Two-dimensional Hydrogen-bonded Network Research Articles

2,4-Di(butylureido)-6-methyl-s-triazine

The formation of a quadruply hydrogen-bonded dimer of the title compound, C14H25N7O2, is prevented by an intramolec­ular hydrogen bond, which disrupts the linear ADADA donor–acceptor array. An infinite two-dimensional hydrogen-bonded network is formed instead.

Ethane-1,2-diammonium bis(4-nitrobenzoate) dihydrate

The structure of the title compound, C2H10N22+·2C7H4NO4−·2H2O, comprises interdigitated two-dimensional hydrogen-bonded networks derived from a repeat unit that contains the bis­ammonium, two benzoates and two water mol­ecules.

Two-Dimensional Hydrogen Bond Networks Supported by CH/π Interaction Leading to a Molecular Packing Appropriate for Topochemical Polymerization of 1,3-Diene Monomers

Strong and weak hydrogen bonds, as intermolecular interactions, are used for the construction of designer crystals with organic small molecules as the building blocks. We report here crystal engineering for the synthetic plan of the topochemical polymerization using the ammonium derivatives of 1,3-diene mono- and dicarboxylic acids on the basis of intermolecular interactions such as NH/O and CH/π interactions. The isomerism of hydrogen bond network structures obstructs the prediction of crystal structure and reactivity, although topochemical polymerization requires that monomer molecules stack in a column with a stacking distance of 5 A in the crystals. The structures of hydrogen bond networks are roughly classified into a two-dimensional type appropriate for topochemical polymerization, and the others consisting of two-dimensional sheets or one-dimensional ladders not for polymerization. We conclude that the CH/π interaction of naphthylmethyl and benzyl substituents promises to give polymerizable lamella...

4-[2-(4-Pyridyl)ethyl]pyridinium nitrate trihydrate

The title compound, C12H13N2+·NO3−·3H2O [where C12H13N2+ is the monoprotonated form of 1,2-bis(4-pyridyl)­ethane (BPEH+)] is monoclinic, space group P21/c, and contains two empirical formulae in the asymmetric unit. The compound has cationic [BPEH]nn+ organic layers, alternating in the b direction with anionic [(NO3)·3H2O]nn− inorganic layers. Hydro­gen bonds between 4-pyridyl and 4-pyridinium groups, and between nitrate ions and water mol­ecules, give rise to chains and two-dimensional hydrogen-bonding networks, respectively.

1′-Deoxy-1′-hydroxymethyl-1,2′-O-isopropylidene-β-D-arabinofuranose

The six-membered ring of the title compound, C9H16O5, adopts a chair conformation, while the furan­ose five-membered ring has an envelope conformation. The packing is stabilized by a two-dimensional network of intermolecular hydrogen bonds.

A Role of Weak interaction between Naphthylmethyl Groups on Crystal Structure And Photopolymerization Reactivity of 1-Naphthylmethylammonium Salts of Unsaturated Carboxylic Acidsin The Crystalline State

We have investigated the crystal structures of several 1-naphthylmethylammonium salts of unsaturated carboxylic acids, i.e., sorbate, crotonate, tiglate, and methacrylate as the diene and vinyl monomers. In the crystals, the monomer molecules stack in a similar fashion to make a lamellar structure consisting of alternating naphthylmethylammonium cation and carboxylate anion layers. For the construction of the lamellar structure, weak intermolecular interaction such as ~ - ~ stacking and CH- ~ interaction is important as well as the formation of robust two-dimensional hydrogen bond network. We discuss the relationship between the molecular packing in the crystals and photopolymerization reactivity of the unsaturated carboxylic acid derivatives in the solid state.

3α,4β-Dihydroxy-5β-androstan-17-one

The ring conformation of the title compound, C19H30O3, is similar to that of the 5α-epimer except for the cis A/B ring junction. Ring D adopts a 13β,14α-half chair conformation. The mol­ecules are linked together by a two-dimensional network of hydrogen bonds involving the carbonyl and hydroxyl groups.

Guaninium dinitrate dihydrate

In the asymmetric unit of the title compound, C5H7N5O2+·2NO3−·2H2O, the guanine base is diprotonated and cocrystallizes with two nitrate anions and two water mol­ecules. The structure is a layered one, and in each layer all H atoms bonded to O and N atoms are involved in a two-dimensional hydrogen-bonding network. Short contacts are observed between parallel layers and ensure the cohesion of the crystals.

Synthesis and crystal structure of nickel complex of N, N-bis(benzimidazol-2-yl-methyl)amine

A new nickel(II) complex, [NiL 2]Cl 2 (L= N, N-bis(benzimidazol-2-yl-methyl)amine), was synthesized and its crystal structure was determined. According to X-ray crystallographic studies, each nickel(II) ion was six-coordinated with six nitrogen atoms of two L ligands. The complex crystallizes in triclinic system, space group P 1 ̄ , a=9.764(3) A ̊ , b=11.032(3) A ̊ , c=16.402(5) A ̊ , α=80.529(6)°, β=79.180(7)°, γ=74.232(6)°, and Z=2. The title complex forms two-dimensional hydrogen bond network structures between the chlorine atoms and the nitrogens of L. The IR and UV spectroscopy were measured. The absorption bands of d–d electron transition are assigned, the values of Dq and B were calculated according to the electronic spectrum of the complex.

Imidazolium trihydrogen-1,2,4,5-benzenetetracarboxylate

The crystal of the title compound, imidazolium tri­hydrogen-1,2,4,5-benzene­tetra­carboxyl­ate, C3H5N2+·C10H5O8−, is built of imidazolium cations and tri­hydrogen-1,2,4,5-benzene­tetra­carboxyl­ate anions. The anions use two of their `active' H atoms to generate hydrogen bonds linking to the neighbouring anions, thus creating a two-dimensional hydrogen-bonding network parallel to the bc plane of the crystal. The third oxy­gen-bound H atom of the anion is involved in an intramolecular hydrogen bond, which closes the six-membered pseudo-ring. The imidazolium cations are linked to the anionic hydrogen-bonded network through N—H⋯O bonds which target two of the O atoms of the carboxyl groups of the anions as acceptors. The mean plane of the imidazolium cation is almost orthogonal to the mean plane of the benzene ring of benzene­tetra­carboxyl­ate, with a dihedral angle of 89.7 (1)°.

Bis(2-methyl-2-propanammonium) chromate

A new organic chromate, [(CH3)3CNH3]2[CrO4], associated with the monoprotonated 2-methyl-2-propan­amine mol­ecule, has been synthesized. The structure of the compound consists of discrete chromate ions stacked in layers perpendicular to the (010) plane, separated by organic layers containing [(CH3)3CNH3]+ groups. The cohesion and stability of the structure are ensured by a two-dimensional network of hydrogen bonds in the (001) plane, where the O atoms of the anion are acceptors from the 2-methyl-2-propan­ammonium N—H groups.

(1SR,2RS,5RS,6SR,8RS)-7,7-Dimethyltricyclo[6.2.1.0(1,6)]undecane-2,5,6-triol: a supramolecular framework built from O-H...O hydrogen bonds.

In the title compound, C(13)H(22)O(3), the asymmetric unit has two independent molecules linked by a strong O-H...O hydrogen bond. The cyclohexane ring is trans fused to the cyclopentane ring bridged through an ethyl moiety. The hydroxyl groups act as donors as well as acceptors, resulting in an extensive two-dimensional hydrogen-bonded network in the (011) plane. Intermolecular O-H...O bonds between centrosymmetrically related molecules form a four-membered supramolecular assembly, leading to infinite chains parallel to the [011] direction, crosslinked in the [100] direction.

(3S,2R)-3-Hydroxy-2-hydroxymethyl-7,9-diazaspiro[4.5]decane-6,8,10-trione

The trans stereochemical relationship of the two substituents of the title compound, C9H12N2O5, a new spiro-nucleoside, has been confirmed. The cyclo­pentane moiety adopts the C3′-endo-type conformation, while the barbiturate ring is almost planar. Molecules interconnected by a two-dimensional network of hydrogen bonds build layers parallel to the ab plane.

(Mu-oxalato-O1,O2:O1',O2')bis[aqua(diethylenetriamine)nickel(II)] bis(hexafluorophosphate) dihydrate.

The title compound, [Ni(2)(C(2)O(4))(C(4)H(13)N(3))(2)(H(2)O)(2)](PF(6))(2).2H(2)O, contains a dinuclear oxalato-bridged nickel(II) complex cation. The structure determination reveals the presence of a centrosymmetric binuclear complex where the oxalate ligand is coordinated in a bis-bidentate mode to the Ni atoms. The distorted octahedral environment of each Ni atom is completed by the three N atoms of the diethylenetriamine ligand in a fac arrangement and by one O atom from a water molecule. PF(6)(-) acts as counter-anion. A two-dimensional network of hydrogen bonds links the cations and anions and stabilizes the structure.

Peptidocalix[4]arene self-assembled nanotubes

The upper rim, C-linked and Cbz-protected cone calix[4]arene bis- l-alanyl derivative 2 forms self-assembled nanotubes in the solid state through a two-dimensional network of hydrogen bonds between the amide chains of adjacent conformers. The crystal lattice is quite different from that of the analogous N-linked derivative 1 which shows calix[4]arene macrocycles piled through van der Waals interactions.

Ring templated nanochannel architecture of imidazolium phosphonoacetate

The supramolecular architecture of imidazolium phosphonoacetate is shown to consist of anionic monolayers that are parallel stacked in the third direction in order to form channels in which the cations are organized. The two-dimensional hydrogen-bonded network, formed via two O–H⋯O interactions, is characterized by large, nano-size cavities that are surrounded by six phosphonoacetate residues. The imidazolium residues fit in the cavities and connect the monolayers via two N–H⋯O hydrogen bonds. Weak C–H⋯O interactions additionally stabilize the channel architecture, locking the imidazolium rings. The rings are intercalated in the channels at a unit cell distance and no stacking or other aromatic interactions exist between them.

Syntheses and physical properties of quasi-one-dimensional halogen-bridged Cu(II)(-)Pt(IV) mixed-metal complexes [Cu(chxn)(2)][PtX(2)(chxn)(2)]X(4).

Quasi-one-dimensional halogen-bridged Cu(II)-Pt(IV) mixed-metal complexes of the form [Cu(chxn)(2)][PtX(2)(chxn)(2)]X(4), where chxn = 1R,2R-diaminocyclohexane and X is either Cl or Br, have been synthesized. The crystal structures of these compounds have been determined by single-crystal X-ray diffraction. The Cl-bridged compound crystallizes in the space group I222 with dimensions a = 24.237(1) A, b = 5.103(1) A, c = 6.854(1) A, and V = 847.7(1) A(3) and with Z = 1. The Br-bridged complex crystallizes in the space group I222 with dimensions a = 23.700(8) A, b = 5.344(5) A, c = 6.978(8) A, and V = 883.8(8) A(3) and with Z = 1. These structures are isomorphic to each other and to homometal [Pt(chxn)(2)][PtX(2)(chxn)(2)]X(4) complexes. In these complexes, the planar [Cu(chxn)(2)] and the octahedral [PtX(2)(chxn)(2)] groups are stacked alternatively with the axial bridging halogen ions, forming linear chain structures. The neighboring [Cu(chxn)(2)] and [PtX(2)(chxn)(2)] moieties along the chains are linked by hydrogen bonds between amino hydrogens and the counteranions (X). Moreover, there are hydrogen bonds among the neighboring chains that form a two-dimensional hydrogen-bonded network parallel to the bc plane. Therefore, the Cu(II) and Pt(IV) units are two-dimensionally ordered. The b axes correspond to the Cu(II)-Pt(IV) separations, which are shorter than those of [Pt(chxn)(2)][PtX(2)(chxn)(2)]X(4) due to the smaller ionic radius of the Cu(II) ions. In the XP spectra, the Pt(IV) 4f(7/2) and Pt(IV) 4f(5/2) binding energies in homometal [Pt(chxn)(2)][PtX(2)(chxn)(2)]X(4) are lower than those of [Cu(chxn)(2)][PtX(2)(chxn)(2)]X(4) (X = Cl and Br), indicating that the electron-phonon interaction in Cu(II)-Pt(IV) compounds is stronger than that in Pt(II)-Pt(IV) compounds. In the Raman spectra, nu(Pt(IV)(-)X) of the homometal Pt(II)-Pt(IV) complexes is lower than that of the Cu(II)-Pt(IV) complexes, indicating again that the electron-phonon interaction in Cu(II)-Pt(IV) compounds is stronger than that of Pt(II)-Pt(IV) compounds. The temperature-dependent magnetic susceptibilities of the Cu(II)-Pt(IV) complexes show weak antiferromagnetic interactions between Cu(II) components along the chain axes.

Surface Stabilized Porphyrin and Phthalocyanine Two-Dimensional Network Connected by Hydrogen Bonds

Using carboxyl functionalized porphyrin and phthalocyanine as building blocks and alkane derivatives as coadsorbates, two-dimensional hydrogen-bonded networks were formed on graphite surface and observed by scanning tunneling microscopy. The configuration of the hydrogen bonding in the 2-D structure of 5,10,15,20-tetrakis (4-carboxylphenyl)-21H,23H-porphyrin (TCPP) is found to be different from that in the 3-D structure in bulk crystal. The difference of these structures from that expected from the bulk crystal is attributed to the effect of minimization of surface free energy in the 2-D system, which leads to close packing symmetry of molecules on the substrate.

Pillared layered hydrogen-bonded network in hexamethylenediammonium hydrogenphosphite

In the structure of the title compound, C6H18N22+·2H2PO3−, the hexa­methyl­enedi­ammonium dication has a center of symmetry and the asymmetric unit contains half of the dication and one hydrogenphosphite anion. The (P—)O—H⋯O(—P) and N—H⋯O(—P) hydrogen bonds link ammonium and hydrogenphosphite groups to form a two-dimensional hydrogen-bonded network. Layers are linked covalently into pillars by bifunctional di­ammonium moieties, making a three-dimensional framework.

Strong supramolecular-based magnetic exchange in pi-stacked radicals. Structure and magnetism of a hydrogen-bonded verdazyl radical:hydroquinone molecular solid.

The X-ray crystal structure and magnetic properties of a molecular crystal consisting of 1,5-dimethyl-3-(2-pyridyl)-6-oxoverdazyl radical and hydroquinone (pyvd:hq) are presented. The structure contains a two-dimensional network of hydrogen bonds involving the hydroquinones and the pyridine ring of the pyvd radical. The radicals adopt an unusual head-over-tail (antiparallel) pi-stacked array perpendicular to the hydrogen-bonded planes. The variable-temperature magnetic susceptibility data can be modeled using a one-dimensional antiferromagnetic chain model, with J = -58 cm(-1). The strength of the magnetic coupling is very unusual because there are no close intermolecular radical-radical contacts to provide conventional pathways for magnetic interactions. A pathway for coupling is proposed involving the mediation of magnetic exchange interactions between radical centers by the pyridine rings. Density functional calculations on the pyvd radical, as well as aggregates thereof based on the X-ray structure, have been employed in attempts to understand the possible mechanisms by which the strong magnetic interactions are achieved.