Abstract
A novel naphthalene-based open-chain crown ether has been synthesized by the etherification of 2-bromo- N-phenylacetamide with 3,6-dibromo-2,7-dihydroxynaphthalene, followed by reduction with sodium borohydride and boron trifluoride ether solution, in 95% total yield. Its crystal structure was determined by X-ray diffraction method. The crystal is of triclinic space group P-1 with a=9.588(3) A, b=10.898(3) A, c=13.060(4) A, α=103.190(4)°, β=93.953(4)°, γ= 115.622(5)°, V=1176.0(6) A 3 , Z=2, Dc=1.571 g/cm 3 , λ=0.71075 A, μ(Mo Kα)=3.472 mm -1 , Mr=353.22 and F(000)= 560. In the structure, one of the N—H groups forms bifurcated N—H…Br and N—H…O hydrogen bonds. These link the molecules into inversion related dimers. The centrosymmetric dimers are aggregated via pairs of C—H…π interactions into two-dimensional sheets parallel to (110). Keywords open-chain crown ethers; synthesis; crystal structure
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