Assisted π-stacking: a strong synergy between weak interactions

2018 ◽  
Vol 54 (86) ◽  
pp. 12186-12189 ◽  
Author(s):  
Soumik Sao ◽  
Sumit Naskar ◽  
Narottam Mukhopadhyay ◽  
Mousumi Das ◽  
Debangshu Chaudhuri
Keyword(s):  
Weak Interactions ◽  
Π Stacking

An exceptionally strong synergy between aromatic π-stacking and n → π* interaction.

Controlling the molecular arrangement of racemates through weak interactions: the synergy between π-interactions and halogen bonds

2021 ◽  
Author(s):  
Carlos Romero-Nieto ◽  
A. de Cózar ◽  
Elzbieta Regulska ◽  
John B. Mullenix ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Weak Interactions ◽  
Halogen Bonds ◽  
Π Interactions ◽  
Molecular Arrangement ◽  
Π Stacking

The combination of halogend bonds from PO and N-moieties with π-stacking leads to sort out R- and S-isomers into homoleptic, porous assemblies.

Weak C—H...O and C—H...π hydrogen bonds and π–π stacking interactions in a series of fourN′-[(E)-(aryl)methylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazides

2015 ◽  
Vol 71 (8) ◽  
pp. 647-652 ◽  
Author(s):  
Thais C. M. Nogueira ◽  
Alessandra C. Pinheiro ◽  
James L. Wardell ◽  
Marcus V. N. de Souza ◽  
Jordan P. Abberley ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Weak Interactions ◽  
The Other ◽  
Stacking Interactions ◽  
Screw Axis ◽  
Chiral Structure ◽  
Π Stacking ◽  
Unit Form ◽  
Protective Groups ◽  
Local Inversion

Oxazolidin-2-ones are widely used as protective groups for 1,2-amino alcohols and chiral derivatives are employed as chiral auxiliaries. The crystal structures of four differently substituted oxazolidinecarbohydrazides, namelyN′-[(E)-benzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12N3O3, (I),N′-[(E)-2-chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12ClN3O3, (II), (4S)-N′-[(E)-4-chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12ClN3O3, (III), and (4S)-N′-[(E)-2,6-dichlorobenzylidene]-N,3-dimethyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C13H13Cl2N3O3, (IV), show that an unexpected mild-condition racemization from the chiral starting materials has occurred in (I) and (II). In the extended structures, the centrosymmetric phases, which each crystallize with two molecules (AandB) in the asymmetric unit, formA+Bdimers linked by pairs of N—H...O hydrogen bonds, albeit with different O-atom acceptors. One dimer is composed of one molecule with anSconfiguration for its stereogenic centre and the other with anRconfiguration, and possesses approximate local inversion symmetry. The other dimer consists of eitherR,RorS,Spairs and possesses approximate local twofold symmetry. In the chiral structure, N—H...O hydrogen bonds link the molecules intoC(5) chains, with adjacent molecules related by a 21screw axis. A wide variety of weak interactions, including C—H...O, C—H...Cl, C—H...π and π–π stacking interactions, occur in these structures, but there is little conformity between them.

scholarly journals Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands

2018 ◽  
Vol 9 (4) ◽  
pp. 360-368
Author(s):  
Ebru Keskin ◽  
Ummuhan Solmaz ◽  
Gun Binzet ◽  
Ilkay Gumus ◽  
Hakan Arslan
Keyword(s):  
Single Crystal ◽  
Weak Interactions ◽  
Platinum Complexes ◽  
Stacking Interactions ◽  
X Ray Diffraction ◽  
Thiourea Derivatives ◽  
X Ray ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
In Cis

Thiourea derivatives [N-(di-n-propylcarbamothioyl)-4-fluorobenzamide (HL1) and N-(di-n-propylcarbamothioyl)-4-bromobenzamide (HL2)] and their platinum complexes have been successfully synthesized and structurally characterized by spectroscopic 1H NMR, 13C NMR, COSY, HMQC, and FT-IR techniques. The structure of both complexes was also confirmed by single crystal X-ray diffraction studies. The study of X-ray single crystal diffraction shows that the supramolecular aggregation of the complexes is stabilized via weak interactions as well as stacking interactions such as C-H···π and π···π. The cis-[Pt(L1-S,O)2 showed C–H···π and π···π stacking interactions, whereas only C–H···π stacking interaction was observed in cis-[Pt(L2-S,O)2]. In addition, the strong classical and non-classical intermolecular hydrogen bonds are not found in the prepared complexes. Therefore, it can be said that the C–H···π and π···π stacking interactions play an important role in the formation of supramolecular structures of the complexes.

scholarly journals Different weak interactions in the crystals of three isomeric (E)-N-methyl-N′-(nitrobenzylidene)-2-(thiophen-2-yl)acetohydrazides

2016 ◽  
Vol 72 (12) ◽  
pp. 1677-1682 ◽  
Author(s):  
Laura N. F. Cardoso ◽  
Thais C. M. Noguiera ◽  
Carlos R. Kaiser ◽  
James L. Wardell ◽  
Marcus V. N. de Souza ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Crystal Structures ◽  
Nitro Group ◽  
Benzene Ring ◽  
Weak Interactions ◽  
Three Dimensional ◽  
Π Stacking

The crystal structures of three isomeric (E)-N-methyl-N′-(nitrobenzylidene)-2-(thiophen-2-yl)acetohydrazides (formula C14H13N3O3S) are described, with the nitro group inortho,metaandparapositions in the benzene ring. In each crystal structure, molecules are linked by various weak interactions (C—H...O and C—H...π bonds, and π–π stacking), leading to three-dimensional networks in each case, but with little similarity between them.

scholarly journals Energy frameworks and a topological analysis of the supramolecular features in in situ cryocrystallized liquids: tuning the weak interaction landscape via fluorination

2016 ◽  
Vol 18 (46) ◽  
pp. 31811-31820 ◽  
Author(s):  
Dhananjay Dey ◽  
Subhrajyoti Bhandary ◽  
Sajesh P. Thomas ◽  
Mark A. Spackman ◽  
Deepak Chopra
Keyword(s):  
Weak Interaction ◽  
Weak Interactions ◽  
Topological Analysis ◽  
Fluorine Substitution ◽  
Π Stacking

The weak interactions assist in tuning the growth of π⋯π stacking with fluorine substitution in in situ cryocrystallized liquids.

scholarly journals 5-(2-Chlorophenyl)-3-(2H-chromen-3-yl)-1,2,4-oxadiazole

IUCrData ◽  
2018 ◽  
Vol 3 (1) ◽  
Author(s):  
Nilofar Baral ◽  
Sabita Nayak ◽  
Satyanarayan Pal ◽  
Seetaram Mohapatra
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Weak Interactions ◽  
Stacking Interactions ◽  
Two Dimensional ◽  
Individual Molecule ◽  
Compound C ◽  
Π Stacking

In the title compound, C17H11ClN2O2, the central oxadiazole ring carries 2H-chromene and 2-chlorophenyl substituents at the 3- and 5-positions, respectively. C—H...O and C—H...Cl hydrogen bonds form two-dimensional sheets parallel to (212), with each individual molecule involved in six of these weak interactions. The sheets are stacked perpendicular to (212) by offset π–π stacking interactions.

scholarly journals Self-assembly of supermolecular species directed by hydrogen bonding and aromatic π–π stacking interactions

2018 ◽  
Vol 33 (2) ◽  
pp. 13
Author(s):  
X. H. Li ◽  
A. F. Jalbout ◽  
W. D. Xiang
Keyword(s):  
Solid State ◽  
Self Assembly ◽  
Weak Interactions ◽  
State Structure ◽  
X Ray Diffraction ◽  
Solid State Structure ◽  
X Ray ◽  
Supramolecular Architectures ◽  
Π Stacking ◽  
Π Stacking Interaction

A new Cu(II) trimers, [Cu3(dcp)2(H2O)8]. 4DMF, with the ligand 3,5-pyrazoledicarboxylic acid monohydrate (H3dcp) has been prepared by solvent method. Its solid-state structure has been characterized by elemental analysis, thermal analysis (TGA and DSC), and single crystal X-ray diffraction. X-ray crystallographic studies reveal that this complex has extended 1-D,2-D and 3-D supramolecular architectures directed by weak interactions (hydrogen bond and aromatic π-π stacking interaction) leading to a sandwich solid-state structure.

Supramolecular structures of rhenium(I) complexes mediated by ligand planarity via the interplay of substituents

2018 ◽  
Vol 74 (9) ◽  
pp. 997-1006 ◽  
Author(s):  
Wun Fui Mark-Lee ◽  
Yan Yi Chong ◽  
Mohammad B. Kassim
Keyword(s):  
Weak Interactions ◽  
Supramolecular Structures ◽  
Molecular Structures ◽  
Planar Geometry ◽  
Centrosymmetric Dimer ◽  
Plane Analysis ◽  
Planar Conformation ◽  
Π Stacking ◽  
Localized Orbital ◽  
Centrosymmetric Dimers

The crystal and molecular structures of two ReI tricarbonyl complexes, namely fac-tricarbonylchlorido[1-(4-fluorocinnamoyl)-3-(pyridin-2-yl-κN)pyrazole-κN 2]rhenium(I), [ReCl(C17H12FN3O)(CO)3], (I), and fac-tricarbonylchlorido[1-(4-nitrocinnamoyl)-3-(pyridin-2-yl-κN)pyrazole-κN 2]rhenium(I) acetone monosolvate, [ReCl(C17H12ClN4O3)(CO)3]·C3H6O, (II), are reported. The complexes form centrosymmetric dimers that are linked into one-dimensional columns by C—H...Cl and N—O...H interactions in (I) and (II), respectively. C—H...Cl interactions in (II) generate two R 2 1(7) loops that merge into a single R 2 1(10) loop. These interactions involve the alkene, pyrazole and benzene rings, hence restricting the ligand rotation and giving rise to a planar conformation. Unlike (II), complex (I) exhibits a twisted conformation of the ligand and a pair of molecules forms a centrosymmetric dimer with an R 2 2(10) loop via C—H...O interactions. The unique supramolecular structures of (I) and (II) are determined by their planarity and weak interactions. The planar conformation of (II) provides a base for appreciable π–π stacking interactions compared to (I). In addition, an N—O...π interaction stabilizes the supramolecular structure of (II). We report herein the first n→π* interactions of ReI tricarbonyl complexes, which account for 0.33 kJ mol−1. Intermolecular C—H...Cl and C—H...O interactions are present in both complexes, with (II) showing a greater preference for these interactions compared to (I), with cumulative contributions of 48.7 and 41.5%, respectively. The influence of inductive (fluoro) and/or resonance (nitro) effects on the π-stacking ability was further supported by LOLIPOP (localized orbital locator-integrated π over plane) analysis. The benzene ring of (II) demonstrated a higher π-stacking ability compared to that of (I), which is supported by the intrinsic planar geometry. The HOMA (harmonic oscillator model of aromaticity) index of (I) revealed more aromaticity with respect to (II), suggesting that NO2 greatly perturbed the aromaticity. The Hirshfeld fingerprint (FP) plots revealed the preference of (II) over (I) for π–π contacts, with contributions of 6.8 and 4.4%, respectively.

scholarly journals Weak interactions in the crystal structures of two indole derivatives

2016 ◽  
Vol 72 (7) ◽  
pp. 964-968
Author(s):  
Jamie R. Kerr ◽  
Laurent Trembleau ◽  
John M. D. Storey ◽  
James L. Wardell ◽  
William T. A. Harrison
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Weak Interactions ◽  
Indole Derivatives ◽  
Halogen Bonds ◽  
Π Interactions ◽  
Π Stacking

We describe the syntheses and crystal structures of two indole derivatives, namely a second monoclinic polymorph of ethyl 5-chloro-1H-indole-2-carboxylate C11H10ClNO2, (I), and ethyl 5-chloro-3-iodo-1H-indole-2-carboxylate, C11H9ClINO2, (II). In their crystal structures, both compounds form inversion dimers linked by pairs of N—H...O hydrogen bonds, which generateR22(10) loops. The dimers are linked into double chains in (I) and sheets in (II) by a variety of weak interactions, including π–π stacking, C—I...π, C—Cl—π interactions and I...Cl halogen bonds.

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