mansilla, H. & Lopez, M. (1988). Tetrahedron, 44, 4585-4589.]).

[Scheme 1]

Experimental

Crystal data
  • C18H24N2O4·H2O

  • Mr = 350.41

  • Monoclinic, P 21

  • a = 9.8073 (2) Å

  • b = 8.2784 (1) Å

  • c = 10.7741 (2) Å

  • [beta] = 95.015 (1)°

  • V = 871.39 (3) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.80 mm-1

  • T = 90 K

  • 0.25 × 0.20 × 0.04 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.836, Tmax = 0.942

  • 10767 measured reflections

  • 2437 independent reflections

  • 2425 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.061

  • S = 1.04

  • 2437 reflections

  • 235 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

  • Absolute structure: Flack parameter determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])

  • Absolute structure parameter: -0.03 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...N2i 0.84 1.93 2.7491 (17) 164
C13-H13B...O1Wii 0.99 2.45 3.388 (2) 157
C15-H15B...O3iii 0.98 2.55 3.282 (2) 131
C16-H16A...O1Wiv 0.95 2.44 3.370 (2) 167
C17-H17A...O3v 0.95 2.54 3.377 (2) 147
C18-H18A...O1v 0.95 2.57 3.5016 (19) 167
O1W-H1W...O4 0.87 (3) 1.93 (3) 2.7928 (17) 173 (3)
O1W-H2W...O3vi 0.85 (3) 2.14 (3) 2.9534 (19) 162 (2)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) [-x+1, y-{\script{1\over 2}}, -z]; (iii) [-x+2, y+{\script{1\over 2}}, -z+1]; (iv) x, y, z+1; (v) x, y-1, z; (vi) x, y, z-1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL2013.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5362 ).


Acknowledgements

This work was supported by NIH/NCI grant CA158275.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Feraly, F. S. (1984). Phytochemistry, 23, 2372-2374.  [ChemPort]
Gonzalez, A. G., Galindo, A., Mar Afonso, M., Mansilla, H. & Lopez, M. (1988). Tetrahedron, 44, 4585-4589.  [ChemPort]
Macias, F. A., Galindo, J. C. G. & Massanet, G. M. (1992). Phytochemistry, 31, 1969-1977.  [ChemPort]
Nasim, S. & Crooks, P. A. (2008). Bioorg. Med. Chem. Lett. 18, 3870-3873.  [CSD] [CrossRef] [PubMed] [ChemPort]
Nasim, S., Pei, S. S., Hagan, F. K., Jordan, C. T. & Crooks, P. A. (2011). Bioorg. Med. Chem. 19, 1515-1519.  [CrossRef] [ChemPort] [PubMed]
Neelakantan, S., Nasim, S., Guzman, M. L., Jordan, C. T. & Crooks, P. A. (2009). Bioorg. Med. Chem. Lett. 19, 4346-4349.  [CrossRef] [PubMed] [ChemPort]
Neukirch, H., Guerriero, A. & Ambrosio, M. D. (2003). Eur. J. Org. Chem. pp. 3969-3975.  [CrossRef]
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Woods, J. R., Mo, H., Bieberich, A. A., Alavanja, T. & Colby, D. A. (2011). J. Med. Chem. 54, 7934-7941.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1734-o1735   [ doi:10.1107/S1600536813029188 ]

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