Crystal engineering with pyrazolyl-thiazole derivatives: structure-directing role of π-stacking and σ-hole interactions

Abstract

The synthesis and X-ray characterization of 1-(2-(3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazol-5-yl)ethanone (7), ethyl 2-(5-(4-bromophenyl)-3-(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazole-4-carboxylate (8) and 2-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-N'-(2-hydroxy-3-methoxybenzylidene)thiazole-4-carbohydrazide (10) is described in this manuscript. The structure-directing role of a variety of noncovalent interactions have been...

Synthesis, Characterization, Crystal Structure and Computational Study of Third‐Order NLO Properties of Schiff bases

“…The Hirshfeld surface plotted over d norm is more important than the other Hirshfeld surfaces as it provides information about the H‐bonding interactions [34,36–39] . HS d norm utilizes blue, white, and red colors to recognize the interatomic contacts, which are longer, at Van der Waals separations, and short interatomic contacts, respectively [40–42] . Figures 4a and 4b are the Hirshfeld surfaces plotted over d norm for 2AP6NO and 2AP4ETH , respectively.…”

“…[34,[36][37][38][39] HS d norm utilizes blue, white, and red colors to recognize the interatomic contacts, which are longer, at Van der Waals separations, and short interatomic contacts, respectively. [40][41][42] Figures 4a and 4b are the Hirshfeld surfaces plotted over d norm for 2AP6NO and 2AP4ETH, respectively. Figure 4a shows close contacts arising from CÀ O� � �H (inside to outside) and H� � �OÀ C (outside to inside) as red circular spots.…”

Synthesis and X‐ray Characterization of 4,5‐Dihydropyrazolyl‐Thiazoles Bearing a Coumarin Moiety: On the Importance of Antiparallel π‐Stacking

“…[33] Similar properties have been also described for substituted pyrazolyl thiazolyl coumarin dyes. [34][35][36] In continuance of our previous work emphasizing the significance of antiparallel displaced π-stacking [37,38] and tetrel bonding [39,40] in crystal engineering, [41] in this manuscript we report the synthesis, spectroscopic and solid state characterization of two new pyrazolyl-thiazole-coumarin hybrids that present an extended π-surface due to the planarity of the pyrazolyl-thiazole-coumarin system that mostly dictate their Xray packing (see Scheme 1). Several π-stacking modes and halogen bonding interactions have been also studied using DFT calculations and characterized by a combination of computational tools, such us molecular electrostatic potential (MEP) surfaces, the quantum theory of atoms-in-molecules and the noncovalent interaction plot (NCIPlot).…”

Acid catalyzed one-pot approach towards the synthesis of curcuminoid systems: unsymmetrical diarylidene cycloalkanones, exploration of their single crystals, optical and nonlinear optical properties

“…Red and blue spots represent short and long contacts, respectively. [38][39][40][41] White spots represent the contacts for which the center to center distance between the atoms is equal to the sum of the van der Waals radii of the atoms involved. Fig.…”