Scientific article
French

Structures cristallines et moléculaires des muscs macrocycliques. II. La trans-civettone et sa 2,4-dinitrophénylhydrazone

Other titleCrystal and Molecular Structure of Macrocyclic Musks. II. trans-Civetone and its 2,4-Dinitrophenylhydrazone
Published inHelvetica chimica acta, vol. 65, no. 3, p. 730-738
Publication date1982-05-05
First online date2004-10-25
Abstract

The trans and cis isomers of civetone (C17H30O) crystallize in isomorphous systems and form plastic crystals (tetragonal, space group I41 a=9.95 (4), c = 32.79 (1) Å, Z = 8). Mixed crystals were prepared with cis-civetone as second component. Accordingly the diffuse structural model obtained for the disordered phase of the cis-isomer [1] is also regarded as representative of that of trans-civetone.

The crystal structure of trans-civetone 2,4-dinitrophenylhydrazone (DNPHTC; C23H34N4, Monoclinic, Space group P21/c, a=8.364(2), b=7.971(1), c=36.025(8) Å, β=91.44 (2)°) was solved by direct methods and refined to a final R of 0.09 (Rw = 0.021). The macrocycle adopts a sexangular conformation [23*434*44*], and its mean plane is approximatively perpendicular to that of the aromatic substituent. Empirical force field calculations have shown that the DNPH substituent has very little influence on the macrocycle conformation. The intermolecular interactions take place essentially between groups of the same type: macrocycle…macrocycle and DNPH…DNPH.

Citation (ISO format)
BERNARDINELLI, Gérald Hugues, GERDIL, Raymond. Structures cristallines et moléculaires des muscs macrocycliques. II. La trans-civettone et sa 2,4-dinitrophénylhydrazone. In: Helvetica chimica acta, 1982, vol. 65, n° 3, p. 730–738. doi: 10.1002/hlca.19820650311
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Journal ISSN0018-019X
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