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Volume 66 
Part 11 
Page o2790  
November 2010  

Received 24 September 2010
Accepted 6 October 2010
Online 9 October 2010

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Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.037
wR = 0.114
Data-to-parameter ratio = 15.1
Details
Open access

Oleanolic acid ethanol monosolvate

Anna Froelicha and Andrzej K. Gzellab*

aDepartment of Organic Chemistry, Poznan University of Medical Sciences, ul. Grunwaldzka 6, 60-780 Poznan, Poland, and bFaculty of Pharmacy, Ludwik Rydygier Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Torun, ul. M. Curie Sklodowskiej 9, 85-094 Bydgoszcz, Poland
Correspondence e-mail: akgzella@ump.edu.pl

Crystals of the title compound (systematic name: 3[beta]-hydroxyolean-12-en-28-oic acid ethanol monosolvate), C30H48O3·C2H5OH, were obtained from unsuccessful co-crystallization trials. The asymmetric unit contains two symmetry-independent oleanolic acid molecules, as well as two ethanol solvent molecules. Intermolecular O-H...O hydrogen bonds stabilize the crystal packing. In the oleanolic acid molecules, ring C has a slightly distorted envelope conformation, while rings A, B, D and E adopt chair conformations and rings D and E are cis-fused. Both independent ethanol molecules are orientationally disordered [occupancy ratios of 0.742 (8):0.258 (8) and 0.632 (12):0.368 (12).

Related literature

For the biological activity of oleanolic acid and its derivatives, see: Liu (1995[Liu, J. (1995). J. Ethnopharmacol. 49, 57-68.], 2005[Liu, J. (2005). J. Ethnopharmacol. 100, 92-94.]). For 1a,3a-dimethylcyclohexane, see: Spirlet et al. (1980[Spirlet, M. R., Dupont, L., Dideberg, O. & Kapundu, M. (1980). Acta Cryst. B36, 1593-1598.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C30H48O3·C2H6O

  • Mr = 502.75

  • Monoclinic, P 21

  • a = 16.3616 (14) Å

  • b = 7.2587 (5) Å

  • c = 25.786 (2) Å

  • [beta] = 107.500 (9)°

  • V = 2920.7 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.57 mm-1

  • T = 130 K

  • 0.34 × 0.11 × 0.08 mm
Data collection

  • Oxford Diffraction SuperNova Atlas diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.901, Tmax = 1.000

  • 21878 measured reflections

  • 11079 independent reflections

  • 10744 reflections with I > 2[sigma](I)

  • Rint = 0.025
Refinement

  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.114

  • S = 1.09

  • 11079 reflections

  • 732 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4907 Friedel pairs

  • Flack parameter: 0.01 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1BA-H1BO...O1B 0.84 (3) 1.81 (3) 2.652 (2) 177 (3)
O1AA-H1AO...O1A 0.82 1.98 2.794 (7) 170
O1A-H11...O2B 0.85 (3) 2.02 (3) 2.8503 (18) 168 (3)
O1B-H12...O2Ai 0.83 (3) 1.89 (3) 2.7204 (18) 174 (3)
O3A-H31...O1BAii 0.95 (3) 1.61 (3) 2.552 (2) 177 (3)
O3B-H32...O1AA 0.96 (4) 1.64 (4) 2.575 (7) 163 (4)
C15A-H15A...O3A 0.97 2.58 3.1222 (19) 116
C15B-H15C...O2B 0.97 2.60 3.152 (2) 116
C23A-H23A...O2B 0.96 2.54 3.375 (2) 145
Symmetry codes: (i) x, y, z-1; (ii) x, y+1, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5364 ).

Acknowledgements

The authors acknowledge financial support from Poznan University of Medical Sciences (grant No. 501-02-03308417-05160-50437).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Liu, J. (1995). J. Ethnopharmacol. 49, 57-68.  [CrossRef] [ChemPort] [PubMed] [ISI]
Liu, J. (2005). J. Ethnopharmacol. 100, 92-94.  [ISI] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Spirlet, M. R., Dupont, L., Dideberg, O. & Kapundu, M. (1980). Acta Cryst. B36, 1593-1598.  [CrossRef] [details] [ISI]

Acta Cryst (2010). E66, o2790  [ doi:10.1107/S1600536810039929 ]

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