The influence of substituents on the geometry of the cyclopropane ring VIII. The molecular and crystal structures of azocyclopropane N,N′-dioxide and 1,1′-dimethylazocyclopropane N,N′-dioxide

✍ Scribed by J. S. A. M. de Boer; H. Schenk

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 219 KB
• Volume: 114
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19951140904

✦ Synopsis

Abstract

Crystals of azocyclopropane N,N′‐dioxide, (C~3~H~5~NO)~2~, (1) are monoclinic, space group C2/c, a = 8.708(2), b = 8.321(1), c = 9.836(2) Å, β = 95.437(3)° (243K). Z = 4. The final R for 479 independent observed reflections is 0.035. The molecules are centrosymmetric and have the bisecting (s‐cis) conformation for the NO group.

Crystals of 1,1′‐dimethylazocyclopropane N,N′‐dioxide, (C~4~H~7~NO)~2~, (2) are monoclinic, space group __P__2~1~/n, a = 10.727(5), b = 7.181(3), c = 5.969(2) Å, β = 90.52 (2)° (223K), Z = 2. The final R for 773 independent observed reflections is 0.046. The molecules are also centrosymmetric but steric interference by the methyl group at C1 prevents them from assuming the bisecting conformation. The effect of the N(O)N(R) group on the geometry of the cyclopropane ring is small to negligeable.