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Volume 69 
Part 3 
Pages o406-o407  
March 2013  

Received 13 December 2012
Accepted 8 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 147 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.075
Data-to-parameter ratio = 12.2
Details
Open access

2,2'-[(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethane-1,2-diyl]bis(isoindoline-1,3-dione) ethanol monosolvate hemihydrate

aDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6, and bDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
Correspondence e-mail: alough@chem.utoronto.ca

In the title compound, C30H20N2O6·C2H6O·0.5H2O, the solvent water molecule lies on a twofold rotation axis. The dihedral angle between the essentially planar isoindole ring systems [maximum deviations = 0.028 (1) and 0.022 (1) Å] is 47.12 (5)°. The dihedral angle between the benzene rings is 81.32 (7)°. In the crystal, the components are linked into a three-dimensional network via O-H...O hydrogen bonds.

Related literature

For the use of chiral bisphenolic ligands in stereoselective catalysis, see: Noyori et al. (1984[Noyori, R., Tomino, I., Tanimoto, Y. & Nishizawa, M. (1984). J. Am. Chem. Soc. 106, 6709-6716.]); Takaya et al. (1989[Takaya, H., Akutagawa, S. & Noyori, R. (1989). Org. Synth. 67, 20-32.]); Liu & Ding (2005[Liu, Y. & Ding, K. (2005). J. Am. Chem. Soc. 127, 10488-10489.]); Xu et al. (2011[Xu, B., Zhu, S.-F., Xie, X.-L., Shen, J.-J. & Zhou, Q.-L. (2011). Angew. Chem. Int. Ed. Engl. 50, 11483-11486.]); Yamaguchi et al. (2009[Yamaguchi, A., Matsunaga, S. & Shibasaki, M. (2009). J. Am. Chem. Soc. 131, 10842-10843.]); Van den Berg et al. (2002[Van den Berg, M., Haak, R. M., Minnaard, A. J., De Vries, A. H. M., De Vries, J. G. & Feringa, B. L. (2002). Adv. Synth. Catal. 344, 1003-1007.]); So et al. (2012[So, S. M., Mui, L., Kim, H. & Chin, J. (2012). Acc. Chem. Res. 45, 1345-1355.]); Kim, Nguyen et al. (2008[Kim, H., Nguyen, Y., Yen, C. P.-H., Chagal, L., Lough, A. J., Kim, B. M. & Chin, J. (2008). J. Am. Chem. Soc. 130, 12184-12191.]); Kim, So et al. (2008[Kim, H., So, S. M., Chin, J. & Kim, B. M. (2008). Aldrichim. Acta, 41, 77-88.]); For related structures, see: Li et al. (2011[Li, C., Fu, X.-K., Wu, C.-L. & Huang, J. (2011). Acta Cryst. E67, o1483.]); Liu et al. (2011[Liu, Z.-J., Fu, X.-K., Hu, Z.-K., Wu, X.-J. & Wu, L. (2011). Acta Cryst. E67, o1562.]). For analysis of the absolute configration, see: Hooft et al. (2008[Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.]).

[Scheme 1]

Experimental

Crystal data
  • C30H20N2O6·C2H6O·0.5H2O

  • Mr = 559.56

  • Tetragonal, P 41 21 2

  • a = 10.6848 (3) Å

  • c = 47.9935 (17) Å

  • V = 5479.2 (3) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.81 mm-1

  • T = 147 K

  • 0.29 × 0.18 × 0.18 mm

Data collection
  • Bruker Kappa APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.696, Tmax = 0.753

  • 35250 measured reflections

  • 4786 independent reflections

  • 4756 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.075

  • S = 1.12

  • 4786 reflections

  • 391 parameters

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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1895 Friedel pairs

  • Flack parameter: 0.03 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...O1W 0.86 (2) 1.89 (2) 2.7263 (13) 165 (2)
O2-H2O...O5i 0.88 (2) 1.95 (2) 2.8238 (15) 177 (2)
O1S-H1SO...O4 1.06 (4) 1.76 (4) 2.7905 (17) 161 (3)
O1W-H1W...O1Sii 1.06 (3) 1.65 (3) 2.6927 (16) 169 (3)
Symmetry codes: (i) [-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 4}}]; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2082 ).


Acknowledgements

Financial support of this research by the NSERC is gratefully acknowledged. DK gratefully acknowledges the sabbatical program of Dongduk Womens University. The University of Toronto thanks the NSERC Canada for funding.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.  [ISI] [CrossRef] [ChemPort] [details]
Kim, H., Nguyen, Y., Yen, C. P.-H., Chagal, L., Lough, A. J., Kim, B. M. & Chin, J. (2008). J. Am. Chem. Soc. 130, 12184-12191.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kim, H., So, S. M., Chin, J. & Kim, B. M. (2008). Aldrichim. Acta, 41, 77-88.
Li, C., Fu, X.-K., Wu, C.-L. & Huang, J. (2011). Acta Cryst. E67, o1483.  [CSD] [CrossRef] [details]
Liu, Y. & Ding, K. (2005). J. Am. Chem. Soc. 127, 10488-10489.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Liu, Z.-J., Fu, X.-K., Hu, Z.-K., Wu, X.-J. & Wu, L. (2011). Acta Cryst. E67, o1562.  [CSD] [CrossRef] [details]
Noyori, R., Tomino, I., Tanimoto, Y. & Nishizawa, M. (1984). J. Am. Chem. Soc. 106, 6709-6716.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
So, S. M., Mui, L., Kim, H. & Chin, J. (2012). Acc. Chem. Res. 45, 1345-1355.  [ISI] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Takaya, H., Akutagawa, S. & Noyori, R. (1989). Org. Synth. 67, 20-32.  [ChemPort]
Van den Berg, M., Haak, R. M., Minnaard, A. J., De Vries, A. H. M., De Vries, J. G. & Feringa, B. L. (2002). Adv. Synth. Catal. 344, 1003-1007.  [ChemPort]
Xu, B., Zhu, S.-F., Xie, X.-L., Shen, J.-J. & Zhou, Q.-L. (2011). Angew. Chem. Int. Ed. Engl. 50, 11483-11486.  [ISI] [CrossRef] [ChemPort] [PubMed]
Yamaguchi, A., Matsunaga, S. & Shibasaki, M. (2009). J. Am. Chem. Soc. 131, 10842-10843.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o406-o407   [ doi:10.1107/S1600536813003978 ]

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