Ethane-1,2-diphosphonic acid as a building block in supramolecular chemistry; a pillared-layer framework and framework-encapsulated cations

2001 ◽  
Vol 57 (1) ◽  
pp. 95-102 ◽  
Author(s):  
Paul S. Wheatley ◽  
Alan J. Lough ◽  
George Ferguson ◽  
Colin J. Burchell ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Building Block ◽  
Three Dimensional ◽  
Single Type ◽  
Water Molecules ◽  
Diphosphonic Acid ◽  
Different Types ◽  
O 175

The 1:1 adduct of piperazine and ethane-1,2-diphosphonic acid is a salt [C4H12N2]2+·[C2H6O6P2]2−, in which both ions lie across centres of inversion in space group P21/c. The anions are linked by a single type of O—H...O hydrogen bond [O...O, 2.562 (3) Å; H...O, 1.73 Å, O—H...O, 169°] into (6, 3) nets built from a single type of R^4_4(22) ring. The cations lie between these nets, linked to them by two types of N—H...O hydrogen bond [N...O, 2.635 (3) and 2.735 (3) Å; H...O 1.72 and 1.82 Å, N—H...O, 175 and 177°] such that the cations link adjacent sheets, thus forming a pillared-layer framework. The aquated adduct formed between trimethylenedipiperidine and ethane-1,2-diphosphonic acid is also a salt [C13H28N2]2+·[C2H6O6P2]2−·2.8[H2O], in which there are 12 different types of hydrogen bond, eight O—H...O and four N—H...O. The anions are linked into chains by pairs of O—H...O hydrogen bonds and these chains are linked by the water molecules into a continuous three-dimensional framework. Within the anion/water framework are large voids which contain pairs of cations, linked to the framework by N—H...O hydrogen bonds.

3,6,9,16,19,22-Hexaazatricyclo[22.2.2.211,14]triconta-1(26),11(29),12,14(30),24,27-hexaene, C24H38N6, as a building block in supramolecular chemistry: structures in two and three dimensions

2000 ◽  
Vol 56 (2) ◽  
pp. 287-298 ◽  
Author(s):  
Christopher Glidewell ◽  
George Ferguson ◽  
Richard M. Gregson ◽  
Alan J. Lough
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Building Block ◽  
Three Dimensional ◽  
Three Dimensions ◽  
Single Type ◽  
Water Molecules ◽  
Minor Components ◽  
Cation Site ◽  
Cation Sites

The adduct (1) formed between the hexaaza macrocycle 3,6,9,16,19,22-hexaazatricyclo[22.2.2.211,14]triconta-1(26),11(29),12,14(30),24,27-hexaene, C24H38N6, and 4,4′-sulfonyldiphenol, O2S(C6H4OH)2, is a salt [(C24H40N6)2+]·2[(HOC6H4SO2C6H4O)−], and the adduct (2) formed by the same macrocyclic amine with 4,4′-biphenol is an aquated salt which also contains neutral biphenol molecules, [(C24H40N6)2+]·2[(HOC6H4C6H4O)−]·(HOC6H4C6H4OH).2H2O. In both compounds the cations lie across centres of inversion: there are two crystallographically distinct cation sites in (1) and the conformations of the cations occupying them are quite different. In (2) the single type of cation site is occupied by a conformationally disordered cation: the major and minor components represent two further distinct conformers. In (1) the anions are linked by O—H...O hydrogen bonds into chains, and each cation is linked by a total of six N—H...O hydrogen bonds to anions in four different chains, so linking the chains into continuous sheets. In (2) the anions and the water molecules are linked into sheets, which are further linked into a continuous three-dimensional framework by both the cations and the neutral biphenol units.

scholarly journals Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-aminophenylarsonate tetrahydrate

2016 ◽  
Vol 72 (5) ◽  
pp. 751-755 ◽  
Author(s):  
Graham Smith ◽  
Urs D. Wermuth
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Network Structure ◽  
Three Dimensional ◽  
Water Molecules ◽  
Arsanilic Acid ◽  
Dimensional Network

In the structure of the brucinium salt of 4-aminophenylarsonic acid (p-arsanilic acid), systematically 2,3-dimethoxy-10-oxostrychnidinium 4-aminophenylarsonate tetrahydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water molecules of solvation are accommodated between the layers and are linked to them through a primary cation N—H...O(anion) hydrogen bond, as well as through water O—H...O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure.

Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry

2003 ◽  
Vol 59 (1) ◽  
pp. 100-117 ◽  
Author(s):  
Katharine F. Bowes ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Fumaric Acid ◽  
Maleic Acid ◽  
Rotation Axis ◽  
Three Dimensional ◽  
Building Blocks ◽  
Ionic Components ◽  
Acid Compound

Maleic acid and fumaric acid both readily form adducts with organic diamines: maleic acid usually forms 2:1 adducts with bases, while fumaric acid usually forms 1:1 adducts, and the supramolecular stuctures within the two series are not simply related. The 1:2 adducts formed by 1,2-bis(4-pyridyl)ethane and by 4,4′-bipyridyl, respectively, with maleic acid, compounds (1) and (2), are salts [{(diamine)H2}2+]·[(C4H3O4)−]2 in which the cations lie across a centre of inversion and a twofold rotation axis, respectively. The ions are linked by N—H...O hydrogen bonds into three-ion aggregates, which are further linked by C—H...O hydrogen bonds into two- and three-dimensional arrays, respectively. In the fumarate salts formed by 2,2′-dipyridylamine (1:1) and 1,4-diazabicyclo[2.2.2]octane (1:2), compounds (3) and (4), the ionic components are linked into molecular ladders. The 1:1 adduct of 4,4′-bipyridyl and fumaric acid, compound (5), contains two neutral components, both of which lie across centres of inversion; these components are linked into chains by a single O—H...N hydrogen bond and thence into sheets by C—H...O hydrogen bonds. The corresponding adduct formed by 1,4-diazabicyclo[2.2.2]octane, compound (6), is a salt that again contains chains linked into sheets by C—H...O hydrogen bonds. In the 1:1 adducts, compounds (7), (8) and (10), that are formed between 1,2-bis(4-pyridyl)ethane, 4,4′-trimethylenedipyridine and hexamethylenetetramine, respectively, with fumaric acid, and in the 1:2 adduct, compound (9), of 2,2′-dipyridylamine and maleic acid, the chains that are generated by the hard hydrogen bonds are linked by C—H...O hydrogen bonds to form, in each case, a single three-dimensional framework. In the 1:1 adduct, compound (11), of 2,2′-bipyridyl and fumaric acid the hydrogen bonds generate two interwoven three-dimensional frameworks.

Crystal Engineering Using Bis- and Tris-phenols. Adducts with 1,4,8,11-Tetraazacyclotetradecane (Cyclam): Isolated Ladders in the Adduct with 4,4'-Thiodiphenol, Tethered Ladders in the Adduct with 4,4'-Sulfonyldiphenol and Two Interwoven Three-Dimensional Networks in the Adduct with 1,1,1-Tris(4-hydroxyphenyl)ethane

1998 ◽  
Vol 54 (2) ◽  
pp. 139-150 ◽  
Author(s):  
G. Ferguson ◽  
C. Glidewell ◽  
R. M. Gregson ◽  
P. R. Meehan
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Engineering ◽  
Three Dimensional ◽  
Dimensional Array ◽  
Different Types ◽  
Molecular Components

The structure of 4,4′-thiodiphenol–1,4,8,11-tetraazacyclotetradecane (2/1), (C12H10O2S)2.C10H24N4 (1), monoclinic, P21/c, a = 11.1602 (12), b = 10.8084 (12), c = 14.001 (2) Å, β = 103.127 (10)°, with Z = 2, contains phenolate anions [HOC6H4SC6H4O]− and diprotonated cyclam cations [C10H26N4]2+: these cations have the centrosymmetric trans-III conformation and the two additional protons are contained within the N4 cavity of the macrocycle, held by three-centre hydrogen bonds. The phenolate anions form chains, held together by O—H...O hydrogen bonds, and pairs of these chains are cross-linked into ladders by the [cyclamH2]2+ cations by means of N—H...O hydrogen bonds. The structure of 4,4′-sulfonyldiphenol–1,4,8,11-tetraazacyclotetradecane (2/1), (C12H10O4S)2.C10H24N4 (2), triclinic, P1¯, a = 10.9345 (10), b = 11.0060 (10), c = 14.350 (2) Å, α = 79.532 (10), β = 86.739 (10), γ = 87.471 (10)°, with Z = 2, contains phenolate anions [HOC6H4SO2C6H4O]− and cyclam dications [C10H26N4]2+: the phenolate anions are linked into antiparallel chains, cross-linked by the cyclam cations. There are two distinct types of ladder in the structure running along (0, y, 0) and (1\over2, y, 1\over2), respectively, and these bundled ladders are tied together by C—H...O hydrogen bonds to form a continuous three-dimensional array. In 1,1,1-tris(4-hydroxyphenyl)ethane–1,4,8,11-tetraazacyclotetradecane–methanol (2/1/1), (C20H18O3)2.C10H24N4.CH4O (3), triclinic, P1¯, a = 8.2208 (11), b = 16.245 (2), c = 17.337 (2) Å, α = 81.694 (13), β = 89.656 (14), γ = 86.468 (12)°, with Z = 2, the structure contains centrosymmetric diprotonated cyclam cations of precisely the same type as found in (1), phenolate anions [(HOC6H4)2C(CH3)C6H4O]− and neutral methanol molecules. The molecular components are linked together by nine different types of hydrogen bond, five of O—H...O type and four of N—H...O type, to form chains running in the [001], [010] (two sets), [211] and [211¯] directions. The combination of these chain motifs generates two independent three-dimensional networks which are fully interwoven, but not bonded to one another.

Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines

2003 ◽  
Vol 59 (2) ◽  
pp. 248-262 ◽  
Author(s):  
Katharine F. Bowes ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Water Molecules ◽  
Two Dimensional ◽  
Phosphonoacetic Acid ◽  
Space Group ◽  
Hydrated Salt ◽  
Hydrogen Bonded

The structures of seven salts formed by phosphonopropionic acid with organic diamines are reported; in these salts, the hydrogen-bonded substructures formed by the anions can be zero-, one- or two-dimensional, while the overall hydrogen-bonded supramolecular structures are three-dimensional. The 1:1 adduct, compound (1), formed between 1,2-bis(4′-pyridyl)ethene and phosphonopropionic acid is a salt, [{(C12H10N2)H2}2+]·[(C12H10N2)]·[(C3H6O5P)−]2, in which both diamine components lie across centres of inversion in space group P21/c. The anions form hydrogen-bonded head-to-head dimers, and these are linked by the two diamine units into sheets, which are themselves linked by C—H...O hydrogen bonds. With 2,2′-dipyridylamine the acid forms the hydrated salt [{(C10H9N3)H}+]·[(C3H6O5P)−]·H2O (2), in which all components are disordered with occupancy 0.5 in space group Fmm2. The anions form head-to-tail dimers, which are linked into sheets by the cations, and the sheets are linked into a three-dimensional framework by the water molecules. The piperazine salt [{(C4H10N2)H2}2+]·[(C3H5O5P)2−] (3) contains simple anion chains linked into a three-dimensional framework by the two independent cations, both of which are centrosymmetric. In the hydrated salt formed by N,N′-dimethylpiperazine, [{(MeNC4H8NMe)H2}2+]·[(C3H6O5P)−]2·(H2O)2 (4), head-to-tail anion chains combine with the water molecules to form a three-dimensional framework, which encloses voids that contain the cations. In the 4,4′-bipyridyl adduct [{(C10H8N2)H0.72}0.72+]·[{(H0.5O)3PCH2CH2COOH0.78}0.72−] (5), there is extensive disorder of the H atoms that are bonded to N and O atoms, and the anion chains are linked by the cations into sheets, which are themselves linked by C—H...O hydrogen bonds. In the 1:2 adduct formed with 1,2-bis(4′-pyridyl)ethane, [{(C12H12N2)H2}2+]·[(C3H6O5P)−]2 (6), where the cation lies across an inversion centre, the anions form molecular ladders. These ladders are linked into sheets by the cations, which are themselves linked by C—H...O hydrogen bonds. In the methanol-solvated salt formed with 2,6-dimethylpiperazine, [{(C6H14N2)H2}2+]·[(C3H6O5P)−]2· (CH4O)0.34 (7), the anions form sheets that are linked into a three-dimensional framework by the cations. The supramolecular structures are compared with those of analogous salts formed by phosphonoacetic acid.

Crystal engineering using bisphenols: interwoven ladders, sheet and framework structures in the binary adducts of 4,4′-sulfonyldiphenol with pyrazine (2/1), 4,4′-bipyridyl (1/1), trans-1,2-bis(4-pyridyl)ethene (1/1), 1,2-bis(4-pyridyl)ethane (1/1) and 4,4′-trimethylenedipyridine (1/1), and in 4,4′-sulfonyldiphenol–4,4′-trimethylenedipiperidine–water (2/2/1)

1999 ◽  
Vol 55 (4) ◽  
pp. 573-590 ◽  
Author(s):  
George Ferguson ◽  
Christopher Glidewell ◽  
Richard M. Gregson ◽  
Emma S. Lavender
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Engineering ◽  
Three Dimensional ◽  
The Other ◽  
Single Type ◽  
Water Molecules ◽  
Two Dimensional ◽  
Double Helices ◽  
The One ◽  
N Vector

The structures of six hydrogen-bonded adducts of 4,4′-sulfonyldiphenol with heteroaromatic amines have been determined. In 4,4′-sulfonyldiphenol–pyrazine (2/1) the pyrazine molecules lie across centres of inversion. The bisphenol molecules are linked into C(8) chains parallel to [100] by means of O—H...O=S hydrogen bonds, and antiparallel pairs of these chains are cross-linked by the pyrazine molecules, via O—H...N hydrogen bonds, to form molecular ladders containing R_6^6(50) rings between the rungs of the ladders. Each ladder is interwoven with two neighbouring ladders, thus producing a continuous two-dimensional sheet. The structure of 4,4′-sulfonyldiphenol–4,4′-bipyridyl (1/1) consists of spiral C_2^2(21) chains parallel to [010] containing alternating bisphenol and bipyridyl molecules linked by O—H...N hydrogen bonds: these chains are linked by two types of C—H...O hydrogen bonds which form C(5) chains along [001] and C_2^2(10) chains along [101], thus generating two interconnected nets characterized in the one case by a chequerboard pattern of R_6^6(44) and R_6^6(52) rings, and in the other by a single type of R_6^6(46) ring. 4,4′-Sulfonyldiphenol–trans-1,2-bis(4-pyridyl)ethene (1/1) [systematic name: 4,4′-sulfonyldiphenol–trans-4,4′-vinylenedipyridine (1/1)] and 4,4′-sulfonyldiphenol–1,2-bis(4-pyridyl)ethane (1/1) [systematic name: 4,4′-sulfonyldiphenol–trans-4,4′-ethylenedipyridine (1/1)] are isomorphous: the 1,2-bis(4-pyridyl)ethene component exhibits orientational disorder, corresponding approximately to a 180° rotation of ca 23% of the molecules about the N...N vector; in each compound the structure is built from C_2^2(23) chains of alternating bisphenol and bis(pyridyl) molecules connected by O—H...N hydrogen bonds, running parallel to [112] and generated by translation. The [112] chains are linked by C—H...O hydrogen bonds which generate C_2^2(12) chains parallel to [101], so forming a two-dimensional net built from R_6^6(50) rings. The structure of 4,4′-sulfonyldiphenol–4,4′-trimethylenedipyridine (1/1) consists of C_2^2(24) chains parallel to [100] generated by translation and consisting of alternating bisphenol and bis(pyridyl) molecules linked by O—H...N hydrogen bonds. Pairs of such chains are coiled together to form double helices, and pairs of such double helices, of opposite hand, are linked together by paired C—H...O hydrogen bonds in R_2^2(10) rings to form pairs of interwoven ladders in which the C_2^2(24) chains form the uprights and the R_2^2(10) rings form the rungs, between which are R_6^6(50) rings: an R_2^2(10) ring belonging to one ladder lies at the centre of an R_6^6(50) ring belonging to the other. 4,4′-Sulfonyldiphenol–4,4′-trimethylenedipiperidine–water (2/2/1) is a salt, 2C13H27N_2^+·2C12H9O4S−·H2O, containing two independent singly protonated diamine cations, two independent bisphenolate anions, and neutral water molecules. The two independent diamine cations are linked by N—H...N hydrogen bonds into C_2^2(24) chains running parallel to [001] and generated by translation, and each type of bisphenolate anion forms an independent spiral C(12) chain, also parallel to [001]. The three types of chain are linked by the water molecules: the two types of bisphenolate chain are linked by water molecules acting as double donors in O—H...O− hydrogen bonds in a C_6^4(32) chain parallel to [100], thus generating a two-dimensional net built from R_8^6(56) rings; the diamine chains are linked to these nets by means of N—H...O hydrogen bonds in which the water molecules act as acceptors and further hydrogen bonds, of N—H...O− and N—H...O=S types, link these two-dimensional nets into a continuous three-dimensional framework.

scholarly journals Crystal structure of 2-amino-4-methylpyridin-1-ium (2R,3R)-3-carboxy-2,3-dihydroxypropanoate monohydrate

2014 ◽  
Vol 70 (9) ◽  
pp. o1036-o1037 ◽  
Author(s):  
J. V. Jovita ◽  
S. Sathya ◽  
G. Usha ◽  
R. Vasanthi ◽  
A. Ramanand
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Tartaric Acid ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Water Molecules ◽  
Asymmetric Unit ◽  
Bond Forming ◽  
Molecular Salt

The title molecular salt, C6H9N2+·C4H5O6−·H2O, crystallized with two 2-amino-4-methylpyridin-1-ium cations, two L-(+)-tartaric acid monoanions [systematic name: (2R,3R)-3-carboxy-2,3-dihydroxypropanoate] and two water molecules in the asymmetric unit. In the crystal, the cations, anions and water molecules are linkedviaa number of O—H...O and N—H...O hydrogen bonds, and a C—H...O hydrogen bond, forming a three-dimensional structure

Chiral versus racemic building blocks in supramolecular chemistry: tartrate salts of organic diamines

2002 ◽  
Vol 58 (2) ◽  
pp. 272-288 ◽  
Author(s):  
Dorcas M. M. Farrell ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Tartaric Acid ◽  
Three Dimensional ◽  
Building Blocks ◽  
Different Types ◽  
Ionic Components

In the 1:1 adducts C12H10N2·C4H6O6 formed between 1,2-bis(4′-pyridyl)ethene and racemic tartaric acid [(I), triclinic P\bar 1, Z′ = 1] and (2R,3R)-tartaric acid [(II), triclinic P1, Z′ = 2], the ionic components are linked by hard hydrogen bonds into single sheets, which are further linked by C—H...O hydrogen bonds. In the analogous adducts C10H18N2·C4H6O6 formed by 4,4′-bipyridyl with racemic tartaric acid [(III), triclinic P\bar 1, Z′ = 1] and the chiral acid [(IV), monoclinic P21, Z′ = 1], the hard hydrogen bonds generate bilayers which are again linked by C—H...O hydrogen bonds. Piperazine forms a 1:1 salt [{(C4H10N2)H2}2+]·[(C4H4O6)2−] with (2R,3R)-tartaric acid [(V), monoclinic P21] sheets, which are linked by the cations to form a pillared-layer framework. In each of the 1:2 salts formed by racemic tartaric acid with piperazine [(VI), monoclinic P21/n, Z′ = 0.5] and 1,4-diazabicyclo[2.2.2]octane (DABCO) [(VII), monoclinic P21/n, Z′ = 0.5], the cation lies across a centre of inversion, with the [{HN(CH2CH2)3NH}2+] cation disordered over two sets of sites: in both (VI) and (VII) the anions form a three-dimensional framework encapsulating large voids which accommodate the cations. The salt formed between DABCO and (2R,3R)-tartaric acid [(VIII), orthorhombic P212121, Z′ = 1] has 3:4 stoichiometry and contains four different types of ion, [{HN(CH2CH2)3NH}2+]2·[N(CH2CH2)3NH]+·3(C4H5O6)−·C4H4O6 2−: the hard hydrogen bonds generate a three-dimensional framework.

scholarly journals (3R,4S)-3,4,8-Trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one monohydrate from Embellisia eureka

2012 ◽  
Vol 68 (6) ◽  
pp. o1874-o1874 ◽  
Author(s):  
Tarik Ouchbani ◽  
Hafid Zouihri ◽  
El Mokhtar Essassi ◽  
Peter Proksch ◽  
Seik Weng Ng
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Hydroxy Group ◽  
Organic Molecules ◽  
Three Dimensional ◽  
Axial Position ◽  
Water Molecules ◽  
Hydrogen Bond Donor ◽  
Dimensional Network

In the title hydrate, C10H10O4·H2O, the six-membered aliphatic ring that is fused to the benzene ring has a sofa shape, with the hydroxy group in the 3-position (that represents the sofa back) of the aliphatic ring occupying a quasi-axial position. The hydroxy group of the aromatic ring is hydrogen-bond donor to the carbonyl O atom; other O—H...O hydrogen bonds link the organic molecules and the water molecules into a three-dimensional network.

scholarly journals Tetraquinolinium ditelluro(VI)octavanadate(V) octahydrate

2013 ◽  
Vol 69 (11) ◽  
pp. m595-m596
Author(s):  
Sirine Toumi ◽  
Samah Akriche Toumi ◽  
Mohamed Rzaigui
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
The Other ◽  
Water Molecules ◽  
Stacking Interactions ◽  
Compound C ◽  
Dimensional Network ◽  
Water Hydrogen

In the title compound, (C9H8N)4[Te2V8O28]·8H2O, the complete heteropolyanion is generated by a crystallographic inversion centre. One of the two quniolinium ions forms an N—H...Op(p = polyoxidometallate) hydrogen bond and the other an N—H...Ow(w = water) hydrogen bond. The water molecules further link the components by O—H...Opand O—H...Owhydrogen bonds. A number of C—H...O interactions and aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.541 (7) Å] are also observed. Together, these generate a three-dimensional network.

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