5,11,17,23,29,35-Hexa-tert-butyl-37,38,39,40,41,42-hexa­kis­(eth­oxy­carbonyl­meth­oxy)calix[6]arene acetonitrile disolvate

Pojarová, M.; Dušek, M.; Budka, J.; Císařová, I.; Makrlík, E.

doi:10.1107/S1600536812015735

Volume 68
Part 5
Pages o1418-o1419
May 2012

Received 28 March 2012
Accepted 11 April 2012
Online 18 April 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.061
wR = 0.183
Data-to-parameter ratio = 18.6
Details

5,11,17,23,29,35-Hexa-tert-butyl-37,38,39,40,41,42-hexakis(ethoxycarbonylmethoxy)calix[6]arene acetonitrile disolvate

Michaela Pojarová,^a ^* Michal Dusek,^a Jan Budka,^b Ivana Císarová ^c and Emanuel Makrlík ^d

^aInstitute of Physics, AS CR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic,^bInstitute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic,^cDepartment of Inorganic Chemistry, Charles University in Prague, Faculty of Natural Sciences, Hlavova 2030/8, Praha, Czech Republic, 128 40, Czech Republic, and ^dFaculty of Environmental Sciences, Czech University of Life Sciences, Prague, Kamýcká 129, 165 21 Prague 6, Czech Republic
Correspondence e-mail: pojarova@fzu.cz

In the title compound, C₉₀H₁₂₀O₁₈·2CH₃CN, the calix[6]arene has a 1,2,3-alternate conformation and possesses inversion symmetry. It crystallizes as an acetonitrile disolvate, with a half-molecule of calix[6]arene and one molecule of solvent in the asymmetric unit. In the crystal, the two solvent molecules are enclosed in voids between the calix[6]arene molecules. They form weak C-HO hydrogen bonds involving an O atom of the lower rim substituent. The cavity of the calix[6]arene itself is enclosed by two opposite phenol rings, which are turned into the cavity due to the presence of a C-H [pi] interaction. The calix[6]arene molecule exhibits disorder of one substituent on its lower rim [occupancy ratio 0.897 (3):0.103 (3)].

Related literature

For general information about calixarenes, see: Gutsche (2008). For their applications in coordination chemistry, see: Homden & Redshaw (2008); Gibson et al. (1998), in supramolecular chemistry, see: Atwood et al. (2002) and in polymerization, see: Ling et al. (2003). For the synthesis of the title compound, see: McKervey et al. (1985).

Experimental

Crystal data

C₉₀H₁₂₀O₁₈·2C₂H₃N
M_r = 1571.97
Triclinic, $[P \overline 1]$
a = 12.6190 (2) Å
b = 13.1500 (3) Å
c = 14.8990 (4) Å
= 75.9037 (11)°
= 67.7646 (11)°
= 74.5815 (19)°
V = 2177.67 (9) Å³
Z = 1
Mo K radiation
= 0.08 mm^-1
T = 150 K
0.3 × 0.3 × 0.25 mm

Data collection

Nonius KappaCCD area-detector diffractometer
19018 measured reflections
9990 independent reflections
7277 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.183
S = 1.03
9990 reflections
538 parameters
12 restraints
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1C-C6C ring.

D-HA	D-H	HA	DA	D-HA
C3-H3EO1C	0.96	2.47	3.250 (4)	139
C7C-H7C2O3B	0.97	2.38	3.312 (3)	160
C12B-H12DO2A	0.97	2.57	3.526 (3)	169
C15B-H15GO3Aⁱ	0.96	2.48	3.398	160
C5C-H5CO1Aⁱⁱ	0.93	2.44	3.190 (2)	138
C11C-H11GO1Bⁱⁱ	0.96	2.56	3.477 (3)	159
C10C-H10ICg1ⁱⁱ	0.96	2.73	3.588 (3)	148
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+2, -z.

Data collection: COLLECT (Hooft, 1998); cell refinement: COLLECT; data reduction: COLLECT and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2398 ).

Acknowledgements

This project was supported by the Praemium Academiae of the Academy of Science of the Czech Republic, by the Grant Agency of the Academy of Sciences of the CR (project No. IAAX08240901) and by the Grant Agency of the Faculty of Environmental Sciences, Czech University of Life Sciences, Prague (project No. 42900/1312/3114 "Environmental Aspects of Sustainable Development of Society").

References

Atwood, J. L., Barbour, L. J., Dalgarno, S., Raston, C. L. & Webb, H. R. (2002). J. Chem. Soc. Dalton Trans. pp. 4351-4356.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gibson, V. C., Redshaw, C., Clegg, W. & Elsegood, M. R. J. (1998). J. Chem. Soc. Chem. Commun. 18, 1969-1970.
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Homden, D. M. & Redshaw, C. (2008). Chem. Rev. 108, 5086-5130.
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Ling, J., Shen, Z. Q. & Zhu, W. P. (2003). J. Polym. Sci. Part A Polym. Chem. 41, 1390-1399.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
McKervey, M. A., Seward, E. M., Ferguson, G., Ruhl, B. & Harris, S. J. (1985). J. Chem. Soc. Chem. Commun. pp. 388-90.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds