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首页> 外文期刊>Acta crystallographica. Section C, Structural chemistry. >Crystal structures of four δ-keto esters and a Cambridge Structural Database analysis of cyano–halogen interactions
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Crystal structures of four δ-keto esters and a Cambridge Structural Database analysis of cyano–halogen interactions

机译：四种δ-酮酸酯的晶体结构和氰基-卤素相互作用的剑桥结构数据库分析

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The revived interest in halogen bonding as a tool in pharmaceutical cocrystals and drug design has indicated that cyano–halogen interactions could play an important role. The crystal structures of four closely related δ-keto esters, which differ only in the substitution at a single C atom (by H, OMe, Cl and Br), are compared, namely ethyl 2-cyano-5-oxo-5-phenyl-3-(piperidin-1-yl)pent-2-enoate, C19H22N2O3, (1), ethyl 2-cyano-5-(4-methoxyphenyl)-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C20H24N2O4, (2), ethyl 5-(4-chlorophenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C19H21ClN2O3, (3), and the previously published ethyl 5-(4-bromophenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C19H21BrN2O3, (4) [Maurya, Vasudev & Gupta (2013). RSC Adv.3, 12955–12962]. The molecular conformations are very similar, while there are differences in the molecular assemblies. Intermolecular C—H...O hydrogen bonds are found to be the primary interactions in the crystal packing and are present in all four structures. The halogenated derivatives have additional aromatic–aromatic interactions and cyano–halogen interactions, further stabilizing the molecular packing. A database analysis of cyano–halogen interactions using the Cambridge Structural Database [CSD; Groom & Allen (2014). Angew. Chem. Int. Ed.53, 662–671] revealed that about 13% of the organic molecular crystals containing both cyano and halogen groups have cyano–halogen interactions in their packing. Three geometric parameters for the C—X...N[triple-bond]C interaction (X?= F, Cl, Br or I), viz. the N...X distance and the C—X...N and C—N...X angles, were analysed. The results indicate that all the short cyano–halogen contacts in the CSD can be classified as halogen bonds, which are directional noncovalent interactions.
机译：对卤素键作为药物共晶体和药物设计工具的兴趣重新显现，表明氰基-卤素相互作用可能起重要作用。比较了四种密切相关的δ-酮酯的晶体结构，它们的区别仅在于在单个C原子上的取代（通过H，OMe，Cl和Br）不同，即乙基2-氰基-5-氧代-5-苯基-3-（哌啶-1-基）戊-2-烯酸酯，C19H22N2O3，（1），2-氰基-5-（4-甲氧基苯基）-5-氧代-3-（哌啶-1-基）戊-乙基2-烯酸酯，C20H24N2O4，（2），5-（4-氯苯基）-2-氰基-5-氧代-3-（哌啶-1-基）戊-2-烯酸酯，C19H21ClN2O3，（3）和以前发表的5-（4-溴苯基）-2-氰基-5-氧代-3-（哌啶-1-基）戊-2-烯酸酯，C19H21BrN2O3，（4）[Maurya，Vasudev＆Gupta（2013）。 RSC Adv.3，12955–12962]。分子构象非常相似，但分子组装有所不同。发现分子间的CHH ... O氢键是晶体堆积中的主要相互作用，并且存在于所有四个结构中。卤代衍生物具有额外的芳族-芳族相互作用和氰基-卤素相互作用，从而进一步稳定了分子堆积。使用剑桥结构数据库[CSD; 2002]进行氰基-卤素相互作用的数据库分析。新郎与艾伦（2014）。 Angew。化学诠释Ed.53，662–671]发现，约有13％的同时含有氰基和卤素基团的有机分子晶体在其堆积中具有氰基-卤素相互作用。 C-X ... N-三键相互作用的三个几何参数（X = F，Cl，Br或I），即。分析了N ... X距离以及C-X ... N和C-N ... X角度。结果表明，CSD中所有的氰基-卤素短接触都可以归为卤素键，这是方向性非共价相互作用。

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