7,11,15,28-Tetra­kis[(2-formyl­phen­oxy)methyl]-1,21,23,25-tetra­methyl­resorcin[4]arene cavitand ethyl acetate clathrate at 173 K

Mc Kay, M.G.; Friedrich, H.B.; Howie, R.A.; Maguire, G.E.M.

doi:10.1107/S1600536809007582

Volume 65
Part 4
Pages o692-o693
April 2009

Received 22 January 2009
Accepted 2 March 2009
Online 6 March 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R = 0.074
wR = 0.230
Data-to-parameter ratio = 13.1
Details

7,11,15,28-Tetrakis[(2-formylphenoxy)methyl]-1,21,23,25-tetramethylresorcin[4]arene cavitand ethyl acetate clathrate at 173 K

Michael G. Mc Kay,^a Holger B. Friedrich,^a R. Alan Howie ^b and Glenn E. M. Maguire ^a ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Durban, 4000, South Africa, and ^bDepartment of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, Scotland
Correspondence e-mail: maguireg@ukzn.ac.za

The title compound, C₆₈H₅₆O₁₆, was synthesized as a novel synthetic intermediate towards deeper and more elaborate resorcin[4]arene cavitands. The structure is the first reported example of a resorcin[4]arene cavitand bearing aromatic aldehyde functional groups at the extra-annular rim of the molecule. The 2-formylphenoxy residues are found to assume two different orientations above the molecular cavity. One half of the resorcin[4]arene cavitand molecule appears in the asymmetric unit; the complete resorcin[4]arene cavitand structure was generated across a mirror plane. In addition, a highly disordered ethyl acetate solvent molecule is present within the molecular cavity.

Related literature

For literature pertaining to the preparation of precursors to the reported compound, see: Middel et al. (2001); Sorrell & Pigge (1993). For related literature on synthetic analogues and other precursors which illustrate the host capabilities of resorcin[4]arene cavitand molecules, see: Friedrich et al. (2007); Mc Kay et al. (2007, 2008). For the implemetation of the SQUEEZE function in PLATON, see: Tam et al. (2005).

Experimental

Crystal data

C₆₈H₅₆O₁₆
M_r = 1183.17
Monoclinic, P 2₁ /m
a = 11.9228 (7) Å
b = 23.2806 (15) Å
c = 12.2320 (7) Å
= 117.005 (3)°
V = 3025.0 (3) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 173 K
0.37 × 0.34 × 0.26 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration (SAINT-NT; Bruker, 2005) T_min = 0.967, T_max = 0.977
24858 measured reflections
5470 independent reflections
3556 reflections with I > 2(I)
R_int = 0.079

Refinement

R[F² > 2(F²)] = 0.074
wR(F²) = 0.230
S = 1.11
5470 reflections
417 parameters
21 restraints
H-atom parameters constrained
_max = 0.64 e Å^-3
_min = -0.48 e Å^-3

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-NT (Bruker, 2005); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2233 ).

Acknowledgements

The financial support of the DST-NRF Centre of Excellence in Catalysis, is duly acknowledged. Our thanks to Dr Manuel Fernandes at the University of the Witwatersrand for performing the data acquisition and structure solution.

References

Bruker (2005). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Friedrich, H. B., Howie, R. A., Maguire, G. E. M. & Mc Kay, M. G. (2007). Acta Cryst. E63, o4346.
McKay, M. G., Friedrich, H. B. & Maguire, G. E. M. (2007). Acta Cryst. E63, o4345.
Mc Kay, M. G., Friedrich, H. B. & Maguire, G. E. M. (2008). Acta Cryst. E64, o98.
Middel, O., Verboom, W. & Reinhoudt, D. N. (2001). J. Org. Chem. 66, 3998-4005.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sorrell, T. N. & Pigge, F. C. (1993). J. Org. Chem. 58, 784-785.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tam, T. F., Leung-Toung, R., Wang, Y., Spino, M. & Lough, A. J. (2005). Acta Cryst. E61, m2601-m2603.