Issue 9, 2014

Experimental and theoretical analysis of lp⋯π intermolecular interactions in derivatives of 1,2,4-triazoles

Abstract

In the present study, we have synthesized and characterized two biologically active 1,2,4-triazole derivatives, a fluoro derivative, namely (E)-3-(4-fluoro-3-phenoxyphenyl)-4-((4-fluorobenzylidene)amino)-1-(morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione (TRZ-1), and a chloro derivative, namely (E)-4-((4-chlorobenzylidene)amino)-3-(4-fluoro-3-phenoxyphenyl)-1-(morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione (TRZ-2), via single crystal and powder X-ray diffraction. The chloro derivative crystallizes in an anhydrous form (TRZ-2A) and a solvated one (TRZ-2B) due to the presence of a toluene molecule in the crystal. This solvatomorphic behavior has been studied in detail using different thermal techniques, namely DSC and TGA, combined with hot stage microscopy (HSM). All of the three crystal structures show the presence of different intermolecular interactions of the type C–H⋯O, C–H⋯S[double bond, length as m-dash]C, C–H⋯π, C–H⋯X (X = –F, –Cl), π⋯π and lp⋯π interactions. The fingerprints for all these interactions were evaluated using Hirshfeld surfaces. The nature and energetics associated with these interactions were characterized using PIXEL and supported by ab initio quantum mechanical calculations using TURBOMOLE. In addition, the calculations performed on the evaluation of the electrostatic potential provide deeper insights into the nature of lp⋯π interactions.

Graphical abstract: Experimental and theoretical analysis of lp⋯π intermolecular interactions in derivatives of 1,2,4-triazoles

Supplementary files

Article information

Article type
Paper
Submitted
08 Nov 2013
Accepted
03 Dec 2013
First published
05 Dec 2013

CrystEngComm, 2014,16, 1702-1713

Author version available

Experimental and theoretical analysis of lp⋯π intermolecular interactions in derivatives of 1,2,4-triazoles

R. Shukla, T. P. Mohan, B. Vishalakshi and D. Chopra, CrystEngComm, 2014, 16, 1702 DOI: 10.1039/C3CE42286K

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