STRUCTURE AND ABSOLUTE-CONFIGURATION OF A HIGH-AFFINITY 5-HT3 RECEPTOR ANTAGONIST, -5A,6,7,8,9,9A-HEXAHYDRO-4-DIBENZOFURANCARBOXAMIDE HYDROCHLORIDE

Authors
AMMON HL YOUSSEFYEH RD AIREY JE STUDT WL CAMPBELL HF POWERS MR GOLEC FA
Citation
Hl. Ammon et al., STRUCTURE AND ABSOLUTE-CONFIGURATION OF A HIGH-AFFINITY 5-HT3 RECEPTOR ANTAGONIST, -5A,6,7,8,9,9A-HEXAHYDRO-4-DIBENZOFURANCARBOXAMIDE HYDROCHLORIDE, Acta crystallographica. Section C, Crystal structure communications, 49, 1993, pp. 1551-1554
Citations number
14
Categorie Soggetti
Crystallography
Journal title
Acta crystallographica. Section C, Crystal structure communications → ACNP
ISSN journal
01082701
Volume
49
Year of publication
1993
Part
8
Pages
1551 - 1554
Database
ISI
SICI code
0108-2701(1993)49:<1551:SAAOAH>2.0.ZU;2-Q
Abstract
The absolute configuration was established as (S,S,S) by the R-factor test and by careful measurement of 197 enantiomorph-sensitive Friedel pairs of reflections. The determination also confirms the absolute ste reochemistry of (-)-3-aminoquinuclidine, a compound used in the prepar ation of the title material. The cyclohexane/tetrahydrofuran ring fusi on is cis. The quinuclidine moiety has almost perfect threefold symmet ry; the front and rear halves are twisted about this axis by 15-degree s. Quinuclidine-N-H...Cl- and amide-N-H...Cl hydrogen bonds link screw -dyad-related molecules along the b axis.