scholarly journals Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C6H5O)2P(O)X [X = NHC7H13 and N(CH2C6H5)2]

2020 ◽  
Vol 76 (1) ◽  
pp. 104-116
Author(s):  
Banafsheh Vahdani Alviri ◽  
Mehrdad Pourayoubi ◽  
Abdul Ajees Abdul Salam ◽  
Marek Nečas ◽  
Arie van der Lee ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Three Dimensional ◽  
Intramolecular Interactions ◽  
Large Contribution ◽  
Scanning Calorimetry ◽  
Π Interactions ◽  
Intermolecular Contacts ◽  
Phenyl Rings ◽  
Dsc Analyses

The crystal structures of diphenyl (cycloheptylamido)phosphate, C19H24NO3P or (C6H5O)2P(O)(NHC7H13), (I), and diphenyl (dibenzylamido)phosphate, C26H24NO3P or (C6H5O)2P(O)[N(CH2C6H5)2], (II), are reported. The NHC7H13 group in (I) provides two significant hydrogen-donor sites in N—H...O and C—H...O hydrogen bonds, needed for a one-dimensional hydrogen-bond pattern along [100] in the crystal, while (II), with a (C6H5CH2)2N moiety, lacks these hydrogen bonds, but its three-dimensional supramolecular structure is mediated by C—H...π interactions. The conformational behaviour of the phenyl rings in (I), (II) and analogous structures from the Cambridge Structural Database (CSD) were studied in terms of flexibility, volume of the other group attached to phosphorus and packing forces. From this study, synclinal (±sc), anticlinal (±ac) and antiperiplanar (±ap) conformations were found to occur. In the structure of (II), there is an intramolecular C ortho —H...O interaction that imposes a +sc conformation for the phenyl ring involved. For the structures from the CSD, the +sc and ±ap conformations appear to be mainly imposed by similar C ortho —H...O intramolecular interactions. The large contribution of the C...H/H...C contacts (32.3%) in the two-dimensional fingerprint plots of (II) is a result of the C—H...π interactions. The differential scanning calorimetry (DSC) analyses exhibit peak temperatures (T m) at 109 and 81 °C for (I) and (II), respectively, which agree with the strengths of the intermolecular contacts and the melting points.

scholarly journals Crystal structures of (E)-(3-ethyl-1-methyl-2,6-diphenylpiperidin-4-ylidene)amino phenyl carbonate and (E)-(3-isopropyl-1-methyl-2,6-diphenylpiperidin-4-ylidene)amino phenyl carbonate

2014 ◽  
Vol 70 (10) ◽  
pp. 199-202 ◽  
Author(s):  
B. Raghuvarman ◽  
R. Sivakumar ◽  
V. Thanikachalam ◽  
S. Aravindhan
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angle ◽  
Intermolecular Interactions ◽  
Three Dimensional ◽  
Piperidine Ring ◽  
Dihedral Angles ◽  
Π Interactions ◽  
Dimensional Network ◽  
Phenyl Rings

In the title compounds, C27H28N2O3, (I), and C28H30N2O3, (II), the conformation about the C=N bond isE. The piperidine rings adopt chair conformations with the attached phenyl rings almost normal to their mean planes, the dihedral angles being 85.82 (8) and 85.84 (7)° in (I), and 87.98 (12) and 86.42 (13)° in (II). The phenyl rings are inclined to one another by 52.87 (8)° in (I) and by 60.51 (14)° in (II). The main difference in the conformation of the two compounds is the angle of inclination of the phenoxycarbonyl ring to the piperidine ring mean plane. In (I), these two planes are almost coplanar, with a dihedral angle of 2.05 (8)°, while in (II), this angle is 45.24 (13)°. In the crystal of (I), molecules are linked by C—H...O hydrogen bonds, forming inversion dimers withR22(14) loops. The dimers are linkedviaC—H...π interactions forming a three-dimensional network. In the crystal of (II), there are no significant intermolecular interactions present.

scholarly journals Crystal structures of (1E,4E)-1,5-bis(5-bromothiophen-2-yl)-2,4-dimethylpenta-1,4-dien-3-one and (E)-4-(5-bromothiophen-2-yl)-1,3-diphenylbut-3-en-2-one

2016 ◽  
Vol 72 (2) ◽  
pp. 199-202
Author(s):  
C. Nithya ◽  
M. Sithambaresan ◽  
M. R. Prathapachandra Kurup
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angle ◽  
Three Dimensional ◽  
Methyl Groups ◽  
Supramolecular Architecture ◽  
Π Interactions ◽  
Phenyl Rings ◽  
Staircase Structure ◽  
Carbonyl Bond

The title compounds, C15H12Br2OS2, (I), and C20H15BrOS, (II), were synthesized by employing Claisen–Schmidt condensation of pentan-3-one and dibenzylacetone with 5-bromothiophene-2-carbaldehyde in the presence of methanolic KOH. Even though 1:2 products were expected in both of the reactions, 1:2 and 1:1 products were obtained as (I) and (II), respectively. In (I), the two methyl groups aretransto each other, 29.5 (7) and 28.7 (7)° away from the central carbonyl bond between them, whereas the two phenyl rings of dibenzylacetone subtend a dihedral angle of 53.09 (18)°. In the crystal of (I), C—H...O hydrogen bonds define molecular chains alongc. A second type of molecular chain is formed alongbby means of C—Br...π interactions. These two families of molecular chains are stacked by π–π interactions, forming a three-dimensional supramolecular architecture. In (II), similar C—H...O hydrogen bonds as in (I) define inversion dimers, whilst C—H....π interactions build a staircase structure along theaaxis.

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 Bis(N′-{(E)-[(2E)-1,3-diphenylprop-2-en-1-ylidene]amino}-N-ethylcarbamimidothioato-κ2N′,S)zinc(II): crystal structure and Hirshfeld surface analysis

2017 ◽  
Vol 73 (7) ◽  
pp. 1001-1008 ◽  
Author(s):  
Ming Yueh Tan ◽  
Karen A. Crouse ◽  
Thahira B. S. A. Ravoof ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Asymmetric Unit ◽  
Tetrahedral Geometry ◽  
Π Interactions ◽  
Distorted Tetrahedral Geometry ◽  
Hirshfeld Surfaces ◽  
Phenyl Rings ◽  
The Impact ◽  
Dimeric Aggregates

The title ZnIIcomplex, [Zn(C18H18N3S)2], (I), features two independent but chemically equivalent molecules in the asymmetric unit. In each, the thiosemicarbazonate monoanion coordinates the ZnIIatomviathe thiolate-S and imine-N atoms, with the resulting N2S2donor set defining a distorted tetrahedral geometry. The five-membered ZnSCN2chelate rings adopt distinct conformations in each independent molecule,i.e.one ring is almost planar while the other is twisted about the Zn—S bond. In the crystal, the two molecules comprising the asymmetric unit are linked by amine-N—H...N(imine) and amine-N—H...S(thiolate) hydrogen bondsviaan eight-membered heterosynthon, {...HNCN...HNCS}. The dimeric aggregates are further consolidated by benzene-C—H...S(thiolate) interactions and are linked into a zigzag supramolecular chain along thecaxisviaamine-N—H...S(thiolate) hydrogen bonds. The chains are connected into a three-dimensional architectureviaphenyl-C—H...π(phenyl) and π–π interactions, the latter occurring between chelate and phenyl rings [inter-centroid separation = 3.6873 (11) Å]. The analysis of the Hirshfeld surfaces calculated for (I) emphasizes the different interactions formed by the independent molecules in the crystal and the impact of the π–π interactions between chelate and phenyl rings.

Different supramolecular architectures mediated by different weak interactions in the crystals of three N-aryl-2,5-dimethoxybenzenesulfonamides

2017 ◽  
Vol 73 (10) ◽  
pp. 833-844 ◽  
Author(s):  
K. Shakuntala ◽  
S. Naveen ◽  
N. K. Lokanath ◽  
P. A. Suchetan ◽  
M. Abdoh
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Weak Interactions ◽  
Three Dimensional ◽  
Shape Index ◽  
Intramolecular Interactions ◽  
Molecular Conformations ◽  
Supramolecular Architectures ◽  
The Relationship

The synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety have attracted interest as these compounds are important pharmacophores. The crystal structures of three closely related N-aryl-2,5-dimethoxybenzenesulfonamides, namely N-(2,3-dichlorophenyl)-2,5-dimethoxybenzenesulfonamide, C14H13Cl2NO4S, (I), N-(2,4-dichlorophenyl)-2,5-dimethoxybenzenesulfonamide, C14H13Cl2NO4S, (II), and N-(2,4-dimethylphenyl)-2,5-dimethoxybenzenesulfonamide, C16H19NO4S, (III), are described. The asymmetric unit of (I) consists of two symmetry-independent molecules, while those of (II) and (III) contain one molecule each. The molecular conformations are stabilized by different intramolecular interactions, viz. C—H...O interactions in (I), N—H...Cl and C—H...O interactions in (II), and C—H...O interactions in (III). The crystals of the three compounds display different supramolecular architectures built by various weak intermolecular interactions of the types C—H...O, C—H...Cl, C—H...π(aryl), π(aryl)–π(aryl) and Cl...Cl. A detailed Hirshfeld surface analysis of these compounds has also been conducted in order to understand the relationship between the crystal structures. The d norm and shape-index surfaces of (I)–(III) support the presence of various intermolecular interactions in the three structures. Analysis of the fingerprint plots reveals that the greatest contribution to the Hirshfeld surfaces is from H...H contacts, followed by H...O/O...H contacts. In addition, comparisons are made with the structures of some related compounds. Putative N—H...O hydrogen bonds are observed in 29 of the 30 reported structures, wherein the N—H...O hydrogen bonds form either C(4) chain motifs or R 2 2(8) rings. Further comparison reveals that the characteristics of the N—H...O hydrogen-bond motifs, the presence of other interactions and the resultant supramolecular architecture is largely decided by the position of the substituents on the benzenesulfonyl ring, with the nature and position of the substituents on the aniline ring exerting little effect. On the other hand, the crystal structures of (I)–(III) display several weak interactions other than the common N—H...O hydrogen bonds, resulting in supramolecular architectures varying from one- to three-dimensional depending on the nature and position of the substituents on the aniline ring.

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.

scholarly journals Crystal structures of bis[2-(diphenylphosphinothioyl)phenyl] ether and bis{2-[diphenyl(selanylidene)phosphanyl]phenyl} ether

2014 ◽  
Vol 70 (12) ◽  
pp. 536-540
Author(s):  
Daron E. Janzen ◽  
Arianna M. Kooyman ◽  
Kayla A. Lange
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Phenyl Ether ◽  
Π Interactions ◽  
Twofold Axis ◽  
Phenyl Rings

The title compounds, C36H28OP2S2, (1), and C36H28OP2Se2, (2), exhibit remarkably similar structures although they are not isomorphous. The whole molecule of compound (2) is generated by twofold symmetry, with the ether O atom located on the twofold axis. Both compounds have intramolecular π–π interactions between terminal phenyl rings with centroid–centroid distances of 3.6214 (16) and 3.8027 (14) Å in (1) and (2), respectively. In the crystal of (1), short C—H...S hydrogen bonds link the molecules, forming chains along [001], while in (2) there are no analogous C—H...Se interactions present.

Tricarbonyl(η5-formylcyclopentadienyl)manganese(I) and tricarbonyl(η5-formylcyclopentadienyl)rhenium(I) containing short π(CO)...π(CO) and π(CO)...π interactions

2012 ◽  
Vol 68 (3) ◽  
pp. m69-m72 ◽  
Author(s):  
Alexander S. Romanov ◽  
Gary F. Angles ◽  
Mikhail Yu. Antipin ◽  
Tatiana V. Timofeeva
Keyword(s):  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Three Dimensional ◽  
The Other ◽  
Carbonyl Groups ◽  
Π Interactions ◽  
Dimensional Network ◽  
Intermolecular Contacts

The structures of tricarbonyl(formylcyclopentadienyl)manganese(I), [Mn(C6H5O)(CO)3], (I), and tricarbonyl(formylcyclopentadienyl)rhenium(I), [Re(C6H5O)(CO)3], (II), were determined at 100 K. Compounds (I) and (II) both possess a carbonyl group in atransposition relative to the substituted C atom of the cyclopentadienyl ring, while the other two carbonyl groups are in almost eclipsed positions relative to their attached C atoms. Analysis of the intermolecular contacts reveals that the molecules in both compounds form stacks due to short attractive π(CO)...π(CO) and π(CO)...π interactions, along the crystallographiccaxis for (I) and along the [201] direction for (II). Symmetry-related stacks are bound to each other by weak intermolecular C—H...O hydrogen bonds, leading to the formation of the three-dimensional network.

scholarly journals Crystal structures of 2,3-bis(4-chlorophenyl)-1,3-thiazolidin-4-one andtrans-2,3-bis(4-chlorophenyl)-1,3-thiazolidin-4-one 1-oxide

2015 ◽  
Vol 71 (3) ◽  
pp. 264-267 ◽  
Author(s):  
Hemant P. Yennawar ◽  
John Tierney ◽  
Patrick D. Hullihen ◽  
Lee J. Silverberg
Keyword(s):  
Carbon Atom ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Opposite Direction ◽  
Dihedral Angles ◽  
Π Interactions ◽  
Centroid Distance ◽  
Phenyl Rings ◽  
Thiazolidine Ring ◽  
Atom Position

In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thiazolidine ring is attached to two chlorophenyl rings. The chlorophenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) istransto the chlorophenyl ring on the 2-carbon. The chlorophenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thiazolidine ring has a twisted conformation on the S—Cmethinebond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), molecules are linked by C—H...O hydrogen bonds, as well as by slipped parallel π–π interactions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), molecules are linkedviaC—H...O and C—H...Cl hydrogen bonds, forming slabs parallel to (001).

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.

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