scholarly journals Crystal structures of two 1,3-thiazolidin-4-one derivatives featuring sulfide and sulfone functional groups

2018 ◽  
Vol 74 (12) ◽  
pp. 1695-1699
Author(s):  
Hemant P. Yennawar ◽  
Lee J. Silverberg ◽  
Kevin Cannon ◽  
Deepa Gandla ◽  
Sandeep K. Kondaveeti ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Functional Groups ◽  
Phenyl Ring ◽  
The Other ◽  
Cyclohexane Ring ◽  
Dihedral Angles ◽  
Sulfone Group ◽  
Closed Ring ◽  
Adjacent Molecule ◽  
Related Compounds

The crystal structures of two closely related compounds, 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, C15H18N2O3S, (1) and 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one 1,1-dioxide, C15H18N2O5S, (2), are presented. These compounds are comprised of three types of rings: thiazolidinone, nitrophenyl and cyclohexyl. In both structures, the rings are close to mutually perpendicular, with interplanar dihedral angles greater than 80° in each case. The thiazolidinone rings in both structures exhibit envelope puckering with the S atom as flap and the cyclohexyl rings are in their expected chair conformations. The two structures superpose fairly well, except for the orientation of the nitro groups with respect to their host phenyl ring, with a difference of about 10° between 1 and 2. The extended structure of 1 has two kinds of weak C—H...O interactions, giving rise to a closed ring formation involving three symmetry-related molecules. Structure 2 has four C—H...O interactions, two of which are exclusively between symmetry-related thiazolidinone dioxide moieties and have a parallel `give-and-take-fashion' counterpart. In the other two interactions, the nitrophenyl ring and the cyclohexane ring each offer an H atom to the two O atoms on the sulfone group. Additionally, a C—H...π interaction between a C—H group of the cyclohexane ring and the nitrophenyl ring of an adjacent molecule helps to consolidate the structure.

scholarly journals Crystal structures of two solvated 2-aryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones

2019 ◽  
Vol 75 (11) ◽  
pp. 1689-1693
Author(s):  
Hemant P. Yennawar ◽  
Eric N. Thompson ◽  
Jennie Li ◽  
Lee J. Silverberg
Keyword(s):  
Crystal Structures ◽  
Phenyl Ring ◽  
The Other ◽  
Dihedral Angles ◽  
Asymmetric Unit ◽  
Racemic Mixtures ◽  
Type C ◽  
Solvent Molecules ◽  
The Individual ◽  
Aromatic Ring Interactions

The synthesis and crystal structures of 2-(4-fluorophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one toluene hemisolvate (1), C19H13FN2OS·0.5C7H8, and 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one isopropanol 0.25-solvate 0.0625-hydrate (2), C19H13N3O3S·0.25C3H7O·0.0625H2O, are reported. Both are racemic mixtures (centrosymmetric crystal structures) of the individual compounds and incorporate solvent molecules in their structures. Compound 2 has four thiazine molecules in the asymmetric unit. All the thiazine rings in this study show an envelope pucker, with the C atom bearing the substituted phenyl ring displaced from the other atoms. The phenyl and aryl rings in each of the molecules are roughly orthogonal to each other, with dihedral angles of about 75°. The extended structures of 1 and 2 are consolidated by C—H...O and C—H...N(π), as well as T-type (C—H...π) interactions. Parallel aromatic ring interactions (π–π stacking) are observed only in 2.

scholarly journals 1-Methyl-3,3-bis(phenylsulfanyl)piperidin-2-one

2012 ◽  
Vol 68 (6) ◽  
pp. o1793-o1794
Author(s):  
Ignez Caracelli ◽  
Paulo R. Olivato ◽  
Carlos R. Cerqueira Jr ◽  
Jean M. M. Santos ◽  
Seik Weng Ng ◽  
...  
Keyword(s):  
Phenyl Ring ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Chair Conformation ◽  
The Other ◽  
Dihedral Angles ◽  
Compound C ◽  
Phenyl Rings ◽  
Twisted Boat ◽  
Supramolecular Chains

The piperidone ring in the title compound, C18H19NOS2, is in a distorted half-chair conformation, distorted towards a twisted boat, with the central methylene C atom of the propyl backbone lying 0.606 (2) Å out of the plane defined by the other five atoms (r.m.s. deviation = 0.1197 Å). One of the S-bound phenyl rings is almost perpendicular to the least-squares plane through the piperidone ring, whereas the other is splayed [dihedral angles = 75.97 (6) and 44.21 (7)°, respectively]. The most prominent feature of the crystal packing is the formation of helical supramolecular chains along the b axis sustained by C—H...O interactions. The chains are consolidated into a three-dimensional architecture via C—H...π interactions whereby one S-bound phenyl ring accepts two C—H...π contacts.

scholarly journals Crystal structures and Hirshfeld surface analysis of a series of 4-O-arylperfluoropyridines

2019 ◽  
Vol 75 (8) ◽  
pp. 1102-1107 ◽  
Author(s):  
Andrew J. Peloquin ◽  
Cynthia A. Corley ◽  
Sonya K. Adas ◽  
Gary J. Balaich ◽  
Scott T. Iacono
Keyword(s):  
Crystal Structures ◽  
Aromatic Ring ◽  
Dihedral Angle ◽  
Surface Analysis ◽  
Phenyl Ring ◽  
Pyridine Ring ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Dihedral Angles ◽  
Twofold Axis

Five new crystal structures of perfluoropyridine substituted in the 4-position with phenoxy, 4-bromophenoxy, naphthalen-2-yloxy, 6-bromonaphthalen-2-yloxy, and 4,4′-biphenoxy are reported, viz. 2,3,5,6-tetrafluoro-4-phenoxypyridine, C11H5F4NO (I), 4-(4-bromophenoxy)-2,3,5,6-tetrafluoropyridine, C11H4BrF4NO (II), 2,3,5,6-tetrafluoro-4-[(naphthalen-2-yl)oxy]pyridine, C15H7F4NO (III), 4-[(6-bromonaphthalen-2-yl)oxy]-2,3,5,6-tetrafluoropyridine, C15H6BrF4NO (IV), and 2,2′-bis[(perfluoropyridin-4-yl)oxy]-1,1′-biphenyl, C22H8F8N2O2 (V). The dihedral angles between the aromatic ring systems in I–IV are 78.74 (8), 56.35 (8), 74.30 (7), and 64.34 (19)°, respectively. The complete molecule of V is generated by a crystallographic twofold axis: the dihedral angle between the pyridine ring and adjacent phenyl ring is 80.89 (5)° and the equivalent angle between the biphenyl rings is 27.30 (5)°. In each crystal, the packing is driven by C—H...F interactions, along with a variety of C—F...π, C—H...π, C—Br...N, C—H...N, and C—Br...π contacts. Hirshfeld surface analysis was conducted to aid in the visualization of these various influences on the packing.

scholarly journals Crystal structure of 1,2-bis(2,6-dimethylphenyl)-3-phenylguanidine

2015 ◽  
Vol 71 (7) ◽  
pp. o506-o507
Author(s):  
Hongfei Han ◽  
Zhiqiang Guo ◽  
Xuehong Wei
Keyword(s):  
Crystal Structure ◽  
Benzene Ring ◽  
Dihedral Angle ◽  
Title Compound ◽  
Phenyl Ring ◽  
Dihedral Angles ◽  
Compound C ◽  
Centroid Distance ◽  
Adjacent Molecule

In the title compound, C23H25N3, the dihedral angles between the planes of the benzene ring and the two substituent dimethylphenyl rings are 60.94 (7)° and 88.08 (7)°, and the dihedral angle between the planes of the two dimethylphenyl rings is 58.01 (7)°. In the crystal, weak C—H...N interactions exist between adjacent molecules. One of the dimethylphenyl rings has a small amount of π–π overlap with the phenyl ring of an adjacent molecule [centroid-to-centroid distance = 3.9631 (12) Å].

scholarly journals Crystal structures of four indole derivatives with a phenyl substituent at the 2-position and a carbonyl group at the 3-position: theC(6) N—H...O chain remains the same, but the weak reinforcing interactions are different

2016 ◽  
Vol 72 (3) ◽  
pp. 363-369 ◽  
Author(s):  
Jamie R. Kerr ◽  
Laurent Trembleau ◽  
John M. D. Storey ◽  
James L. Wardell ◽  
William T. A. Harrison
Keyword(s):  
Crystal Structures ◽  
Carbonyl Group ◽  
Phenyl Ring ◽  
Narrow Range ◽  
Weak Interactions ◽  
Ring System ◽  
Dihedral Angles ◽  
Indole Derivatives ◽  
Indole Ring ◽  
Ring Plane

We describe the crystal structures of four indole derivatives with a phenyl ring at the 2-position and different carbonyl-linked substituents at the 3-position, namely 1-(2-phenyl-1H-indol-3-yl)ethanone, C16H13NO, (I), 2-cyclohexyl-1-(2-phenyl-1H-indol-3-yl)ethanone, C22H23NO, (II), 3,3-dimethyl-1-(2-phenyl-1H-indol-3-yl)butan-1-one, C20H21NO, (III), and 3-benzoyl-2-phenyl-1H-indole, C21H15NO, (IV). In each case, the carbonyl-group O atom lies close to the indole-ring plane and points towards the benzene ring. The dihedral angles between the indole ring system and 2-phenyl ring for these structures are clustered in a narrow range around 65°. The dominant intermolecular interaction in each case is an N—H...O hydrogen bond, which generates aC(6) chain, although each structure possesses a different crystal symmetry. TheC(6) chains are consolidated by different (C—H...O, C—H...π and π–π stacking) weak interactions, with little consistency between the structures.

scholarly journals Crystal structure of 2-((1E)-{2-[bis(2-methylbenzylsulfanyl)methylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol

2015 ◽  
Vol 71 (4) ◽  
pp. o242-o243 ◽  
Author(s):  
Enis Nadia Md Yusof ◽  
Thahira Begum S. A. Ravoof ◽  
Mohamed Ibrahim Mohamed Tahir ◽  
Edward R. T. Tiekink
Keyword(s):  
Phenyl Ring ◽  
Three Dimensional ◽  
The Other ◽  
Dihedral Angles ◽  
Central Plane ◽  
Π Interactions ◽  
Compound C ◽  
Centroid Distance ◽  
Phenyl Rings ◽  
Methyl Phenyl

In the title compound, C25H26N2O2S2, the central CN2S2atoms are almost coplanar (r.m.s. deviation = 0.0058 Å). One phenyl ring clearly lies to one side of the central plane, while the other is oriented in the plane but splayed. Despite the different relative orientations, the phenyl rings form similar dihedral angles of 64.90 (3) and 70.06 (3)° with the central plane, and 63.28 (4)° with each other. The benzene ring is twisted with respect to the central plane, forming a dihedral angle of 13.17 (7)°. The S2C=N, N—N and N—N=C bond lengths of 1.2919 (19), 1.4037 (17) and 1.2892 (19) Å, respectively, suggest limited conjugation over these atoms; the configuration about the N—N=C bond isE. An intramolecular O—H...N hydrogen bond is noted. In the crystal, phenyl–methoxy C—H...O and phenyl–phenyl C—H...π interactions lead to supramolecular double chains parallel to thebaxis. These are connected into a layerviamethyl–phenyl C—H...π interactions, and layers stack along theaaxis, being connected by weak π–π interactions between phenyl rings [inter-centroid distance = 3.9915 (9) Å] so that a three-dimensional architecture ensues.

35Cl NQR and Structural Studies on Substituted Amides, XyC6H5–yNHCOR (X = H or Cl; y = 0, 1 or 2 and R = C(CH3)3, CHClCH3, C6H5 or 2-ClC6H4)

2003 ◽  
Vol 58 (4) ◽  
pp. 225-230 ◽  
Author(s):  
B. Thimme Gowda ◽  
K. Jyothi ◽  
Helmut Paulus ◽  
Hartmut Fuess
Keyword(s):  
Bond Length ◽  
Crystal Structures ◽  
The Other ◽  
Side Chain ◽  
Structural Studies ◽  
Lattice Constants ◽  
Alkyl Groups ◽  
The Family ◽  
35Cl Nqr ◽  
Related Compounds

35Cl NQR frequencies of some N-(substitutedphenyl)-amides represented by the general formula, XyC6H5−yNHCOR (where X = H or Cl; y = 0, 1 or 2 and R = H, CH3, CH2CH3, CH(CH3)2, C(CH3)3, CH2Cl, CHCl2 or CCl3) have been measured and compared with those of other compounds in the family to analyse the effect of substitution in the side chain on the frequencies. Comparison of 35Cl NQR frequencies of all the N-(2-chlorophenyl)- and N-(2,6-dichlorophenyl)-amides reveals that the presence of alkyl groups in the side chain lowers the frequency, while that of aryl or chlorosubstituted alkyl groups enhance the frequencies to some extent, when compared to the frequencies of either N-(2-chlorophenyl)-acetamide or N-(2,6-dichlorophenyl)-acetamide. In addition, the crystal structures of N-(phenyl)-2-chloro-2-methylacetamide (C6H5NHCOCHClCH3) and N-(phenyl)-2- chloro-benzamide (C6H5NHCO-(2-ClC6H4)) have been determined and the data analysed along with the crystal structures of related compounds. The data (lattice constants in Å) of the new structures are: C6H5NHCO- CHClCH3: monoclinic, P21/c, Z = 4, a = 10.879(2), b = 9.561(2), c = 10.067(2), β = 116.080(10)°; C6H5NHCO-(2-ClC6H4): tetragonal, P4(3), Z = 4, a = 8.795(4), b = 8.795(4), c = 15.115(6), β = 90.0°. It is evident from a comparison, that the side chain substitution influences the C(S)-C(O) bond length, while the effect on the other bond lengths is not significant except for benzanilide. Similarly, only the side chain angles are affected to some extent. The variations do not show definite trends, probably due to the differences in the crystallisations.

scholarly journals (RP)-5-Methyl-2-(propan-2-yl)cyclohexyl phenyl{phenyl[(1-phenylethyl)amino]methyl}phosphinate

2012 ◽  
Vol 68 (8) ◽  
pp. o2328-o2328 ◽  
Author(s):  
Meng Yang ◽  
Yong-Ming Sun ◽  
Qing-Gao Hou ◽  
Chang-Qiu Zhao
Keyword(s):  
Title Compound ◽  
Phenyl Ring ◽  
Bond Angle ◽  
The Other ◽  
Dihedral Angles ◽  
Compound C ◽  
Phenyl Rings

In the title compound, C31H40NO2P, the P atom has a distorted tetrahedral stereochemistry [bond-angle range about P = 103.33 (6)–115.24 (15)°] and hasRPchirality, which was confirmed crystallographically. The dihedral angles between the P-bonded phenyl ring and the other two phenyl rings are 40.4 (3) and 12.2 (2)°. In the crystal, a C—H...O interaction links molecules into chains which extend along [100].

scholarly journals Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position

2018 ◽  
Vol 74 (10) ◽  
pp. 1509-1512 ◽  
Author(s):  
Ahmed Nuriye ◽  
Hemant Yennawar ◽  
Kevin Cannon ◽  
John Tierney
Keyword(s):  
Carbon Atom ◽  
Crystal Structures ◽  
Benzene Ring ◽  
Unit Cell Parameter ◽  
Phenyl Ring ◽  
Cell Parameter ◽  
Unit Cell ◽  
Dihedral Angles ◽  
Π Interactions ◽  
Chiral Carbon

The title compounds 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-one (C10H8Cl3NOS),1and 3-(4-chlorophenyl)-2-trichloromethyl-1,3-thiazolidin-4-one (C10H7Cl4NOS)2, are structurally related with one atom substitution difference in theparaposition of the benzene ring. In both structures, the thiazolidinone ring adopts an envelope conformation with the S atom as the flap. The dihedral angles between the rings [48.72 (11) in1and 48.42 (9)° in2] are very similar and the molecules are almost superimposable. In both crystal structures, C—H...O `head-to-tail' interactions between the chiral carbon atoms and the thiazolidinone oxygen atoms result in infinite monochiral chains along the direction of the shortest unit-cell parameter, namelyain1andbin2. C—H...π interactions between the thiazolidinone carbon atom at the 4-position and the phenyl ring of the neighboring enantiomer also help to stabilize the packing in each case, although the crystals are not isostructural.

scholarly journals Crystal structure and theoretical study of N,N-bis[(5-chloro-2-oxo-2,3-dihydrobenzo[d]oxazol-3-yl)methyl]-2-phenylethanamine

2018 ◽  
Vol 74 (5) ◽  
pp. 757-760
Author(s):  
Abdullah Aydın ◽  
Zeynep Soyer ◽  
Mehmet Akkurt ◽  
Orhan Büyükgüngör
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Phenyl Ring ◽  
Theoretical Study ◽  
The Other ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Compound C ◽  
The Mean

In the molecular structure of the title compound, C24H19Cl2N3O4, the three C atoms of the central N,N-dimethylmethanamine moiety are bonded to the N atoms of the two 5-chloro-1,3-benzoxazol-2(3H)-one groups and to the methyl C atom of the methylbenzene group. One of the nine-membered 2,3-dihydro-1,3-benzoxazole rings and the phenyl ring are almost parallel to each other, making a dihedral angle of 5.30 (18)°, but they are almost normal to the mean plane of the other nine-membered 2,3-dihydro-1,3-benzoxazole ring, subtending dihedral angles of 89.29 (16) and 85.41 (18)°, respectively. The crystal structure features C—H...O hydrogen bonds and π–π stacking interactions [centroid-to-centroid distances = 3.5788 (19) Å, slippage = 0.438 and 3.7773 (16) Å, and slippage = 0.716 Å].

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