X-ray crystal structure analysis of nitroxazepine: 10-(3-dimethylaminopropyl)-2-nitro-10,11-dihydrodibenz [b,f][l,4]oxazepin-11-one

Johnson, O. ; Jones, D. W. ; Nagarajan, K. ; Bhadbhade, M. M. ; Venkatesan, K. (1992) X-ray crystal structure analysis of nitroxazepine: 10-(3-dimethylaminopropyl)-2-nitro-10,11-dihydrodibenz [b,f][l,4]oxazepin-11-one Journal of Chemical Crystallography, 22 (5). pp. 579-583. ISSN 1074-1542

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Official URL: http://www.springerlink.com/content/w1753326u28u0l...

Related URL: http://dx.doi.org/10.1007/BF01161343

Abstract

The title compound, C18H19O4N3, Mr=341, the base (I) of the dibenzoxazepine anti-depressant drug Sintamil, crystallizes in the orthorhombic space group, Pbca with Z=8 in a cell a=8.636(2), b=23.687(3), c=16.787Å3, Vc=3434 Å3. The structure was solved by direct methods and refined to R=0.102 (Rw=0.093) with 1348 observed Cu Kα reflections. The tricyclic framework takes up a saddle shape with the heterocyclic ring in boat conformation; the flanking planar aromatic rings make angles 148.2(3), 150.8(3)° with the central ring plane, compared with 143.5(5), 158.1(5)° in Sintamil monohydrate (II). Both I and II have extended-CNMe2 side chains (with appreciable thermal motion); this conformation, and the distances of the -N(CH3)3 nitrogen to the centers of aromatic rings (6.4 and 7.8 Å in I), are consistent with inhibition of uptake mechanisms underlying the pharmacological action.

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