[Journal logo]

Volume 70 
Part 5 
Page o506  
May 2014  

Received 11 March 2014
Accepted 25 March 2014
Online 2 April 2014

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.067
wR = 0.153
Data-to-parameter ratio = 16.1
Details
Open access

(±)-4,12,15,18,26-Penta­hydroxy-13,17-dioxahepta­cyclo­[14.10.0.03,14.04,12.06,11.018,26.019,24]hexa­cosa-1,3(14),6(11),7,9,15,19,21,23-nona­ene-5,25-dione methanol disolvate

aThe Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel
Correspondence e-mail: almog@mail.huji.ac.il

The title compound, C24H14O9·2CH3OH, displays a chair-shaped form. The two di­hydro­indenone ring systems are located above and below the central fused-ring system, the dihedral angles between the mean planes of di­hydro­indenone ring systems and the mean plane of central fused-ring system are 67.91 (5) and 73.52 (4)°, respectively. In the crystal, extensive O-H...O hydrogen bonds, weak C-H...O hydrogen bonds and C-H...[pi] inter­actions link the mol­ecules into a three-dimensional supra­molecular architecture.

Related literature

For an isomer of the title compound possessing a cup-shaped form, see: Mahmood et al. (2011[Mahmood, K., Yaqub, M., Tahir, M. N., Shafiq, Z. & Qureshi, A. M. (2011). Acta Cryst. E67, o910-o911.]). For a related structure, see: Almog et al. (2009[Almog, J., Rozin, R., Klein, A., Shamoilov-Levinton, G. & Cohen, S. (2009). Tetrahedron, 65, 7954-7962.]).

[Scheme 1]

Experimental

Crystal data
  • C24H14O9·2CH4O

  • Mr = 510.44

  • Triclinic, [P \overline 1]

  • a = 8.8243 (13) Å

  • b = 10.3974 (16) Å

  • c = 14.348 (2) Å

  • [alpha] = 72.936 (3)°

  • [beta] = 74.639 (2)°

  • [gamma] = 75.792 (3)°

  • V = 1193.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 295 K

  • 0.20 × 0.13 × 0.08 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • 13982 measured reflections

  • 5549 independent reflections

  • 3395 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.153

  • S = 1.01

  • 5549 reflections

  • 345 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
O1-H1O...O8i 0.82 1.92 2.702 (2) 160
O3-H3O...O5ii 0.82 1.91 2.725 (2) 171
O5-H5O...O10 0.82 1.80 2.610 (3) 171
O7-H7O...O1iii 0.82 2.14 2.916 (2) 158
O9-H9O...O4iv 0.82 1.95 2.751 (2) 166
O10-H10O...O11iv 0.82 (1) 1.85 (2) 2.650 (4) 163 (5)
O11-H11O...O7 0.83 (1) 2.31 (3) 3.010 (3) 142 (4)
O11-H11O...O9 0.83 (1) 2.15 (3) 2.873 (3) 145 (4)
C18-H18...O6iii 0.93 2.56 3.370 (3) 146
C21-H21...O1v 0.93 2.57 3.231 (3) 129
C11-H11...Cgvi 0.93 2.63 3.501 (3) 156
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+2; (iv) -x+1, -y+1, -z+1; (v) x-1, y, z; (vi) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]); software used to prepare material for publication: SHELXL97.


Supporting information for this paper is available from the IUCr electronic archives (Reference: XU5780 ).


Acknowledgements

This project was supported financially by a joint grant from The Israel Atomic Energy Commission and The Israel Council of Higher Education.

References

Almog, J., Rozin, R., Klein, A., Shamoilov-Levinton, G. & Cohen, S. (2009). Tetrahedron, 65, 7954-7962.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mahmood, K., Yaqub, M., Tahir, M. N., Shafiq, Z. & Qureshi, A. M. (2011). Acta Cryst. E67, o910-o911.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o506  [ doi:10.1107/S1600536814006643 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.