scholarly journals Some chalcones derived from thiophene-3-carbaldehyde: synthesis and crystal structures

2019 ◽  
Vol 75 (7) ◽  
pp. 957-963 ◽  
Author(s):  
Trung Vu Quoc ◽  
Duong Tran Thi Thuy ◽  
Thuan Dang Thanh ◽  
Thanh Phung Ngoc ◽  
Vuong Nguyen Thien ◽  
...  
Keyword(s):  
Potassium Hydroxide ◽  
Thiophene Ring ◽  
Three Dimensional ◽  
Ethanol Solution ◽  
Molecular Structures ◽  
Chain Formation ◽  
Axis Direction ◽  
Crystal And Molecular Structures ◽  
Phenyl Rings ◽  
Thiophene Derivatives

The synthesis, spectroscopic data and crystal and molecular structures of four 3-(3-phenylprop-1-ene-3-one-1-yl)thiophene derivatives, namely 1-(4-hydroxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C13H10O2S, (1), 1-(4-methoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C14H12O2S, (2), 1-(4-ethoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C15H14O2S, (3), and 1-(4-bromophenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C13H9BrOS, (4), are described. The four chalcones have been synthesized by reaction of thiophene-3-carbaldehyde with an acetophenone derivative in an absolute ethanol solution containing potassium hydroxide, and differ in the substituent at the para position of the phenyl ring: –OH for 1, –OCH3 for 2, –OCH2CH3 for 3 and –Br for 4. The thiophene ring in 4 was found to be disordered over two orientations with occupancies 0.702 (4) and 0.298 (4). The configuration about the C=C bond is E. The thiophene and phenyl rings are inclined by 4.73 (12) for 1, 12.36 (11) for 2, 17.44 (11) for 3 and 46.1 (6) and 48.6 (6)° for 4, indicating that the –OH derivative is almost planar and the –Br derivative deviates the most from planarity. However, the substituent has no real influence on the bond distances in the α,β-unsaturated carbonyl moiety. The molecular packing of 1 features chain formation in the a-axis direction by O—H...O contacts. In the case of 2 and 3, the packing is characterized by dimer formation through C—H...O interactions. In addition, C—H...π(thiophene) interactions in 2 and C—H...S(thiophene) interactions in 3 contribute to the three-dimensional architecture. The presence of C—H...π(thiophene) contacts in the crystal of 4 results in chain formation in the c-axis direction. The Hirshfeld surface analysis shows that for all four derivatives, the highest contribution to surface contacts arises from contacts in which H atoms are involved.

scholarly journals Crystal structure of two N′-(1-phenylbenzylidene)-2-(thiophen-3-yl)acetohydrazides

2019 ◽  
Vol 75 (8) ◽  
pp. 1090-1095
Author(s):  
Trung Vu Quoc ◽  
Linh Nguyen Ngoc ◽  
Duong Tran Thi Thuy ◽  
Manh Vu Quoc ◽  
Thien Vuong Nguyen ◽  
...  
Keyword(s):  
Torsion Angle ◽  
Phenyl Ring ◽  
Spectroscopic Data ◽  
Crystal Packing ◽  
Thiophene Ring ◽  
Hirshfeld Surface ◽  
Molecular Structures ◽  
Dihedral Angles ◽  
Crystal And Molecular Structures ◽  
Phenyl Rings

The synthesis, spectroscopic data, crystal and molecular structures of two N′-(1-phenylbenzylidene)-2-(thiophen-3-yl)acetohydrazides, namely N′-[1-(4-hydroxyphenyl)benzylidene]-2-(thiophen-3-yl)acetohydrazide, C13H10N2O2S, (3a), and N′-[1-(4-methoxyphenyl)benzylidene]-2-(thiophen-3-yl)acetohydrazide, C14H14N2O2S, (3b), are described. Both compounds differ in the substituent at the para position of the phenyl ring: –OH for (3a) and –OCH3 for (3b). In (3a), the thiophene ring is disordered over two orientations with occupancies of 0.762 (3) and 0.238 (3). The configuration about the C=N bond is E. The thiophene and phenyl rings are inclined by 84.0 (3) and 87.0 (9)° for the major- and minor-occupancy disorder components in (3a), and by 85.89 (12)° in (3b). Although these dihedral angles are similar, the conformation of the linker between the two rings is different [the C—C—C—N torsion angle is −ac for (3a) and −sc for (3b), while the C6—C7—N9—N10 torsion angle is +ap for (3a) and −sp for (3b)]. A common feature in the crystal packing of (3a) and (3b) is the presence of N—H...O hydrogen bonds, resulting in the formation of chains of molecules running along the b-axis direction in the case of (3a), or inversion dimers for (3b). The most prominent contributions to the surface contacts are those in which H atoms are involved, as confirmed by an analysis of the Hirshfeld surface.

scholarly journals 4-Fluoro-N-(4-hydroxybenzylidene)aniline

2014 ◽  
Vol 70 (8) ◽  
pp. o860-o860
Author(s):  
L. Jothi ◽  
G. Anuradha ◽  
G. Vasuki ◽  
R. Ramesh Babu ◽  
K. Ramamurthi
Keyword(s):  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Schiff Bases ◽  
Title Compound ◽  
Three Dimensional ◽  
Dihedral Angles ◽  
Axis Direction ◽  
Compound C ◽  
Dimensional Network ◽  
Phenyl Rings

In the title compound, C13H10FNO, the benzene ring planes are inclined at an angle of 50.52 (8)°. A characteristic of aromatic Schiff bases withN-aryl substituents is that the terminal phenyl rings are twisted relative to the plane of the HC=N link between them. In this case, the HC=N unit makes dihedral angles of 10.6 (2) and 40.5 (2)° with the hydroxybenzene and flurobenzene rings, respectively. In the crystal, O—H...N and C—H...F hydrogen bonds lead to the formation of chains along thec-andb-axis directions, respectively. C—H...π contacts link molecules alongaand these contacts combine to generate a three-dimensional network with molecules stacked along theb-axis direction.

scholarly journals {2-[(4-Nitrobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}(phenyl)methanone

2014 ◽  
Vol 70 (6) ◽  
pp. o738-o739 ◽  
Author(s):  
Manpreet Kaur ◽  
Jerry P. Jasinski ◽  
Channappa N. Kavitha ◽  
H. S. Yathirajan ◽  
K. Byrappa
Keyword(s):  
Title Compound ◽  
Thiophene Ring ◽  
Three Dimensional ◽  
Chair Conformation ◽  
Dihedral Angles ◽  
Compound C ◽  
Cyclohexene Ring ◽  
Benzoyl Group ◽  
Phenyl Rings ◽  
The Mean

In the title compound, C22H18N2O3S, disorder is found in the benzoyl group (AandB), as well as for four C atoms of the cyclohexene ring. Two orientations were modeled in a 0.583 (5):0.417 (5) ratio. The cyclohexene ring is in a distorted chair conformation. The dihedral angles between the mean plane of the thiophene ring and the 4-nitrobenzene and phenyl rings are 30.9 (8) and 64.8 (3) (A) and 62.4 (7)° (B). The mean planes of the 4-nitrobenzene and the phenyl rings are almost perpendicular to each other, with dihedral angles of 85.4 (1) (A) and 83.9 (8)° (B). An extensive array of weak C—H...O interactions consolidate molecules into a three-dimensional architecture, forming chains along [001] and [010] and layers parallel to (011).

THE CRYSTAL AND MOLECULAR STRUCTURES OF m-DINITROBENZENE AND p-DINITROBENZENE

1961 ◽  
Vol 39 (8) ◽  
pp. 1638-1644 ◽  
Author(s):  
J. Trotter
Keyword(s):  
Three Dimensional ◽  
Molecular Structures ◽  
Steric Effects ◽  
Crystal And Molecular Structures

The structures of m-dinitrobenzene and p-dinitrobenzene have been refined by three-dimensional (Fo—Fc) syntheses. The results indicate that both nitro groups in each molecule are twisted 11° out of the aromatic plane, about the C—N bonds, in contrast to nitrobenzene, where the whole molecule is completely planar. These molecular configurations are shown to be in accord with those which might be expected from intramolecular steric effects. The dimensions of the three molecules have also been compared.

scholarly journals Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium

2018 ◽  
Vol 74 (12) ◽  
pp. 1735-1740 ◽  
Author(s):  
James L. Wardell ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Molecular Structures ◽  
Double Layers ◽  
Crystal And Molecular Structures ◽  
Ammonium N ◽  
Molecular Salts ◽  
Benzene Rings ◽  
The Common ◽  
Supramolecular Aggregation

The crystal and molecular structures of the title molecular salts, C4H12NO+·C7H5N2O4 −, (I), C6H16NO+·C7H5N2O4 −, (II), and C4H12NO3 +·C7H5N2O4 −, (III), are described. The common feature of these salts is the presence of the 2-amino-4-nitrobenzoate anion, which exhibit non-chemically significant variations in the conformational relationships between the carboxylate and nitro groups, and between these and the benzene rings they are connected to. The number of ammonium-N—H H atoms in the cations increases from one to three in (I) to (III), respectively, and this variation significantly influences the supramolecular aggregation patterns in the respective crystals. Thus, a linear supramolecular chain along [100] sustained by charge-assisted tertiary-ammonium-N—H...O(carboxylate), hydroxy-O—H...O(carboxylate) and amino-N—H...O(carboxylate) hydrogen-bonds is apparent in the crystal of (I). Chains are connected into a three-dimensional architecture by methyl-C—H...O(hydroxy) and π–π interactions, the latter between benzene rings [inter-centroid separation = 3.5796 (10) Å]. In the crystal of (II), a supramolecular tube propagating along [901] arises as a result of charge-assisted secondary-ammonium-N—H...O(carboxylate) and hydroxy-O—H...O(carboxylate) hydrogen-bonding. These are connected by methylene- and methyl-C—H...O(nitro) and π–π stacking between benzene rings [inter-centroid separation = 3.5226 (10) Å]. Finally, double-layers parallel to (100) sustained by charge-assisted ammonium-N—H...O(carboxylate), ammonium-N—H...O(hydroxy) and hydroxy-O—H...O(carboxylate) hydrogen-bonds are apparent in the crystal of (III). These are connected in a three-dimensional architecture by amine-N—H...O(nitro) hydrogen-bonds.

scholarly journals Crystal structures and Hirshfeld surface analyses of bis[N,N-bis(2-methoxyethyl)dithiocarbamato-κ2S,S′]di-n-butyltin(IV) and [N-(2-methoxyethyl)-N-methyldithiocarbamato-κ2S,S′]triphenyltin(IV)

2018 ◽  
Vol 74 (3) ◽  
pp. 302-308 ◽  
Author(s):  
Rapidah Mohamad ◽  
Normah Awang ◽  
Nurul Farahana Kamaludin ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structures ◽  
Metal Atom ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Molecular Structures ◽  
Site Symmetry ◽  
Tetrahedral Geometry ◽  
Twofold Axis ◽  
Distorted Tetrahedral Geometry ◽  
Crystal And Molecular Structures

The crystal and molecular structures of the two title organotin dithiocarbamate compounds, [Sn(C4H9)2(C7H14NO2S2)2], (I), and [Sn(C6H5)3(C5H10NOS2)], (II), are described. Both structures feature asymmetrically bound dithiocarbamate ligands leading to a skew-trapezoidal bipyramidal geometry for the metal atom in (I) and a distorted tetrahedral geometry in (II). The complete molecule of (I) is generated by a crystallographic twofold axis (Sn site symmetry 2). In the crystal of (I), molecules self-assemble into a supramolecular array parallel to (10-1)viamethylene-C—H...O(methoxy) interactions. In the crystal of (II), supramolecular dimers are formedviapairs of weak phenyl-C—H...π(phenyl) contacts. In each of (I) and (II), the specified assemblies connect into a three-dimensional architecture without directional interactions between them. Hirshfeld surface analyses confirm the importance of H...H contacts in the molecular packing of each of (I) and (II), and in the case of (I), highlight the importance of short methoxy-H...H(butyl) contacts between layers.

scholarly journals 3-(4-Amino-3-ethyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one

IUCrData ◽  
2017 ◽  
Vol 2 (1) ◽  
Author(s):  
Jianchao Xu ◽  
Hewen Wang
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Triazole Ring ◽  
Dihedral Angles ◽  
Axis Direction ◽  
Π Interactions ◽  
Compound C ◽  
Dimensional Network ◽  
Phenyl Rings

In the title compound, C19H20N4OS, the 1,2,4-triazole ring forms dihedral angles of 58.64 (9) and 87.68 (9)° with the phenyl rings, which are inclined to one another by 43.30 (6)°. In the crystal, molecules are linked by N—H...O, N—H...S and C—H...S hydrogen bonds, forming chains propagating along thec-axis direction. Neighbouring chains are linked by three C—H...π interactions, forming layers parallel to thebcplane. Finally, the layers are linked by a fourth C—H...π interaction, forming a three-dimensional network.

scholarly journals The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

2020 ◽  
Vol 76 (1) ◽  
pp. 102-110 ◽  
Author(s):  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonds ◽  
Benzoic Acid ◽  
Computational Study ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Molecular Structures ◽  
Amide Hydrogen ◽  
Title 1 ◽  
Crystal And Molecular Structures ◽  
Hirshfeld Surfaces

The crystal and molecular structures of the title 1:2 co-crystal, C14H14N4O2·2C7H6O2, are described. The oxalamide molecule has a (+)-antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555 Å). The benzoic acid molecules have equivalent, close to planar conformations [C6/CO2 dihedral angle = 6.33 (14) and 3.43 (10)°]. The formation of hydroxy-O—H...N(pyridyl) hydrogen bonds between the benzoic acid molecules and the pyridyl residues of the diamide leads to a three-molecule aggregate. Centrosymmetrically related aggregates assemble into a six-molecule aggregate via amide-N—H...O(amide) hydrogen bonds through a 10-membered {...HNC2O}2 synthon. These are linked into a supramolecular tape via amide-N—H...O(carbonyl) hydrogen bonds and 22-membered {...HOCO...NC4NH}2 synthons. The contacts between tapes to consolidate the three-dimensional architecture are of the type methylene-C—H...O(amide) and pyridyl-C—H...O(carbonyl). These interactions are largely electrostatic in nature. Additional non-covalent contacts are identified from an analysis of the calculated Hirshfeld surfaces.

scholarly journals (E)-2-{[(2-Aminophenyl)imino]methyl}-5-(benzyloxy)phenol and (Z)-3-benzyloxy-6-{[(5-chloro-2-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one

2018 ◽  
Vol 74 (5) ◽  
pp. 737-742
Author(s):  
Nadir Ghichi ◽  
Ali Benboudiaf ◽  
Chawki Bensouici ◽  
Yacine DJebli ◽  
Hocine Merazig
Keyword(s):  
Hydrogen Bond ◽  
Schiff Base ◽  
Density Functional ◽  
Tautomeric Form ◽  
Three Dimensional ◽  
Molecular Structures ◽  
Compound I ◽  
Phenyl Rings ◽  
Imine Bond ◽  
Compound Ii

The title Schiff base compounds, C20H18N2O2(I) and C20H16ClNO3(II), were synthesized from 4-benzyloxy-2-hydroxybenzaldehyde by reaction with 1,2-diaminobenzene for (I), and condensation with 2-amino-4-chlorophenol for (II). Compound (I) adopts the enol–imine tautomeric form with anEconfiguration about the C=N imine bond. In contrast, theo-hydroxy Schiff base (II), is in the keto–imine tautomeric form with aZconfiguration about the CH—NH bond. Neither molecule is planar. In (I), the central benzene ring makes dihedral angles of 46.80 (10) and 78.19 (10)° with the outer phenylamine and phenyl rings, respectively, while for (II), the corresponding angles are 5.11 (9) and 58.42 (11)°, respectively. The molecular structures of both compounds are affected by the formation of intramolecular contacts, an O—H...N hydrogen bond for (I) and an N—H...O hydrogen bond for (II); each contact generates anS(6) ring motif. In the crystal of (I), strong N—H...O hydrogen bonds form zigzag chains of molecules along theb-axis direction. Molecules are further linked by C—H...π interactions and offset π–π contacts and these combine to form a three-dimensional network. The density functional theory (DFT) optimized structure of compound (II), at the B3LYP/6–311+G(d) level, confirmed that the keto tautomeric form of the compound, as found in the structure determination, is the lowest energy form. The antioxidant capacities of both compounds were determined by the cupric reducing antioxidant capacity (CUPRAC) process.

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