Acta Crystallographica Section C

Crystal Structure Communications

Volume 63, Part 7 (July 2007)

organic compounds

gg3095 scheme

Acta Cryst. (2007). C63, o426-o430 [ doi:10.1107/S0108270107024420 ]

4-(2-Hydroxyphenyl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepine and the 2-(2,3-dimethoxyphenyl)-, 2-(3,4-dimethoxyphenyl)- and 2-(2,5-dimethoxyphenyl)-substituted derivatives

C. A. Escobar, O. Donoso-Tauda, R. Araya-Maturana and A. Vega

Abstract: The 1,5-benzodiazepine ring system exhibits a puckered boat-like conformation for all four title compounds [4-(2-hydroxyphenyl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepine, C₂₁H₁₈N₂O, (I), 2-(2,3-dimethoxyphenyl)-4-(2-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine, C₂₃H₂₂N₂O₃, (II), 2-(3,4-dimethoxyphenyl)-4-(2-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine, C₂₃H₂₂N₂O₃, (III), and 2-(2,5-dimethoxyphenyl)-4-(2-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine, C₂₃H₂₂N₂O₃, (IV)]. The stereochemical correlation of the two C₆ aromatic groups with respect to the benzodiazepine ring system is pseudo-equatorial-equatorial for compounds (I) (the phenyl group), (II) (the 2,3-dimethoxyphenyl group) and (III) (the 3,4-dimethoxyphenyl group), while for (IV) (the 2,5-dimethoxyphenyl group) the system is pseudo-axial-equatorial. An intramolecular hydrogen bond between the hydroxyl OH group and a benzodiazepine N atom is present for all four compounds and defines a six-membered ring, whose geometry is constant across the series. Although the molecular structures are similar, the supramolecular packing is different; compounds (I) and (IV) form chains, while (II) forms dimeric units and (III) displays a layered structure. The packing seems to depend on at least two factors: (i) the nature of the atoms defining the hydrogen bond and (ii) the number of intermolecular interactions of the types O-HO, N-HO, N-H [pi] (arene) or C-H [pi] (arene).

Formula: C₂₁H₁₈N₂O and three isomers of C₂₃H₂₂N₂O₃


	Structure factor file (CIF format) (142.1 kbytes) [ doi:10.1107/S0108270107024420/gg3095Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (163.3 kbytes) [ doi:10.1107/S0108270107024420/gg3095IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (166.8 kbytes) [ doi:10.1107/S0108270107024420/gg3095IIIsup4.hkl ] Contains datablock III

	Structure factor file (CIF format) (204.9 kbytes) [ doi:10.1107/S0108270107024420/gg3095IVsup5.hkl ] Contains datablock IV

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