Received 15 May 2013
The reaction of tetrakis(allyloxy)calixarene with the first-generation Grubbs catalyst, followed by catalytic hydrogenation, gave the novel bis-calixarene 15,20,46,51,64,69,74,79-octaoxatridecacyclo[126.96.36.199,28.113,53.122,44.09,14.021,26.038,70.040,45.052,57.059,63.07,80.032,73]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 calixarene units connected by four-carbon chains at each of the four O atoms on their narrow rims, to form a cage. Each of the calixarene 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.
For literature related to the use of calixarenes as easily isolable reaction products, see: Asfari et al. (2001); Gutsche (2008). For literature related to the preparation of bridged calixarenes, see: Yang & Swager (2007); Hailu et al. (2012). For literature related to the conformation of calixarenes, see: Arduini et al. (1995, 1996); Drew et al. (1997). For literature related to starting material and catalyst used, see: Ho et al. (1996); Vougioukalakis & Grubbs (2010).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5315 ).
RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer. STH wishes to acknowledge the Howard University Graduate School for a Teaching Assistantship.
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.
Arduini, A., Fanni, S., Manfredi, G., Pochini, A., Ungaro, R., Sicuri, A. R. & Ugozzoli, F. (1995). J. Org. Chem. 60, 1448-1453.
Arduini, A., McGregor, W. M., Pochini, A., Secchi, A., Ugozzoli, F. & Ungaro, R. (1996). J. Org. Chem. 61, 6881-6887.
Asfari, Z., Böhmer, V., Harrowfield, J. & Vicens, J. (2001). In Calixarenes 2001. Dordrecht: Kluwer Academic Publishers.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Drew, M. G. B., Beer, P. D. & Ogden, M. I. (1997). Acta Cryst. C53, 472-474.
Gutsche, C. D. (2008). Calixarenes: An Introduction, 2nd ed., Monographs in Supramolecular Chemistry, edited by J. F. Stoddard. Cambridge: The Royal Society of Chemistry.
Hailu, S. T., Butcher, R. J., Hudrlik, P. F. & Hudrlik, A. M. (2012). Acta Cryst. E68, o1833-o1834.
Ho, Z., Ku, M., Shu, C. & Lin, L. (1996). Tetrahedron, 52, 13189-13200.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vougioukalakis, G. C. & Grubbs, R. H. (2010). Chem. Rev. 110, 1746-1787.
Yang, Y. & Swager, T. M. (2007). Macromolecules, 40, 7437-7440.