[Journal logo]

Volume 69 
Part 12 
Pages o1789-o1790  
December 2013  

Received 28 October 2013
Accepted 5 November 2013
Online 20 November 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.025
wR = 0.067
Data-to-parameter ratio = 13.9
Details
Open access

13-(N,N-Di­methyl­amino)­micheliolide 0.08-hydrate

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

The title compound, C17H27NO3·0.08H2O {sytematic name: (3R,3aS,9R,9aS,9bS)-3-[(di­methyl­amino)­meth­yl]-9-hy­droxy-6,9-dimethyl-3,3a,4,5,7,8,9,9a-octa­hydro­azuleno[4,5-b]furan-2(9bH)-one 0.08-hydrate}, exhibits intra­molecular O-H...O hydrogen bonding to form a ring of graph-set motif S(6). As well as this intra­molecular hydrogen bond with the lactone-ring O atom, the hy­droxy H atom forms an O-H...O hydrogen bond to the low-occupancy partial water mol­ecule [occupancy = 0.078 (2)]. The water mol­ecule is correlated with disorder of the N(CH3)2 group [major-minor occupancy factors are 0.922 (2):0.078 (2)]. The dihedral angle between the mean planes of the trans-fused seven-membered ring and the lactone ring is 4.42 (9)°.

Related literature

For the biological activity of 13-N,N-di­methyl­amino michel­iolide, see: Rodriguez et al. (1976[Rodriguez, E., Towers, G. H. N. & Mitchell, J. C. (1976). Phytochemistry, 15, 1573-1580.]); Sethi et al. (1984[Sethi, V. K., Thappat, R. K., Dhar, K. L. & Atal, C. K. (1984). Planta Med. 50, 364.]); Acosta & Fixher (1993[Acosta, J. & Fixher, N. (1993). J. Nat. Prod. 56, 90-98.]); Zhang et al. (2012[Zhang, Q., Lu, Y., Ding, Y., Zhai, J., Ji, Q., Ma, W., Yang, M., Fan, H., Long, J., Tong, Z., Shi, Y., Jia, Y., Han, B., Zhang, W., Qiu, C., Ma, X., Li, Q., Shi, Q., Zhang, H., Li, D., Zhang, J., Lin, J., Li, L. Y., Gao, Y. & Chen, Y. (2012). J. Med. Chem. 55, 8757-8769.]). For the crystal structure of a similar mol­ecule, see: Acosta et al. (1991[Acosta, J. C., Fronczek, F. R. & Fischer, N. H. (1991). Acta Cryst. C47, 2702-2704.]). The structure was checked with PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and with an R-tensor (Parkin, 2000[Parkin, S. (2000). Acta Cryst. A56, 157-162.]).

[Scheme 1]

Experimental

Crystal data
  • C17H27NO3·0.08H2O

  • Mr = 295.01

  • Orthorhombic, P 21 21 21

  • a = 9.1329 (2) Å

  • b = 10.5227 (2) Å

  • c = 16.7194 (3) Å

  • V = 1606.78 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.66 mm-1

  • T = 90 K

  • 0.18 × 0.16 × 0.12 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). Acta Cryst. A64, 112-122.]) Tmin = 0.854, Tmax = 0.942

  • 20070 measured reflections

  • 2925 independent reflections

  • 2908 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.067

  • S = 1.07

  • 2925 reflections

  • 211 parameters

  • 41 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

  • Absolute structure: Flack parameter determined using 1227 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: -0.01 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O2 0.84 2.35 2.9578 (15) 129
O1W-H1W1...O3i 0.84 2.16 2.845 (12) 139
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}].

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). SADABS. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). SADABS. University of Göttingen, Germany.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). SADABS. University of Göttingen, Germany.]); software used to prepare material for publication: SHELXL2013.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5365 ).


Acknowledgements

This work was supported by the NIH/NCI (grant No. CA158275).

References

Acosta, J. & Fixher, N. (1993). J. Nat. Prod. 56, 90-98.  [PubMed] [Web of Science]
Acosta, J. C., Fronczek, F. R. & Fischer, N. H. (1991). Acta Cryst. C47, 2702-2704.  [CSD] [CrossRef] [IUCr Journals]
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Parkin, S. (2000). Acta Cryst. A56, 157-162.  [CrossRef] [IUCr Journals]
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.  [CrossRef] [ChemPort] [IUCr Journals]
Rodriguez, E., Towers, G. H. N. & Mitchell, J. C. (1976). Phytochemistry, 15, 1573-1580.  [CrossRef] [ChemPort] [Web of Science]
Sethi, V. K., Thappat, R. K., Dhar, K. L. & Atal, C. K. (1984). Planta Med. 50, 364.  [CrossRef] [PubMed] [Web of Science]
Sheldrick, G. M. (2008a). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008b). SADABS. University of Göttingen, Germany.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zhang, Q., Lu, Y., Ding, Y., Zhai, J., Ji, Q., Ma, W., Yang, M., Fan, H., Long, J., Tong, Z., Shi, Y., Jia, Y., Han, B., Zhang, W., Qiu, C., Ma, X., Li, Q., Shi, Q., Zhang, H., Li, D., Zhang, J., Lin, J., Li, L. Y., Gao, Y. & Chen, Y. (2012). J. Med. Chem. 55, 8757-8769.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1789-o1790   [ doi:10.1107/S1600536813030304 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.