Crystal structure, DFT study and Hirshfeld surface analysis of 1-nonyl-2,3-di-hydro-1 H-indole-2,3-dione

Ibtissam Rayni; Youness El Bakri; Chin-Hung Lai; Jihad Sebhaoui; El Mokhtar Essassi; Joel T Mague

doi:10.1107/S2056989019009691

Crystal structure, DFT study and Hirshfeld surface analysis of 1-nonyl-2,3-di-hydro-1 H-indole-2,3-dione

Acta Crystallogr E Crystallogr Commun. 2019 Jul 12;75(Pt 8):1140-1144. doi: 10.1107/S2056989019009691. eCollection 2019 Aug 1.

Authors

Ibtissam Rayni¹, Youness El Bakri², Chin-Hung Lai^{3

4}, Jihad Sebhaoui¹, El Mokhtar Essassi¹, Joel T Mague⁵

Affiliations

¹ Laboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des Médicaments, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco.
² Organic Chemistry Department, Faculty of Science, RUDN University, Miklukho-Maklaya St. 6, 117198 Moscow, Russian Federation.
³ Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung 40241, Taiwan.
⁴ Department of Medical Education, Chung Shan Medical University Hospital, 402 Taichung, Taiwan.
⁵ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

Abstract

In the title mol-ecule, C₁₇H₂₃NO₂, the di-hydro-indole portion is planar (r.m.s. deviation = 0.0157 Å) and the nonyl substituent is in an 'extended' conformation. In the crystal, the nonyl chains inter-calate and the di-hydro-indole-dione units are associated through C-H⋯O hydrogen bonds to form micellar blocks. Based on the Hirshfeld surface analysis, the most important inter-molecular inter-action is the H⋯H inter-action.

Keywords: crystal structure; dihydroindoledione; hydrogen bond; micelle; π-stacking.

Grants and funding

This work was funded by RUDN University grant . National Science Foundation grant 1228232. Tulane University grant .