Dibenzylammonium hydrogen maleate and a redetermination at 120 K of bis(dibenzylamino)methane

In dibenzylammonium hydrogen maleate [or dibenzylammonium (2Z)‐3‐carboxyprop‐2‐enoate], C₁₄H₁₆N⁺·C₄H₃O₄⁻, (I), the anion contains a fairly short and nearly linear O—H...O hydrogen bond, with an O...·O distance of 2.4603 (16) Å, but with the H atom clearly offset from the mid‐point of the O...O vector. The counter‐ions in (I) are linked by two N—H...O hydrogen bonds to form C₂²(6) chains and these chains are weakly linked into sheets by a C—H...O hydrogen bond. Bis(dibenzylamino)methane, C₂₉H₃₀N₂, (II), crystallizes with two independent molecules lying across twofold rotation axes in the space group C2/c, and the molecules are conformationally chiral; there are no direction‐specific intermolecular interactions in the crystal structure of (II).     

Hydrogen‐bonded sheets in benzylmethylammonium hydrogen maleate

In the title compound, C₈H₁₂N⁺·C₄H₃O₄⁻, there is a short and almost linear but asymmetric O—H...O hydrogen bond in the anion. The ions are linked into C₂²(6) chains by two short and nearly linear N—H...O hydrogen bonds and the chains are further weakly linked into sheets by a single C—H...O hydrogen bond.     

Hydrogen‐bonded chains of rings in 1‐(4‐chloroanilinomethyl)‐5‐(4‐chlorophenyl)‐1,3,5‐triazinane‐2‐thione and hydrogen‐bonded sheets in 1‐anilinomethyl‐5‐phenyl‐1,3,5‐triazinane‐2‐thione

In 1‐(4‐chloroanilinomethyl)‐5‐(4‐chlorophenyl)‐1,3,5‐triazinane‐2‐thione, C₁₆H₁₆Cl₂N₄S, there are two independent molecules in the asymmetric unit which form inversion dimers via two weak N—H...S hydrogen bonds. The dimers are then linked into C(9)C(14) chains by a C—H...S hydrogen bond and a C—H...Cl contact. In 1‐(anilinomethyl)‐5‐phenyl‐1,3,5‐triazinane‐2‐thione, C₁₆H₁₈N₄S, molecules are linked into complex sheets via a combination of N—H...S and C—H...π hydrogen bonds.     

A hydrogen‐bonded chain of rings in 5‐amino‐1‐(4‐methoxybenzoyl)‐3‐methylpyrazole and a three‐dimensional hydrogen‐bonded framework in 5‐amino‐3‐methyl‐1‐(2‐nitrobenzoyl)pyrazole

The molecules of 5‐amino‐1‐(4‐methoxybenzoyl)‐3‐methylpyrazole, C₁₂H₁₃N₃O₂, (I), and 5‐amino‐3‐methyl‐1‐(2‐nitrobenzoyl)pyrazole, C₁₁H₁₀N₄O₃, (II), both contain intramolecular N—H...O hydrogen bonds. The molecules of (I) are linked into a chain of rings by a combination of N—H...N and N—H...π(arene) hydrogen bonds, while those of (II) are linked into a three‐dimensional framework structure by N—H...N and C—H...O hydrogen bonds.     

N‐(2,6‐Dibromophenyl)formamide

In the crystal structure of the title compound, C₇H₅Br₂NO, molecules related by translation are linked through N—H...O hydrogen bonds to form chains in the crystallographic a direction, with the aryl rings stacked parallel to each other along the chain. Besides the N—H...O hydrogen bonds, Br...O and Br...Br intermolecular interactions complete the packing of molecules in the crystal structure.     

Cocrystals of 6‐propyl‐2‐thiouracil: N—H...O versus N—H...S hydrogen bonds

In order to investigate the relative stability of N—H...O and N—H...S hydrogen bonds, we cocrystallized the antithyroid drug 6‐propyl‐2‐thiouracil with two complementary heterocycles. In the cocrystal pyrimidin‐2‐amine–6‐propyl‐2‐thiouracil (1/2), C₄H₅N₃·2C₇H₁₀N₂OS, (I), the `base pair' is connected by one N—H...S and one N—H...N hydrogen bond. Homodimers of 6‐propyl‐2‐thiouracil linked by two N—H...S hydrogen bonds are observed in the cocrystal N‐(6‐acetamidopyridin‐2‐yl)acetamide–6‐propyl‐2‐thiouracil (1/2), C₉H₁₁N₃O₂·2C₇H₁₀N₂OS, (II). The crystal structure of 6‐propyl‐2‐thiouracil itself, C₇H₁₀N₂OS, (III), is stabilized by pairwise N—H...O and N—H...S hydrogen bonds. In all three structures, N—H...S hydrogen bonds occur only within R₂²(8) patterns, whereas N—H...O hydrogen bonds tend to connect the homo‐ and heterodimers into extended networks. In agreement with related structures, the hydrogen‐bonding capability of C=O and C=S groups seems to be comparable.     

Two N,N′‐diaryl‐2,2,2‐trichloroethane‐1,1‐diamines: hydrogen‐bonded supramolecular structures in one and two dimensions

The molecules of 2,2,2‐trichloro‐N,N′‐diphenylethane‐1,1‐diamine, C₁₄H₁₃Cl₃N₂, are linked into (040) sheets by a combination of C—H...Cl and C—H...π(arene) hydrogen bonds. In 2,2,2‐trichloro‐N,N′‐bis(4‐methylphenyl)ethane‐1,1‐diamine, C₁₆H₁₇Cl₃N₂, the molecules are linked into C(7) chains by two independent C—H...Cl hydrogen bonds and one Cl...Cl contact.     

Hydrogen‐bonding patterns in two aroylthiocarbamates and two aroylimidothiocarbonates

In O‐ethyl N‐benzoylthiocarbamate, C₁₀H₁₁NO₂S, the molecules are linked into sheets by a combination of two‐centre N—H...O and C—H...S hydrogen bonds and a three‐centre C—H...(O,S) hydrogen bond. A combination of two‐centre N—H...O and C—H...O hydrogen bonds links the molecules of O‐ethyl N‐(4‐methylbenzoyl)thiocarbamate, C₁₁H₁₃NO₂S, into chains of rings, which are linked into sheets by an aromatic π–π stacking interaction. In O,S‐diethyl N‐(4‐methylbenzoyl)imidothiocarbonate, C₁₃H₁₇NO₂S, pairs of molecules are linked into centrosymmetric dimers by pairs of symmetry‐related C—H...π(arene) hydrogen bonds, while the molecules of O,S‐diethyl N‐(4‐chlorobenzoyl)imidothiocarbonate, C₁₂H₁₄ClNO₂S, are linked by a single C—H...O hydrogen bond into simple chains, pairs of which are linked by an aromatic π–π stacking interaction to form a ladder‐type structure.     

The effect of partial methylation of the glycine amino group on crystal structure in N,N‐dimethylglycine and its hemihydrate

N,N‐Dimethylglycine, C₄H₉NO₂, and its hemihydrate, C₄H₉NO₂·0.5H₂O, are discussed in order to follow the effect of the methylation of the glycine amino group (and thus its ability to form several hydrogen bonds) on crystal structure, in particular on the possibility of the formation of hydrogen‐bonded `head‐to‐tail' chains, which are typical for the crystal structures of amino acids and essential for considering amino acid crystals as mimics of peptide chains. Both compounds crystallize in centrosymmetric space groups (Pbca and C2/c, respectively) and have two N,N‐dimethylglycine zwitterions in the asymmetric unit. In the anhydrous compound, there are no head‐to‐tail chains but the zwitterions form R₄⁴(20) ring motifs, which are not bonded to each other by any hydrogen bonds. In contrast, in the crystal structure of N,N‐dimethylglycinium hemihydrate, the zwitterions are linked to each other by N—H...O hydrogen bonds into infinite C₂²(10) head‐to‐tail chains, while the water molecules outside the chains provide additional hydrogen bonds to the carboxylate groups.     

1‐(2‐Aminophenyl)‐3‐(4‐pyridyl)prop‐2‐en‐1‐one: a three‐dimensional framework structure built from N—H...N,C—H...O and C—H...π(arene) hydrogen bonds

The intramolecular dimensions of the title compound, C₁₄H₁₂N₂O, provide evidence for a polarized electronic structure. The molecule, which is almost completely planar, contains an intramolecular N—H...O hydrogen bond, and the molecules are linked by a combination of N—H...N, C—H...O and C—H...π(arene) hydrogen bonds to form a three‐dimensional framework structure.     

2,6‐Bis[(2‐hydroxy‐3‐methoxybenzylidene)hydrazinocarbonyl]pyridine monohydrate

In the title compound, C₂₃H₁₉N₅O₆·H₂O, the two components are linked into complex chains by a combination of two independent O—H...O and two independent N—H...O hydrogen bonds. The complex chains are linked into a two‐dimensional sheet network viaπ–π stacking interactions and C—H...O hydrogen bonds.     

Crystal structure of a silver(I) complex {[Ag(N-methylthiourea)2]NO3}n exhibiting infinite chains of AgS4 tetrahedra

A polymeric silver(I) complex, bis(N-methylthiourea)silver(I) nitrate, {[Ag(Metu)₂]NO₃} _n is prepared and its crystal structure is determined. The compound crystallizes in the monoclinic C2/c space group. In the structure, distorted AgS₄ tetrahedra are linked through the sulfur atoms of the Metu ligand to form isolated infinite chains of the type [Ag(SR)₂] _n ⁿ⁺. The cationic chains are separated from each other by nitrate ions that do not coordinate to the metal ion. The chains are bridged via N-H...O hydrogen bonds involving the nitrate ions. The complex exhibits an Ag—Ag separation of ∼3.21 ? indicating the existence of significant argentophilic interactions. An upfield shift in the >C=S resonance of Metu in ¹³C NMR and downfield shift in the N-H resonance in ¹H NMR are consistent with sulfur coordination to silver(I).     

3‐{[4‐Amino‐6‐methoxy‐2‐(methylsulfanyl)pyrimidin‐5‐yl]amino}‐1,2′‐biindenylidene‐1′,3′‐dione dimethyl sulfoxide solvate: π‐stacked sheets of hydrogen‐bonded chains of edge‐fused rings

In the title compound, C₂₄H₁₈N₄O₃S·C₂H₆OS, the biindenylidene component shows evidence of polarization of the electronic structure. The dimethyl sulfoxide solvent molecules are disordered over two sites, and they are linked to the biindenylidenedione components via N—H...O and C—H...O hydrogen bonds. A combination of N—H...N and N—H...O hydrogen bonds links the nonsolvent components into a chain of edge‐fused centrosymmetric R₂²(8) and R₂²(22) rings, and these chains are linked into sheets by a single aromatic π–π stacking interaction.     

Hydrogen bonded complexes of cyanuric acid with pyridine and guanidinium carbonate

Hydrogen bonded complexes of cyanuric acid (CA) with pyridine, [C₃N₃H₃O₃:C₅H₅N], 1, and guanidinium carbonate [C₃H₂N₃][C(NH₂)₃],2, have been prepared at room temperature and characterized by single-crystal X-ray diffraction. Structure of 1 shows pyridine molecules substituting the inter-tape hydrogen bond in CA by N-H… N and C-H…O hydrogen bonds. The structure reveals CA-pyridine hydrogen-bonded single helices held together by dimeric N-H…O hydrogen bonding between CA molecules. In2, the CA tapes, resembling a sine wave interact with the guanidinium cations through N-H…O and N-H…N hydrogen bonds forming guanidinium cyanurate sheets.     

Tolterodinium (+)‐(2R,3R)‐hydrogen tartrate

In the crystal structure of (R)‐N,N‐diisopropyl‐3‐(2‐hydroxy‐5‐methyl­phenyl)‐3‐phenyl­propyl­aminium (2R,3R)‐hydrogen tartrate, C₂₂H₃₂NO⁺·C₄H₅O₆⁻, the hydrogen tartrate anions are linked by O—H⋯O hydrogen bonds to form helical chains built from (9) rings. These chains are linked by the tolterodine molecules via N—H⋯O and O—H⋯O hydrogen bonds to form separate sheets parallel to the (101) plane.     

2‐(2‐Oxoimidazolidinyl)ethyl 2‐methyl­prop‐2‐enoate

In the crystal structure of the title compound, C₉H₁₄N₂O₃, the molecules are linked by N—H?O=C bonds into chains parallel to [001]. Large crystals are readily obtained, presumably because of the hydrogen bonds and an energetically stable conformation of the mol­ecule.     

Two similarly substituted benzo[h]pyrazolo[3,4‐b]quinoline‐5,6(10H)‐diones: supramolecular structures in two and three dimensions

The molecules of 8‐methyl‐7,10‐diphenyl‐5H‐benzo[h]pyrazolo[3,4‐b]quinoline‐5,6(10H)‐dione, C₂₇H₁₇N₃O₂, (I), are weakly linked into chains by a single C—H...O hydrogen bond, and these chains are linked into sheets by a π–π stacking interaction involving pyridyl and aryl rings. In 8‐methyl‐7‐(4‐methylphenyl)‐10‐phenyl‐5H‐benzo[h]pyrazolo[3,4‐b]quinoline‐5,6(10H)‐dione, C₂₈H₁₉N₃O₂, (II), the molecules are linked into a three‐dimensional framework structure by a combination of C—H...N, C—H...O and C—H...π(arene) hydrogen bonds, together with a π–π stacking interaction analogous to that in (I).     

Two mononuclear octahedral complexes with benzimidazole‐2‐carboxylate: supramolecular networks constructed by hydrogen bonds

The title compounds, trans‐bis(1H‐benzimidazole‐2‐carboxylato‐κ²N³,O)bis(ethanol‐κO)cadmium(II), [Cd(C₈H₅N₂O₂)₂(C₂H₆O)₂], (I), and trans‐bis(1H‐benzimidazole‐κN³)bis(1H‐benzimidazole‐2‐carboxylato‐κ²N³,O)nickel(II), [Ni(C₈H₅N₂O₂)₂(C₇H₆N₂)₂], (II), are hydrogen‐bonded supramolecular complexes. In (I), the Cd^II ion is six‐coordinated by two O atoms from two ethanol molecules, and by two O and two N atoms from two bidentate benzimidazole‐2‐carboxylate (HBIC) ligands, giving a distorted octahedral geometry. The combination of O—H...O and N—H...O hydrogen bonds results in two‐dimensional layers parallel to the ab plane. In (II), the six‐coordinated Ni^II atom, which lies on an inversion centre, shows a similar distorted octahedral geometry to the Cd^II ion in (I); two benzimidazole molecules occupy the axial sites and the equatorial plane contains two chelating HBIC ligands. Pairs of N—H...O hydrogen bonds between pairs of HBIC anions connect adjacent Ni^II coordination units to form a one‐dimensional chain parallel to the a axis. Moreover, these one‐dimensional chains are further linked via N—H...O hydrogen bonds between HBIC anions and benzimidazole molecules to generate a three‐dimensional supramolecular framework. The two compounds show quite different supramolecular networks, which may be explained by the fact that different co‐ligands occupy the axial sites in the coordination units.     

Unexpected conformational consequences of weak hydrogen bonds on 1,3,7,9,13,15,19,21‐octaazapentacyclo[19.3.1.13,7.19,13.115,19]octacosane monohydrate

In the title compound, C₂₀H₄₀N₈·H₂O, the organic molecule crystallizes with one water molecule located within the molecular cavity of the octaaza macrocycle. The two molecules are linked via two weak O—H...N hydrogen bonds. The assembly has noncrystallographic C₂ axial symmetry.     

(E)‐N‐{[6‐Chloro‐4‐(4‐chlorophenyl)‐3‐methyl‐1‐phenyl‐1H‐pyrazolo[3,4‐b]pyridin‐5‐yl]methylene}benzene‐1,2‐diamine: a three‐dimensional framework structure built from only two hydrogen bonds

The molecules of the title compound, C₂₆H₁₉Cl₂N₅, are conformationally chiral, with none of the aryl groups coplanar with the pyrazolo[3,4‐b]pyridine core of the molecule. A single unique N—H...N hydrogen bond links the molecules into two symmetry‐related sets of C(11) chains running parallel to the [011] and [01] directions, respectively, and these two sets of chains are linked into a continuous three‐dimensional framework structure by a single unique C—H...N hydrogen bond which forms a chain parallel to the [100] direction.