Insight into supramolecular self-assembly directed by weak interactions in acetophenone derivatives: crystal structures and Hirshfeld surface analyses

Seth, Saikat Kumar; Sarkar, Debayan; Roy, Amalesh; Kar, Tanusree

doi:10.1039/c1ce05670k

Cited by 173 publications

(41 citation statements)

References 109 publications

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“…13a,17,18 The wings at the top left (d e > d i ) correspond to the points on the surface around the C-H donor, while those at the bottom right (d e < d i ) correspond to the surface around the π-acceptor. The shape of the surfaces clearly reflects this contact, 18,19 through a broad depression in the surface above the π-electron cloud of the aryl ring. The proportions of C π ···H/H···C π contacts comprise 20.3% and 20.1% of the total Hirshfeld surface areas of each molecule in 3 and 4, respectively.…”

Section: Hirshfeld Surfacesmentioning

confidence: 95%

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Crystallographic and computational study of 1-(arylamino)-1,2,3-triazole-4-carbohydrazides

Seth¹,

Lee

Yana

et al. 2015

CrystEngComm

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1 Graphical AbstractSystematic analysis reveals the influence of the aryl substituents upon the formation of supramolecular synthons based on N-H···N and N-H···O hydrogen bonding. AbstractCrystallography on mono-p-substituted derivatives of 1-(arylamino)-1,2,3-triazole-4-carbohydrazides, 1 (X = H), 2 (F), 3 (Cl) and 4 (Br), and a 2,5-dichloro (5) analogue, shows the molecular structures to be similar. Distinct hydrogen bonding patterns based on N-H···N and N-H···O are observed in their crystal structures with 1, having two independent molecules comprising the asymmetric unit, displaying one pattern, 2 and 5 another, and 3 and 4 yet another.Geometry optimisation calculations indicate any conformational differences in the solid-state do not persist in the gas-phase, and that no influence of the substituents is seen in the geometric parameters. A Natural Population Analysis, for both experimental and optimised structures, shows the charge on the triazole-N3 atom is at a maximum for 1, as opposed to 2-5, an observation correlated with its distinctive packing based around a supramolecular synthon not seen in the other structures. For the molecules having electronegative substituents, Molecular Electrostatic Potentials show the energies of the amine-H4n atoms are reduced for 2 and 5, compared to 3 and 4. A further distinction in 2-5 is indicated by the Hirshfeld surface analysis which highlights the importance of π···π interactions in 2 and 5, i.e. with the more electronegative substituents. Clearly, there is interplay between various factors but all correlated with the influence of the electronegativity of the substituent(s).

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Section: Hirshfeld Surfacesmentioning

confidence: 95%

“…where there is a small twist in the N1-N2-C1-O1 torsion angle, -8.03 (18)º. In 4, an intramolecular N1-H···O1 hydrogen bond is formed that closes an S(5) loop but this is not formed in the other molecules, based on the distance criteria incorporated in PLATON; 9 see Table 2 for geometric details.…”

Section: Molecular Structuresmentioning

confidence: 99%

Crystallographic and computational study of 1-(arylamino)-1,2,3-triazole-4-carbohydrazides

Seth¹,

Lee

Yana

et al. 2015

CrystEngComm

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“…The intermolecular interactions [31][32][33][37][38][39][40][41][42][43][44] in the crystal structure were quantified using Hirshfeld surface analysis and the associated 2D fingerprint plots [45][46][47] were calculated via the Crystal Explorer 3.0 [48] , which accepts a structure input file in the CIF format. This approach has been built on the electron distribution calculated as the sum of spherical atom electron densities [49,50] .…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

A new non-centrosymmetric microporous fluorinated iron phosphate: Structural elucidation, spectroscopic study and Hirshfeld surface analysis

Bouzidia

Hamdi

Salah

2016

Chem. Res. Chin. Univ.

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The crystal structure of a new non-centrosymmetric microporous fluorinated iron phosphate, (H 3 O) 2 [Fe 4 (H 2 O) 2 F 4 (PO 4 ) 2 (HPO 4 ) 2 ](H 2 O), was determined by single crystal X-ray diffraction analysis and the result reveals that it belongs to the orthorhombic system with four molecules in the unit cell(space group P2 1 2 1 2 1 ). Thus, the complex was characterized by powder X-ray diffraction, spectroscopic techniques(Fourier transform infrared and Fourier transform Raman) and 19 F MAS NMR. The elemental analysis of the sample was also carried out. The chiral inorganic sheets, which stacked along [100] showed the presence of FeF 2 O 4 as well as FeF 2 O 3 H 2 O octahedra, PO 4 besides HPO 4 tetrahedra, hydronium ions(H 3 O + ) and isolated water molecules. Hirshfeld surface analysis, especially d nom surface and fingerprint plots, were used for decoding the intermolecular interactions in the crystal network and the contribution of component units for the construction of the 3D architecture. From the Hirshfeld surfaces and 2D fingerprint analysis, it was found that the subtle interactions, such as H···H associating the third intense interaction of all intercontacts, provide extra stabilization in addition to the presence of the strong hydrogen bonds mentioned above.

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“…When the cif files of crystals 1 and 2 were read into the CrystalExplorer program for analysis, all bond lengths to hydrogen were automatically modified to typical standard neutron values (C-H = 1.083 Å and N-H = 1.009 Å ). The 2D fingerprint plots [33][34][35] were displayed by using the standard 0.5-2.5 Å view with the d e and d i distance scales were displayed on the graph axes.…”

Section: Hirshfeld Surface Calculationsmentioning

confidence: 99%

Crystals of 4-(2-benzimidazole)-1,2,4-triazole and its hydrate: preparations, crystal structure and Hirshfeld surfaces analysis

Wang

Yang

et al. 2015

Res Chem Intermed

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Single crystals of compound L (C 9 H 7 N 5 ): 4-(2-benzimidazole)-1,2,4-triazole and its hydrate were obtained via slow evaporation. The structures of the crystals were characterized by IR, TGA/DSC and X-ray diffraction analysis. Molecules in crystal 1 are linked by a combination of N-HÁÁÁN and C-HÁÁÁN hydrogen bonds into 2D layers, and further stacked into a 3D structure by pÁÁÁp stacking interactions. Compared to crystal 1, the water molecules play a key role in the construction of the crystal structure of hydrate 2. The 2D layers were formed via O-HÁÁÁN, O-HÁÁÁO, N-HÁÁÁN hydrogen bonds, and further stacked by O-HÁÁÁO hydrogen bonds and pÁÁÁp stacking interactions in crystal 2. A detailed analysis of the intermolecular interactions and crystal packing via Hirshfeld surface analysis and fingerprint plots reveals that the structures are stabilized mainly by NÁÁÁH/HÁÁÁN, CÁÁÁH/HÁÁÁC hydrogen bonds, HÁÁÁH weak interactions and pÁÁÁp stacking interactions.

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Insight into supramolecular self-assembly directed by weak interactions in acetophenone derivatives: crystal structures and Hirshfeld surface analyses

Cited by 173 publications

References 109 publications

Crystallographic and computational study of 1-(arylamino)-1,2,3-triazole-4-carbohydrazides

Crystallographic and computational study of 1-(arylamino)-1,2,3-triazole-4-carbohydrazides

A new non-centrosymmetric microporous fluorinated iron phosphate: Structural elucidation, spectroscopic study and Hirshfeld surface analysis

Crystals of 4-(2-benzimidazole)-1,2,4-triazole and its hydrate: preparations, crystal structure and Hirshfeld surfaces analysis

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