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Volume 69 
Part 10 
Pages o1494-o1495  
October 2013  

Received 26 July 2013
Accepted 26 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.078
Data-to-parameter ratio = 8.6
Details
Open access

(3S,3aS,6R,6aR)-2-Oxohexahydrofuro[3,2-b]furan-3,6-diyl dibenzoate

aDipartimento di Scienze Chimiche, Università degli Studi 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, angela.tuzi@unina.it

The title compound, C20H16O7, contains a cis-fused [gamma]-lactone tetrahydrofuran ring system functionalized with two benzoyloxy groups. Both rings adopt an envelope conformation. The molecule assumes an elongated shape and exibits non-crystallographic C2 symmetry. The benzoyloxy groups are almost planar [maximum deviations of 0.0491 (15) and 0.0336 (17) Å for the O atoms] and their mean planes are inclined to one another by 16.51 (4)°. The crystal packing features weak C-H...O interactions. The aryl groups of adjacent molecules are parallel shifted with face-to-face contacts and a shortest intermolecular C...C distance of 3.482 (4) Å.

Related literature

For the use of carbohydrate in the synthesis of complex natural chiral substances, see: Hanessian (1993[Hanessian, S. (1993). Total synthesis of natural products `Chiron approach'. Organic Chemistry Series, edited by J. E. Baldwin. New York: Pergamon Press.]). For mannitol as chiral reagent and as a precursor of biologically active derivatives, see: Masaki et al. (1999[Masaki, Y., Arasaki, H. & Itoh, A. (1999). Tetrahedron Lett. 40, 4829-4832.]); Lohray et al. (1999[Lohray, B. B., Baskaran, S., Rao, B. S., Reddy, B. Y. & Rao, I. N. (1999). Tetrahedron Lett. 40, 4855-4856.]). For oxidative processes mediated by transition metal oxo-species, see: De Champdorè et al.. (1998[De Champdorè, M., Lasalvia, M. & Piccialli, V. (1998). Tetrahedron Lett. 39, 9781-9784.]); Piccialli (2007[Piccialli, V. (2007). Synthesis, pp. 2585-2607.]); Piccialli, Oliviero et al. (2013[Piccialli, V., Oliviero, G., Borbone, N., Centore, R. & Tuzi, A. (2013). Acta Cryst. E69, o879-o880.]); Piccialli, Tuzi et al. (2013[Piccialli, V., Tuzi, A., Oliviero, G., Borbone, N. & Centore, R. (2013). Acta Cryst. E69, o1109-o1110.]). For the catalytic use of chlorochromatoperiodate, see: 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.]); Piccialli et al. (2012[Piccialli, V., Zaccaria, S., Oliviero, G., D'Errico, S., D'Atri, V. & Borbone, N. (2012). Eur. J. Org. Chem. pp. 4293-4305.]). For the synthesis of the precursor, see: Hockett et al. (1946[Hockett, R. C., Fletcher, H. G. Jr, Sheffield, E., Goepp, R. M. Jr & Soltzberg, S. (1946). J. Am. Chem. Soc. pp. 930-935.]).

[Scheme 1]

Experimental

Crystal data
  • C20H16O7

  • Mr = 368.33

  • Orthorhombic, P 21 21 21

  • a = 7.4870 (7) Å

  • b = 10.2050 (14) Å

  • c = 22.232 (2) Å

  • V = 1698.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 K

  • 0.50 × 0.40 × 0.08 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker . (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.947, Tmax = 0.991

  • 8078 measured reflections

  • 2108 independent reflections

  • 1797 reflections with I > 2[sigma](I)

  • Rint = 0.032

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

  • wR(F2) = 0.078

  • S = 1.07

  • 2108 reflections

  • 244 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O6i 1.00 2.34 2.974 (2) 121
C3-H3...O4ii 1.00 2.51 3.356 (3) 142
C10-H10...O7iii 0.95 2.48 3.353 (3) 154
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iii) x, y-1, z.

Data collection: COLLECT (Nonius, 1999[Nonius, B. V. (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: ZP2007 ).


Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico-Fisiche, Università degli Studi di Napoli "Federico II" for X-ray and NMR facilities.

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.
De Champdorè, M., Lasalvia, M. & Piccialli, V. (1998). Tetrahedron Lett. 39, 9781-9784.
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]
Hanessian, S. (1993). Total synthesis of natural products `Chiron approach'. Organic Chemistry Series, edited by J. E. Baldwin. New York: Pergamon Press.
Hockett, R. C., Fletcher, H. G. Jr, Sheffield, E., Goepp, R. M. Jr & Soltzberg, S. (1946). J. Am. Chem. Soc. pp. 930-935.  [CrossRef] [Web of Science]
Lohray, B. B., Baskaran, S., Rao, B. S., Reddy, B. Y. & Rao, I. N. (1999). Tetrahedron Lett. 40, 4855-4856.  [Web of Science] [CrossRef] [ChemPort]
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]
Masaki, Y., Arasaki, H. & Itoh, A. (1999). Tetrahedron Lett. 40, 4829-4832.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Nonius, B. V. (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Piccialli, V. (2007). Synthesis, pp. 2585-2607.  [Web of Science] [CrossRef]
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., Tuzi, A., Oliviero, G., Borbone, N. & Centore, R. (2013). Acta Cryst. E69, o1109-o1110.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Piccialli, V., Zaccaria, S., Oliviero, G., D'Errico, S., D'Atri, V. & Borbone, N. (2012). Eur. J. Org. Chem. pp. 4293-4305.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1494-o1495   [ doi:10.1107/S160053681302391X ]

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