Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 4 (April 2009)

organic compounds

Acta Cryst. (2009). C65, o140-o145 [ doi:10.1107/S0108270109005265 ]

(2R,4S)-7-Bromo-2-phenyl-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, (2RS,4SR)-7-bromo-2-(4-chlorophenyl-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine and (2RS,4SR)-2-(4-fluorophenyl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine: hydrogen-bonded structures in two and three dimensions

A. Palma, A. Bahsas, A. F. Yépes, J. Cobo, M. B. Hursthouse and C. Glidewell

Abstract: (2R,4S)-7-Bromo-2-phenyl-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C₂₀H₁₆BrNO, (I), exhibits evidence of a modest degree (ca 10%) of inversion twinning, while both (2RS,4SR)-7-bromo-2-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C₂₀H₁₅BrClNO, (II), and (2RS,4SR)-2-(4-fluorophenyl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C₂₀H₁₆FNO, (III), crystallize as genuine racemic mixtures. The molecules of (I) are linked into sheets by a combination of one C-HO hydrogen bond and two C-H [pi] (arene) hydrogen bonds, while those of (II) are linked into sheets of [pi] -stacked hydrogen-bonded chains. A combination of one C-HO hydrogen bond and four independent C-H [pi] (arene) hydrogen bonds links the molecules of (III) into a three-dimensional framework. The significance of this study lies in its finding, via comparison with the structures of some closely-related epoxybenzazepine analogues, of significant changes in crystal structures consequent upon small changes in the peripheral substituents.

Formula: C₂₀H₁₆BrNO, C₂₀H₁₅BrClNO and C₂₀H₁₆FNO


	Structure factor file (CIF format) (153.7 kbytes) [ doi:10.1107/S0108270109005265/sk3295Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (179.5 kbytes) [ doi:10.1107/S0108270109005265/sk3295IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (170.1 kbytes) [ doi:10.1107/S0108270109005265/sk3295IIIsup4.hkl ] Contains datablock III

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