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Volume 69 
Part 7 
Pages o1109-o1110  
July 2013  

Received 28 May 2013
Accepted 11 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.047
wR = 0.107
Data-to-parameter ratio = 8.4
Details
Open access

3[beta],6[alpha]-Diacetoxy-5,9[alpha]-dihydroxy-5[alpha]-cholest-7-en-11-one

aDipartimento di Scienze Chimiche, Università di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy, and bDipartimento di Farmacia, Università degli Studi di Napoli 'Federico II', Via D. Montesano 49, 80131 Napoli, Italy
Correspondence e-mail: vinpicci@unina.it, roberto.centore@unina.it

The title compound, C31H48O7, a polyoxygenated steroid, was obtained by chemical oxidation of 7-dehydrocholesteryl acetate. The molecular geometry features trans A/B and C/D junctions at the steroid core with the acetyl groups in the equatorial position and a fully extended conformation for the alkyl side chain. A chair conformation is observed for rings A and C while ring B adopts a half-chair conformation. The five-membered ring D has an envelope conformation, with the C atom bearing the methyl group at the flap. The terminal isopropyl group and one acetyl group are disordered over two sets of sites with 0.774 (8):0.226 (8) and 0.843 (7):0.157 (7) ratios, respectively. An intramolecular S(6) O-H...O hydrogen-bonding motif involving a hydroxy donor and acceptor is observed. In the crystal, chains of molecules running along the b axis are formed via O-H...O hydrogen bonds between hydroxy donors and carbonyl acceptors of the ordered acetyl group, giving rise to a C(14) motif. The chains are wrapped around the 21 screw axes.

Related literature

For general information on the isolation of polyoxygenated steroids from marine source, see: Notaro et al. (1991[Notaro, G., Piccialli, V., Sica, D. & Corriero, G. (1991). J. Nat. Prod. 54, 1570-1575.], 1992[Notaro, G., Piccialli, V., Sica, D. & Pronzato, R. (1992). J. Nat. Prod. 55, 773-779.]). For the synthesis of polyoxygenated steroids, see: Migliuolo et al. (1992[Migliuolo, A., Piccialli, V. & Sica, D. (1992). Steroids, 57, 344-347.]). For new selective oxidation protocols, see: Piccialli et al. (1993[Piccialli, V., Smaldone, D. M. A. & Sica, D. (1993). Tetrahedron, 49, 4211-4228.]); Notaro et al. (1994[Notaro, G., Piccialli, V., Sica, D. & Smaldone, D. M. A. (1994). Tetrahedron, 50, 4835-4852.]); Caserta et al. (2005[Caserta, T., Piccialli, V., Gomez-Paloma, L. & Bifulco, G. (2005). Tetrahedron, 61, 927-939.]); Piccialli, D'Errico et al. (2013[Piccialli, V., D'Errico, S., Borbone, N., Oliviero, G., Centore, R. & Zaccaria, S. (2013). Eur. J. Org. Chem. pp. 1781-1789.]). For recent examples of hydrogen bonding in crystals, see: Centore, Fusco, Jazbinsek et al. (2013[Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm, 15, 3318-3325.]); Centore et al. (2013a[Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.],b[Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.]); Centore, Fusco, Capobianco et al. (2013[Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. doi:10.1002/ejoc.201201653.]). For the structure and packing of the 6[beta] isomeric steroid see: Piccialli, Oliviero et al. (2013[Piccialli, V., Oliviero, G., Borbone, N., Centore, R. & Tuzi, A. (2013). Acta Cryst. E69, o879-o880.]).

[Scheme 1]

Experimental

Crystal data
  • C31H48O7

  • Mr = 532.69

  • Monoclinic, P 21

  • a = 10.964 (2) Å

  • b = 9.155 (1) Å

  • c = 14.740 (2) Å

  • [beta] = 92.98 (1)°

  • V = 1477.5 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.60 × 0.35 × 0.05 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.996

  • 9976 measured reflections

  • 3498 independent reflections

  • 2502 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.107

  • S = 1.07

  • 3498 reflections

  • 414 parameters

  • 43 restraints

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H1D...O1 0.84 (4) 1.89 (4) 2.619 (3) 145 (4)
O1-H1C...O7i 0.76 (4) 2.04 (4) 2.782 (3) 166 (4)
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z].

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2632 ).


Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico-Fisiche, Università degli Studi di Napoli "Federico II".

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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Caserta, T., Piccialli, V., Gomez-Paloma, L. & Bifulco, G. (2005). Tetrahedron, 61, 927-939.  [Web of Science] [CrossRef] [ChemPort]
Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. doi:10.1002/ejoc.201201653.
Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm, 15, 3318-3325.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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]
Migliuolo, A., Piccialli, V. & Sica, D. (1992). Steroids, 57, 344-347.  [CrossRef] [PubMed] [ChemPort]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Notaro, G., Piccialli, V., Sica, D. & Corriero, G. (1991). J. Nat. Prod. 54, 1570-1575.  [CrossRef] [ChemPort] [Web of Science]
Notaro, G., Piccialli, V., Sica, D. & Pronzato, R. (1992). J. Nat. Prod. 55, 773-779.  [CrossRef] [Web of Science]
Notaro, G., Piccialli, V., Sica, D. & Smaldone, D. M. A. (1994). Tetrahedron, 50, 4835-4852.  [CrossRef] [ChemPort] [Web of Science]
Piccialli, V., D'Errico, S., Borbone, N., Oliviero, G., Centore, R. & Zaccaria, S. (2013). Eur. J. Org. Chem. pp. 1781-1789.  [CSD] [CrossRef]
Piccialli, V., Oliviero, G., Borbone, N., Centore, R. & Tuzi, A. (2013). Acta Cryst. E69, o879-o880.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Piccialli, V., Smaldone, D. M. A. & Sica, D. (1993). Tetrahedron, 49, 4211-4228.  [CrossRef] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1109-o1110   [ doi:10.1107/S1600536813016206 ]

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