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Volume 69 
Part 12 
Pages o1799-o1800  
December 2013  

Received 25 October 2013
Accepted 12 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.084
Data-to-parameter ratio = 16.4
Details
Open access

A P212121 polymorph of (+)-clusianone

aCenter for Natural and Medicinal Product Research, School of Pharmacy, Faculty of Science, University of Nottingham Malaysia Campus, Jalan Broga, 43500 Semenyih, Selangor, Malaysia,bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Malaysia, and cDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, Malaysia
Correspondence e-mail: tengjin.khoo@nottingham.edu.my

The title compound, C33H42O4 [systematic name: (1S,5S,7R)-3-benzoyl-4-hy­droxy-8,8-dimethyl-1,5,7-tris­(3-methyl­but-2-­enyl)bi­cyclo­[3.3.1]nona-3-ene-2,9-dione], has a central bi­cyclo­[3.3.1]nonane-2,4,9-trione surrounded by tetra­prenyl­ated and benzoyl groups. The compound was recrystallized several times in methanol using both a slow evaporation method and with a crystal-seeding technique. This subsequently produced diffraction-quality crystals which crystallize in the ortho­rhom­bic space group P212121, in contrast to a previous report of a structure determination in the Pna21 space group [McCandlish et al. (1976[McCandlish, L. E., Hanson, J. C. & Stout, G. H. (1976). Acta Cryst. B32, 1793-1801.]). Acta Cryst. B32, 1793-1801]. The title compound has a melting point of 365-366 K, and a specific rotation [[alpha]]20 value of +51.94°. A strong intra­molecular O-H...O hydrogen bond is noted. In the crystal, mol­ecules are assembled in the ab plane by weak C-H...O inter­actions.

Related literature

For related structural studies, see: McCandlish et al. (1976[McCandlish, L. E., Hanson, J. C. & Stout, G. H. (1976). Acta Cryst. B32, 1793-1801.]); Santos et al. (1998[Santos, M. H., Speziali, N. L., Nagem, T. J. & Oliveira, T. T. (1998). Acta Cryst. C54, 1990-1992.], 2001[Santos, M. H., Nagem, T. J., Braz-Filho, R., Lula, I. S. & Speziali, N. L. (2001). Magn. Reson. Chem. 39, 155-159.]). For background to Clusiaceae metabolites, see: Monache et al. (1991[Monache, F. D., Monache, G. D. & Gacs-Baitz, E. (1991). Phytochemistry, 30, 2003-2005.]); de Oliveira et al. (1996[Oliveira, C. M. A. de, Porto, A. M., Bittrich, V., Vencato, I. & Marsaioli, A. J. (1996). Tetrahedron Lett. 37, 6427-6430.]). For discussion of polycyclic polyprenylated acyl­phloroglucinols, including their biological properties, see: Piccinelli et al. (2005[Piccinelli, A. L., Cuesta-Rubio, O., Chica, M. B., Mahmood, N., Pagano, B., Pavone, M., Barone, V. & Rastrelli, L. (2005). Tetrahedron, 61, 8206-8211.]); Garnsey et al. (2011[Garnsey, M. R., Matous, J. A., Kwiek, J. J. & Coltart, D. M. (2011). Bioorg. Med. Chem. Lett. 21, 2406-2409.]); Simpkins (2013[Simpkins, N. S. (2013). Chem. Commun. 49, 1042-1051.]).

[Scheme 1]

Experimental

Crystal data
  • C33H42O4

  • Mr = 502.69

  • Orthorhombic, P 21 21 21

  • a = 9.2035 (2) Å

  • b = 13.4629 (2) Å

  • c = 22.9607 (5) Å

  • V = 2844.96 (10) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.59 mm-1

  • T = 100 K

  • 0.21 × 0.14 × 0.08 mm

Data collection
  • Oxford Diffraction Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2002[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.86, Tmax = 0.95

  • 39826 measured reflections

  • 5498 independent reflections

  • 5269 reflections with I > 2.0[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.084

  • S = 0.96

  • 5498 reflections

  • 335 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2383 Friedel pairs

  • Absolute structure parameter: -0.04 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O11-H1...O1 0.98 1.48 2.4227 (14) 158
C27-H273...O1i 0.99 2.63 3.330 (2) 128
C36-H363...O1ii 0.94 2.67 3.523 (2) 151
C8-H81...O11iii 0.95 2.62 3.300 (2) 129
C21-H211...O17iv 0.96 2.70 3.610 (2) 158
Symmetry codes: (i) x-1, y, z; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]; Cooper et al., 2010[Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5270 ).


Acknowledgements

The authors would like to thank the Ministry of Science, Technology and Innovation in Malaysia (MOSTI 02-02-12-SF0055) for providing a grant for this study. Professor C. Moody is thanked for access to instrumentation at the University of Nottingham, UK.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [Web of Science] [CrossRef] [IUCr Journals]
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Garnsey, M. R., Matous, J. A., Kwiek, J. J. & Coltart, D. M. (2011). Bioorg. Med. Chem. Lett. 21, 2406-2409.  [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
McCandlish, L. E., Hanson, J. C. & Stout, G. H. (1976). Acta Cryst. B32, 1793-1801.  [CSD] [CrossRef] [IUCr Journals] [Web of Science]
Monache, F. D., Monache, G. D. & Gacs-Baitz, E. (1991). Phytochemistry, 30, 2003-2005.  [CrossRef]
Oliveira, C. M. A. de, Porto, A. M., Bittrich, V., Vencato, I. & Marsaioli, A. J. (1996). Tetrahedron Lett. 37, 6427-6430.
Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Piccinelli, A. L., Cuesta-Rubio, O., Chica, M. B., Mahmood, N., Pagano, B., Pavone, M., Barone, V. & Rastrelli, L. (2005). Tetrahedron, 61, 8206-8211.  [Web of Science] [CrossRef] [ChemPort]
Santos, M. H., Nagem, T. J., Braz-Filho, R., Lula, I. S. & Speziali, N. L. (2001). Magn. Reson. Chem. 39, 155-159.
Santos, M. H., Speziali, N. L., Nagem, T. J. & Oliveira, T. T. (1998). Acta Cryst. C54, 1990-1992.  [CSD] [CrossRef] [IUCr Journals]
Simpkins, N. S. (2013). Chem. Commun. 49, 1042-1051.  [CrossRef] [ChemPort]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1799-o1800   [ doi:10.1107/S1600536813031036 ]

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