Calixarene-based molecular capsule from olefin metathesis

Shimelis T Hailu,Ray J Butcher,Paul F Hudrlik,Anne M Hudrlik

doi:10.1107/s1600536813014438

Shimelis T Hailu, Ray J Butcher + Show 2 more

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https://doi.org/10.1107/s1600536813014438

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Abstract

The reaction of tetrakis(allyloxy)calix[4]arene with the first-generation Grubbs catalyst, followed by catalytic hydrogenation, gave the novel bis-calixarene 15,20,46,51,64,69,74,79-octaoxatridecacyclo[32.28.8.83,28.113,53.122,44.09,14.021,26.038,70.040,45.052,57.059,63.07,80.032,73]octaconta-1(63),3,5,7(80),9(14),10,12,21,23,25,28(73),29,31,34,36,38(70),40,42,44,52,54,56,59,61-tetracosaene benzene monosolvate, C72H72O8·C6H6. The structure consists of two calix[4]arene units connected by four-carbon chains at each of the four O atoms on their narrow rims, to form a cage. Each of the calix[4]arene units has a flattened cone conformation in which two of the opposite aryl groups are closer together and nearly parallel [dihedral angle between planes = 7.35 (16)°], and the other two aryl groups are splayed outward [dihedral angle between planes = 72.20 (8)°]. While the cavity contains no solvent or other guest molecule, there is benzene solvent molecule in the lattice. Two of the alkyl linking arms were disordered over two conformations with occupancies of 0.582 (3)/0.418 (3) and 0.33 (4)/0.467 (4). They were constrained to have similar metrical and thermal parameters.

Highlights

Structure ReportsKey indicators: single-crystal X-ray study; T = 123 K; mean (C–C) = 0.005 Å; disorder in main residue; R factor = 0.078; wR factor = 0.249; data-to-parameter ratio = 24.0
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5315)
The structure consists of two calix[4]arene units connected by four-carbon chains at each of the four O atoms on their narrow rims, to form a cage

Summary

Structure Reports

Key indicators: single-crystal X-ray study; T = 123 K; mean (C–C) = 0.005 Å; disorder in main residue; R factor = 0.078; wR factor = 0.249; data-to-parameter ratio = 24.0. The reaction of tetrakis(allyloxy)calix[4]arene with the firstgeneration Grubbs catalyst, followed by catalytic hydrogenation, gave the novel bis-calixarene 15,20,46,51,64,69,74,79octaoxatridecacyclo[32.28.8.83,28.113,53.122,44.09,14.021,26.038,70.040,45.052,57.059,63.07,80.032,73]octaconta-1(63),3,5,7(80),9(14),10,12,21,23,25,28(73),29,31,34,36,38(70),40,42,44,52,54,56,59,61-tetracosaene benzene monosolvate, C72H72O8C6H6. The structure consists of two calix[4]arene units connected by four-carbon chains at each of the four O atoms on their narrow rims, to form a cage. Each of the calix[4]arene units has a flattened cone conformation in which two of the opposite aryl groups are closer together and nearly parallel [dihedral angle between planes = 7.35 (16) ], and the other two aryl groups are splayed outward [dihedral angle between planes = 72.20 (8) ].

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