Crystal and molecular structures of methyl 2,3-anhydro-4-deoxy-α-dl-ribo- and -α-dl-lyxo-hexopyranosides

Janusz W. Krajewski, Przemysław Gluziński, Zofia Urbańczyk-Lipkowska, Anna Banaszek, László Párkányi, Alajos Kálmán

Research output: Contribution to journalArticle

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Abstract

Single crystals of methyl 2,3-anhydro-4-deoxy-α-dl-ribo- (1) and -α-dl-lyxo-hexopyranoside (2) have been investigated by X-ray diffraction methods. Compound 1 crystallises in the monoclinic system, space group P21/c, with cell dimensions a = 7.694(1), b = 12.954(1), c = 8.415(1) Å, and β = 110.34(1)°. Compound 2 crystallises in the tetragonal system, space group I41/a (No. 88, origin at 1), with cell dimensions a = 22.995(2) and c = 6.086(1) Å. The intensity data were collected in a four-circle CAD-4D automatic diffractometer, with 1623 reflections for 1, and 2421 for 2. The structures were solved by direct methods. The atomic parameters were refined in an anisotropic mode by the full-matrix, least-squares procedure against 1456 and 1109 observed reflections for 1 and 2, respectively, resulting in R = 0.049 for 1, and R = 0.042 for 2. A hybrid conformation 5E + 5H0 was found for the anhydrohexopyranose ring in 1, whereas a slightly deformed 5H0 conformation was assigned to that in 2. Relatively strong intermolecular hydrogen-bonds were observed in each compound. In 1 (acceptor atom O-5), they result in dimers of pairs of enantiomeric molecules; in 2 (acceptor atom O-6), the molecules form helices around the four-fold screw axes in the crystal.

Original languageEnglish
Pages (from-to)13-22
Number of pages10
JournalCarbohydrate Research
Volume144
Issue number1
DOIs
Publication statusPublished - Nov 15 1985

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Molecular Structure
Molecular structure
Conformations
Crystal structure
Atoms
Molecules
Diffractometers
Dimers
Computer aided design
Hydrogen bonds
Single crystals
Least-Squares Analysis
X-Ray Diffraction
X ray diffraction
Crystals
Hydrogen

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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Crystal and molecular structures of methyl 2,3-anhydro-4-deoxy-α-dl-ribo- and -α-dl-lyxo-hexopyranosides. / Krajewski, Janusz W.; Gluziński, Przemysław; Urbańczyk-Lipkowska, Zofia; Banaszek, Anna; Párkányi, László; Kálmán, Alajos.

In: Carbohydrate Research, Vol. 144, No. 1, 15.11.1985, p. 13-22.

Research output: Contribution to journalArticle

Krajewski, Janusz W. ; Gluziński, Przemysław ; Urbańczyk-Lipkowska, Zofia ; Banaszek, Anna ; Párkányi, László ; Kálmán, Alajos. / Crystal and molecular structures of methyl 2,3-anhydro-4-deoxy-α-dl-ribo- and -α-dl-lyxo-hexopyranosides. In: Carbohydrate Research. 1985 ; Vol. 144, No. 1. pp. 13-22.
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abstract = "Single crystals of methyl 2,3-anhydro-4-deoxy-α-dl-ribo- (1) and -α-dl-lyxo-hexopyranoside (2) have been investigated by X-ray diffraction methods. Compound 1 crystallises in the monoclinic system, space group P21/c, with cell dimensions a = 7.694(1), b = 12.954(1), c = 8.415(1) {\AA}, and β = 110.34(1)°. Compound 2 crystallises in the tetragonal system, space group I41/a (No. 88, origin at 1), with cell dimensions a = 22.995(2) and c = 6.086(1) {\AA}. The intensity data were collected in a four-circle CAD-4D automatic diffractometer, with 1623 reflections for 1, and 2421 for 2. The structures were solved by direct methods. The atomic parameters were refined in an anisotropic mode by the full-matrix, least-squares procedure against 1456 and 1109 observed reflections for 1 and 2, respectively, resulting in R = 0.049 for 1, and R = 0.042 for 2. A hybrid conformation 5E + 5H0 was found for the anhydrohexopyranose ring in 1, whereas a slightly deformed 5H0 conformation was assigned to that in 2. Relatively strong intermolecular hydrogen-bonds were observed in each compound. In 1 (acceptor atom O-5), they result in dimers of pairs of enantiomeric molecules; in 2 (acceptor atom O-6), the molecules form helices around the four-fold screw axes in the crystal.",
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AU - Krajewski, Janusz W.

AU - Gluziński, Przemysław

AU - Urbańczyk-Lipkowska, Zofia

AU - Banaszek, Anna

AU - Párkányi, László

AU - Kálmán, Alajos

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N2 - Single crystals of methyl 2,3-anhydro-4-deoxy-α-dl-ribo- (1) and -α-dl-lyxo-hexopyranoside (2) have been investigated by X-ray diffraction methods. Compound 1 crystallises in the monoclinic system, space group P21/c, with cell dimensions a = 7.694(1), b = 12.954(1), c = 8.415(1) Å, and β = 110.34(1)°. Compound 2 crystallises in the tetragonal system, space group I41/a (No. 88, origin at 1), with cell dimensions a = 22.995(2) and c = 6.086(1) Å. The intensity data were collected in a four-circle CAD-4D automatic diffractometer, with 1623 reflections for 1, and 2421 for 2. The structures were solved by direct methods. The atomic parameters were refined in an anisotropic mode by the full-matrix, least-squares procedure against 1456 and 1109 observed reflections for 1 and 2, respectively, resulting in R = 0.049 for 1, and R = 0.042 for 2. A hybrid conformation 5E + 5H0 was found for the anhydrohexopyranose ring in 1, whereas a slightly deformed 5H0 conformation was assigned to that in 2. Relatively strong intermolecular hydrogen-bonds were observed in each compound. In 1 (acceptor atom O-5), they result in dimers of pairs of enantiomeric molecules; in 2 (acceptor atom O-6), the molecules form helices around the four-fold screw axes in the crystal.

AB - Single crystals of methyl 2,3-anhydro-4-deoxy-α-dl-ribo- (1) and -α-dl-lyxo-hexopyranoside (2) have been investigated by X-ray diffraction methods. Compound 1 crystallises in the monoclinic system, space group P21/c, with cell dimensions a = 7.694(1), b = 12.954(1), c = 8.415(1) Å, and β = 110.34(1)°. Compound 2 crystallises in the tetragonal system, space group I41/a (No. 88, origin at 1), with cell dimensions a = 22.995(2) and c = 6.086(1) Å. The intensity data were collected in a four-circle CAD-4D automatic diffractometer, with 1623 reflections for 1, and 2421 for 2. The structures were solved by direct methods. The atomic parameters were refined in an anisotropic mode by the full-matrix, least-squares procedure against 1456 and 1109 observed reflections for 1 and 2, respectively, resulting in R = 0.049 for 1, and R = 0.042 for 2. A hybrid conformation 5E + 5H0 was found for the anhydrohexopyranose ring in 1, whereas a slightly deformed 5H0 conformation was assigned to that in 2. Relatively strong intermolecular hydrogen-bonds were observed in each compound. In 1 (acceptor atom O-5), they result in dimers of pairs of enantiomeric molecules; in 2 (acceptor atom O-6), the molecules form helices around the four-fold screw axes in the crystal.

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