NDLI: Hydrogen-bonding patterns in 3-alkyl-3-hydroxyindolin-2-ones

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Hydrogen-bonding patterns in 3-alkyl-3-hydroxyindolin-2-ones

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Hydrogen-bonding patterns in 3-alkyl-3-hydroxyindolin-2-ones

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Becerra, Diana Insuasty, Braulio Cobo, Justo Glidewell, Christopher
Description	Country affiliation: Colombia Author Affiliation: Becerra D ( Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.)
Abstract	The molecules of racemic 3-benzoylmethyl-3-hydroxyindolin-2-one, C $_{16}H$ $_{13}NO$ $_{3},$ (I), are linked by a combination of N-H O and O-H O hydrogen bonds into a chain of centrosymmetric edge-fused R $_{2}$ $^{2}(10)$ and R $_{4}$ $^{4}(12)$ rings. Five monosubstituted analogues of (I), namely racemic 3-hydroxy-3-[(4-methylbenzoyl)methyl]indolin-2-one, C $_{17}H$ $_{15}NO$ $_{3},$ (II), racemic 3-[(4-fluorobenzoyl)methyl]-3-hydroxyindolin-2-one, C $_{16}H$ $_{12}FNO$ $_{3},$ (III), racemic 3-[(4-chlorobenzoyl)methyl]-3-hydroxyindolin-2-one, C $_{16}H$ $_{12}ClNO$ $_{3},$ (IV), racemic 3-[(4-bromobenzoyl)methyl]-3-hydroxyindolin-2-one, C $_{16}H$ $_{12}BrNO$ $_{3},$ (V), and racemic 3-hydroxy-3-[(4-nitrobenzoyl)methyl]indolin-2-one, C $_{16}H$ $_{12}N$ $_{2}O$ $_{5},$ (VI), are isomorphous in space group P . In each of compounds (II)-(VI), a combination of N-H O and O-H O hydrogen bonds generates a chain of centrosymmetric edge-fused R $_{2}$ $^{2}(8)$ and R $_{2}$ $^{2}(10)$ rings, and these chains are linked into sheets by an aromatic - stacking interaction. No two of the structures of (II)-(VI) exhibit the same combination of weak hydrogen bonds of C-H O and C-H (arene) types. The molecules of racemic 3-hydroxy-3-(2-thienylcarbonylmethyl)indolin-2-one, C $_{14}H$ $_{11}NO$ $_{3}S,$ (VII), form hydrogen-bonded chains very similar to those in (II)-(VI), but here the sheet formation depends upon a weak - stacking interaction between thienyl rings. Comparisons are drawn between the crystal structures of compounds (I)-(VII) and those of some recently reported analogues having no aromatic group in the side chain.
File Format	HTM / HTML
e-ISSN	20532296
Journal	Acta Crystallographica Section C Crystal Structure Communications
Issue Number	Pt 2
Volume Number	66
Language	English
Publisher	IUCr/Wiley
Publisher Date	2010-02-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Discipline Analytical Chemistry Discipline Crystallography
Content Type	Text
Resource Type	Article

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