Solid-state supramoecular assembly via C–H ⋯ O hydrogen bonds: crystal structures of the complexes of 1,3,5-trinitrobenzene with dibenzylideneacetone and 2,5-dibenzylidenecyclopentanone

1993 ◽  
pp. 1473-1475 ◽  
Author(s):  
Kumar Biradha ◽  
C. V. Krishnamohan Sharma ◽  
Kaliyamoorthy Panneerselvam ◽  
Liat Shimoni ◽  
H. L. Carrell ◽  
...  
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures

Supramolecular architectures in two 1:1 cocrystals of 5-fluorouracil with 5-bromothiophene-2-carboxylic acid and thiophene-2-carboxylic acid

2017 ◽  
Vol 73 (6) ◽  
pp. 481-485 ◽  
Author(s):  
Marimuthu Mohana ◽  
Packianathan Thomas Muthiah ◽  
Colin D. McMillen
Keyword(s):  
Solid State ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
X Ray Diffraction ◽  
Base Pairs ◽  
X Ray ◽  
Supramolecular Architectures ◽  
Acid Acid ◽  
Carboxylic Acid Dimer

In solid-state engineering, cocrystallization is a strategy actively pursued for pharmaceuticals. Two 1:1 cocrystals of 5-fluorouracil (5FU; systematic name: 5-fluoro-1,3-dihydropyrimidine-2,4-dione), namely 5-fluorouracil–5-bromothiophene-2-carboxylic acid (1/1), C5H3BrO2S·C4H3FN2O2, (I), and 5-fluorouracil–thiophene-2-carboxylic acid (1/1), C4H3FN2O2·C5H4O2S, (II), have been synthesized and characterized by single-crystal X-ray diffraction studies. In both cocrystals, carboxylic acid molecules are linked through an acid–acid R 2 2(8) homosynthon (O—H...O) to form a carboxylic acid dimer and 5FU molecules are connected through two types of base pairs [homosynthon, R 2 2(8) motif] via a pair of N—H...O hydrogen bonds. The crystal structures are further stabilized by C—H...O interactions in (II) and C—Br...O interactions in (I). In both crystal structures, π–π stacking and C—F...π interactions are also observed.

scholarly journals Exploration and exploitation of homologous series of bis(acrylamido)alkanes containing pyridyl and phenyl groups: β-sheetversustwo-dimensional layers in solid-state photochemical [2 + 2] reactions

IUCrJ ◽  
2015 ◽  
Vol 2 (5) ◽  
pp. 523-533 ◽  
Author(s):  
Mousumi Garai ◽  
Kumar Biradha
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Crystal Structures ◽  
Homologous Series ◽  
Bonding Layer ◽  
Two Dimensional ◽  
Systematic Analysis ◽  
Small Change

The homologous series of phenyl and pyridyl substituted bis(acrylamido)alkanes have been synthesized with the aim of systematic analysis of their crystal structures and their solid-state [2 + 2] reactivities. The changes in the crystal structures with respect to a small change in the molecular structure, that is by varying alkyl spacers between acrylamides and/or by varying the end groups (phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl) on the C-terminal of the amide, were analyzed in terms of hydrogen-bonding interference (N—H...NpyversusN—H...O=C) and network geometries. In this series, a greater tendency towards the formation of N—H...O hydrogen bonds (β-sheets and two-dimensional networks) over N—H...N hydrogen bonds was observed. Among all the structures seven structures were found to have the required alignments of double bonds for the [2 + 2] reaction such that the formations of single dimer, double dimer and polymer are facilitated. However, only four structures were found to exhibit such a solid-state [2 + 2] reaction to form a single dimer and polymers. The two-dimensional hydrogen-bonding layerviaN—H...O hydrogen bonds was found to promote solid-state [2 + 2] photo-polymerization in a single-crystal-to-single-crystal manner. Such two-dimensional layers were encountered only when the spacer between acryl amide moieties is butyl. Only four out of the 16 derivatives were found to form hydrates, two each from 2-pyridyl and 4-pyridyl derivatives. The water molecules in these structures govern the hydrogen-bonding networks by the formation of an octameric water cluster and one-dimensional zigzag water chains. The trends in the melting points and densities were also analyzed.

Aminkomplexe von Silber(I)-disulfonylamiden, Teil I: Sekund¨are Amine [1]

2011 ◽  
Vol 66 (5) ◽  
pp. 449-458
Author(s):  
Eva-Maria Zerbe ◽  
Christoph Wölper ◽  
Peter G. Jones
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Secondary Amine ◽  
Linear Arrays ◽  
Bond Angles ◽  
Bond Lengths ◽  
Ionic Compounds ◽  
State 1 ◽  
Molecular Compounds

We report the crystal structures of five amine-complexed silver(I) disulfonylamides of composition L2AgX (L = secondary amine, X = disulfonylamide anion) [1: bis(2,2,6,6-tetramethylpiperidine)- silver(I) dimesylamide, 2: bis(2,2,6,6-tetramethylpiperidine)(1,1,3,3-tetraoxo-1,3,2-benzodithiazolido) silver(I), 3: bis(diethylamine)(dimesylamido)silver(I), 4: bis(diethylamine)silver(I) 1,1,3,3-tetraoxo- 1,3,2-benzodithiazolide, 5: bis(dicyclohexylamine)silver(I) 1,1,3,3-tetraoxo-1,3,2-benzodithiazolide]. In the solid state 1, 4 and 5 are ionic compounds, whereas 2 and 3 appear to be molecular, but with long Ag-Ndisulfonylamide bonds (ca. 2.5 Å ), almost linear Namine-Ag-Namine bond angles (171, 158°) and S-N bond lengths more typical of purely ionic disulfonylamides. The packing of these complexes is governed by the formation of chains via motifs of Ag・ ・ ・O contacts and classical hydrogen bonds. The interaction motifs vary slightly depending on the steric demand of the amine substituents. For the molecular compounds, either new motifs appear (3) or intramolecular classical hydrogen bonds are formed, and linear arrays of molecules are generated by non-classical hydrogen bonds (2)

scholarly journals Solid-state conformations of linear depsipeptide amides with an alternating sequence of α,α-disubstituted α-amino acid and α-hydroxy acid

2019 ◽  
Vol 76 (1) ◽  
pp. 1-9
Author(s):  
Anthony Linden ◽  
J. E. Florian Magirius ◽  
Heinz Heimgartner
Keyword(s):  
Amino Acid ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Hydroxy Acid ◽  
Mandelic Acid ◽  
Type I ◽  
Two Dimensional ◽  
Phenyllactic Acid ◽  
Torsion Angles

Depsipeptides and cyclodepsipeptides are analogues of the corresponding peptides in which one or more amide groups are replaced by ester functions. Reports of crystal structures of linear depsipeptides are rare. The crystal structures and conformational analyses of four depsipeptides with an alternating sequence of an α,α-disubstituted α-amino acid and an α-hydroxy acid are reported. The molecules in the linear hexadepsipeptide amide in (S)-Pms-Acp-(S)-Pms-Acp-(S)-Pms-Acp-NMe2 acetonitrile solvate, C47H58N4O9·C2H3N, (3b), as well as in the related linear tetradepsipeptide amide (S)-Pms-Aib-(S)-Pms-Aib-NMe2, C28H37N3O6, (5a), the diastereoisomeric mixture (S,R)-Pms-Acp-(R,S)-Pms-Acp-NMe2/(R,S)-Pms-Acp-(R,S)-Pms-Acp-NMe2 (1:1), C32H41N3O6, (5b), and (R,S)-Mns-Acp-(S,R)-Mns-Acp-NMe2, C30H37N3O6, (5c) (Pms is phenyllactic acid, Acp is 1-aminocyclopentanecarboxylic acid and Mns is mandelic acid), generally adopt a β-turn conformation in the solid state, which is stabilized by intramolecular N—H...O hydrogen bonds. Whereas β-turns of type I (or I′) are formed in the cases of (3b), (5a) and (5b), which contain phenyllactic acid, the torsion angles for (5c), which incorporates mandelic acid, indicate a β-turn in between type I and type III. Intermolecular N—H...O and O—H...O hydrogen bonds link the molecules of (3a) and (5b) into extended chains, and those of (5a) and (5c) into two-dimensional networks.

scholarly journals Crystal structures of the hexafluoridophosphate salts of the isomeric 2-, 3- and 4-cyano-1-methylpyridinium cations and determination of solid-state interaction energies

2018 ◽  
Vol 74 (9) ◽  
pp. 1322-1329
Author(s):  
Joel T. Mague ◽  
Erin Larrabee ◽  
David Olivier ◽  
Francesca Vaccaro ◽  
Kevin E. Riley ◽  
...  
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Density Functional ◽  
Cyano Group ◽  
Three Dimensional ◽  
Axis Direction ◽  
Dimensional Network ◽  
Molecular Salts ◽  
Anion Interaction

The synthesis and crystal structures of the isomeric molecular salts 2-, 3- and 4-cyano-1-methylpyridinium hexafluoridophosphate, C7H7N2 +·PF6 −, are reported. In 2-cyano-1-methylpyridinium hexafluoridophosphate, C—H...F hydrogen bonds form chains extending along the c-axis direction, which are associated through C—H...F hydrogen bonds and P—F...π(ring) interactions into stepped layers. For 3-cyano-1-methylpyridinium hexafluoridophosphate, corrugated sheets parallel to [001] are generated by C—H...F hydrogen bonds and P—F...π(ring) interactions. The sheets are weakly associated by a weak interaction of the cyano group with the six-membered ring of the cation. In 4-cyano-1-methylpyridinium hexafluoridophosphate, C—H...F hydrogen bonds form a more open three-dimensional network in which stacks of cations and of anions are aligned with the b-axis direction. Dispersion-corrected density functional theory (DFT-D) calculations were carried out in order to elucidate some of the energetic aspects of the solid-state structures. The results indicate that the distribution of charge within a molecular ionic cation can play a large role in determining the strength of a cation–anion interaction within a crystal structure. Crystals of 2-cyano-1-methylpyridinium hexafluoridophosphate are twinned by a 180° rotation about the c* axis. The anion in 3-cyano-1-methylpyridinium hexafluoridophosphate is rotationally disordered by 38.2 (1)° in an 0.848 (3):0.152 (3) ratio.

Structures and Photochemistry of Inclusion Compounds of 9,10-Dihydro-9,10-ethenoanthracene-11,12-bis(diphenylmethanol)

1997 ◽  
Vol 53 (2) ◽  
pp. 300-305 ◽  
Author(s):  
T. Y. Fu ◽  
J. R. Scheffer ◽  
J. Trotter
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Solid State Reaction ◽  
Inclusion Compounds ◽  
Host Molecule ◽  
Molecular Rearrangement ◽  
Intermolecular Hydrogen Bonds ◽  
Solvent Molecules

Crystal structures have been determined for inclusion complexes of the host molecule 9,10-dihydro-9,10-ethenoanthracene-11,12-bis(diphenylmethanol), with acetone, ethanol and toluene as guest solvent molecules. The host molecule exhibits an intramolecular O--H...O hydrogen bond in each of the complexes, with intermolecular hydrogen bonds to the acetone and ethanol guests. Different photoproducts are obtained from solution and solid-state photolyses; the solid-state reaction involves a relatively small amount of molecular rearrangement, for which a mechanism is proposed.

Notizen: The Crystal Structures of Pyridinium Chloride Revisited: Evidence for Extensive C–H ••• Cl Hydrogen-Bond Interactions

1993 ◽  
Vol 48 (7) ◽  
pp. 1023-1026 ◽  
Author(s):  
Christer B. Aakeröy ◽  
Kenneth R. Seddon
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Pyridinium Chloride ◽  
Structural Role ◽  
Hydrogen Bond Interactions

A reinvestigation of the previously determined structures of two polymorphs of pyridinium chloride shows that both polymorphs contain several aromatic C– H-H···Cl hydrogen-bond interactions. These hydrogen bonds, hitherto unrecognized, may play a significant structural role, both in solution and in the solid-state.

A solid-state oxidation of 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfinate to 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfonate

2013 ◽  
Vol 69 (7) ◽  
pp. 778-780 ◽  
Author(s):  
Åsmund Kaupang ◽  
Carl Henrik Görbitz ◽  
Tore Bonge-Hansen
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Organic Acid ◽  
Crystal Structures ◽  
Monoclinic Space Group ◽  
Acid Base ◽  
Space Group ◽  
Base Complex ◽  
Oxidation In Air

The organic acid–base complex 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfonate, C5H14N3+·C7H7O3S−, was obtained from the corresponding 1,1,3,3-tetramethylguanidinium 4-methylbenzenesulfinate complex, C5H14N3+·C7H7O2S−, by solid-state oxidation in air. Comparison of the two crystal structures reveals similar packing arrangements in the monoclinic space groupP21/c, with centrosymmetric 2:2 tetramers being connected by four strong N—H...O=S hydrogen bonds between the imine N atoms of two 1,1,3,3-tetramethylguanidinium bases and the O atoms of two acid molecules.

scholarly journals Investigation of solid-state photochemical nitro–nitrito linkage isomerization: crystal structures of trans-bis(ethylenediamine)(isothiocyanato)nitritocobalt(III) salts: thiocyanate, chloride monohydrate, and perchlorate–thiocyanate(0.75/0.25)

2018 ◽  
Vol 74 (10) ◽  
pp. 1526-1531 ◽  
Author(s):  
Shigeru Ohba ◽  
Masanobu Tsuchimoto ◽  
Saeko Kurachi
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Building Block ◽  
Main Building ◽  
Linkage Isomerization ◽  
The Common ◽  
Chloride Monohydrate

The reaction cavities of the nitro groups in the crystals of the title compounds, trans-[Co(NO2)(NCS)(C2H8N2)2]·X, X = SCN− (I), Cl−·H2O (II), and (ClO4 −)0.75(SCN−)0.25 (III), have been investigated, revealing that the geometry of the intermolecular N—H...O hydrogen bonds in (I) is unsuitable for nitro–nitrito photo-isomerization. The common main building block of these crystal structures is a centrosymmetric pair of complex cations connected by pairwise N—H...O(nitro) hydrogen bonds forming an R 2 2(4) ring, which is a narrow diamond shape in (I) but is approximately square in (II) and (III). The structure of (I) was reported earlier [Börtin (1976). Acta Chem. Scand. A, 30, 503–506] but is described here with an improved disorder model for the thiocyanate anions and to higher precision.

Polysulfonylamine, CXII. Neues aus der Festkörperchemie der 2-Pyridone: Isolierung und Röntgenstrukturen von Bis(2-pyridon)hydrogen(I)- und Bis(6-methyl-2-pyridon)hydrogen(I)-dimesylamid / Polysulfonylamines, CXII. A Novel Solid-State Aspect of 2-Pyridones: Isolation and X-Ray Structures of Bis(2-pyridone)hydrogen(I) and Bis(6-methyl-2-pyridone)hydrogen(I) Dimesylamides

1999 ◽  
Vol 54 (5) ◽  
pp. 643-648 ◽  
Author(s):  
Karna Wijaya ◽  
Oliver Moers ◽  
Armand Blaschette ◽  
Peter G. Jones
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Monoclinic Space Group ◽  
Space Group ◽  
X Ray ◽  
Crystal Packings

The compounds (2-pyridone)2H+(MeSO2)2N- (1, monoclinic, space group P21/n ) and (6- methyl-2-pyridone)2H+(MeSO2)2N- (2, triclinic, P1) crystallize selectively and in good yields when the parent 2-pyridones (2-hydroxypyridines) are treated with the strong NH acid dimesylamine in acetonitrile or acetone. The corresponding 2-hydroxypyridinium salts could not be obtained. In the unprecedented crystal structures of 1 and 2, two pyridone units are linked by a proton to form very short and approximately symmetric O⋯H+ ⋯O hydrogen bonds, the adjacent C-O distances being appreciably elongated as compared to “free” pyridones [1: O ⋯ O 241.8(2), C -O 127.8(3) and 129.1(2) pm; 2: O ⋯ O 243.8(2), C -O 128.1(2) and 129.2(2) pm]. In both crystal packings, the homoconjugate cations and the dimesylamide anions are alternately associated into chains by an N - H ⋯ N “ and an N - H ⋯ O hydrogen bond.

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