Structure of 3-methyl-1,2,3,4,5,6-hexahydro-1,6-methano-3-benzazocinium hydrogen oxalate.
C13H18N+.C2HO4-, Mr = 277.3, orthorhombic, P2(1)2(1)2(1), a = 5.752 (1), b = 15.502 (2), c = 15.910 (2) A, V = 1418.6 (6) A3, Z = 4, Dx = 1.298 g cm-3, Mo K alpha (lambda = 0.71069 A), mu = 1.01 cm-1, F(000) = 592, T = 295 K. Final R = 0.035, wR = 0.042 for 1003 reflections with I greater than 3 sigma(I). The compound is an ammonium hydrogen oxalate. Both O atoms of the ionized carboxyl group act as acceptors in the formation of two hydrogen bonds: (a) an N--H...O bond linking the cation and anion with N...O and H...O distances of 2.722 (4) and 1.78 (5) A and (b) a strong O--H...O bond linking a chain of oxalate ions along a with O...O and H...O distances of 2.578 (4) and 1.59 (6) A. The relative stereochemistry of the heterocyclic and aromatic rings in the cation is similar to that in morphine.
Department of Chemistry and Biochemistry, University of Maryland, College Park 20742.
H L
HL
Ammon
S M
SM
Prasad
P H
PH
Mazzocchi
A M
AM
Harrison
D000701:Analgesics, Opioid / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000737:chemistry*; D015394:Molecular Structure; D014961:X-Ray Diffraction
D000701:Analgesics, Opioid; D001952:Bridged-Ring Compounds; C071566:3-methyl-1,2,3,4,5,6-hexahydro-1,6-methano-3-benzazocinium