4-and 5-nitroindane

Article abstract of DOI:10.1007/BF01670314

Mononitration of indane produces a mixture of 4- and 5- nitroindanes. Crystallization from mixtures occurs after distillation improves composition of a major component to above 80%. 4-Nitroindane: triclinic, space group P1 (#2), a = 7.332(4) A, b = 8.304(4) A, c = 8.358(4) A, α = 61.43(4)°, β = 67.60(4)°, γ = 70.15(4)°, V = 405.4(4) A³, Z = 2. Non-H-atoms are nearly planar, aliphatic H's are eclipsed. 5-Nitroindane: monoclinic, space group P2₁/c (#14), a = 10.946(8) A, b = 15.643(10) A, c = 9.415(6) A, β = 92.34(5)°, V = 1611(2) A3, Z = 8. Non-H-atoms in the two molecules differ in torsion of the nitro group with respect to indane and fold of the nonbenzylic methylene group. Semiempirical calculations (PM3) suggest that distorsion from planarity may be associated with the two lowest energy vibrational modes. Uv, ir, ms, proton, and ¹³C-nmr spectra are correlated with the solid state structures.