Neoaustin: a meroterpene produced by Penicillium sp. Julio Zukerman-Schpector, a * Stella H. Maganhi, a Taicia Pacheco Fill, a Edson Rodrigues-Fo a and Ignez Caracelli b a Department of Chemistry, Universidade Federal de Sa ˜o Carlos, 13565-905 Sa ˜o Carlos, SP, Brazil, and b Physics Department, Universidade Estadual Paulista, "Ju ´ lio de Mesquita Filho", UNESP, 17033-360 Bauru, SP, Brazil Correspondence e-mail: julio@power.ufscar.br Received 15 February 2009; accepted 23 February 2009 Key indicators: single-crystal X-ray study; T = 290 K; mean (C–C) = 0.003 A ˚; R factor = 0.039; wR factor = 0.106; data-to-parameter ratio = 9.2. The title meroterpene neoaustin {systematic name: (1 0 S,2 0 R,3S,7 0 R,9 0 S,11 0 S,12 0 R)-11 0 -hydroxy-2,2,2 0 ,9 0 ,12 0 -penta- methyl-6 0 ,15 0 -dimethylene-2,6-dihydro-13 0 -oxaspiro[pyran- 3,5 0 -tetracyclo[7.5.1.0 1,11 .0 2,7 ]pentadecane]-6,10 0 ,14 0 -trione}, C 25 H 30 O 6 , comprises five rings, three six-membered and two five-membered. The absolute configuration was established based on [ D ] = +166.91 (c 1.21, CH 2 Cl 2 ). In the crystal, the molecules are connected into a supramolecular helical chain via O—HO hydrogen bonds reinforced by C—HO contacts. Related literature For related literature, see: dos Santos & Rodrigues-Fo (2002, 2003); Maganhi et al. 2009. For ring conformation analysis, see: Cremer & Pople (1975); Iulek & Zukerman-Schpector (1997). Experimental Crystal data C 25 H 30 O 6 M r = 426.49 Orthorhombic, P2 1 2 1 2 1 a = 11.2152 (4) A ˚ b = 13.2870 (5) A ˚ c = 14.3914 (7) A ˚ V = 2144.55 (15) A ˚ 3 Z =4 Mo Kradiation = 0.09 mm 1 T = 290 K 0.49 0.39 0.21 mm Data collection Bruker APEXII CCD area-detector diffractometer Absorption correction: none 18157 measured reflections 2622 independent reflections 2453 reflections with I >2(I) R int = 0.048 Refinement R[F 2 >2(F 2 )] = 0.039 wR(F 2 ) = 0.106 S = 1.07 2622 reflections 286 parameters H-atom parameters constrained Á max = 0.17 e A ˚ 3 Á min = 0.13 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—HA D—H HA DA D—HA O4—H1O4O2 i 0.82 2.06 2.852 (3) 162 C5—H5O3 ii 0.93 2.63 3.386 (3) 139 Symmetry codes: (i) x 1 2 ; y þ 3 2 ; z þ 2; (ii) x þ 1 2 ; y þ 3 2 ; z þ 2. Data collection: APEX2, COSMO and BIS (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al. , 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995). We thank FAPESP, CNPq and CAPES for financial support. Publication costs were met by FAPESP (Proc. 2008/02531–5). Professor R. A. Burrow of the Federal University of Santa Maria is gratefully acknowledged for helping with the collec- tion of the intensity data. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2374). References Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Bruker (2006). APEX2, COSMO, BIS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Iulek, J. & Zukerman-Schpector, J. (1997). Qui. Nova, 20, 433–434. Maganhi, S. H., Fill, T. P., Rodrigues-Fo, E., Caracelli, I. & Zukerman- Schpector, J. (2009). Acta Cryst. E65, o221. Nardelli, M. (1995). J. Appl. Cryst. 28, 659. Santos, R. M. G. dos & Rodrigues-Fo, E. (2002). Phytochemistry, 61, 907–912. Santos, R. M. G. dos & Rodrigues-Fo, E. (2003). J. Braz. Chem. Soc. 14, 722– 727. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. organic compounds o612 Zukerman-Schpector et al. doi:10.1107/S1600536809006618 Acta Cryst. (2009). E65, o612 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368