Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 9 (September 2008)

organic compounds

gg3181 scheme

Acta Cryst. (2008). C64, o524-o528 [ doi:10.1107/S0108270108026176 ]

Three tetrahydro-1,4-epoxy-1-benzazepines carrying pendent heterocyclic substituents: supramolecular structures in zero, one or two dimensions

M. C. Blanco, W. Raysth, A. Palma, J. Cobo, J. N. Low and C. Glidewell

Abstract: (2SR,4RS)-7-Fluoro-2-exo-(2-furyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₄H₁₂FNO₂, (I), crystallizes with Z' = 2 in the space group P2₁/c. A combination of three C-HO hydrogen bonds and one C-HN hydrogen bond links the molecules into a complex chain of rings, and pairs of such chains are linked into a tube-like structure by two C-H [pi] (arene) hydrogen bonds. There are no hydrogen bonds in the structure of racemic (2SR,4RS)-2-exo-(5-bromo-2-thienyl)-7-fluoro-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₄H₁₁BrFNOS, (II), while the molecules of (2S,4R)-2-exo-(5-bromo-2-thienyl)-7-trifluoromethoxy-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₅H₁₄BrF₃NO₂S, (III), are linked into sheets by a combination of two C-HO hydrogen bonds and one C-H [pi] (arene) hydrogen bond. The significance of this study lies in its observation of the wide variation in the patterns of supramolecular aggregation, consequent upon modest changes in the peripheral substituents.

Formula: C₁₄H₁₂FNO₂, C₁₄H₁₁BrFNOS and C₁₅H₁₁BrF₃NO₂S


	Structure factor file (CIF format) (251.3 kbytes) [ doi:10.1107/S0108270108026176/gg3181Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (142.5 kbytes) [ doi:10.1107/S0108270108026176/gg3181IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (166.4 kbytes) [ doi:10.1107/S0108270108026176/gg3181IIIsup4.hkl ] Contains datablock III

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