Acta Crystallographica Section C

Volume 65, Part 7 (July 2009)


organic compounds



sk3325 scheme

Acta Cryst. (2009). C65, o326-o330    [ doi:10.1107/S0108270109019556 ]

Conformational and configurational disorder in 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one and 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8-one: a hydrogen-bonded chain of rings and [pi]-stacked hydrogen-bonded chains

P. Cuervo, R. Abonía, J. Cobo and C. Glidewell

Abstract: In 6-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8(5H)-one, C19H19NO6, (I), the six-membered heterocyclic ring adopts a conformation intermediate between envelope and half-chair forms; it is disordered over two enantiomeric configurations, with occupancies of 0.879 (3) and 0.121 (3), leading to positional disorder of the 3,4,5-trimethoxyphenyl unit. In 6-(1,3-benzodioxol-5-yl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinolin-8-one, C17H13NO5, (II), the molecules are similarly disordered, with occupancies of 0.866 (4) and 0.134 (4). The molecules in (I) are linked by one three-centre N-H...(O)2 hydrogen bond and one two-centre C-H...O hydrogen bond to form a complex chain of rings whose formation is reinforced by two independent aromatic [pi]-[pi] stacking interactions. In (II), a single N-H...O hydrogen bond links the molecules into a simple chain, and pairs of chains are linked by a single aromatic [pi]-[pi] stacking interaction.

Formula: C19H19NO6 and C17H13NO5


hkldisplay filedownload file

Structure factor file (CIF format) (188.4 kbytes)
[ doi:10.1107/S0108270109019556/sk3325Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (151.1 kbytes)
[ doi:10.1107/S0108270109019556/sk3325IIsup3.hkl ]
Contains datablock II


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