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Volume 68 
Part 12 
Page o3423  
December 2012  

Received 11 October 2012
Accepted 19 November 2012
Online 24 November 2012

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.052
wR = 0.161
Data-to-parameter ratio = 15.6
Details
Open access

31-Benzyloxy-5,11,17,23,29-penta-tert-butylcalix[5]arene-32,33,34,35-tetraol

Claudia Gargiulli,a Giuseppe Gattuso,a Anna Notti,a* Francesco Nicolóa and Andrea Pappalardob

aDipartimento di Scienze Chimiche, Università di Messina, Viale F. Stagno d'Alcontres 31, 98166 Messina, Italy, and bDipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy
Correspondence e-mail: anotti@unime.it

The title compound, C62H76O5, known to be one of the most versatile synthetic precursors/intermediates of calix[5]arene derivatives, adopts an approximate Cs-symmetric cone-in conformation. The aryloxybenzyl ring is tilted in such a way that the p-tert-butyl group fills the macrocycle cavity, while the benzyl group moves away from the cavity axis. In the crystal, this conformational arrangement is secured by intra- and intermolecular O-H...O hydrogen bonds forming inversion dimers. Four tert-butyl groups are disordered over two orientations, with occupancy ratios of 0.745 (6):0.255 (6), 0.837 (5):0.163 (5), 0.850 (5):0.150 (5) and 0.845 (8):0.155 (8).

Related literature

For the synthesis of the title compound, see: Stewart et al. (1995[Stewart, D. R., Krawiec, M., Kashyap, R. P., Watson, W. H. & Gutsche, C. D. (1995). J. Am. Chem. Soc. 117, 586-601.]). For calix[5]arene molecules derived from the title compound, see: Garozzo et al. (2005[Garozzo, D., Gattuso, G., Notti, A., Pappalardo, A., Pappalardo, S., Parisi, M. F., Perez, M. & Pisagatti, I. (2005). Angew. Chem. Int. Ed. 44, 4892-4896.]); Capici et al. (2011[Capici, C., Cohen, Y., D'Urso, A., Gattuso, G., Notti, A., Pappalardo, A., Pappalardo, S., Parisi, M. F., Purrello, R., Slovak, S. & Villari, V. (2011). Angew. Chem. Int. Ed. 50, 11956-11961.]); Pappalardo et al. (2012[Pappalardo, A., Ballistreri, F. P., Li Destri, G., Mineo, P. G., Tomaselli, G. A., Toscano, R. M. & Trusso Sfrazzetto, G. (2012). Macromolecules, 45, 7549-7556.]). For the structures of calix[5]arene/alkylammonium complexes, see: Gattuso et al. (2012[Gattuso, G., Notti, A., Pappalardo, A., Parisi, M. F., Pilati, T., Resnati, G. & Terraneo, G. (2012). CrystEngComm, 14, 2621-2625.]).

[Scheme 1]

Experimental

Crystal data

  • C62H76O5

  • Mr = 901.23

  • Triclinic, [P \overline 1]

  • a = 14.1467 (8) Å

  • b = 14.3235 (9) Å

  • c = 15.2179 (9) Å

  • [alpha] = 70.653 (3)°

  • [beta] = 78.776 (3)°

  • [gamma] = 71.573 (3)°

  • V = 2746.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.38 × 0.18 × 0.10 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • 75089 measured reflections

  • 10532 independent reflections

  • 5343 reflections with I > 2[sigma](I)

  • Rint = 0.044
Refinement

  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.161

  • S = 0.96

  • 10532 reflections

  • 677 parameters

  • 120 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O5i 0.82 2.04 2.7197 (19) 140
O4-H4...O3 0.82 2.04 2.847 (2) 168
O5-H5...O4 0.82 2.00 2.803 (2) 168
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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: XPW (Siemens, 1996[Siemens (1996). XPW. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); 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: IS5208 ).

Acknowledgements

MIUR (PRIN-2009 A5Y3N9 project) is gratefully acknowledged for financial support.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Capici, C., Cohen, Y., D'Urso, A., Gattuso, G., Notti, A., Pappalardo, A., Pappalardo, S., Parisi, M. F., Purrello, R., Slovak, S. & Villari, V. (2011). Angew. Chem. Int. Ed. 50, 11956-11961.  [ISI] [CrossRef] [ChemPort]
Garozzo, D., Gattuso, G., Notti, A., Pappalardo, A., Pappalardo, S., Parisi, M. F., Perez, M. & Pisagatti, I. (2005). Angew. Chem. Int. Ed. 44, 4892-4896.  [ISI] [CrossRef] [ChemPort]
Gattuso, G., Notti, A., Pappalardo, A., Parisi, M. F., Pilati, T., Resnati, G. & Terraneo, G. (2012). CrystEngComm, 14, 2621-2625.  [ISI] [CSD] [CrossRef] [ChemPort]
Pappalardo, A., Ballistreri, F. P., Li Destri, G., Mineo, P. G., Tomaselli, G. A., Toscano, R. M. & Trusso Sfrazzetto, G. (2012). Macromolecules, 45, 7549-7556.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). XPW. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Stewart, D. R., Krawiec, M., Kashyap, R. P., Watson, W. H. & Gutsche, C. D. (1995). J. Am. Chem. Soc. 117, 586-601.  [CrossRef] [ChemPort] [ISI]

Acta Cryst (2012). E68, o3423  [ doi:10.1107/S1600536812047435 ]

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