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The structure of a 1:4 adduct between 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) and thiourea

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Abstract

The structure of 18-crown-6·4 thiourea has been determined by single crystal X-ray methods. The unit cell is monoclinic and the space group isP21, witha=9.251(3),b=19.285(8),c=16.556(7) Å and β=90.85(6)°. There are two formula units, C12H24O6·4CH4N2S, in the asymmetric unit; finalR=0.086. One thiourea is attached at either side of the macrocycle (‘biangular’ conformation) via N−N...O bonds and the patterns in the two crystallographically-independent adductsA andB differ slightly, involving two bifurcated hydrogen bonds inA. Core adducts are linked by additional thiourea molecules via N−H...S bonds. As compared to the analogous 18-crown-6·5 urea, the present 1:4 stoichiometry might be attributed to the longer S...N hydrogen bonding distance, i.e., to the bigger van der Waals radius of sulphur.

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Supplementary Data relating to this article are deposited with the British Library as Supplementary Publication No. SUP 82004 (31 pages). To obtain copies, see p. ii of this issue.

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Weber, G. The structure of a 1:4 adduct between 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) and thiourea. Journal of Inclusion Phenomena 1, 339–347 (1984). https://doi.org/10.1007/BF00665477

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Key words

  • X-ray analysis
  • hydrogen bonds
  • molecular complexes
  • crown ethers