[Journal logo]

Volume 69 
Part 7 
Pages o1155-o1156  
July 2013  

Received 18 June 2013
Accepted 20 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Some non-H atoms missing,
R = 0.036
wR = 0.095
Data-to-parameter ratio = 16.9
Details
Open access

Pallidol hexaacetate ethyl acetate monosolvate

aSchool of Agriculture, Food and Wine, The University of Adelaide, Waite Campus, PMB 1, Glen Osmond, SA 5064, Australia,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

The entire molecule of pallidol hexaacetate {systematic name: (±)-(4bR,5R,9bR,10R)-5,10-bis[4-(acetyloxy)phenyl]-4b,5,9b,10-tetrahydroindeno[2,1-a]indene-1,3,6,8-tetrayl tetraacetate} is completed by the application of twofold rotational symmetry in the title ethyl acetate solvate, C40H34O12·C4H8O2. The ethyl acetate molecule was highly disordered and was treated with the SQUEEZE routine [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155]; the crystallographic data take into account the presence of the solvent. In pallidol hexaacetate, the dihedral angle between the fused five-membered rings (r.m.s. deviation = 0.100 Å) is 54.73 (6)°, indicating a significant fold in the molecule. Significant twists between residues are also evident as seen in the dihedral angle of 80.70 (5)° between the five-membered ring and the pendent benzene ring to which it is attached. Similarly, the acetate residues are twisted with respect to the benzene ring to which they are attached [C-O(carboxy)-C-C torsion angles = -70.24 (14), -114.43 (10) and -72.54 (13)°]. In the crystal, a three-dimensional architecture is sustained by C-H...O interactions which encompass channels in which the disordered ethyl acetate molecules reside.

Related literature

For synthetic protocols, see: Takaya et al. (2005[Takaya, Y., Terashima, K., Ito, J., He, Y.-H., Tateoka, M., Yamaguchi, N. & Niwa, M. (2005). Tetrahedron, 61, 10285-10290.]); Moss et al. (2013[Moss, R., Mao, Q., Taylor, D. K. & Saucier, C. (2013). Rapid Commun. Mass Spectrom. DOI: 10.1002/rcm.6636.]). For the spectroscopic characteristics of pallidol hexaacetate, see: Khan et al. (1986[Khan, M. A., Nabi, S. G., Prakash, S. & Zaman, A. (1986). Phytochemistry, 25, 1945-1948.]).

[Scheme 1]

Experimental

Crystal data
  • C40H34O12·C4H8O2

  • Mr = 794.78

  • Monoclinic, C 2/c

  • a = 13.1495 (1) Å

  • b = 12.7439 (1) Å

  • c = 24.0386 (2) Å

  • [beta] = 97.186 (1)°

  • V = 3996.65 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.83 mm-1

  • T = 100 K

  • 0.30 × 0.10 × 0.10 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.790, Tmax = 0.922

  • 27173 measured reflections

  • 4029 independent reflections

  • 3714 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.095

  • S = 1.02

  • 4029 reflections

  • 238 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10...O6i 1.00 2.51 3.5053 (14) 179
C15-H15...O4ii 0.95 2.59 3.4834 (12) 158
C20-H20A...O6iii 0.98 2.52 3.2708 (15) 133
C20-H20B...O2ii 0.98 2.28 3.2318 (16) 162
Symmetry codes: (i) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iii) [-x+2, y, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SU2614 ).


Acknowledgements

This project was supported in part by the School of Agriculture, Food and Wine, The University of Adelaide, and by Australia's grape-growers and winemakers through their investment body, the Grape and Wine Research and Development Corporation, with matching funds from the Australian Government. QM thanks the Faculty of Science for a PhD scholarship. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM·C/HIR-MOHE/SC/03).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Khan, M. A., Nabi, S. G., Prakash, S. & Zaman, A. (1986). Phytochemistry, 25, 1945-1948.  [CrossRef] [ChemPort] [Web of Science]
Moss, R., Mao, Q., Taylor, D. K. & Saucier, C. (2013). Rapid Commun. Mass Spectrom. DOI: 10.1002/rcm.6636.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Takaya, Y., Terashima, K., Ito, J., He, Y.-H., Tateoka, M., Yamaguchi, N. & Niwa, M. (2005). Tetrahedron, 61, 10285-10290.  [Web of Science] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1155-o1156   [ doi:10.1107/S160053681301708X ]

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.