Weak C—H...O and C—H...π hydrogen bonds and π–π stacking interactions in a series of fourN′-[(E)-(aryl)methylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazides

2015 ◽  
Vol 71 (8) ◽  
pp. 647-652 ◽  
Author(s):  
Thais C. M. Nogueira ◽  
Alessandra C. Pinheiro ◽  
James L. Wardell ◽  
Marcus V. N. de Souza ◽  
Jordan P. Abberley ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Weak Interactions ◽  
The Other ◽  
Stacking Interactions ◽  
Screw Axis ◽  
Chiral Structure ◽  
Π Stacking ◽  
Unit Form ◽  
Protective Groups ◽  
Local Inversion

Oxazolidin-2-ones are widely used as protective groups for 1,2-amino alcohols and chiral derivatives are employed as chiral auxiliaries. The crystal structures of four differently substituted oxazolidinecarbohydrazides, namelyN′-[(E)-benzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12N3O3, (I),N′-[(E)-2-chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12ClN3O3, (II), (4S)-N′-[(E)-4-chlorobenzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12H12ClN3O3, (III), and (4S)-N′-[(E)-2,6-dichlorobenzylidene]-N,3-dimethyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C13H13Cl2N3O3, (IV), show that an unexpected mild-condition racemization from the chiral starting materials has occurred in (I) and (II). In the extended structures, the centrosymmetric phases, which each crystallize with two molecules (AandB) in the asymmetric unit, formA+Bdimers linked by pairs of N—H...O hydrogen bonds, albeit with different O-atom acceptors. One dimer is composed of one molecule with anSconfiguration for its stereogenic centre and the other with anRconfiguration, and possesses approximate local inversion symmetry. The other dimer consists of eitherR,RorS,Spairs and possesses approximate local twofold symmetry. In the chiral structure, N—H...O hydrogen bonds link the molecules intoC(5) chains, with adjacent molecules related by a 21screw axis. A wide variety of weak interactions, including C—H...O, C—H...Cl, C—H...π and π–π stacking interactions, occur in these structures, but there is little conformity between them.

scholarly journals Fluoren-9-one oxime

2014 ◽  
Vol 70 (3) ◽  
pp. o265-o265
Author(s):  
Bernhard Bugenhagen ◽  
Yosef Al Jasem ◽  
Mariam Al-Azani ◽  
Thies Thiemann
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Interplanar Distance ◽  
Maximum Deviation ◽  
Stacking Interactions ◽  
Oxime Group ◽  
Screw Axis ◽  
Π Stacking ◽  
Title Molecule ◽  
Unit Translation

In the title molecule, C13H9NO, the fluorene system and the oxime group non-H atoms are essentially coplanar, with a maximum deviation from the fluorene mean plane of 0.079 (2) Å for the oxime O atom. A short intramolecular C—H...O generates anS(6) ring. In the crystal, molecules related by a twofold screw axis are connected by O—H...N hydrogen bonds, forming [100] chains Within these chains, molecules related by a unit translation along [100] show π–π stacking interactions between their fluorene ring systems with an interplanar distance of 3.347 (2) Å. The dihedral angle between the fluorene units of adjacent molecules along the helix is 88.40 (2)°. There is a short C—H...π contact between the fluorene groups belonging to neighbouring chains.

scholarly journals (E)-3-{4-[(7-Chloroquinolin-4-yl)oxy]-3-methoxyphenyl}-1-(4-methylphenyl)prop-2-en-1-one: a ladder-like structure resulting solely from π–π stacking interactions

2014 ◽  
Vol 70 (7) ◽  
pp. 677-680
Author(s):  
Alba Montoya ◽  
Braulio Insuasty ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
The Other ◽  
Stacking Interactions ◽  
Quinoline Ring ◽  
Compound C ◽  
Π Stacking ◽  
Quinoline Fragment ◽  
Molecular Skeleton

In the title compound, C26H20ClNO3, the quinoline fragment is nearly orthogonal to the adjacent aryl ring, while the rest of the molecular skeleton is close to being planar. The crystal structure contains no hydrogen bonds of any sort, but there are two π–π stacking interactions present. One, involving the quinoline ring, links molecules related by inversion, while the other, involving the two nonfused aryl rings, links molecules related by translation, so together forming a ladder-type arrangement

scholarly journals 5-(2-Chlorophenyl)-3-(2H-chromen-3-yl)-1,2,4-oxadiazole

IUCrData ◽  
2018 ◽  
Vol 3 (1) ◽  
Author(s):  
Nilofar Baral ◽  
Sabita Nayak ◽  
Satyanarayan Pal ◽  
Seetaram Mohapatra
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Weak Interactions ◽  
Stacking Interactions ◽  
Two Dimensional ◽  
Individual Molecule ◽  
Compound C ◽  
Π Stacking

In the title compound, C17H11ClN2O2, the central oxadiazole ring carries 2H-chromene and 2-chlorophenyl substituents at the 3- and 5-positions, respectively. C—H...O and C—H...Cl hydrogen bonds form two-dimensional sheets parallel to (212), with each individual molecule involved in six of these weak interactions. The sheets are stacked perpendicular to (212) by offset π–π stacking interactions.

scholarly journals 3-Hydroxy-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-2,3-dihydro-1H-indol-2-one

IUCrData ◽  
2017 ◽  
Vol 2 (2) ◽  
Author(s):  
Joel T. Mague ◽  
Shaaban K. Mohamed ◽  
Mehmet Akkurt ◽  
Mohamed Shaker S. Adam ◽  
Farouq E. Hawaiz
Keyword(s):  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Crystal Packing ◽  
Membered Ring ◽  
The Other ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Title Molecule

The conformation of the title molecule, C16H12N2O3, is partly determined by an intramolecular C=O...π interaction between one carbonyl group and the five-membered ring of the other indolinone moiety. The crystal packing consists of layers parallel to (001) formed by a combination of N—H...O and O—H...O hydrogen bonds and π–π stacking interactions. Both the N—H...O and O—H...O hydrogen bonds generate inversion dimers.

scholarly journals Bis(thiocyanato-κN)[tris(pyridin-2-ylmethyl)amine-κ4N]iron(II)

2014 ◽  
Vol 70 (2) ◽  
pp. m35-m35
Author(s):  
Jing-Wei Dai ◽  
Zhao-Yang Li ◽  
Osamu Sato
Keyword(s):  
Hydrogen Bonds ◽  
Octahedral Geometry ◽  
Title Complex ◽  
Stacking Interactions ◽  
Supramolecular Architecture ◽  
Two Dimensional ◽  
Π Stacking ◽  
Centroid Distance ◽  
Solvent Molecules ◽  
Amine Ligand

In the title complex, [Fe(NCS)2(C18H18N4)], the FeIIcation is chelated by a tris(2-pyridylmethyl)amine ligand and coordinated by two thiocyanate anions in a distorted N6octahedral geometry. In the crystal, weak C—H...S hydrogen bonds and π–π stacking interactions between parallel pyridine rings of adjacent molecules [centroid–centroid distance = 3.653 (3) Å] link the molecules into a two-dimensional supramolecular architecture. The structure contains voids of 124 (9) Å3, which are free of solvent molecules.

scholarly journals Crystal structure of 2-bromo-1,4-dihydroxy-9,10-anthraquinone

2014 ◽  
Vol 70 (10) ◽  
pp. o1130-o1130 ◽  
Author(s):  
Wataru Furukawa ◽  
Munenori Takehara ◽  
Yoshinori Inoue ◽  
Chitoshi Kitamura
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Compound C ◽  
Π Stacking ◽  
Dimensional Network

In an attempt to brominate 1,4-dipropoxy-9,10-anthraquinone, a mixture of products, including the title compound, C14H7BrO4, was obtained. The molecule is essentially planar (r.m.s. deviation = 0.029 Å) and two intramolecular O—H...O hydrogen bonds occur. In the crystal, the molecules are linked by weak C—H...O hydrogen bonds, Br...O contacts [3.240 (5) Å], and π–π stacking interactions [shortest centroid–centroid separation = 3.562 (4) Å], generating a three-dimensional network.

Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, I...O interactions and aromatic π...π stacking interactions

2001 ◽  
Vol 58 (1) ◽  
pp. 94-108 ◽  
Author(s):  
Craig J. Kelly ◽  
Janet M. S. Skakle ◽  
James L. Wardell ◽  
Solange M. S. V. Wardell ◽  
John N. Low ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Space Group ◽  
Rotation Axes ◽  
Π Stacking ◽  
Structural Database ◽  
A Chain

Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O2NC6H4NHSO2C6H4I-4′ (1), are linked by three-centre I...O2N interactions into chains and these chains are linked into a three-dimensional framework by C—H...O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4NHSO2C6H4NO2-4′ (2), the chains generated by the I...O2N interactions are again linked into a three-dimensional framework by C—H...O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4N(SO2C6H4NO2-3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I...O=S interactions: these chains are linked into sheets by a C—H...O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π...π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline, 3-O2NC6H4NHSO2C6H4I-4′ (4), there are R^2_2(8) rings formed by hard N—H...O=S hydrogen bonds and R^2_2(24) rings formed by two-centre I...nitro interactions, which together generate a chain of fused rings: the combination of a C—H...O hydrogen bond and aromatic π...π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonyl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO2C6H4I-4′ (5), are linked by N—H...O=S and C—H...O(nitro) hydrogen bonds into a chain containing alternating R^2_2(8) and R^2_2(10) rings, but there are no I...O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O2NC6H4NHSO2C6H4I-4′ (6), and the combination of an I...O=S interaction and a hard N—H...O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C—H...O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

Polymorphs of phenazine hexacyanoferrate(II) hydrate: supramolecular isomerism in a 2D hydrogen-bonded network

2021 ◽  
Vol 77 (2) ◽  
pp. 211-218
Author(s):  
Ivica Cvrtila ◽  
Vladimir Stilinović
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
The Other ◽  
Two Dimensional ◽  
Structural Motifs ◽  
Supramolecular Isomerism ◽  
Other Hand ◽  
Π Stacking ◽  
Hydrogen Bonded

The crystal structures of two polymorphs of a phenazine hexacyanoferrate(II) salt/cocrystal, with the formula (Hphen)3[H2Fe(CN)6][H3Fe(CN)6]·2(phen)·2H2O, are reported. The polymorphs are comprised of (Hphen)2[H2Fe(CN)6] trimers and (Hphen)[(phen)2(H2O)2][H3Fe(CN)6] hexamers connected into two-dimensional (2D) hydrogen-bonded networks through strong hydrogen bonds between the [H2Fe(CN)6]2− and [H3Fe(CN)6]− anions. The layers are further connected by hydrogen bonds, as well as through π–π stacking of phenazine moieties. Aside from the identical 2D hydrogen-bonded networks, the two polymorphs share phenazine stacks comprising both protonated and neutral phenazine molecules. On the other hand, the polymorphs differ in the conformation, placement and orientation of the hydrogen-bonded trimers and hexamers within the hydrogen-bonded networks, which leads to different packing of the hydrogen-bonded layers, as well as to different hydrogen bonding between the layers. Thus, aside from an exceptional number of symmetry-independent units (nine in total), these two polymorphs show how robust structural motifs, such as charge-assisted hydrogen bonding or π-stacking, allow for different arrangements of the supramolecular units, resulting in polymorphism.

5-Nitrosalicylaldehyde (2-hydroxybenzoyl)hydrazone

2006 ◽  
Vol 62 (7) ◽  
pp. o3026-o3027 ◽  
Author(s):  
Hong-Mei Xu ◽  
Shi-Xiong Liu
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Crystal Packing ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Aromatic Rings ◽  
Compound C ◽  
Π Stacking

The molecule of the title compound, C14H11N3O5, is approximately planar, the dihedral angles between the two aromatic rings being 4.63 (7)°. O—H...N, N—H...O and O—H...O hydrogen bonds and π–π stacking interactions help to consolidate the crystal packing.

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