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Volume 69 
Part 9 
Pages o1487-o1488  
September 2013  

Received 21 August 2013
Accepted 22 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.139
Data-to-parameter ratio = 15.6
Details
Open access

3,3-Dimethyl-cis-9a,13a-diphenyl-2,3,9a,11,12,13a-hexahydro-1H-benzo[h][1,4]dioxino[2',3':5,6][1,4]dioxino[2,3-f]chromene

aDepartamento de Química, Universidade Federal Rural do Rio de Janeiro, 23851-970 Seropédica, RJ, Brazil,bInstituto de Tecnologia em Fármacos-Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, RJ, Brazil,cDepartment of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland,dCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

In the title dihydrodioxin, C31H28O5, the dioxane ring has a chair conformation, whereas each of the pyran and dioxine rings has an envelope conformation with methylene and quaternary C atoms, respectively, being the flap atoms. The phenyl rings are cis and form a dihedral angle of 82.11 (10)°. The molecular structure is stabilized by C-H...O contacts. In the crystal packing, supramolecular layers parallel to (101) are sustained by C-H...[pi] interactions.

Related literature

For the biological activity of lapachol and its isomers, see: de Almeida (2009[Almeida, E. R. de (2009). Open Nat. Prod. J. 2, 42-47.]); Ferreira et al. (2010[Ferreira, S. B., Gonzaga, D. T. G., Santos, W. C., Araújo, K. G. L. & Ferreira, V. F. (2010). Rev. Virtual Quím. 2, 140-169.]); Medeiros et al. (2010[Medeiros, C. S., Pontes-Filho, N. T., Camara, C. A., Lima-Filho, J. V., Oliveira, P. C., Lemos, S. A., Leal, A. F. G., Brandão, J. O. C. & Neves, R. P. (2010). Braz. J. Med. Biol. Res. 43, 345-349.]); Neves-Pinto et al. (2002[Neves-Pinto, C., Malta, V. R., Pinto, M., do, C., Santos, R. H., de Castro, S. L. & Pinto, A. V. (2002). J. Med. Chem. 45, 2112-2115.]). For reactions of the quinone O atoms in lapachol, see: da Silva et al. (2011[Silva, A. R. da, Herbst, M. H., Ferreira, A. B. B., da Silva, A. M. & Visentin, L. C. (2011). Molecules, 16, 1192-1200.]); Ferreira et al. (2006[Ferreira, V. F., Jorqueira, A., Leal, K. Z., Pimentel, H. R., Seidl, P. R., da Silva, M. N., da Souza, M. C., Pinto, A. V., Wardell, J. L. & Wardell, S. M. S. V. (2006). Magn. Reson. Chem. 44, 481-490.]); Neves-Pinto et al. (2002[Neves-Pinto, C., Malta, V. R., Pinto, M., do, C., Santos, R. H., de Castro, S. L. & Pinto, A. V. (2002). J. Med. Chem. 45, 2112-2115.]). For the preparation of dihydrodioxins, see: Schönberg & Mustafa (1944[Schönberg, A. & Mustafa, A. (1944). J. Chem. Soc. p. 387.]), and for their DNA photo-cleavage, see: Mack et al. (2004[Mack, E. T., Carle, A. B., Liang, J. T.-M., Coyle, W. & Wilson, R. M. (2004). J. Am. Chem. Soc. 126, 15324-15325.]). For the synthesis, see: Summerbell & Berger (1959[Summerbell, R. K. & Berger, D. R. (1959). J. Am. Chem. Soc. 81, 633-639.]). For the crystal structure of [beta]-lapachone, see: Cunha-Filho et al. (2006[Cunha-Filho, M. S. S., Landin, M., Martinez-Pacheco, R. & Dacunha-Marinho, B. (2006). Acta Cryst. C62, o473-o475.]).

[Scheme 1]

Experimental

Crystal data
  • C31H28O5

  • Mr = 480.53

  • Monoclinic, P 21 /n

  • a = 15.1335 (6) Å

  • b = 9.6048 (2) Å

  • c = 16.9739 (6) Å

  • [beta] = 97.384 (1)°

  • V = 2446.77 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 120 K

  • 0.36 × 0.28 × 0.07 mm

Data collection
  • Bruker-Nonius Roper CCD camera on a [kappa]-goniostat diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.831, Tmax = 1.000

  • 23103 measured reflections

  • 5549 independent reflections

  • 3390 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.139

  • S = 1.02

  • 5549 reflections

  • 355 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4A,C5,C6,C6A,C10A,C10B benzene ring.

D-H...A D-H H...A D...A D-H...A
C18-H18...O3 0.95 2.36 3.001 (3) 124
C22-H22...O4 0.95 2.32 2.683 (3) 102
C24-H24...O4 0.95 2.44 3.071 (2) 124
C8-H8...Cg1i 0.95 2.65 3.3134 (19) 128
C15-H15A...Cg1ii 0.99 2.39 3.336 (2) 161
Symmetry codes: (i) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x, -y, -z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5343 ).


Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. BB and JLW thank CAPES (Brazil) for support. Dr Maira Fasciotti, Inmetro (Brazil), is gratefuly acknowledged for the HRMS analysis. Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR-MOHE/SC/12) is also gratefully acknowledged.

References

Almeida, E. R. de (2009). Open Nat. Prod. J. 2, 42-47.  [CrossRef]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cunha-Filho, M. S. S., Landin, M., Martinez-Pacheco, R. & Dacunha-Marinho, B. (2006). Acta Cryst. C62, o473-o475.  [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ferreira, S. B., Gonzaga, D. T. G., Santos, W. C., Araújo, K. G. L. & Ferreira, V. F. (2010). Rev. Virtual Quím. 2, 140-169.  [ChemPort]
Ferreira, V. F., Jorqueira, A., Leal, K. Z., Pimentel, H. R., Seidl, P. R., da Silva, M. N., da Souza, M. C., Pinto, A. V., Wardell, J. L. & Wardell, S. M. S. V. (2006). Magn. Reson. Chem. 44, 481-490.  [CrossRef] [PubMed] [ChemPort]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Mack, E. T., Carle, A. B., Liang, J. T.-M., Coyle, W. & Wilson, R. M. (2004). J. Am. Chem. Soc. 126, 15324-15325.  [CrossRef] [PubMed] [ChemPort]
Medeiros, C. S., Pontes-Filho, N. T., Camara, C. A., Lima-Filho, J. V., Oliveira, P. C., Lemos, S. A., Leal, A. F. G., Brandão, J. O. C. & Neves, R. P. (2010). Braz. J. Med. Biol. Res. 43, 345-349.  [CrossRef] [ChemPort] [PubMed]
Neves-Pinto, C., Malta, V. R., Pinto, M., do, C., Santos, R. H., de Castro, S. L. & Pinto, A. V. (2002). J. Med. Chem. 45, 2112-2115.  [PubMed] [ChemPort]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Schönberg, A. & Mustafa, A. (1944). J. Chem. Soc. p. 387.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Silva, A. R. da, Herbst, M. H., Ferreira, A. B. B., da Silva, A. M. & Visentin, L. C. (2011). Molecules, 16, 1192-1200.  [CrossRef] [PubMed]
Summerbell, R. K. & Berger, D. R. (1959). J. Am. Chem. Soc. 81, 633-639.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1487-o1488   [ doi:10.1107/S1600536813023660 ]

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