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Hydrogen-bonding patterns in 3-alkyl-3-hydroxyindolin-2-ones
- Source :
- Acta Crystallographica Section C Crystal Structure Communications. 66:o79-o86
- Publication Year :
- 2010
- Publisher :
- International Union of Crystallography (IUCr), 2010.
-
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-1. 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 pi-pi 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...pi(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 pi-pi 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.
Details
- ISSN :
- 01082701
- Volume :
- 66
- Database :
- OpenAIRE
- Journal :
- Acta Crystallographica Section C Crystal Structure Communications
- Accession number :
- edsair.doi.dedup.....732c084ea1e9f26a0cd8d032aaa7b4cb