Crystal Structure and Hirshfeld Analysis of Di--butyl 2,2'-[(ethyl-aza-nedi-yl)bis-(methyl-ene)]bis-(1-pyrrole-1-carboxyl-ate)

Overview

Journal Acta Crystallogr E Crystallogr Commun

Date 2021 Feb 1

PMID 33520262

Authors

Elizaveta A Kvyatkovskaya

Zeliha Atioglu

Mehmet Akkurt

Polina P Epifanova

Karina S Valchuk

Victor N Khrustalev

Ajaya Bhattarai

Affiliations

Soon will be listed here.

Abstract

The title compound, CHNO, crystallizes in the triclinic space group with two mol-ecules in a unit cell. The two pyrrole rings are essentially planar (r.m.s. deviation = 0.002 Å) and they form a dihedral angle of 81.24 (10)° with each other. The crystal packing is stabilized by C-H⋯π inter-actions and π-π stacking inter-actions, forming a three-dimensional network. The Hirshfeld surface analysis and two-dimensional fingerprint plots reveal that the most important contributions for the crystal packing are from H⋯H (74.3%), C⋯H/H⋯C (11.5%) and O⋯H/H⋯O (9.1%) contacts.

References

Winkler J . Tandem Dielsminus signAlder Cycloadditions in Organic Synthesis. Chem Rev. 1996; 96(1):167-176. DOI: 10.1021/cr950029z. View

Spek A . validation ALERTS: what they mean and how to respond. Acta Crystallogr E Crystallogr Commun. 2020; 76(Pt 1):1-11. PMC: 6944088. DOI: 10.1107/S2056989019016244. View

Evans P . Scaling and assessment of data quality. Acta Crystallogr D Biol Crystallogr. 2005; 62(Pt 1):72-82. DOI: 10.1107/S0907444905036693. View

Wang R, Liang Y, Liu G, Pu S . Aggregation-induced emission compounds based on 9,10-diheteroarylanthracene and their applications in cell imaging. RSC Adv. 2022; 10(4):2170-2179. PMC: 9048432. DOI: 10.1039/c9ra09290k. View

Borisova K, Nikitina E, Novikov R, Khrustalev V, Dorovatovskii P, Zubavichus Y . Diels-Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control. Chem Commun (Camb). 2018; 54(23):2850-2853. DOI: 10.1039/c7cc09466c. View

Butler , Hammond , Johnston , Sun , Malpass , Fawcett . In-Line Proximity Effects in Extended 7-Azanorbornanes. 1. A New Concept for Modifying Effector Group Separation Based on the Control of N-Invertomer Geometry. Org Lett. 2000; 2(6):721-724. DOI: 10.1021/ol9910969. View

Domingo , Picher , Andres . Toward an understanding of the selectivity in domino reactions. A DFT study of the reaction between acetylenedicarboxylic acid and 1, 3-Bis(2-furyl)propane. J Org Chem. 2000; 65(11):3473-7. DOI: 10.1021/jo000030k. View

Groom C, Bruno I, Lightfoot M, Ward S . The Cambridge Structural Database. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016; 72(Pt 2):171-9. PMC: 4822653. DOI: 10.1107/S2052520616003954. View

Karmakar A, Rubio G, Paul A, Guedes da Silva M, Mahmudov K, Guseinov F . Lanthanide metal organic frameworks based on dicarboxyl-functionalized arylhydrazone of barbituric acid: syntheses, structures, luminescence and catalytic cyanosilylation of aldehydes. Dalton Trans. 2017; 46(26):8649-8657. DOI: 10.1039/c7dt01056g. View

10.

Battye T, Kontogiannis L, Johnson O, Powell H, Leslie A . iMOSFLM: a new graphical interface for diffraction-image processing with MOSFLM. Acta Crystallogr D Biol Crystallogr. 2011; 67(Pt 4):271-81. PMC: 3069742. DOI: 10.1107/S0907444910048675. View

11.

Bruno I, Cole J, Edgington P, Kessler M, Macrae C, McCabe P . New software for searching the Cambridge Structural Database and visualizing crystal structures. Acta Crystallogr B. 2002; 58(Pt 3 Pt 1):389-97. DOI: 10.1107/s0108768102003324. View

12.

Mahmudov K, Kopylovich M, Guedes da Silva M, Pombeiro A . Chalcogen bonding in synthesis, catalysis and design of materials. Dalton Trans. 2017; 46(31):10121-10138. DOI: 10.1039/c7dt01685a. View

13.

Borisova K, Kvyatkovskaya E, Nikitina E, Aysin R, Novikov R, Zubkov F . Classical Example of Total Kinetic and Thermodynamic Control: The Diels-Alder Reaction between DMAD and Bis-furyl Dienes. J Org Chem. 2018; 83(8):4840-4850. DOI: 10.1021/acs.joc.8b00336. View

14.

McKinnon J, Jayatilaka D, Spackman M . Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces. Chem Commun (Camb). 2008; (37):3814-6. DOI: 10.1039/b704980c. View

15.

Zhang J, Kang H, Li N, Zhou S, Sun H, Yin S . Organic solid fluorophores regulated by subtle structure modification: color-tunable and aggregation-induced emission. Chem Sci. 2017; 8(1):577-582. PMC: 5351801. DOI: 10.1039/c6sc02875f. View

16.

Lautens M, Fillion E . An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction. J Org Chem. 1997; 62(13):4418-4427. DOI: 10.1021/jo9701593. View