Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

2018 ◽  
Vol 74 (3) ◽  
pp. 325-331
Author(s):  
Robert Swinton Darious ◽  
Nithianantham Jeeva Jasmine ◽  
Ammasai Karthikeyan ◽  
Packianathan Thomas Muthiah ◽  
Franc Perdih
Keyword(s):  
Hydrogen Bonds ◽  
Pyrimidine Ring ◽  
Hydrogen Sulfate ◽  
X Ray Diffraction ◽  
Sulfate Ion ◽  
Sulfate Ions ◽  
Supramolecular Architectures ◽  
Hydrated Salt ◽  
Sheet Structure ◽  
Hydrogen Bonded

Aminopyrimidine derivatives are biologically important as they are components of nucleic acids and drugs. The crystals of two new salts, namely cytosinium 6-chloronicotinate monohydrate, C4H6N3O+·C6H3ClNO2−·H2O, (I), and 5-bromo-6-methylisocytosinium hydrogen sulfate (or 2-amino-5-bromo-4-oxo-6-methylpyrimidinium hydrogen sulfate), C5H7BrN3O+·HSO4−, (II), have been prepared and characterized by single-crystal X-ray diffraction. The pyrimidine ring of both compounds is protonated at the imine N atom. In hydrated salt (I), the primaryR22(8) ring motif (supramolecular heterosynthon) is formedviaa pair of N—H...O(carboxylate) hydrogen bonds. The cations, anions and water molecule are hydrogen bonded through N—H...O, N—H...N, O—H...O and C—H...O hydrogen bonds, formingR22(8),R32(7) andR55(21) motifs, leading to a hydrogen-bonded supramolecular sheet structure. The supramolecular double sheet structure is formedviawater–carboxylate O—H...O hydrogen bonds and π–π interactions between the anions and the cations. In salt (II), the hydrogen sulfate ions are linkedviaO—H...O hydrogen bonds to generate zigzag chains. The aminopyrimidinium cations are embedded between these zigzag chains. Each hydrogen sulfate ion bridges two cationsviapairs of N—H...O hydrogen bonds andvice versa, generating twoR22(8) ring motifs (supramolecular heterosynthon). The cations also interact with one anotherviahalogen–halogen (Br...Br) and halogen–oxygen (Br...O) interactions.

Supramolecular interactions in carboxylate and sulfonate salts of 2,6-diamino-4-chloropyrimidinium

2017 ◽  
Vol 73 (7) ◽  
pp. 536-540
Author(s):  
Marimuthu Mohana ◽  
Packianathan Thomas Muthiah ◽  
Ray J. Butcher
Keyword(s):  
Hydrogen Bonds ◽  
Water Molecule ◽  
Pyrimidine Ring ◽  
Molecular Structures ◽  
Supramolecular Interactions ◽  
Sulfonate Group ◽  
X Ray Diffraction ◽  
Hydrated Salt ◽  
Sulfonate Salts ◽  
Ring Motif

Two new salts, namely 2,6-diamino-4-chloropyrimidinium 2-carboxy-3-nitrobenzoate, C4H6ClN4 +·C8H4NO6 −, (I), and 2,6-diamino-4-chloropyrimidinium p-toluenesulfonate monohydrate, C4H6ClN4 +·C7H7O3S−·H2O, (II), have been synthesized and characterized by single-crystal X-ray diffraction. In both crystal structures, the N atom in the 1-position of the pyrimidine ring is protonated. In salt (I), the protonated N atom and the amino group of the pyrimidinium cation interact with the carboxylate group of the anion through N—H...O hydrogen bonds to form a heterosynthon with an R 2 2(8) ring motif. In hydrated salt (II), the presence of the water molecule prevents the formation of the familiar R 2 2(8) ring motif. Instead, an expanded ring [i.e. R 3 2(8)] is formed involving the sulfonate group, the pyrimidinium cation and the water molecule. Both salts form a supramolecular homosynthon [R 2 2(8) ring motif] through N—H...N hydrogen bonds. The molecular structures are further stabilized by π–π stacking, and C=O...π, C—H...O and C—H...Cl interactions.

scholarly journals Cyclooctanaminium hydrogen succinate monohydrate

2012 ◽  
Vol 68 (4) ◽  
pp. o1204-o1204 ◽  
Author(s):  
Sanaz Khorasani ◽  
Manuel A. Fernandes
Keyword(s):  
Hydrogen Bonds ◽  
Water Molecule ◽  
Ammonium Cation ◽  
Water Molecules ◽  
Hydrated Salt ◽  
A Chain ◽  
Hydrogen Bonded

In the title hydrated salt, C8H18N+·C4H5O4−·H2O, the cyclooctyl ring of the cation is disordered over two positions in a 0.833 (3):0.167 (3) ratio. The structure contains various O—H.·O and N—H...O interactions, forming a hydrogen-bonded layer of molecules perpendicular to thecaxis. In each layer, the ammonium cation hydrogen bonds to two hydrogen succinate anions and one water molecule. Each hydrogen succinate anion hydrogen bonds to neighbouring anions, forming a chain of molecules along thebaxis. In addition, each hydrogen succinate anion hydrogen bonds to two water molecules and the ammonium cation.

scholarly journals A new one-dimensional NiIIcoordination polymer with a two-dimensional supramolecular architecture

2017 ◽  
Vol 73 (2) ◽  
pp. 192-195
Author(s):  
Kai-Long Zhong
Keyword(s):  
Hydrogen Bonds ◽  
Water Molecule ◽  
Two Dimensional ◽  
X Ray Diffraction ◽  
Sulfate Ions ◽  
Sulfate Anion ◽  
One Dimensional ◽  
X Ray ◽  
Distorted Octahedral ◽  
Metal Organic

A new one-dimensional NiIIcoordination polymer of 1,3,5-tris(imidazol-1-ylmethyl)benzene, namelycatena-poly[[aqua(sulfato-κO)hemi(μ-ethane-1,2-diol-κ2O:O′)[μ3-1,3,5-tris(1H-imidazol-1-ylmethyl)benzene-κ3N3,N3′,N3′′]nickel(II)] ethane-1,2-diol monosolvate monohydrate], {[Ni(SO4)(C18H18N6)(C2H6O2)0.5(H2O)]·C2H6O2·H2O}n, was synthesized and characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction. The NiIIcation is coordinated by three N atoms of three different 1,3,5-tris(imidazol-1-ylmethyl)benzene ligands, one O atom of an ethane-1,2-diol molecule, by a sulfate anion and a water molecule, forming a distorted octahedral NiN3O3coordination geometry. The tripodal 1,3,5-tris(imidazol-1-ylmethyl)benzene ligands link the NiIIcations, generating metal–organic chains running along the [100] direction. Adjacent chains are further connected by O—H...O hydrogen bonds, resulting in a two-dimensional supermolecular architecture running parallel to the (001) plane. Another water molecule and a second ethane-1,2-diol molecule are non-coordinating and are linked to the coordinating sulfate ionsviaO—H...O hydrogen bonds.

scholarly journals Neutron and high-pressure X-ray diffraction study of hydrogen-bonded ferroelectric rubidium hydrogen sulfate

2016 ◽  
Vol 72 (6) ◽  
pp. 855-863 ◽  
Author(s):  
Jack Binns ◽  
Garry J McIntyre ◽  
Simon Parsons
Keyword(s):  
High Pressure ◽  
Applied Pressure ◽  
Ferroelectric Material ◽  
Ferroelectric Materials ◽  
Hydrogen Sulfate ◽  
X Ray Diffraction ◽  
Temperature Dependent ◽  
X Ray ◽  
Pressure Phase ◽  
Hydrogen Bonded

The pressure- and temperature-dependent phase transitions in the ferroelectric material rubidium hydrogen sulfate (RbHSO4) are investigated by a combination of neutron Laue diffraction and high-pressure X-ray diffraction. The observation of disordered O-atom positions in the hydrogen sulfate anions is in agreement with previous spectroscopic measurements in the literature. Contrary to the mechanism observed in other hydrogen-bonded ferroelectric materials, H-atom positions are well defined and ordered in the paraelectric phase. Under applied pressure RbHSO4undergoes a ferroelectric transition before transforming to a third, high-pressure phase. The symmetry of this phase is revised to the centrosymmetric space groupP21/c, resulting in the suppression of ferroelectricity at high pressure.

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.

Dimer oder nicht dimer, das ist hier die Frage: Zwei benachbarte I3–--Ionen eingeschlossen in Hohlr¨aumen einer komplexen Wirtsstruktur

2010 ◽  
Vol 65 (12) ◽  
pp. 1462-1466 ◽  
Author(s):  
Michaela K. Meyer ◽  
Jürgen Graf ◽  
Guido J. Reiß
Keyword(s):  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Two Dimensional ◽  
X Ray Diffraction ◽  
Space Group ◽  
X Ray ◽  
Dimensional Network ◽  
Oder Nicht ◽  
Bonding Interaction ◽  
Hydrogen Bonded

[Me(HO)2P-(CH2)10-P(O)OHMe]2[I3]2・MeHO(O)P-(CH2)10-P(O)OHMe (1) was synthesized and characterized by IR, Raman and NMR spectroscopy. Its structure was determined by singlecrystal X-ray diffraction (T = 100 K; space group P1̄). The structure consists of decane-1,10-diyl-bis- (methylphosphinic acid) molecules and the analogous mono-protonated cations in a ratio 1:2 connected with each other by strong O-H···O hydrogen bonds to form a two-dimensional network. Between these hydrogen-bonded layers, there are elongated cavities each containing two triiodide anions. The intermolecular I· · · I distance of the two enclosed triiodide anions is 3.6317(4) Å and should be considered as an interhalogen bonding interaction.

scholarly journals Sulfate-bridged dimeric trinuclear copper(II)–pyrazolate complex with three different terminal ligands

2016 ◽  
Vol 72 (8) ◽  
pp. 1064-1067 ◽  
Author(s):  
Gellert Mezei
Keyword(s):  
Hydrogen Bonds ◽  
Copper Cation ◽  
Coordination Geometry ◽  
Two Dimensional ◽  
Sulfate Ion ◽  
Dimeric Molecule ◽  
Apical Position ◽  
Sulfate Ions ◽  
Dimensional Network ◽  
Solvent Molecules

The reaction of CuSO4·5H2O, 4-chloropyrazole (4-Cl-pzH) and triethylamine (Et3N) in dimethylformamide (DMF) produced crystals of diaquahexakis(μ-4-chloropyrazolato-κ2N:N′)bis(N,N-dimethylformamide)di-μ3-hydroxido-bis(μ4-sulfato-κ4O:O′:O′′:O′′)hexacopper(II)N,N-dimethylformamide tetrasolvate dihydrate, [Cu3(OH)(SO4)(C3H2ClN2)3(C3H7NO)(H2O)]2·4C3H7NO·2H2O. The centrosymmetric dimeric molecule consists of two trinuclear copper–pyrazolate units bridged by two sulfate ions. The title compound provides the first example of a trinuclear copper–pyrazolate complex with three different terminal ligands on the Cu atoms, and also the first example of such complex with a strongly binding basal sulfate ion. Within each trinuclear unit, the CuIIatoms are bridged by μ-pyrazolate groups and a central μ3-OH group, and are coordinated by terminal sulfate, H2O and DMF ligands, respectively. Moreover, the sulfate O atoms coordinate at the apical position to the Cu atoms of the symmetry-related unit, providing square–pyramidal coordination geometry around each copper cation. The metal complex and solvent molecules are involved in O—H...O hydrogen bonds, leading to a two-dimensional network parallel to (10-1).

A new polymorph of bis(2-aminopyridinium) fumarate–fumaric acid (1/1) from powder X-ray diffraction

2013 ◽  
Vol 69 (8) ◽  
pp. 896-900 ◽  
Author(s):  
Shuichao Dong ◽  
Yaqiu Tao ◽  
Xiaodong Shen ◽  
Zhigang Pan
Keyword(s):  
Hydrogen Bonds ◽  
Fumaric Acid ◽  
Diffraction Method ◽  
Monoclinic Space Group ◽  
Asymmetric Unit ◽  
X Ray Diffraction ◽  
Acta Cryst ◽  
Space Group ◽  
X Ray ◽  
Hydrogen Bonded

A new polymorph of bis(2-aminopyridinium) fumarate–fumaric acid (1/1), 2C5H7N2+·C4H2O42−·C4H4O4, was obtained and its crystal structure determined by powder X-ray diffraction. The new polymorph (form II) crystallizes in the triclinic system (space groupP\overline{1}), while the previous reported polymorph [form I; Ballabh, Trivedi, Dastidar & Suresh (2002).CrystEngComm,4, 135–142; Büyükgüngör, Odabaşoğlu, Albayrak & Lönnecke (2004).Acta Cryst.C60, o470–o472] is monoclinic (space groupP21/c). In both forms I and II, the asymmetric unit consists of one 2-aminopyridinium cation, half a fumaric acid molecule and half a fumarate dianion. The fumarate dianion is involved in hydrogen bonding with two neighbouring 2-aminopyridinium cations to form a hydrogen-bonded trimer in both forms. In form II, the hydrogen-bonded trimers are interlinked across centres of inversionviapairs of N—H...O hydrogen bonds, whereas such trimers are joinedviasingle N—H...O hydrogen bonds in form I, leading to different packing modes for forms I and II. The results demonstrate the relevance and application of the powder diffraction method in the study of polymorphism of organic molecular materials.

scholarly journals Crystal structure of tris(piperidinium) hydrogen sulfate sulfate

2015 ◽  
Vol 71 (12) ◽  
pp. 1444-1446 ◽  
Author(s):  
Tamara J. Lukianova ◽  
Vasyl Kinzhybalo ◽  
Adam Pietraszko
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Chair Conformation ◽  
Hydrogen Sulfate ◽  
Sulfate Ion ◽  
Sulfate Anion ◽  
Dimensional Network ◽  
Molecular Salt

In the title molecular salt, 3C5H12N+·HSO4−·SO42−, each cation adopts a chair conformation. In the crystal, the hydrogen sulfate ion is connected to the sulfate ion by a strong O—H...O hydrogen bond. The packing also features a number of N—H...O hydrogen bonds, which lead to a three-dimensional network structure. The hydrogen sulfate anion accepts four hydrogen bonds from two cations, whereas the sulfate ion, as an acceptor, binds to five separate piperidinium cations, forming seven hydrogen bonds.

scholarly journals Crystal structure ofN′-hydroxypyrimidine-2-carboximidamide

2014 ◽  
Vol 70 (10) ◽  
pp. o1107-o1108 ◽  
Author(s):  
Nithianantham Jeeva Jasmine ◽  
Packianathan Thomas Muthiah ◽  
Nithianantham Stanley
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Pyrimidine Ring ◽  
Stacking Interactions ◽  
Compound C ◽  
Centroid Distance ◽  
Sheet Structure ◽  
Ring Motif

The title compound, C5H6N4O, is approximately planar, with an angle of 11.04 (15)° between the planes of the pyrimidine ring and the non-H atoms of the carboximidamide unit. The molecule adopts anEconfiguration about the C=N double bond. In the crystal, adjacent molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with anR22(10) ring motif. The dimers are further linkedviaN—H...N and O—H...N hydrogen bonds into a sheet structure parallel to theacplane. The crystal structure also features N—H...O and weak C—H...O hydrogen bonds and offset π–π stacking interactions between adjacent pyrimidine rings [centroid–centroid distance = 3.622 (1) Å].

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