Monatshefte für Chemie / Chemical Monthly

, Volume 117, Issue 12, pp 1413–1422 | Cite as

Synthese und Röntgenkristallstruktur eines (15E)-Dihydrobilatrien-abc-Derivats

  • Ulrike Gabriella Wagner
  • Christoph Kratky
  • Heinz Falk
  • Gerhard Kapl
Organische Chemie Und Biochemie

Synthesis and X-ray crystal structure of a (15E)-dihydrobilatriene-abc-derivate


The crystal structure of the (15E)-configurated 2,3-dihydrobilatriene-abc2, representing a model compound for the active form of the phytochrome chromophore, was determined at room temperature and at 97 K. Compared to the crystal structure of the corresponding (15Z)-derivative1, the molecule of2 shows a similar helix conformation, but with considerably larger helix pitch. The azide hydrogen atoms are localized at the nitrogen atoms of rings A, C and D. The distribution of bond lengths and bond angles is compatible with previous crystal structures and with the canonical formula. Tautomeric form, conformation and crystal packing are understandable on the basis of the observed intra- and intermolecular hydrogen bonds.


Crystal structure of (15E)-2,3 dihydrobilatriene-abc Dihydrobilatriene-abc Phytochrome model compound 


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  1. [1]
    Als Übersicht (1983) Photomorphogenesis. Encyclop Plant Physiol 16Google Scholar
  2. [2]
    Falk H, Grubmayr K, Kapl G, Müller N, Zrunek U (1983) Monatsh Chem 114: 753Google Scholar
  3. [3]
    Kratky C, Jorde C, Falk H, Thirring K (1983) Tetrahedron 39: 1859–1863Google Scholar
  4. [4]
    Kratky C, Falk H, Grubmayr K (1985) Monatsh Chem 116: 745–760Google Scholar
  5. [5]
    Kratky C, Falk H, Grubmayr K, Zrunek U (1985) Monatsh Chem 116: 761Google Scholar
  6. [6]
    Hirshfeld FL (1971) Acta Cryst A27: 157Google Scholar
  7. [7]
    Rosenfield RE, Trueblood KN, Dunitz JD (1978) Acta Cryst A34: 328Google Scholar
  8. [8]
    Kratky C, Falk H, Zrunek U (1985) Monatsh Chem 116: 607Google Scholar
  9. [9]
    Allen FH, Kennard O, Taylor R (1983) Acc Chem Res 16: 146Google Scholar
  10. [10]
    Sheldrick WS (1983) Isr J Chem 23: 162Google Scholar
  11. [11]
    Dunitz JD (1979) X-Ray analysis and the structure of organic molecules. Cornell University PressGoogle Scholar
  12. [12]
    Falk H, Grubmayr K, Kapl G, Zrunek U (1982) Monatsh Chem 113: 1329Google Scholar
  13. [13]
    Gossauer A, Blacha-Puller M, Zeisberger R, Wray V (1981) Ann Chem 1981: 342Google Scholar
  14. [14]
    German G, Main P, Woolfson MM (1971) Acta Cryst A27: 368Google Scholar
  15. [15]
    Sheldrick GM (1976) Shelx 76, a program for crystal structure determination. University of Cambridge, EnglandGoogle Scholar
  16. [16]
    Motherwell S (1976) program Pluto. University of Cambridge, EnglandGoogle Scholar
  17. [17]
    Johnson CK (1976) Ortep report ORNL 5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, U.S.A.Google Scholar

Copyright information

© Springer-Verlag 1986

Authors and Affiliations

  • Ulrike Gabriella Wagner
    • 1
  • Christoph Kratky
    • 1
  • Heinz Falk
    • 2
  • Gerhard Kapl
    • 2
  1. 1.Institut für Physikalische ChemieKarl-Franzens-Universität GrazGrazÖsterreich
  2. 2.Institut für ChemieJohannes-Kepler-Universität LinzLinzÖsterreich

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