Hydrogen-bonded assemblies in the molecular crystals of 2,2′-thiodiacetic acid with ethylenediamine ando-phenylenediamine

Carboxylate molecular crystals have been of interest due to the presence of hydrogen bonding, which plays a significant role in chemical and crystal engineering, as well as in supramolecular chemistry. Acid–base adducts possess hydrogen bonds which increase the thermal and mechanical stability of the crystal. 2,2′-Thiodiacetic acid (Tda) is a versatile ligand that has been widely explored, employing its multidendate and chelating coordination abilities with many metals; however, charge-transfer complexes of thiodiacetic acid have not been reported. Two salts, namely ethylenediaminium 2,2′-thiodiacetate, C2H10N22+·C4H4O4S22−, denoted Tdaen, and 2-aminoanilinium 2-(carboxymethylsulfanyl)acetate, C6H9N2+·C4H5O4S−, denoted Tdaophen, were synthesized and characterized by IR,1H and13C NMR spectroscopies, and single-crystal X-ray diffraction. In these salts, Tda reacts with the aliphatic (ethylenediamine) and aromatic (o-phenylenediamine) diamines, and deprotonates them to form anions with different valencies and different supramolecular networks. In Tdaen, the divalent Tda2−anions form one-dimensional linear supramolecular chains and these are extended into a three-dimensional sandwich-type supramolecular network by interaction with the ethylenediaminium cations. However, in Tdaophen, the monovalent Tda−anions form one-dimensional zigzag supramolecular chains, which are extended into a three-dimensional supramolecular network by interaction with the 2-aminoanilinium cations. Thus, both three-dimensional structures display different ring motifs. The structures of these diamines, which are influenced by hydrogen-bonded assemblies in the molecular crystals, are discussed in detail.

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Synthesis, Crystal Structure, and Spectral Characterization of Novel Three-dimensional Supramolecular Networks with One-dimensional Channels Based on Keggin-type Polyoxoanions and Mixed-Valence Dibenzotetrathiafulvalenes

Zeitschrift für Naturforschung B ◽

10.1515/znb-2007-0208 ◽

2007 ◽

Vol 62 (2) ◽

pp. 195-199 ◽

Cited By ~ 5

Author(s):

Dongmei Shi ◽

Haijun Pang ◽

Fanxia Meng ◽

Yu Sun ◽

Kun Liu ◽

...

Keyword(s):

Mixed Valence ◽

Three Dimensional ◽

Radical Cations ◽

Water Molecules ◽

Supramolecular Network ◽

X Ray Diffraction ◽

One Dimensional ◽

X Ray ◽

Keggin Type ◽

Supramolecular Networks

A new organic/inorganic salt formed by mixed-valence dibenzotetrathiafulvalene (DBTTF) radical cations and the spherical Keggin-type polyoxometalate anions [H3BW12O40]2− was obtained by electrochemical oxidation of the donor in an acetonitrile and a 1,2-dichloroethane solution containing the polyanion. The compound has been characterized by X-ray diffraction, elemental analysis, EPR, IR and Raman spectroscopy. X-Ray diffraction experiments have revealed that the compound consists of heteropolyanions, water molecules and DBTTF radical cations. The organic radicals form trimers and dimers via π-π stacking; moreover, the polyoxoanions and the organic donors are also held together by hydrogen bonding interactions. In their packing arrangement, a three-dimensional supramolecular network with one-dimensional channels along the b axis is established with uncoordinated water molecules residing in the channels.

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Reliability of π–π Stacking Interactions in Crystal Engineering: Synthesis and Structure of a Hemidirected Lead Complex

Journal of Chemical Research ◽

10.3184/030823408x361084 ◽

2008 ◽

Vol 2008 (10) ◽

pp. 578-580

Author(s):

Tao Li ◽

Hai-bin He ◽

Mao-Sheng Jiang ◽

Ming-Jie Huang ◽

Xiang-Yang Cai

Keyword(s):

Crystal Engineering ◽

Three Dimensional ◽

Lone Pair ◽

Supramolecular Network ◽

Aromatic Rings ◽

One Dimensional ◽

The One ◽

Lead Complex ◽

Single Crystal Analysis ◽

Polymeric Framework

A new three-dimensional polymeric supramolecular PbII complex, {[Pb3(bpy)3(ip)3](H2O)}n, (bpy = 2,2′-bipyridine and ip = isophthalate), has been synthesised and characterised. Single-crystal analysis shows that {[Pb3(bpy)3(ip)3](H2O)}n contains a one-dimensional chain polymeric framework and all the Pb centres with a coordination number of six possess an electron lone pair. The coordination sphere is hemidirected which gives a highly distorted geometry. The arrangement of O- and N- atoms towards Pb atoms suggests a gap or hole in the coordination geometry around these atoms. Moreover, there are three types of π–π interactions between aromatic rings and the one-dimensional chains, which are connected by these interactions to form a three dimensional supramolecular network with the channels occupied by water molecules.

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A one-dimensional ladder-like six-coordinate cadmium polymer: catena-poly[bis[(S)-2-methylpiperazine-1,4-diium] [bis[trichloridocadmium(II)]-di-μ3-chlorido]]

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s205322961400655x ◽

2014 ◽

Vol 70 (5) ◽

pp. 445-448 ◽

Cited By ~ 2

Author(s):

De-Hong Wu

Keyword(s):

Crystal Structure ◽

Hydrogen Bonds ◽

Title Compound ◽

Three Dimensional ◽

Supramolecular Network ◽

One Dimensional ◽

Compound C ◽

Distorted Octahedral ◽

Graph Set ◽

Hydrogen Bonded

The crystal structure of the title compound {(C5H14N2)2[Cd2Cl8]} n , (I), consists of hydrogen-bonded 2-methylpiperazinediium (H2MPPA2+) cations in the presence of one-dimensional polymeric {[CdCl3(μ3-Cl)]2−} n anions. The CdII centres are hexacoordinated by three terminal chlorides and three bridging chlorides and have a slightly distorted octahedral CdCl3(μ3-Cl)3 arrangement. The alternating CdCl6 octahedra form four-membered Cd2Cl2 rings by the sharing of neighbouring Cd–Cl edges to give rise to extended one-dimensional ladder-like chains parallel to the b axis, with a Cd...Cd distance of 4.094 (2) Å and a Cd...Cd...Cd angle of 91.264 (8)°. The H2MPPA2+ cations crosslink the [CdCl3(μ3-Cl)] n chains by the formation of two N—H...Cl hydrogen bonds to each chain, giving rise to one-dimensional ladder-like H2MPPA2+–Cl2 hydrogen-bonded chains [graph set R 4 2(14)]. The [CdCl3(μ3-Cl)] n chains are interwoven with the H2MPPA2+–Cl2 hydrogen-bonded chains, giving rise to a three-dimensional supramolecular network.

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Concomitant polymorphs of 1,3-bis(3-fluorophenyl)urea

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229616013565 ◽

2016 ◽

Vol 72 (9) ◽

pp. 692-696 ◽

Cited By ~ 4

Author(s):

Christina A. Capacci-Daniel ◽

Jeffery A. Bertke ◽

Shoaleh Dehghan ◽

Rupa Hiremath-Darji ◽

Jennifer A. Swift

Keyword(s):

Hydrogen Bonding ◽

Crystal Engineering ◽

Structural Motif ◽

Parallel Orientation ◽

One Dimensional ◽

Monoclinic Form ◽

Engineering Studies ◽

Hydrogen Bonded

Hydrogen bonding between urea functionalities is a common structural motif employed in crystal-engineering studies. Crystallization of 1,3-bis(3-fluorophenyl)urea, C13H10F2N2O, from many solvents yielded concomitant mixtures of at least two polymorphs. In the monoclinic form, one-dimensional chains of hydrogen-bonded urea molecules align in an antiparallel orientation, as is typical of many diphenylureas. In the orthorhombic form, one-dimensional chains of hydrogen-bonded urea molecules have a parallel orientation rarely observed in symmetrically substituted diphenylureas.

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Syntheses and crystal structures of two magnesium–tetrazole compounds in salt and polymeric forms

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229615002727 ◽

2015 ◽

Vol 71 (3) ◽

pp. 222-228 ◽

Cited By ~ 1

Author(s):

Mohamed Abdellatif Bensegueni ◽

Aouatef Cherouana ◽

Slimane Dahaoui

Keyword(s):

Alkaline Earth ◽

Three Dimensional ◽

Polymer Chains ◽

Magnesium Ion ◽

Water Molecules ◽

Compound I ◽

Hydrothermal Conditions ◽

One Dimensional ◽

Polymeric Chains ◽

Hydrogen Bonded

Two alkaline earth–tetrazole compounds, namelycatena-poly[[[triaquamagnesium(II)]-μ-5,5′-(azanediyl)ditetrazolato-κ3N1,N1′:N5] hemi{bis[μ-5,5′-(azanediyl)ditetrazolato-κ3N1,N1′:N2]bis[triaquamagnesium(II)]} monohydrate], {[Mg(C2HN9)(H2O)3][Mg2(C2HN9)2(H2O)6]0.5·H2O}n, (I), and bis[5-(pyrazin-2-yl)tetrazolate] hexaaquamagnesium(II), (C5H3N6)[Mg(H2O)6], (II), have been prepared under hydrothermal conditions. Compound (I) is a mixed dimer–polymer based on magnesium ion centres and can be regarded as the first example of a magnesium–tetrazolate polymer in the crystalline form. The structure shows a complex three-dimensional hydrogen-bonded network that involves magnesium–tetrazolate dimers, solvent water molecules and one-dimensional magnesium–tetrazolate polymeric chains. The intrinsic cohesion in the polymer chains is ensured by N—H...N hydrogen bonds, which formR22(7) rings, thus reinforcing the propagation of the polymer chain along theaaxis. The crystal structure of magnesium tetrazole salt (II) reveals a mixed ribbon of hydrogen-bonded rings, of typesR22(7),R22(9) andR24(10), running along thecaxis, which are linked byR24(16) rings, generating a 4,8-cflunet.

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Synthesis and crystal structure of a 6-chloronicotinate salt of a one-dimensional cationic nickel(II) coordination polymer with 4,4′-bipyridine

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989020004193 ◽

2020 ◽

Vol 76 (5) ◽

pp. 599-604

Author(s):

Nives Politeo ◽

Mateja Pisačić ◽

Marijana Đaković ◽

Vesna Sokol ◽

Boris-Marko Kukovec

Keyword(s):

Molecular Structure ◽

Coordination Polymer ◽

Three Dimensional ◽

Polymeric Chain ◽

Water Molecules ◽

Sulfate Heptahydrate ◽

Synthesis And Crystal Structure ◽

One Dimensional ◽

Polymeric Chains ◽

Hydrogen Bonded

A 6-chloronicotinate (6-Clnic) salt of a one-dimensional cationic nickel(II) coordination polymer with 4,4′-bipyridine (4,4′-bpy), namely, catena-poly[[[tetraaquanickel(II)]-μ-4,4′-bipyridine-κ2 N:N′] bis(6-chloronicotinate) tetrahydrate], {[Ni(C10H8N2)(H2O)4](C6H3ClNO2)2·4H2O} n or {[Ni(4,4′-bpy)(H2O)4](6-Clnic)2·4H2O} n , (1), was prepared by the reaction of nickel(II) sulfate heptahydrate, 6-chloronicotinic acid and 4,4′-bipyridine in a mixture of water and ethanol. The molecular structure of 1 comprises a one-dimensional polymeric {[Ni(4,4′-bpy)(H2O)4]2+} n cation, two 6-chloronicotinate anions and four water molecules of crystallization per repeating polymeric unit. The nickel(II) ion in the polymeric cation is octahedrally coordinated by four water molecule O atoms and by two 4,4′-bipyridine N atoms in the trans position. The 4,4′-bipyridine ligands act as bridges and, thus, connect the symmetry-related nickel(II) ions into an infinite one-dimensional polymeric chain extending along the b-axis direction. In the extended structure of 1, the polymeric chains of {[Ni(4,4′-bpy)(H2O)4]2+} n , the 6-chloronicotinate anions and the water molecules of crystallization are assembled into an infinite three-dimensional hydrogen-bonded network via strong O—H...O and O—H...N hydrogen bonds, leading to the formation of the representative hydrogen-bonded ring motifs: tetrameric R 2 4(8) and R 4 4(10) loops, a dimeric R 2 2(8) loop and a pentameric R 4 5(16) loop.

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Metal-Controlled Assembly Tuning Coordination Polymers with Flexible 2-(1H-imidazole-1-yl)acetic Acid (Hima)

Australian Journal of Chemistry ◽

10.1071/ch06183 ◽

2006 ◽

Vol 59 (9) ◽

pp. 647 ◽

Cited By ~ 9

Author(s):

Yong-Tao Wang ◽

Gui-Mei Tang ◽

Da-Wei Qin

Keyword(s):

Coordination Polymers ◽

Weak Interactions ◽

Critical Role ◽

Three Dimensional ◽

Supramolecular Network ◽

Water Medium ◽

New Materials ◽

X Ray Diffraction ◽

X Ray ◽

Supramolecular Networks

Three new inorganic–organic coordination polymers based on a versatile linking unit 2-(1H-imidazole-1-yl)acetate (Hima) and divalent Mn(ii), Ni(ii), and Cu(ii) ions, exhibiting two kinds of two dimensionalities with different topological structures, have been prepared in water medium and structurally characterized by single-crystal X-ray diffraction analysis. Reaction of MnCl2·4H2O and Ni(NO3)2·6H2O with Hima yielded neutral two-dimensional (2D) coordination polymers [M(ima)2]n, M = Mn(ii) 1, and Ni(ii) 2 with isostructural 2D coordination polymers possessing (3,6) topology structures, which further stack into three-dimensional (3D) supramolecular networks through C–H···O weak interactions. However, when Cu(NO3)2·4H2O was used, a neutral 2D coordination polymer [Cu(ima)2]n 3 consisting of rhombus units was generated, which showed a 3D supramolecular network through C–H···O weak interactions. Among these polymers, the building block ima anion exhibits different coordination modes. These results indicate that the versatile nature of this flexible ligand, together with the coordination preferences of the metal ions, plays a critical role in construction of these novel coordination polymers. Spectral and thermal properties of these new materials have also been investigated.

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A novel one-dimensional CoIIcoordination polymer:catena-poly[[hexaaquacobalt(II)] [[diaquabis(sulfato-κO)cobalt(II)]-μ-4,4′-bipyridine-κ2N:N′] [[triaqua(sulfato-κO)cobalt(II)]-μ-4,4′-bipyridine-κ2N:N′]]

Acta Crystallographica Section C Crystal Structure Communications ◽

10.1107/s0108270112034385 ◽

2012 ◽

Vol 68 (9) ◽

pp. m265-m268 ◽

Cited By ~ 5

Author(s):

Kai-Long Zhong ◽

Ming-Yi Qian

Keyword(s):

Crystal Structure ◽

Three Dimensional ◽

The Other ◽

Water Molecules ◽

Supramolecular Network ◽

Sulfate Ion ◽

Sulfate Ions ◽

One Dimensional ◽

The Third ◽

Hydrogen Bonding Interactions

The title compound, {[Co(H2O)6][Co(SO4)(C10H8N2)(H2O)3][Co(SO4)2(C10H8N2)(H2O)2]}n, contains three crystallographically unique CoIIcentres, all of which are in six-coordinated environments. One CoIIcentre is coordinated by two bridging 4,4′-bipyridine (4,4′-bipy) ligands, one sulfate ion and three aqua ligands. The second CoIIcentre is surrounded by two N atoms of two 4,4′-bipy ligands and four O atoms,i.e.two O atoms from two monodentate sulfate ions and two from water molecules. The third CoIIcentre forms part of a hexaaquacobalt(II) ion. In the crystal structure, there are two different one-dimensional chains, one being anionic and the other neutral, and adjacent chains are arranged in a cross-like fashion around the mid-point of the 4,4′-bipy ligands. The structure features O—H...O hydrogen-bonding interactions between sulfate anions and water molecules, resulting in a three-dimensional supramolecular network.

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An organic–inorganic hybrid compound containing imidazolium cations and a one-dimensional lithium hexacyanidocobaltate-based anionic framework

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229614011541 ◽

2014 ◽

Vol 70 (6) ◽

pp. 603-605 ◽

Cited By ~ 6

Author(s):

Xiu-Dan Shao ◽

Chun-Hua Yu

Keyword(s):

Three Dimensional ◽

Chain Structure ◽

Supramolecular Network ◽

Monoclinic Space Group ◽

Zigzag Chain ◽

Imidazolium Chloride ◽

Hybrid Compound ◽

Inorganic Hybrid ◽

One Dimensional ◽

Imidazolium Cations

An organic–inorganic hybrid compound,catena-poly[bis(3H-imidazol-1-ium) [[tetracyanido-κ4C-cobalt(III)]-μ-cyanido-κ2C:N-[diaqualithium(I)]-μ-cyanido-κ2N:C]], {(C3H5N2)2[CoLi(CN)6(H2O)2]}n, was synthesized by the reaction of Li3[Co(CN)6] with imidazolium chloride in aqueous solution. The compound crystallizes in the monoclinic space groupC2/c(data collected at 273 K). In the crystal structure, neighbouring [Co(CN)6]3−anionic units are linked by Li+cations through the cyanide groups in atransmode, forming a one-dimensional zigzag chain structure extending along thecaxis. A three-dimensional supramolecular network is formed through hydrogen-bonding interactions and is further stabilized by weak CN...π interactions between the cyanide groups and the imidazolium cations.

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