Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 9 (September 2008)

organic compounds

gg3177 scheme

Acta Cryst. (2008). C64, o514-o518 [ doi:10.1107/S0108270108025638 ]

Three styryl-substituted tetrahydro-1,4-epoxy-1-benzazepines: configurations, conformations and hydrogen-bonded chains

L. M. Acosta, A. Bahsas, A. Palma, J. Cobo, J. N. Low and C. Glidewell

Abstract: (2SR,4RS)-7-Chloro-2-exo-[(E)-styryl]-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₈H₁₆ClNO, (I), crystallizes as a racemic twin in the space group P2₁ and the molecules are linked into a chain of edge-fused R₃³(9) rings by a combination of C-HO and C-HN hydrogen bonds. The diastereoisomer (2RS,4RS)-7-chloro-2-endo-[(E)-styryl]-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (II), also crystallizes as a racemic twin, but in the space group P2₁2₁2₁, and a two-centre C-HN hydrogen bond and a three-centre C-H(O,N) hydrogen bond combine to link the molecules into a complex chain of rings. In (2R,4R)-7-fluoro-2-endo-[(E)-styryl]-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₈H₁₆FNO, (III), which is not isomorphous with (II), the molecules are linked by a single C-HO hydrogen bond into simple chains, but the molecular arrangements in (II) and (III) are nonetheless very similar. The significance of this study lies in its observation of the variations in molecular configuration and conformation, and in the variation in the supramolecular aggregation, consequent upon modest changes in the peripheral substituents.

Formula: C₁₈H₁₆ClNO, C₁₈H₁₆ClNO and C₁₈H₁₆FNO


	Structure factor file (CIF format) (162.1 kbytes) [ doi:10.1107/S0108270108025638/gg3177Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (166.0 kbytes) [ doi:10.1107/S0108270108025638/gg3177IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (84.5 kbytes) [ doi:10.1107/S0108270108025638/gg3177IIIsup4.hkl ] Contains datablock III

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