Document Type

Article

Original Publication Date

1979

Journal/Book/Conference Title

Acta Crystallographica

Volume

35

DOI of Original Publication

10.1107/S0567740879008955

Comments

Originally published at http://dx.doi.org/10.1107/S0567740879008955

Date of Submission

October 2014

Abstract

CsH~2NO2+.C1 -, m.p. 441-449 K (from ethyl acetate), P212~2 l, a = 7.363 (2), b = 21.824 (6), c = 5.790 (2)/~, Z = 4, D x = 1.354, D m = 1.356 Mg m -3 (flotation: CC14-C6H6). The structure was solved by MULTAN. Full-matrix least-squares refinement converged to R = 0.057 for the R configuration and to R = 0.056 for the S configuration (P < 0.05). This is consistent with spontaneous resolution of the title compound, single crystals of which provided optically active aqueous solutions. A partially occupied oxygen site O(1)' is attributed to the oxidation of the alkyl hydroxyl group to a ketone during the data collection. The CI- is hydrogen bonded to H2(N)554, H3(N)555, and 1-t(O2)655 (2.37, 2-19, and 2.10 A). Both O(1) and 0(2) are internally hydrogen bonded [HI(N)...O(1), 2.41 and H(O1)...O(2) = 2.24 A]. Intramolecular hydrogen bonding may account for the unusual pharmacological properties of this compound in which only the N-C(1)-C(2)-O(1) and the O(1)-C(2)- C(3)-C(4) and O(1)-C(2)-C(3)-C(8) torsion angles (-41, -60, +122 ° ) differ significantly from those of other phenylethanolamines.

Rights

© 1979 International Union of Crystallography

Is Part Of

Publications from the Office of the Dean of the VCU School of Pharmacy

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