Structures of a pair of diastereomeric salts of ephedrine and fluoro-substituted cyclic phosphoric acid

H. J. B. Slot, F. J. J. Leusen, A. D. van der Haest, F. van Bolhuis

Research output: Contribution to journalComment/Letter to the editorAcademicpeer-review

4 Citations (Scopus)

Abstract

(1) Salt of (S)-(-)-5,5-dimethyl-4-omicron-fluorophenyl-2-hydroxy-1,3,2-dioxaphosphorinane 2-oxide and (1S,2R)-(+)-alpha-[(1-methylamino)ethyl]-benzyl alcohol, (+)-C10H16NO+.(-)-C11H13FO4P-, M(r) = 425.436, monoclinic, P2(1), a = 10.122 (1), b = 7.826 (1), c = 13.715 (1) angstrom, beta = 92.99 (1)-degrees, V = 1085.0 (2) angstrom 3, Z = 2, D(x) = 1.302 Mg m-3, Mo K-alpha radiation (graphite monochromator), lambda = 0.71073 angstrom, mu = 0.1599 mm-1, F(000) = 452, T = 130 K, final conventional R = 0.040, wR = 0.042 for 3487 observed unique reflections and 272 variables. (2) Salt of (S)-(-)-5,5-dimethyl-4-omicron-fluorophenyl-2-hydroxy-1,3,2-dioxaphosphorinane 2-oxide and (1R,2S)-(-)-alpha-[(1-methylamino)ethyl]benzyl alcohol, (-)-C10H16NO+.(-)-C11H13FO4P-, M(r) = 425.436, monoclinic, P2(1), a = 9.679 (1), b = 8.115 (1), c = 13.797 (1) angstrom, beta = 98.14 (2)-degrees, V = 1072.8 (2) angstrom 3, Z = 2, D(x) = 1.317 Mg m-3, Mo K-alpha radiation (graphite monochromator), lambda = 0.71073 angstrom, mu = 0.1617 mm-1, F(000) = 452, T = 130 K, final conventional R = 0.041, wR = 0.043 for 3117 observed unique reflections and 272 variables. For both (1) and (2), the phosphorinane ring is in the usual chair conformation and the ephedrine is in the usual extended form. The crystal packings of (1) and (2) can be regarded as chains parallel to the b axis consisting of phosphorinane and ephedrine linked by hydrogen bonds. (1) and (2) are isostructural; only minor differences in the packing of the ephedrine phenyl moieties are observed.
Original languageEnglish
Pages (from-to)587-590
Number of pages4
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume48
DOIs
Publication statusPublished - 15-Mar-1992

Keywords

  • DIASTEREOISOMERIC SALT
  • (1S,2R)-(+)-ALPHA-<(1-METHYLAMINO)ETHYL>BENZYL ALCOHOL
  • (+)-4-ORTHO-CHLOROPHENYL-2-HYDROXY-5,5-DIMETHYL-2-OXO-1,3,2-DIOXAPHOSPHORINANE
  • (+)-2-HYDROXY-5,5-DIMETHYL-2-OXO-4-PHENYL-1,3,2-DIOXAPHOSPHORINANE

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