Crystal structure of DL-Tryptophan at 173K

Ch B. Hübschle, Marc Messerschmidt, P. Luger

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The crystal structure of pure DL-tryptophan has been determined at 173 K, using large but thin plate formed crystals of C11H12N 2O2, which were grown by cooling down a saturated solution of DL-tryptophan in isopropanole/formic acid. The crystals are monoclinic, space group P 21/c, with the unit cell constants: a = 18.899(2), b = 5.7445(6), c = 9.309(1) Å, β = 101.776(2), V = 989.4(4), D calc = 1.371, Z = 4, F(000) = 432, λ.(MoKα) = 0.71073 Å, μ = 0.096 mm-1. The crystal structure was solved by direct methods and refined by full-matrix least squares to a final R-factor = 4.03% with 3343 unique reflections of which 2104 were observed. The molecule is zwitterionic in the crystal with the protonated amino group and the carboxylate group in unusual conformations with respect to the indole ring system compared to other tryptophan derivatives. A D- and L- molecular pair forms a dimer by N - H ... O hydrogen bonds via a crystallographic inversion center. The dimers are linked by further N - H ... O hydrogen bonds to form a head to head bilayer arrangement of the molecules in the crystal lattice. Except for weak van der Waals contacts there is no relation between indole tails of neighboured bilayers.

Original languageEnglish (US)
Pages (from-to)274-278
Number of pages5
JournalCrystal Research and Technology
Volume39
Issue number3
DOIs
StatePublished - Mar 1 2004
Externally publishedYes

Fingerprint

tryptophan
Tryptophan
formic acid
Crystal structure
indoles
Dimers
Crystals
crystal structure
R388
Hydrogen bonds
dimers
hydrogen bonds
crystals
Molecules
thin plates
Formic acid
crystal lattices
Crystal lattices
carboxylates
Conformations

Keywords

  • Amino acid
  • Crystal structure
  • Tryptophan

ASJC Scopus subject areas

  • Condensed Matter Physics

Cite this

Crystal structure of DL-Tryptophan at 173K. / Hübschle, Ch B.; Messerschmidt, Marc; Luger, P.

In: Crystal Research and Technology, Vol. 39, No. 3, 01.03.2004, p. 274-278.

Research output: Contribution to journalArticle

Hübschle, Ch B. ; Messerschmidt, Marc ; Luger, P. / Crystal structure of DL-Tryptophan at 173K. In: Crystal Research and Technology. 2004 ; Vol. 39, No. 3. pp. 274-278.
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AB - The crystal structure of pure DL-tryptophan has been determined at 173 K, using large but thin plate formed crystals of C11H12N 2O2, which were grown by cooling down a saturated solution of DL-tryptophan in isopropanole/formic acid. The crystals are monoclinic, space group P 21/c, with the unit cell constants: a = 18.899(2), b = 5.7445(6), c = 9.309(1) Å, β = 101.776(2), V = 989.4(4), D calc = 1.371, Z = 4, F(000) = 432, λ.(MoKα) = 0.71073 Å, μ = 0.096 mm-1. The crystal structure was solved by direct methods and refined by full-matrix least squares to a final R-factor = 4.03% with 3343 unique reflections of which 2104 were observed. The molecule is zwitterionic in the crystal with the protonated amino group and the carboxylate group in unusual conformations with respect to the indole ring system compared to other tryptophan derivatives. A D- and L- molecular pair forms a dimer by N - H ... O hydrogen bonds via a crystallographic inversion center. The dimers are linked by further N - H ... O hydrogen bonds to form a head to head bilayer arrangement of the molecules in the crystal lattice. Except for weak van der Waals contacts there is no relation between indole tails of neighboured bilayers.

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