A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en-2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui).

IF 0.8 4区 化学
Cristian Paz, José Becerra, Mario Silva, Eleonora Freire, Ricardo Baggio
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引用次数: 8

Abstract

The title compound [systematic name: (4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en-2-yl)(1H-indol-3-yl)methanone], C20H22N2O, (II), was obtained from mother liquors extracted from Aristotelia chilensis (commonly known as maqui), a native Chilean tree. The compound is a polymorphic form of that obtained from the same source and reported by Watson, Nagl, Silva, Cespedes & Jakupovic [Acta Cryst. (1989), C45, 1322-1324], (Ia). The molecule consists of an indolyl ketone fragment and a nested three-ring system, with both groups linked by a C-C bridge. Comparison of both forms shows that they do not differ in their gross features but in the relative orientation of the two ring systems, due to different rotations around the bridge, as measured by the O=C-C=N torsion angle [130.0 (7)° in (Ia) and 161.6 (2)° in (II)]. The resulting slight conformational differences are reflected in a number of intramolecular contacts being observed in (II) but not in (Ia). Regarding intermolecular interactions, both forms share a similar N-H···O synthon but with differing hydrogen-bonding strength, leading in both cases to C(6) catemers with different chain motifs. There are marked differences between the two forms regarding colour and the (de)localization of a double bond, which allows speculation about the possible existence of different variants of this type of molecule.

4,4-二甲基-8-亚甲基-3-氮杂环[3.3.1]非2-烯-2-基-3-吲哚基酮的多态形式,一种从亚里斯多德中提取的吲哚类生物碱。
标题化合物[系统名称:(4,4-二甲基-8-亚甲基-3- azabicycloo [3.3.1]non-2-en-2-yl)(1h -吲哚-3-yl)甲烷],C20H22N2O, (II),从智利原生树种亚硝酸木(俗称maqui)的母液中提取。该化合物是从相同来源获得并由Watson, Nagl, Silva, Cespedes和Jakupovic [Acta crystal]报道的化合物的多态形式。[j] . (1989), C45, 1322-1324。该分子由吲哚酮片段和嵌套的三环体系组成,两个基团通过C-C桥连接。两种形式的比较表明,它们在总体特征上没有区别,但由于围绕桥的旋转不同,两个环体系的相对取向不同,通过O=C-C=N扭转角[130.0(7)°in (Ia)和161.6(2)°in (II)]来测量。由此产生的轻微构象差异反映在(II)中观察到的一些分子内接触中,而在(Ia)中没有。在分子间相互作用方面,这两种形式具有相似的N-H···O合子,但氢键强度不同,导致两种形式的C(6)双链化合物具有不同的链基序。这两种形式在颜色和双键的(去)定位方面存在显著差异,这使得人们可以推测这类分子可能存在不同的变体。
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来源期刊
自引率
12.50%
发文量
0
审稿时长
1 months
期刊介绍: Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.
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