Crystal Structure of N-Cinnamoyl-8-oxa-6-azabicyclo[3.2.1]octan-7-one

• Published in: Bulletin of the Chemical Society of Japan Vol. 65; no. 4; pp. 1138 - 1140
• Main Authors: Yamane, Takashi, Ashida, Tamaichi, Hashimoto, Kazuhiko, Sumitomo, Hiroshi
• Format: Journal Article
• Language: English
• Published: Tokyo The Chemical Society of Japan 01.04.1992; Chemical Society of Japan
• Subjects: Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Organic compounds; Physics; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Molecular structure; Lactam; Bicyclic compound; Carboxamide; Benzenic compound; Experimental study; X ray diffraction; Organic compounds; Oxygen nitrogen heterocycle; Crystalline structure
• ISSN: 0009-2673; 1348-0634
• DOI: 10.1246/bcsj.65.1138

The crystal structure of the title compound has been determined in order to study the structure-reactivity relationship of a bicyclo compound. C15H15O3, M 257.29, monoclinic, space group P21/a, a = 24.122(6), b = 6.990(2), c = 7.800(2) Å, β = 94.27(2)°, V = 1311.5(6) Å3, Z = 4, Dx = 1.304 g cm−3, μ = 7.56 cm−1 for Kα. The final R-value is 0.062 for 1948 reflections. The molecular structure is essentially the same as that of the N-benzoyl derivative of the bicyclo compound. An elongation of the C–N bond distance in the lactam-amide moiety, which had been found in the N-benzoyl derivative, was observed and compared with that in the unmodified bicyclo compound. There seems to be little extension of the conjugation of the olefinic group to the carbonyl or phenyl groups in a cinnamoyl moiety, according to the C=C and Csp2–Csp2 distances.