Acta Crystallographica Section C

Volume 66, Part 4 (April 2010)

organic compounds

 

Hydrogen-bonded dimers, chains and rings in six differently substituted 2-vinyltetrahydro-1,4-epoxy-1-benzazepines

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

Abstract: In (2SR,4RS)-2-exo-vinyl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₂H₁₃NO, (I), the molecules are linked by two independent C-H(arene) hydrogen bonds to form sheets, such that all of the molecules in a given sheet are of the same configuration. The molecules of (2SR,4RS)-7-chloro-2-exo-(2-methylprop-1-enyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₄H₁₆ClNO, (II), are linked by a C-HO hydrogen bond into C(4) chains, where all the molecules in a given chain are of the same configuration, whereas the molecules of (2SR,4RS)-8-chloro-9-methyl-2-exo-(2-methylprop-1-enyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₅H₁₈ClNO, (III), are linked into centrosymmetric dimers by pairs of symmetry-related C-H(arene) hydrogen bonds. (2RS,4RS)-8-Chloro-9-methyl-2-endo-(2-methylprop-1-enyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₅H₁₈ClNO, (IV), is a diastereoisomer of (III) and, as for (II), a single C-HO hydrogen bond links the molecules into C(4) chains, each containing molecules of a single configuration. The structure of (2SR,4RS)-8-chloro-9-methyl-2-exo-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₄H₁₆ClNO, (V), contains a C-HO hydrogen bond which links pairs of molecules into centrosymmetric R₂²(6) dimers. (2SR,4RS)-7,9-Dichloro-2-exo-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C₁₃H₁₃Cl₂NO, (VI), is an inversion twin containing both the (2S,4R) and (2R,4S) enantiomers in the space group P2₁, and a C-HO hydrogen bond links molecules of a given configuration into simple C(3) chains.

Formula: C₁₂H₁₃NO, C₁₄H₁₆ClNO, C₁₅H₁₈ClNO, C₁₅H₁₈ClNO, C₁₄H₁₆ClNO and C₁₃H₁₃Cl₂NO

	Structure factor file (CIF format) (108.2 kbytes) [ doi:10.1107/S0108270110009017/sk3373Isup2.hkl ] Contains datablock I
	Structure factor file (CIF format) (136.7 kbytes) [ doi:10.1107/S0108270110009017/sk3373IIsup3.hkl ] Contains datablock II
	Structure factor file (CIF format) (135.5 kbytes) [ doi:10.1107/S0108270110009017/sk3373Vsup6.hkl ] Contains datablock V
	Structure factor file (CIF format) (113.4 kbytes) [ doi:10.1107/S0108270110009017/sk3373IIIsup4.hkl ] Contains datablock III
	Structure factor file (CIF format) (147.5 kbytes) [ doi:10.1107/S0108270110009017/sk3373IVsup5.hkl ] Contains datablock IV
	Structure factor file (CIF format) (135.0 kbytes) [ doi:10.1107/S0108270110009017/sk3373VIsup7.hkl ] Contains datablock VI

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