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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—H...O, N—H...O, N—H...π(arene) or C—H...π(arene).
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