Planarity of substituted pyrrole and furan rings in (3R*, 1'S*, 3'R*)-3-(1'-tert-butylamino-1'H, 3'H-benzo[c] furan-3'- yl)-2-tert-butyl-2,3-dihydro-1H-benzo[c] pyrrol-1-one

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F17%3A00485892" target="_blank" >RIV/61388955:_____/17:00485892 - isvavai.cz</a>

Alternative codes found

RIV/68378271:_____/17:00485892 RIV/00216208:11310/17:10360426

Result on the web

<a href="http://dx.doi.org/10.1515/zkri-2016-2001" target="_blank" >http://dx.doi.org/10.1515/zkri-2016-2001</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1515/zkri-2016-2001" target="_blank" >10.1515/zkri-2016-2001</a>

Result language

angličtina

Original language name

Planarity of substituted pyrrole and furan rings in (3R*, 1'S*, 3'R*)-3-(1'-tert-butylamino-1'H, 3'H-benzo[c] furan-3'- yl)-2-tert-butyl-2,3-dihydro-1H-benzo[c] pyrrol-1-one

Original language description

The title structure, (3R*, 1' S*, 3' R*)-3-(1'-tertbutylamino- 1' H, 3' H-benzo[c] furan-3'-yl)-2-tert-butyl-2,3dihydro- 1H-benzo[c] pyrrol-1-one has been determined at 290 and 150 K by single-crystal X-ray diffraction. The structure comprises two symmetry independent molecules with very similar conformations which differ mostly by orientations of the tert-butyl groups, situated at the periphery of these molecules. The molecules are composed of two parts, the cores of which are isoindolinone and isobenzofuran rings being bound by C-C bonds. The planarities of the pyrrolone and furan rings are compared with the known structures retrieved from the Cambridge Crystal Structure Database. It transpires in the title molecules, the planarity of the carbonyl-substituted pyrrole rings is exceptionally distorted in contrast to the furan rings. This fact is just the opposite of the tendency inferred from the Cambridge Crystal Structure Database. The reason may be the influence of the voluminous tertbutyl group which is attached to the nitrogen of the pyrrole group, as well as short centroid-centroid distances between the carbonyl-substituted pyrrole and furan rings. Cohesion forces between the molecules and their parts are provided by weak interactions only: The packing suggests C-H center dot center dot center dot O, pi-pi-electron ring interactions, N-H center dot center dot center dot p-electron ring as well as C-H center dot center dot center dot pi-pi-electron ring interactions. The structure determination of the title compound, the product of the reaction of o-phthalaldehyde with tert-butylamine, has provided indication about the mechanism of a chemical reaction which resulted in the formation of the title molecule.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10403 - Physical chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Zeitschrift fur Kristallographie-Crystalline Materials

ISSN

2194-4946

e-ISSN

—

Volume of the periodical

232

Issue of the periodical within the volume

6

Country of publishing house

DE - GERMANY

Number of pages

12

Pages from-to

441-452

UT code for WoS article

000402380200004

EID of the result in the Scopus database

2-s2.0-85020725764