Crystal Structures of Synthetic Analgesics. VI. Normethadone Hydrochloride.

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Abstract
The weak analgetic normethadone crystallizes as a hydrochloride in the triclinic space group P1, with unit cell dimensions a = 9.142(2) .ANG.; b = 9.438(2) .ANG.; c = 13.318(3) .ANG.; .alpha. = 69.31(2).degree.; .beta. = 87.82(2).degree.; .gamma. = 62.27(2).degree. and 2 independent molecules in the asymmetric unit. The structure was determined by a combination of the heavy atom techniques and direct methods and was refined to R = 0.039 for 2424 observed reflections. The mean e.s.d''s in bond lengths and angles are 0.006 .ANG. and 0.4.degree., respectively. The 2 molecules A and B are practically identical. The propylamino chain is nearly fully extended, the pertinent dihedral angle C4-C5-C6-N being -165.3 and -167.1.degree. for molecule A and B, respectively. Comparatively strong N-H.cntdot..cntdot..cntdot.Cl H bonds of 2.93 and 2.97 .ANG. link the organic cations to the Cl-. A relation between the interplanar angle and the bond angle at the bridging C atom is discussed for bridged diphenyl and triphenyl compounds.

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