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Volume 69 
Part 9 
Pages o1396-o1397  
September 2013  

Received 24 July 2013
Accepted 2 August 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.035
wR = 0.073
Data-to-parameter ratio = 7.8
Details
Open access

(3R,3aR,6R,6aR)-Hexahydrofuro[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, C20H18O6, prepared from D-mannitol by a two-step procedure, is a functionalized fused bis-tetrahydrofuran. In the central fragment, consisting of two fused tetrahydrofuran rings, one O atom and its two adjacent C atoms, a methylene and a bridgehead C atom, are disordered over two sets of sites with an occupancy ratio of 0.735 (9):0.265 (9). In the major component, the ring containing the disordered O atom is a half-chair conformation with twisted methylene and benzoate-substituted C atoms, whereas the other ring has a half-chair or T-form conformation. In the minor component, the ring with the disordered O atom has an envelope conformation, with the O atom as the flap, and the other ring has a half-chair conformation, with the O atom and the other bridgehead CH atom being twisted. The two aromatic rings are inclined to one another by 20.00 (12)°. In the crystal, adjacent molecules are linked via C-H...[pi] interactions, forming chains propagating along [010].

Related literature

For the use of carbohydrates 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 a chiral reagent and for its biologically active derivatives, see: Babjak et al. (2002[Babjak, M., Kapitan, P. & Gracza, T. (2002). Tetrahedron Lett. 43, 6983-6985.]); 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 of oxo-species, see: 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.]); 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 title compound, 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
  • C20H18O6

  • Mr = 354.34

  • Monoclinic, P 21

  • a = 10.0914 (15) Å

  • b = 8.2388 (11) Å

  • c = 10.7592 (10) Å

  • [beta] = 108.913 (10)°

  • V = 846.24 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 173 K

  • 0.50 × 0.20 × 0.10 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.990

  • 7903 measured reflections

  • 2059 independent reflections

  • 1757 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.073

  • S = 1.11

  • 2059 reflections

  • 263 parameters

  • 12 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C15-C20 ring.

D-H...A D-H H...A D...A D-H...A
C1-H1A...Cgi 0.99 2.60 3.419 (3) 149
Symmetry code: (i) x, y+1, 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.]); 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: YK2098 ).


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.  [ISI] [CrossRef] [ChemPort] [details]
Babjak, M., Kapitan, P. & Gracza, T. (2002). Tetrahedron Lett. 43, 6983-6985.  [ISI] [CrossRef] [ChemPort]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.  [ISI] [CrossRef] [ChemPort] [details]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [ISI] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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] [ISI]
Lohray, B. B., Baskaran, S., Rao, B. S., Reddy, B. Y. & Rao, I. N. (1999). Tetrahedron Lett. 40, 4855-4856.  [ISI] [CrossRef] [ChemPort]
Masaki, Y., Arasaki, H. & Itoh, A. (1999). Tetrahedron Lett. 40, 4829-4832.  [ISI] [CSD] [CrossRef] [ChemPort]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
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] [details]
Piccialli, V., Tuzi, A., Oliviero, G., Borbone, N. & Centore, R. (2013). Acta Cryst. E69, o1109-o1110.  [CrossRef] [ChemPort] [details]
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] [details]


Acta Cryst (2013). E69, o1396-o1397   [ doi:10.1107/S1600536813021612 ]

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