Investigation of the crystal structures and Hirshfeld surfaces of three closely related N-(2-fluorobenzoyl)-arylsulfonamides

2016 ◽  
Vol 231 (6) ◽  
Author(s):  
Parameshwar Adimule Suchetan ◽  
Gundagallu Madanagopala Reddy Supriya ◽  
Kalavala Shivaprakash Srivishnu ◽  
Hanumanahalli Nagaraju Lakshmikantha ◽  
Shivalingegowda Naveen ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Compound I ◽  
One Dimensional ◽  
Π Interactions ◽  
Hirshfeld Surfaces ◽  
3D Network ◽  
2D Arrays ◽  
2D Network

AbstractThe investigation of the crystal structures of three closely related sulfonamides, namely N-(2-fluorobenzoyl)-2-methylbenzenesulfonamide (I), N-(2-fluorobenzoyl)-4-methylbenzenesulfonamide (II) and N-(2-fluorobenzoyl)-2-chlorobenzenesulfonamide (III) by analysing intermolecular interactions and the packing patterns, and also by Hirshfeld surface analyses is presented. Compound (I) has a three-dimensional (3D) network, in which N–H···O and C–H···F chains build up two-dimensional (2D) arrays, which are extended into a 3D network through C–H···π interactions. In (II), alternating N–H···O and C–H···O rings form one-dimensional (1D) ribbons, which are interconnected by C–H···π interactions to build a 2D network. In (III), 2D sheets comprising N–H···O rings, C–H···π chains, Cl···F and F···F contacts are stacked by π···π interactions to form a 3D network. Hirshfeld surface analyses, comprising d

Crystal structures and Hirshfeld surface analysis of four 1,4-bis(methoxyphenyl)-2,3-diazabuta-1,3-dienes: comparisons of the intermolecular interactions in related compounds

2019 ◽  
Vol 234 (1) ◽  
pp. 59-71 ◽  
Author(s):  
Ligia R. Gomes ◽  
John N. Low ◽  
Nathasha R. de L. Correira ◽  
Thais C.M. Noguiera ◽  
Alessandra C. Pinheiro ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Dimensional Structure ◽  
Intermolecular Hydrogen Bonds ◽  
Π Interactions ◽  
Isomeric Compound ◽  
Related Compounds

Abstract The crystal structures of four azines, namely 1-3-bis(4-methoxyphenyl)-2,3-diaza-1,4-butadiene, 1, 1,3-bis(2,3-dimethoxyphenyl)-2,3-diaza-1,4-butadiene, 2, 1,3-bis(2-hydroxy-3-methoxyphenyl)-2,3-diaza-1,4-butadiene, 3, and 1,3-bis(2-hydroxy-4-methoxyphenyl)-2,3-diaza-1,4-butadiene, 4, are reported. Molecules of 3 and 4, and both independent molecules of 2, Mol A and Mol B, possess inversion centers. The central C=N–N=C units in each molecule is planar with an (E,E) conformation. The intermolecular interactions found in the four compounds are C–H···O, C–H–N, C–H---π and π---π interactions. However, there is no consistent set of intermolecular interactions for the four compounds. Compound, 1, has a two-dimensional undulating sheet structure, generated from C–H···O and C–H···N intermolecular hydrogen bonds. The only recognized intermolecular interaction in 2 is a C–H···O hydrogen bond, which results in a zig-zag chain of alternating molecules, Mol A and Mol B. While 3 forms a puckered sheet of molecules, solely via C–H···π interactions, its isomeric compound, 4, has a more elaborate three-dimensional structure generated from a combination of C–H···O hydrogen bonds, C–H···π and π···π interactions. The findings in this study, based on both PLATON and Hirshfeld approaches, for the four representative compounds match well the reported structural findings in the literature of related compounds, which are based solely on geometric parameters.

scholarly journals Crystal structures of three 6-aryl-2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazoles

2020 ◽  
Vol 76 (1) ◽  
pp. 18-24
Author(s):  
Sadashivamurthy Shamanth ◽  
Kempegowda Mantelingu ◽  
Haruvegowda Kiran Kumar ◽  
Hemmige S. Yathirajan ◽  
Sabine Foro ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Three Dimensional ◽  
Asymmetric Unit ◽  
Compound I ◽  
Π Interactions ◽  
Reductive Condensation ◽  
Independent Molecules ◽  
Compound Ii

Three title compounds, namely, 2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]-6-phenylimidazo[2,1-b][1,3,4]thiadiazole, C26H19ClN4S, (I), 2-(4-chlorobenzyl)-6-(4-fluorophenyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole, C26H18ClFN4S, (II), and 6-(4-bromophenyl)-2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole, C26H18BrClN4S, (III), have been prepared using a reductive condensation of indole with the corresponding 6-aryl-2-(4-chlorobenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehydes (aryl = phenyl, 4-fluorophenyl or 4-bromophenyl), and their crystal structures have been determined. The asymmetric unit of compound (I) consists of two independent molecules and one of the molecules exhibits disorder of the 4-chlorobenzyl substituent with occupancies 0.6289 (17) and 0.3711 (17). Each type of molecule forms a C(8) chain motif built from N—H...N hydrogen bonds, which for the fully ordered molecule is reinforced by C—H...π interactions. In compound (II), the chlorobenzyl unit is again disordered, with occupancies 0.822 (6) and 0.178 (6), and the molecules form C(8) chains similar to those in (I), reinforced by C—H...π interactions involving only the major disorder component. The chlorobenzyl unit in compound (III) is also disordered with occupancies of 0.839 (5) and 0.161 (5). The molecules are linked by a combination of one N—H...N hydrogen bond and four C—H...π interactions, forming a three-dimensional framework.

Pb···π Aryl Interactions as Supramolecular Synthons

2010 ◽  
Vol 63 (4) ◽  
pp. 535 ◽  
Author(s):  
Edward R. T. Tiekink ◽  
Julio Zukerman-Schpector
Keyword(s):  
Crystal Structures ◽  
Molecular Orbital ◽  
Three Dimensional ◽  
Lone Pair ◽  
Supramolecular Synthon ◽  
Aryl Ring ◽  
One Dimensional ◽  
Π Interactions ◽  
Lowest Unoccupied Molecular Orbital ◽  
Electron Donation

A survey of lead (Pb) structures containing Pb···π aryl interactions has been conducted. Such contacts usually lead to zero- or one-dimensional aggregates with rare examples of two- and three-dimensional architectures. The Pb···π aryl interactions are found only in crystal structures containing lead(ii) centres and arise as a result of electron donation of the lead-bound lone pair of electrons to the lowest unoccupied molecular orbital of the accepting aryl ring. The prevalence of Pb···π interactions as a supramolecular synthon is relatively low, occurring in ~3% of all structures containing lead and at least one aryl ring, but these are more likely to form compared with Sn···π interactions.

scholarly journals Crystal structures of isomeric 3,5-dichloro-N-(2,3-dimethylphenyl)benzenesulfonamide, 3,5-dichloro-N-(2,6-dimethylphenyl)benzenesulfonamide and 3,5-dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide

2017 ◽  
Vol 73 (5) ◽  
pp. 673-677 ◽  
Author(s):  
K. Shakuntala ◽  
S. Naveen ◽  
N. K. Lokanath ◽  
P. A. Suchetan
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Molecular Conformation ◽  
Three Dimensional ◽  
Aromatic Rings ◽  
One Dimensional ◽  
Π Interactions ◽  
Hydrogen Bonded

The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-dichloro-N-(2,3-dimethylphenyl)-benzenesulfonamide (I), 3,5-dichloro-N-(2,6-dimethylphenyl)benzenesulfonamide (II) and 3,5-dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide (III) are described. The molecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The molecular conformation of (II) is stabilized by intramolecular C—H...O hydrogen bonds and C—H...π interactions. The crystal structure of (I) features N—H...O hydrogen-bondedR22(8) loops interconnectedvia C(7) chains of C—H...O interactions, forming a three-dimensional architecture. The structure also features π–π interactions [Cg...Cg= 3.6970 (14) Å]. In (II), N—H...O hydrogen-bondedR22(8) loops are interconnectedviaπ–π interactions [intercentroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to theaaxis. In (III), adjacentC(4) chains of N—H...O hydrogen-bonded molecules running parallel to [010] are connectedviaC—H...π interactions, forming sheets parallel to theabplane. Neighbouring sheets are linkedviaoffset π–π interactions [intercentroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.

scholarly journals Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzylidene-N-methyl-2-(thiophen-2-yl)acetohydrazides

2017 ◽  
Vol 73 (11) ◽  
pp. 1636-1641 ◽  
Author(s):  
Laura N. F. Cardoso ◽  
Thais C. M. Noguiera ◽  
Carlos R. Kaiser ◽  
James L. Wardell ◽  
Marcus V. N. de Souza ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Benzene Ring ◽  
Three Dimensional ◽  
Asymmetric Unit ◽  
Π Interactions ◽  
Fingerprint Plots ◽  
Cyanide Group ◽  
Hirshfeld Surfaces ◽  
Dimensional Network ◽  
Contact Surfaces

The syntheses and crystal structures of (E)-N′-(3-cyanobenzylidene)-N-methyl-2-(thiophen-2-yl)acetohydrazide, C15H13N3OS, (I), and (E)-N′-(4-methoxybenzylidene)-N-methyl-2-(thiophen-2-yl)acetohydrazide, C15H16N2O2S, (II), with different substituents in themetaandparaposition of the benzene ring are described. Compounds (I) and (II) both crystallize with two molecules in the asymmetric unit, with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280 Å, respectively] that approximate to L-shapes. The thiophene rings in (I) are well ordered, whereas those in (II) exhibit `flip' rotational disorder [occupancies 0.662 (2) and 0.338 (2) for molecule 1, and 0.549 (3) and 0.451 (3) for molecule 2]. The packing for (I) features short C—H...O interactions arising from the C—H grouping adjacent to the cyanide group and C—H...Nc(c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C—H...π interactions interlink the chains into a three-dimensional network. The packing for (II) features numerous C—H...O and C—H...π interactions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II).

scholarly journals Crystal structures and Hirshfeld surfaces of two 1,3-benzoxathiol-2-one derivatives

2018 ◽  
Vol 74 (1) ◽  
pp. 78-82
Author(s):  
Eliza de L. Chazin ◽  
Paola de S. Sanches ◽  
Thatyana R. A. Vasconcelos ◽  
Claudia R. B. Gomes ◽  
James L. Wardell ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Three Dimensional ◽  
Heterocyclic Ring ◽  
Stacking Interactions ◽  
Compound I ◽  
Hirshfeld Surfaces ◽  
Dimensional Network ◽  
Fused Ring ◽  
Fused Ring System

The crystal structures of 6-methoxy-1,3-benzoxathiol-2-one, C9H8O3S, (I), and 2-oxo-1,3-benzoxathiol-6-yl acetate, C9H6O4S, (II), are described. Compound (I) is almost planar (r.m.s. deviation for the non-H atoms = 0.011 Å), whereas (II) shows a substantial twist between the fused-ring system and the acetate substituent [dihedral angle = 74.42 (3)°]. For both structures, the bond distances in the heterocyclic ring suggest that little if any conjugation occurs. In the crystal of (I), C—H...O hydrogen bonds link the molecules into [1-11] chains incorporating alternatingR22(8) andR22(12) inversion dimers. The extended structure of (II) featuresC(7) [201] chains linked by C—H...O hydrogen bonds, with further C—H...O bonds and weak π–π stacking interactions connecting the chains into a three-dimensional network. Hirshfeld fingerprint analyses for (I) and (II) are presented and discussed.

scholarly journals Crystal structure and Hirshfeld surface analysis of (Z)-4-(4-hydroxybenzylidene)-3-methylisoxazol-5(4H)-one

2018 ◽  
Vol 74 (7) ◽  
pp. 926-930
Author(s):  
Wissem Zemamouche ◽  
Rima Laroun ◽  
Noudjoud Hamdouni ◽  
Ouarda Brihi ◽  
Ali Boudjada ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Π Interactions ◽  
Compound C ◽  
Hirshfeld Surfaces

The title compound, C11H9NO3, contains an isoxazole and a hydroxybenzylidene ring, which are inclined to each another by 3.18 (8)°. There is an intramolecular C—H...O contact forming an S(7) ring. In the crystal, molecules stack head-to-tail in columns along the b-axis direction, linked by offset π–π interactions [intercentroid distances of 3.676 (1) and 3.723 (1) Å]. The columns are linked by O—H...O and O—H...N hydrogen bonds, forming layers parallel to the ab plane. The layers are linked by C—H...O hydrogen bonds, forming a supramolecular three-dimensional framework. An analysis of the Hirshfeld surfaces points to the importance of the O—H...O and O—H...N hydrogen bonding in the packing mechanism of the crystal structure.

scholarly journals The crystal structures of three pyrazine-2,5-dicarboxamides: three-dimensional supramolecular structures

2017 ◽  
Vol 73 (5) ◽  
pp. 729-734
Author(s):  
Dilovan S. Cati ◽  
Helen Stoeckli-Evans
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Supramolecular Structure ◽  
Three Dimensional ◽  
Molecular Structures ◽  
Monoclinic Space Group ◽  
Inversion Symmetry ◽  
Compound I ◽  
Space Group ◽  
Π Interactions

The complete molecules of the title compounds,N2,N5-bis(pyridin-2-ylmethyl)pyrazine-2,5-dicarboxamide, C18H16N6O2(I), 3,6-dimethyl-N2,N5-bis(pyridin-2-ylmethyl)pyrazine-2,5-dicarboxamide, C20H20N6O2(II), andN2,N5-bis(pyridin-4-ylmethyl)pyrazine-2,5-dicarboxamide, C18H16N6O2(III), are generated by inversion symmetry, with the pyrazine rings being located about centres of inversion. Each molecule has an extended conformation with the pyridine rings inclined to the pyrazine ring by 89.17 (7)° in (I), 75.83 (8)° in (II) and by 82.71 (6)° in (III). In the crystal of (I), molecules are linked by N—H...N hydrogen bonds, forming layers lying parallel to thebcplane. The layers are linked by C—H...O hydrogen bonds, forming a three-dimensional supramolecular structure. In the crystal of (II), molecules are also linked by N—H...N hydrogen bonds, forming layers lying parallel to the (10-1) plane. As in (I), the layers are linked by C—H...O hydrogen bonds, forming a three-dimensional supramolecular structure. In the crystal of (III), molecules are again linked by N—H...N hydrogen bonds, but here form corrugated sheets lying parallel to thebcplane. Within the sheets, neighbouring pyridine rings are linked by offset π–π interactions [intercentroid distance = 3.739 (1) Å]. The sheets are linked by C—H...O hydrogen bonds, forming a three-dimensional supramolecular structure. Compound (I) crystallizes in the monoclinic space groupP21/c. Another monoclinic polymorph, space groupC2/c, has been reported on by Cockrielet al.[Inorg. Chem. Commun.(2008),11, 1–4]. The molecular structures of the two polymorphs are compared.

scholarly journals Crystal structure and Hirshfeld surface analysis of (E)-N′-benzylidene-4-chlorobenzenesulfonohydrazide and of its (E)-4-chloro-N′-(ortho- and para-methylbenzylidene)benzenesulfonohydrazide derivatives

2018 ◽  
Vol 74 (11) ◽  
pp. 1613-1618 ◽  
Author(s):  
Akshatha R. Salian ◽  
Sabine Foro ◽  
B. Thimme Gowda
Keyword(s):  
Crystal Structure ◽  
Crystal Structures ◽  
Parent Compound ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Aromatic Rings ◽  
Compound I ◽  
Methyl Derivative ◽  
Torsion Angles ◽  
Hirshfeld Surfaces

(E)-N′-Benzylidene-4-chlorobenzenesulfonohydrazide, C13H11ClN2O2S, (I), and its ortho- and para-methylsubstituted derivatives, C14H13ClN2O2S, namely (E)-4-chloro-N′-(2-methylbenzylidene)benzenesulfonohydrazide, (II), and (E)-4-chloro-N′-(4-methylbenzylidene)benzenesulfonohydrazide, (III), have been synthesized, characterized spectroscopically and their crystal structures determined to investigate the effect of the substitution site of the benzylidene group on the structural and supramolecular features in these compounds. Compounds (I) and (II) are isotypic while compound (III) is different. All three molecules are bent at the S atom with C—S—N—N torsion angles of −66.0 (3), −66.0 (3) and −58.4 (2)° for (I), (II) and (III), respectively. The hydrazone portions of the molecules, S—N—N=C, are slightly twisted from planarity, with a torsion angle of 166.5 (3)° in (I), 165.4 (3)° in (II) and 157.9 (2)° in (III). The two aromatic rings present in the compounds are inclined to each other by 78.4 (2), 74.8 (2) and 76.9 (1)° in (I), (II) and (III), respectively. In the crystal structure of the parent compound (I), and of the ortho-methyl derivative (II), an N—H...O hydrogen bond links the molecules into chains along [001], which are interconnected by weak intermolecular C—H...O interactions, generating layers lying parallel to the bc plane. In the crystal of the para derivative (III), however, the packing is significantly different. Here molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are then linked by C—Cl...π interactions, forming ribbons propagating along [1\overline{1}0]. Hirshfeld surface analyses show that the van der Waals interactions constitute the major contribution to the intermolecular interactions in the crystal structures of all three compounds. The fingerprint plots indicate that the H...H contacts make the largest contributions to the Hirshfeld surfaces.

scholarly journals Crystal structures ofN-(3-fluorobenzoyl)benzenesulfonamide andN-(3-fluorobenzoyl)-4-methylbenzenesulfonamide

2016 ◽  
Vol 72 (4) ◽  
pp. 428-431
Author(s):  
P. A. Suchetan ◽  
S. Naveen ◽  
N. K. Lokanath ◽  
H. N. Lakshmikantha ◽  
K. S. Srivishnu ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angle ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
One Dimensional ◽  
Π Interactions ◽  
Π Stacking ◽  
Benzene Rings

The crystal structures of twoN-(arylsulfonyl)arylamides, namelyN-(3-fluorobenzoyl)benzenesulfonamide, C13H10FNO3S, (I), andN-(3-fluorobenzoyl)-4-methylbenzenesulfonamide, C14H12FNO3S, (II), are described and compared with related structures. The dihedral angle between the benzene rings is 82.73 (10)° in (I) compared to 72.60 (12)° in (II). In the crystal of (I), the molecules are linked by C—H...O and C—H...π interactions, resulting in a three-dimensional grid-like architecture, while C—H...O interactions lead to one-dimensional ribbons in (II). The crystals of both (I) and (II) feature strong but non-structure-directing N—H...O hydrogen bonds withR22(8) ring motifs. The structure of (I) also features π–π stacking interactions.

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