4-(2-Hydroxy-phen-yl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepine and the 2-(2,3-dimethoxy-phen-yl)-, 2-(3,4-dimethoxy-phen-yl)- and 2-(2,5-dimeth-oxy- phen-yl)-substituted derivatives

Carlos A. Escobar, Oscar Donoso-Tauda, Ramiro Araya-Maturana, Andrés Vega

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

8 Citas (Scopus)

Resumen

The 1,5-benzodiazepine ring system exhibits a puckered boat-like conformation for all four title compounds [4-(2-hydroxy-phen-yl)-2-phenyl-2,3- dihydro-1H-1,5-benzodiazepine, C21H18N2O, (I), 2-(2,3-dimethoxy-phen-yl)-4-(2- hydroxy-phen-yl)-2,3-dihydro-1H-1,5-benzodiazepine, C23H22N2O3, (II), 2-(3,4-dimeth-oxy-phen-yl)-4-(2-hydroxy-phen-yl)-2,3-dihydro-1H-1, 5-benzodiazepine, C23H22N2O3, (III), and 2-(2,5-dimethoxy-phen-yl)-4-(2-hydroxy- phen-yl)-2,3-dihydro-1H-1,5-benzo-diaze-pine, 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-dimeth-oxy-phenyl group) and (III) (the 3,4-dimethoxy-phenyl group), while for (IV) (the 2,5-dimethoxy-phenyl group) the system is pseudo-axial-equatorial. An intra-molecular 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 mol-ecular structures are similar, the supra-molecular 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 inter-molecular inter-actions of the types O - H⋯O, N - H⋯O, N - H⋯π(arene) or C - H⋯π(arene).

Idioma originalInglés
Páginas (desde-hasta)o426-o430
PublicaciónActa Crystallographica Section C: Crystal Structure Communications
Volumen63
N.º7
DOI
EstadoPublicada - 14 jun 2007

Áreas temáticas de ASJC Scopus

  • Bioquímica, genética y biología molecular (todo)

Huella

Profundice en los temas de investigación de '4-(2-Hydroxy-phen-yl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepine and the 2-(2,3-dimethoxy-phen-yl)-, 2-(3,4-dimethoxy-phen-yl)- and 2-(2,5-dimeth-oxy- phen-yl)-substituted derivatives'. En conjunto forman una huella única.

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