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Ol Monohydrate organic compounds Acta Crystallographica Section E b = 11.380 (3) A˚ Mo K radiation Structure Reports c = 16.943 (5) A˚ = 0.08 mmÀ1 V = 1559.2 (8) A˚ 3 T = 293 K Online Z =4 0.31 Â 0.13 Â 0.07 mm ISSN 1600-5368 Data collection Bruker SMART CCD area-detector 8291 measured reflections 1b,10a:4b,5a-Diepoxy-7aH-germacran- diffractometer 1759 independent reflections Absorption correction: multi-scan 1281 reflections with I >2(I) 6b-ol monohydrate (SADABS; Sheldrick, 2000) Rint = 0.080 Tmin = 0.757, Tmax = 1.000 Meng-Hui He,a Quan Yangb* and Jie Sunc Refinement 2 2 aSchool of Life Science, Foshan University, Foshan 528231, People’s Republic of R[F >2(F )] = 0.062 H atoms treated by a mixture of 2 China, bSchool of Chinese Medicine, Guangdong Pharmaceutical University, wR(F ) = 0.148 independent and constrained Guangzhou 510006, People’s Republic of China, and cShanghai Institute of Organic S = 1.06 refinement ˚ À3 1759 reflections Ámax = 0.16 e A Chemistry, Chinese Academy of Sciences, Shanghai 20032, People’s Republic of ˚ À3 186 parameters Ámin = À0.15 e A China Correspondence e-mail: [email protected] Received 28 September 2010; accepted 17 November 2010 Table 1 Hydrogen-bond geometry (A˚ , ). Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.006 A˚; D—HÁÁÁAD—H HÁÁÁADÁÁÁAD—HÁÁÁA R factor = 0.062; wR factor = 0.148; data-to-parameter ratio = 9.5. O2—H3ÁÁÁO4i 0.82 2.03 2.819 (4) 160 O4—H4ÁÁÁO2ii 0.94 (6) 1.92 (6) 2.836 (5) 164 (5) O4—H4CÁÁÁO3 0.93 (4) 2.10 (5) 3.013 (4) 166 (4) In the title compound, C15H26O3ÁH2O, a sesquiterpenoid 1 1 1 3 molecule with a germacrene backbone that contains two Symmetry codes: (i) Àx þ 2; Ày þ 2; z À 2; (ii) Àx; y À 2; Àz þ 2. epoxide groups and one hydroxyl group. Intermolecular O— HÁÁÁO hydrogen bonds between the epoxy groups and solvent Data collection: SMART (Bruker, 2007); cell refinement: SAINT water molecules give rise to an infinite three-dimensional (Bruker, 2007); data reduction: SAINT; program(s) used to solve supramolecular structure. structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for Related literature publication: SHELXTL. For the biosystematic and ecological evaluation of the title This work was supported financially by a grant from the compound, see: Al Yousuf et al. (1999). For the isolation, see Guangdong Pharmaceutical University Foundation for Young Li et al. (2009). For the determination of its absolute structure, Teachers. see: Aguilar-Guadarrama & Rios (2004), Moodley et al. (2004). For related structures, see Takahashi et al. (1983), Barrero et al. (1999). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2065). References Aguilar-Guadarrama, A. B. & Rios, M. Y. (2004). J. Nat. Prod. 67, 914–917. Al Yousuf, M. H., Bashir, A. K., Crabb, T. A., Blunden, G. & Yang, M.-H. (1999). Biochem. System. Ecol. 27, 107–109. Barrero, A. F., Herrador, M. M., Quilez, J. F., Alvarez-Manzaneda, R., Portal, D., Gavin, J. A., Gravalos, D. G., Simmonds, M. S. J. & Blaney, W. M. (1999). Phytochemistry, 51, 529–541. Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Li, S. M., Yang, X. W., Li, Y. L., Shen, Y. H., Feng, L., Wang, Y. H., Zeng, H. W., Liu, X. H., Zhang, C. S., Long, C. L. & Zhang, W. D. (2009). Planta Med. 75, 1591–1596. Moodley, N., Mulholland, D. A. & Crouch, N. R. (2004). J. Nat. Prod. 67, 918– Experimental 920. Sheldrick, G. M. (2000). SADABS. University of Go¨ttingen, Germany. Crystal data Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Takahashi, T., Nemoto, H., Tsuji, J. & Miura, I. (1983). Tetrahedron Lett. 24, C15H26O3ÁH2O Orthorhombic, P212121 3485–3488. ˚ Mr = 272.37 a = 8.087 (2) A Acta Cryst. (2010). E66, o3263 doi:10.1107/S1600536810047732 He et al. o3263 supporting information supporting information Acta Cryst. (2010). E66, o3263 [https://doi.org/10.1107/S1600536810047732] 1β,10α:4β,5α-Diepoxy-7αH-germacran-6β-ol monohydrate Meng-Hui He, Quan Yang and Jie Sun S1. Comment Terpenoids are large naturally-occuring organic molecules derived from five-carbon isoprene units assembled and modified in numerous ways. A sesquiterpenoid is a 15-carbon modified multicyclic terpenoid hydrocarbon molecule that differs from one another in its functional groups. The title compound, C15H26O3, H2O, is a sesquiterpenoid molecule with a germacrene backbone that contains two epoxide groups at the 1–10 and 4–5 ring positions and one alcohol group at the C6 position, respectively (Fig. 1). Crystal packing hss been stabilized as a result of a single water molecule that has crystallized in the unit cell giving rise to O—H···O intermolecular hydrogen bonds between the epoxy groups and the adjacent water molecules (Table 1). This forms an infinite 3-D supramolecular structure (Fig. 2). S2. Experimental The title compound was synthesized by the method of Li et al. (2009). It was purified by repeated column chromatography over silica gel, ODS, and sephadex LH-20. It was then dissolved in a mixed solution of chloroform and methanol (ca 5:1). Colorless needle-like crystals were formed by slow evaporation of the solution in air. S3. Refinement All the H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H (methine) distances of 0.98 Å, C—H (methylene) 0.97 Å, C—H (methyl) 0.96Å, and an O—H distance of 0.82 Å, with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(O). A rotating group model was used for the OH group. Acta Cryst. (2010). E66, o3263 sup-1 supporting information Figure 1 The molecular structure of the title compound, showing 30% displacement ellipsoids. Figure 2 Packing diagram of the title compound viewed down the a axis. Dashed lines indicate O—H—O hydrogen bonds. Acta Cryst. (2010). E66, o3263 sup-2 supporting information 1β,10α:4β,5α-Diepoxy-7αH-germacran-6β-ol monohydrate Crystal data C15H26O3·H2O F(000) = 600 −3 Mr = 272.37 Dx = 1.160 Mg m Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å Hall symbol: P 2ac 2ab Cell parameters from 1361 reflections a = 8.087 (2) Å θ = 4.8–39.9° b = 11.380 (3) Å µ = 0.08 mm−1 c = 16.943 (5) Å T = 293 K V = 1559.2 (8) Å3 Prismatic, colorless Z = 4 0.31 × 0.13 × 0.07 mm Data collection Bruker SMART CCD area-detector 8291 measured reflections diffractometer 1759 independent reflections Radiation source: fine-focus sealed tube 1281 reflections with I > 2σ(I) Graphite monochromator Rint = 0.080 φ and ω scans θmax = 26.0°, θmin = 2.2° Absorption correction: multi-scan h = −9→9 (SADABS; Sheldrick, 2000) k = −14→11 Tmin = 0.757, Tmax = 1.000 l = −20→20 Refinement Refinement on F2 Hydrogen site location: inferred from Least-squares matrix: full neighbouring sites R[F2 > 2σ(F2)] = 0.062 H atoms treated by a mixture of independent wR(F2) = 0.148 and constrained refinement 2 2 2 S = 1.06 w = 1/[σ (Fo ) + (0.0727P) ] 2 2 1759 reflections where P = (Fo + 2Fc )/3 186 parameters (Δ/σ)max = 0.005 −3 0 restraints Δρmax = 0.16 e Å −3 Primary atom site location: structure-invariant Δρmin = −0.15 e Å direct methods Extinction correction: SHELXL97 (Sheldrick, Secondary atom site location: difference Fourier 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 map Extinction coefficient: 0.010 (3) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) xyzUiso*/Ueq O1 0.3976 (4) 1.2287 (2) 0.77838 (15) 0.0499 (8) O2 0.3551 (4) 1.2022 (2) 0.59240 (17) 0.0540 (9) H3 0.4081 1.2005 0.5512 0.081* Acta Cryst. (2010). E66, o3263 sup-3 supporting information O3 0.1549 (4) 0.7702 (2) 0.79520 (15) 0.0519 (8) O4 −0.0212 (5) 0.7428 (3) 0.9509 (2) 0.0686 (11) C1 0.2708 (6) 0.8691 (3) 0.7992 (2) 0.0402 (10) H1 0.3781 0.8546 0.7742 0.048* C2 0.2798 (6) 0.9355 (3) 0.8767 (2) 0.0505 (12) H2A 0.3750 0.9079 0.9063 0.061* H2B 0.1818 0.9180 0.9075 0.061* C3 0.2933 (6) 1.0692 (3) 0.8662 (2) 0.0527 (12) H3A 0.1844 1.1006 0.8545 0.063* H3B 0.3303 1.1038 0.9154 0.063* C4 0.4113 (6) 1.1048 (3) 0.8008 (2) 0.0420 (10) C5 0.3410 (5) 1.1380 (3) 0.7247 (2) 0.0396 (10) H5 0.2204 1.1304 0.7220 0.048* C6 0.4256 (5) 1.1207 (3) 0.64782 (19) 0.0402 (10) H6 0.5433 1.1386 0.6542 0.048* C7 0.4075 (5) 0.9917 (3) 0.6206 (2) 0.0432 (11) H7 0.4511 0.9430 0.6635 0.052* C8 0.2216 (5) 0.9560 (4) 0.6100 (2) 0.0482 (11) H8A 0.1534 1.0230 0.6240 0.058* H8B 0.2026 0.9393 0.5546 0.058* C9 0.1633 (7) 0.8502 (4) 0.6583 (2) 0.0534 (12) H9A 0.0630 0.8198 0.6344 0.064* H9B 0.2467 0.7892 0.6547 0.064* C10 0.1297 (5) 0.8741 (3) 0.7439 (2) 0.0427 (10) C11 0.5160 (6) 0.9655
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