Hartite from Bilina

In the Bilina Mine (Czech Republic), a very chemically pure material corres ponding to hartite was found as a product of distillation into the peloside rite nodule during coalification of a lignite seam in the Miocene or later. The amount of the material available allowed characterizing this natural m ineral equivalent of the hydrocarbon (+)-phyllocladane [16 alpha(H)-phylloc ladane] thoroughly. Elementary analysis of hartite from Bilina gave C = 87.45 wt% and H = 12.55 wt%, which corresponds to the formula C20H34. The IR spectrum demonstrated the presence of gem-dimethyl groups (doublet delta(5)CH(3) at 1369 and 138 3 cm(-1)). Other bands indicated the presence of methyl and methylene grou ps. NMR studies showed that the hydrocarbon (hartite) molecule contains fou r CH3 groups, nine CH2 groups, four CH groups, and three quaternary carbon atoms. The sample exhibits a well-defined melting point between 71 and 71.5 degrees C. Measurements of optical rotation gave [alpha](D) = +24.2 degree s (CHCl3, c = 0.7). Lattice parameters from single-crystal study measured a t 293(2) K were a = 11.407 (1), b = 20.952 (2), c = 7.4060 (8) Angstrom, al pha = 93.941 (9)degrees, beta = 100.750 (8)degrees, and gamma = 80.499 (9)d egrees. The crystal system is triclinic with space group P1, Z = 4, V = 171 3.8 (3) Angstrom(3). Densities are D-m = 1.04 g/cm(3) and D-x = 1.064 g/cm( 3), respectively. Isotopic composition of C in hartite from Bilina gave del ta(13)C((PDB)) = -24.4(1) parts per thousand, a common value for coal and o rganic sedimentary material derived from higher plants.