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Cyclododeca-2,8-diyne-1,10-diol, (6), C12H16O2, and 1,10-dimethylcyclododeca-2,8-diyne-1,10-diol, (11), C14H20O2, have been prepared and their structures determined. Both crystallize in centrosymmetric space groups and the molecules have approximate C2 symmetry. For compound (6), the lengths of the triple bonds are 1.184 (3) (C2[triple bond]C3) and 1.189 (3) Å (C8[triple bond]C9). The bond angles at the triple bonds (C1—C2[triple bond]C3 and C8[triple bond]C9—C10) deviate by less than 6° from 180°. For compound (11), the bond lengths of the triple bonds are 1.190 (3) (C2[triple bond]C3) and 1.188 (3) Å (C8[triple bond]C9), and the bond angles at the triple bonds are close to 175.5°. In both compounds, the two 3-hexyne chains maintain a `crossed' arrangement whereas the two alkylene chains are arranged in a manner similar to that described for unsubstituted cyclododecane.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks 6, 11, global

fcf

Structure factor file (CIF format)
Contains datablock 6

fcf

Structure factor file (CIF format)
Contains datablock rac6

CCDC references: 128305; 128306

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