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Structures cristallines et moléculaires des muscs macrocycliques III. La muscone et sa 2,4‐dinitrophénylhydrazone
Author(s) -
Bernardinelli Gérald,
Gerdil Raymond
Publication year - 1982
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19820650422
Subject(s) - triclinic crystal system , chemistry , orthorhombic crystal system , crystallography , conformational isomerism , crystal structure , crystal (programming language) , stereochemistry , group (periodic table) , molecule , organic chemistry , computer science , programming language
Crystal and Molecular Structure of Macrocyclic Musks. III. Muscone and its 2, 4‐Diuitrophenylhydrazone Muscone (3‐methylcyclopentadecanone C 16 H 30 O) forms orthorhombic plastic‐crystals with Z = 2 ( a = 5.560(4), b = 8.176(6), c = 17,168(20) Å). Single crystals are obtained by zone melting at 258 °K. The high degree of disorder and the ambiguity of space group have precluded a structural determination by X‐ray diffraction methods. The crystal structure of muscone 2,4‐dinitrophenylhydrazone (DNPHM; C 22 H 34 N 4 O 4 , triclinic, space group P¯, a = 8.015 (4), b = 8.235 (2), c = 17.409 (4) Å. α = 102.69 (4), β; = 93.86 (3), γ = 96.03 (3)° Z = 2) was solved by direct methods and refined to a final R of 0.155 (R ω = 0.102). The macrocycle shows static disorder, which could be partially resolved by analysis of the anisotropy of the atomic vibrational parameters. Eight possible conformers with reasonable geometries emerged from the subsequent refinements and were used as starting models in force‐field calculations, which converged to four quinquangular conformations ([25233]; [34233]; [21423*4]; [3423*4]) with similar energies. In the molecular packing, the interactions between macrocycles and substituents are minimized. They are comparable to those described for the cis ‐ and trans ‐civetone DNPH derivatives [1] [2].