Becerra Diana, Insuasty Braulio, Cobo Justo, Glidewell Christopher
Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.
Acta Crystallogr C. 2010 Feb;66(Pt 2):o79-86. doi: 10.1107/S0108270110001058. Epub 2010 Jan 22.
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.
外消旋的3-苯甲酰甲基-3-羟基吲哚啉-2-酮（C₁₆H₁₃NO₃，(I)）分子通过N-H…O和O-H…O氢键的组合连接成由中心对称的边稠合R₂²(10)和R₄⁴(12)环组成的链。(I)的五个单取代类似物，即外消旋的3-羟基-3-[(4-甲基苯甲酰基)甲基]吲哚啉-2-酮（C₁₇H₁₅NO₃，(II)）、外消旋的3-[(4-氟苯甲酰基)甲基]-3-羟基吲哚啉-2-酮（C₁₆H₁₂FNO₃，(III)）、外消旋的3-[(4-氯苯甲酰基)甲基]-3-羟基吲哚啉-2-酮（C₁₆H₁₂ClNO₃，(IV)）、外消旋的3-[(4-溴苯甲酰基)甲基]-3-羟基吲哚啉-2-酮（C₁₆H₁₂BrNO₃，(V)）和外消旋的3-羟基-3-[(4-硝基苯甲酰基)甲基]吲哚啉-2-酮（C₁₆H₁₂N₂O₅，(VI)），在空间群P-1中是同构的。在化合物(II)-(VI)的每一个中，N-H…O和O-H…O氢键的组合产生了由中心对称的边稠合R₂²(8)和R₂²(10)环组成的链，并且这些链通过芳香π-π堆积相互作用连接成片。(II)-(VI)的结构中没有两个具有相同类型的C-H…O和C-H…π(芳烃)弱氢键组合。外消旋的3-羟基-3-(2-噻吩基羰基甲基)吲哚啉-2-酮（C₁₄H₁₁NO₃S，(VII)）分子形成了与(II)-(VI)中非常相似的氢键链，但在这里片层的形成取决于噻吩环之间的弱π-π堆积相互作用。对化合物(I)-(VII)的晶体结构与一些最近报道的侧链中没有芳香基团的类似物的晶体结构进行了比较。
