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In the crystal of the title compound, C7H5FN4S, the molecules are non-planar, with dihedral angle formed by least-squares planes of tetrazole and benzene rings of 59.94 (8) °. The crystal packing is formed by N—H...S hydrogen bonds, which link the molecules into centrosymmetric dimers with an R 2 2(8) ring motif, and by the offset face-to-face π–π stacking interactions between the benzene rings, which join the dimers into layers parallel to (100). The Hirshfeld surface analysis shows that the most important contributions to the surface contacts are from N...H/H...N (21.9%), S...H/H...S (21.1%), H...H (14.6%), F...H/H...F (11.8%) and C...H/H...C (9.5%) interactions.

In the title com­pound, the dihedral angle between the planes of the bi­pyridine and carbazole moieties connected by an O atom is 68.45 (3)°. The bi­pyridine ring system, with two meth­oxy substituents, is approximately planar. The pyridine ring in the pyridyl-substituted carbazole fragment is tilted by 56.65 (4)° with respect to the mean plane of the carbazole moiety. The title com­pound exhibits a high energy gap and triplet energy., In the title com­pound, C29H22N4O3, the carbazole system forms a dihedral angle of 68.45 (3)° with the mean plane of the bi­pyridine ring system. The bi­pyridine ring system, with two meth­oxy substituents, is approximately planar (r.m.s. deviation = 0.0670 Å), with a dihedral angle of 7.91 (13)° between the planes of the two pyridine rings. Intra­molecular C—H⋯O/N hydrogen bonds may promote the planarity of the bipyridyl ring system. In the pyridyl-substituted carbazole fragment, the pyridine ring is tilted by 56.65 (4)° with respect to the mean plane of the carbazole system (r.m.s. deviation = 0.0191 Å). In the crystal, adjacent mol­ecules are connected via C—H⋯O/N hydrogen bonds and C—H⋯π inter­actions, resulting in the formation of a three-dimensional (3D) supra­molecular network. In addition, the 3D structure contains inter­molecular π–π stacking inter­actions, with centroid–centroid distances of 3.5634 (12) Å between pyridine rings. The title com­pound exhibits a high energy gap (3.48 eV) and triplet energy (2.64 eV), indicating that it could be a suitable host material in organic light-emitting diode (OLED) applications.

The dihedral angle between the aromatic rings in the title compound is 31.84 (8)°; N—H⋯O and C—H⋯O hydrogen bonds and π–π stacking inter­actions connect mol­ecules in the crystal, producing a three-dimensional network., In the title compound, C16H12F5N3O, the dihedral angle between the aromatic rings is 31.84 (8)°. In the crystal, the mol­ecules are linked into dimers possessing crystallographic twofold symmetry by pairwise N—H⋯O hydrogen bonds and weak C—H⋯O hydrogen bonds and aromatic π–π stacking inter­actions link the dimers into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from F⋯H/H⋯F (41.1%), H⋯H (21.8%), C⋯H/H⋯C (9.7%) C⋯C (7.1%) and O⋯H/H⋯O (7.1%) contacts. The contribution of some disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9–18] in PLATON. The solvent contribution was not included in the reported mol­ecular weight and density.

The synthesis, structural characterization and influence of solvents on the crystal packing of solvated complexes of ethacridine with phthalic acid: 6,9-diamino-2-ethoxyacridinium phthalate methanol solvate (1), 6,9-diamino-2-ethoxyacridinium phthalate ethanol solvate (2), 6,9-diamino-2-ethoxyacridinium phthalate isobutanol solvate (3), and 6,9-diamino-2-ethoxyacridinium phthalate tert-butanol solvate monohydrate (4) are described in this article. Single-crystal XRD measurements revealed that the compounds 14 crystallized in the triclinic P-1 space group, and the 6,9-diamino-2-ethoxyacridinium cations, phthalic acid anions and solvent molecules interact via strong N&ndash, H&middot, &middot, O, O&ndash, O, C&ndash, O hydrogen bonds, and C&ndash, &pi, and &pi, &ndash, interactions to form different types of basic structural motifs, such as: heterotetramer bis[&middot, cation&middot, anion&middot, ] in compound 1 and 2, heterohexamer bis[&middot, alcohol&middot, ] in compound 3, and heterohexamer bis[&middot, water&middot, ] in compound 4. Presence of solvents molecule(s) in the crystals causes different supramolecular synthons to be obtained and thus has an influence on the crystal packing of the compounds analyzed.

In order to determine the influence of halogen substituent on the self-assembly of the 6,9-diamino-2-ethoxyacridinium cations and 3-halobenzoate anions in the crystals formed from ethacridine and halobenzoic acids, the series of ethacridinium meta-halobenzoates dihydrates: ethacridinium 3-chlorobenzoate dihydrate (1), ethacridinium 3-bromobenzoate dihydrate (2), and ethacridinium 3-iodobenzoate dihydrate (3), were synthesized and structurally characterized. Single-crystal X-ray diffraction measurements showed that the title compounds crystallized in the monoclinic P21/c space group and are isostructural. In the crystals of title compounds, the ions and water molecules interact via N&ndash, H⋯O, O&ndash, H⋯O and C&ndash, H⋯O hydrogen bonds and &pi, &ndash, &pi, stacking interactions to produce blocks. The relationship between the distance X⋯O between the halogen atom (X=Cl, Br, I) of meta-halobenzoate anion and the O-atom from the ethoxy group of cation from neighbouring blocks and crystal packing is observed in the crystals of the title compounds.

The compound, prepared by the NaBH4 reduction of 4,8,9,10-tetra­kis­(4-fluoro­phen­yl)-1,3-di­aza­adamantan-6-one in chloro­form and ethanol as solvent, crystallizes in the monoclinic space group P21/n with four mol­ecules in the unit cell., The title compound, C32H26F4N2O, crystallizes in the monoclinic space group P21/n with four mol­ecules in the unit cell. The compound was prepared by the NaBH4 reduction of 4,8,9,10-tetra­kis­(4-fluoro­phen­yl)-1,3-di­aza­adamantan-6-one in chloro­form and ethanol as solvent. The piperidine rings exhibit chair and boat conformations, and all four fluoro­phenyl groups are oriented in the equatorial direction. The crystal structure features C—H⋯F hydrogen bonds, C—H⋯π, N—H⋯π and π–π inter­actions. Hirshfeld surface and two-dimensional fingerprint analysis show that van der Waals inter­actions constitute a major contribution to the inter­molecular inter­actions, with H⋯H contacts accounting for 37.9% of the surface.

In the title compound, [Cd(C16H16O3)2(C12H8N2)]·4H2O, the Cd ion lies on a twofold rotation axis and is chelated by two monodeprotonated residues of the L-tyrosine-derived ligand (S)-2-[(2-hydroxybenzyl)amino]-3-(4-hydroxyphenyl)propanoic acid (L) in a κ2 N,O amino acid chelating mode, exhibiting an (N,N′)-trans disposition, and by 1,10-phenanthroline in a κ2 N,N′ mode. The latter ligand is also located about the twofold rotation axis that bisects the central six-members ring. The phenolic groups remain protonated and non-coordinating and take part as acceptors in the intramolecular hydrogen bonds with the amino groups of the acido ligands. The Cd ion is six-coordinated in a distorted octahedral environment. In the crystal, O—H...O hydrogen bonds result in the formation of three-dimensional network structures. The title complex has also been characterized by IR and 1H NMR spectroscopy and DFT studies. The crystal studied was refined as an inversion twin.

In the title compound, C16H9FO4, (I), the benzene ring is oriented at an acute angle of 59.03 (15)° relative to the coumarin plane (r.m.s deviation = 0.009 Å). This conformation of (I) is stabilized by an intramolecular C—H...O hydrogen bond, which closes a five-membering ring. In the crystal, molecules of (I) form infinite zigzag chains along the b-axis direction, linked by C—H...O hydrogen bonds. Furthermore, the crystal structure is supported by π–π stacking interactions between neighbouring pyrone and benzene or coumarin rings [centroid–centroid distances in the range 3.5758 (18)–3.6115 (16) Å], as well as C=O...π interactions [O...centroid distances in the range 3.266 (3)–3.567 (3) Å]. The theoretical data for (I) obtained from quantum chemical calculations are in good agreement with the observed structure, although the calculated C—O—C—C torsion angle between the coumarin fragment and the benzene ring (73.7°) is somewhat larger than the experimental value [63.4 (4)°]. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions.

The crystal structures of two multidentate CMPO-containing organic ligands are described. Both compounds feature N—H⋯O hydrogen bonds in the solid state., Two bis-carbamoyl­methyl­phosphine oxide compounds, namely {[(3-{[2-(di­phen­yl­phosphino­yl)ethanamido]­meth­yl}benz­yl)carbamo­yl]meth­yl}di­phenyl­phos­phine oxide, C36H34N2O4P2, (I), and diethyl [({2-[2-(di­eth­oxy­phosphino­yl)ethanamido]­eth­yl}carbamo­yl)meth­yl]phospho­nate, C14H30N2O8P2, (II), were synthesized via nucleophilic acyl substitution reactions between an ester and a primary amine. Hydrogen-bonding inter­actions are present in both crystals, but these inter­actions are intra­molecular in the case of compound (I) and inter­molecular in compound (II). Intra­molecular π–π stacking inter­actions are also present in the crystal of compound (I) with a centroid–centroid distance of 3.9479 (12) Å and a dihedral angle of 9.56 (12)°. Inter­molecular C—H⋯π inter­actions [C⋯centroid distance of 3.622 (2) Å, C—H⋯centroid angle of 146°] give rise to supra­molecular sheets that lie in the ab plane. Key geometric features for compound (I) involve a nearly planar, trans-amide group with a C—N—C—C torsion angle of 169.12 (17)°, and a torsion angle of −108.39 (15)° between the phosphine oxide phospho­rus atom and the amide nitro­gen atom. For compound (II), the electron density corresponding to the phosphoryl group was disordered, and was modeled as two parts with a 0.7387 (19):0.2613 (19) occupancy ratio. Compound (II) also boasts a trans-amide group that approaches planarity with a C—N—C—C torsion angle of −176.50 (16)°. The hydrogen bonds in this structure are inter­molecular, with a D⋯A distance of 2.883 (2) Å and a D—H⋯A angle of 175.0 (18)° between the amide hydrogen atom and the P=O oxygen atom. These non-covalent inter­actions create ribbons that run along the b-axis direction.

The title compound, C10H8N2O2·H2O, consists of an N-hydroxyquinoline-2-carboxamide molecule in the keto tautomeric form and a water molecule connected through an O—H...O hydrogen bond. The N-hydroxyquinoline-2-carboxamide molecule has a nearly planar structure [maximum deviation = 0.062 (1) Å] and only the hydroxy H atom deviates significantly from the molecule plane. In the crystal, π–π stacking between the aromatic rings [intercentroid distance = 3.887 (1) Å] and intermolecular O—H...O hydrogen bonds organize the crystal components into columns extending along the b-axis direction.

The title compound, C12H6N4, crystallizes with four independent molecules (A, B, C and D) in the asymmetric unit. The dihedral angles between the two pyridine rings in each molecule are 25.25 (8)° in A, 5.51 (9)° in B, 11.11 (9)° in C and 16.24 (8)° in D. In the crystal, molecules A and B are linked by C—H...N hydrogen bonds to form layers extending parallel to the ab plane, while molecules C and D are linked by C—H...N hydrogen bonds forming –C–D–C–D– chains propagating along the b-axis direction. The layers and the chains are stacked alternately along the c axis through offset π–π and C[triple-bond]N...π [N-to-pyridine-centroid distance = 3.882 (2) Å] interactions, resulting in the formation of a supramolecular framework.

In the title compound, C8H5ClN2Se, the dihedral angle between the planes of the selenadiazole and chlorophenyl rings is 16.6 (2)°. In the crystal, the packing of the molecules is consolidated by weak C—H...N hydrogen bonds, which generate [001] chains, and π–π stacking interactions are observed between the phenyl and selenadiazole rings, with a centroid–centroid distance of 3.884 (2) Å. There is also a short Se...Cl contact of 3.468 (1) Å

The asymmetric unit of the mononuclear mixed-ligand title complex, [Cd(C13H18NO3)2(C12H8N2)]·2H2O, contains two crystallographically independent molecules that differ insignificantly in their geometrical parameters. In both, the CdII cation lies on a twofold rotation axis and is coordinated in a distorted octahedral fashion to two monodeprotonated residues of the L-leucine-derived ligand (S)-2-(2-hydroxybenzylamino)-4-methylpentanoic acid (L), as well as to a 1,10-phenanthroline ligand in a κ2 N,N′ mode. The former coordinate in an N,O-chelating mode, exhibiting a trans-N,N′ mutual disposition. The phenolic oxygen donor groups remain protonated and do not coordinate to the cation but take part in intra- and intermolecular hydrogen bonds. In the crystal, O—H...O hydrogen bonding results in the formation of a three-dimensional network structure. The contribution to the electron density of two disordered water molecules was removed with the SQUEEZE procedure in PLATON [Spek (2015). Acta Cryst. C71, 9–18]. The studied crystal was refined as a two-component inversion twin. The title complex was also characterized by IR and 1H NMR spectroscopic methods.

In the solvated dinuclear complex [Cu2Br2(ATU)(dppm)2]·2CH3CN, both Cu+ ions adopt distorted tetra­hedral geometries, being coordinated by one terminal Br atom, one μ2-S atom of the bridging ATU ligand and two P atoms of the bridging dppm ligands. Within the complex, intra­molecular C—H⋯S, C—H⋯π, N—H⋯Br and π–π stacking inter­actions are observed. In the crystal, the components are linked by N—H⋯Br and C—H⋯N hydrogen bonds and weak π–π stacking inter­actions, generating chains propagating in the [100] direction., The reaction of cuprous bromide with a mixture of 1,1-bis­(di­phenyl­phosphan­yl)methane (dppm: C25H22P2) and N-allyl­thio­urea (ATU: C4H8N2S) in aceto­nitrile yielded the title solvated dinuclear complex, [Cu2Br2(C4H8N2S)(C25H22P2)2]·2C2H3N or [Cu2Br2(ATU)(dppm)2]·2CH3CN. Both Cu+ ions adopt distorted tetra­hedral geometries, being coordinated by one terminal Br atom, one μ2-S atom of the bridging ATU ligand and two P atoms of the bridging dppm ligands. Within the complex, intra­molecular C—H⋯S, C—H⋯π, N—H⋯Br and π–π stacking inter­actions are observed. In the crystal, the components are linked by N—H⋯Br and C—H⋯N hydrogen bonds and weak π–π stacking inter­actions, generating chains propagating in the [100] direction.

The title fused heterocycles arose from an unexpected intra­molecular cyclization reaction. Each mol­ecule features an intra­molecular O—H⋯O hydrogen bond. In the crystal, chains mediated by C—H⋯O inter­actions arise., The title compounds, 6-(2-hy­droxy­benz­yl)-5H-thia­zolo[3,2-a]pyrimidin-5-one, C13H8N2O3S, (1), and 6-(2-hy­droxy­benz­yl)-3-methyl-5H-thia­zolo[3,2-a]pyrimidin-5-one, C14H10N2O3S, (2), were synthesized when a chromone-3-carb­oxy­lic acid, activated with (benzotriazol-1-yl­oxy)tripyrrolidinyl­phospho­nium hexa­fluorido­phosphate (PyBOP), was reacted with a primary heteromamine. Instead of the expected amidation, the unusual title thia­zolo­pyrimidine-5-one derivatives were obtained serendipitously and a mechanism of formation is proposed. Both compounds present an intra­molecular O—H⋯O hydrogen bond, which generates an S(6) ring. The dihedral angles between the heterocyclic moiety and the 2-hydroxybenzoyl ring are 55.22 (5) and 46.83 (6)° for (1) and (2), respectively. In the crystals, the mol­ecules are linked by weak C—H⋯O hydrogen bonds and π–π stacking inter­actions.

Five closely related (2-chloro­quinlin-3-yl)methyl ethers all exhibit different patterns of direction-specific inter­molecular inter­actions, leading to the formation of different types of chain in four of them and sheets in the fifth., In the mol­ecules of the title compounds, methyl 5-bromo-2-[(2-chloro­quinolin-3-yl)meth­oxy]benzoate, C18H13BrClNO3, (I), methyl 5-bromo-2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, C19H15BrClNO3, (II), methyl 2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, C19H16ClNO3, (III), which crystallizes with Z′ = 4 in space group P212121, and 2-chloro-3-[(naphthalen-1-yl­oxy)meth­yl]quinoline, C20H14ClNO, (IV), the non-H atoms are nearly coplanar, but in {5-[(2-chloro­quinolin-3-yl)meth­oxy]-4-(hy­droxy­meth­yl)-6-methyl­pyridin-3-yl}methanol, C18H17ClN2O3, (V), the planes of the quinoline unit and of the unfused pyridine ring are almost parallel, although not coplanar. The mol­ecules of (I) are linked by two independent π–π stacking inter­actions to form chains, but there are no hydrogen bonds present in the structure. In (II), the mol­ecules are weakly linked into chains by a single type of π–π stacking inter­action. In (III), three of the four independent mol­ecules are linked by π–π stacking inter­actions but the other mol­ecule does not participate in such inter­actions. Weak C—H⋯O hydrogen bonds link the mol­ecules into three types of chains, two of which contain just one type of independent mol­ecule while the third type of chain contains two types of mol­ecule. The mol­ecules of (IV) are linked into chains by a C—H⋯π(arene) hydrogen bond, but π–π stacking inter­actions are absent. In (V), there is an intra­molecular O—H⋯O hydrogen bond, and mol­ecules are linked into sheets by a combination of O—H⋯N hydrogen bonds and π–π stacking inter­actions.

The crystal structure and supra­molecular features of 3-chloro-2-(4-methyl­phen­yl)-2H-pyrazolo­[3,4-b]quinoline are reported., In the mol­ecule of 3-chloro-2-(4-methyl­phen­yl)-2H-pyrazolo­[3,4-b]quinoline, C17H12ClN3, (I), the dihedral angle between the planes of the pyrazole ring and the methyl­ated phenyl ring is 54.25 (9)°. The bond distances in the fused tricyclic system provide evidence for 10-π delocalization in the pyrazolo­pyridine portion of the mol­ecule, with diene character in the fused carbocyclic ring. In the crystal, mol­ecules of (I) are linked by two independent C—H⋯N hydrogen bonds, forming sheets containing centrosymmetric R 2 2(16) and R 6 4(28) rings, and these sheets are all linked together by π–π stacking inter­actions with a ring-centroid separation of 3.5891 (9) Å.

In the crystal, mol­ecules pack in a centrosymmetric fashion and inter­act via a mixture of weak π–π stacking inter­actions, weak C—H⋯O hydrogen bonding, and Br⋯Br halogen bonding. This induces a geometry quite different than that predicted by theory., In the title compound, C14H10Br2O4, the dihedral angle between the aromatic rings is 67.29 (19)°. Both meth­oxy-group C atoms lie close to the plane of their attached ring [deviations = −0.130 (4) and 0.005 (5) Å]. In the crystal, mol­ecules pack in a centrosymmetric fashion and inter­act via a mixture of weak π–π stacking inter­actions [centroid–centoid separations = 4.044 (2) and 4.063 (3) Å], weak C—H⋯O hydrogen bonding, and Br⋯Br halogen bonding. This induces a geometry quite different than that predicted by theory.

The molecular structure of the title compound, [FePt(CN)4(C14H8N2)2(H2O)2]n, consists of one-dimensional polymeric [–Fe–NC–Pt(CN)2–CN–]∞chains. Two water molecules and two monodentate 1,4-bis(pyridin-4-yl)buta-1,3-diyne (bpb) ligand molecules complete the octahedral coordination sphere of the FeIIatoms. The Fe—N(py) bond length (py is pyridine) is 2.2700 (15) Å, Fe—N(cyanide) is 2.1185 (16) Å and the Fe—O distance is 2.1275 (14) Å. The water molecules are hydrogen bonded to either bpb ligands or cyanide groups of the planar [Pt(CN)4]2−anion of adjacent polymeric chains. These O—H...N hydrogen bonds, in conjunction with offset and tilted π–π stacking interactions between bpb ligands and cyanide groups, extend the one-dimensional chains into a three-dimensional assembly.

Three photoluminescent complexes containing either ZnII or CdII have been synthesized and their structures determined. Bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2 N 1,N 5]bis(dicyanamido-κN 1)zinc(II), [Zn(C12H10N6)2(C2N3)2], (I), bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2 N 1,N 5]bis(dicyanamido-κN 1)cadmium(II), [Cd(C12H10N6)2(C2N3)2], (II), and bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2 N 1,N 5]bis(tricyanomethanido-κN 1)cadmium(II), [Cd(C12H10N6)2(C4N3)2], (III), all crystallize in the space group P\overline{1}, with the metal centres lying on centres of inversion, but neither analogues (I) and (II) nor CdII complexes (II) and (III) are isomorphous. A combination of N—H...N and C—H...N hydrogen bonds and π–π stacking interactions generates three-dimensional framework structures in (I) and (II), and a sheet structure in (III). The photoluminescence spectra of (I)–(III) indicate that the energies of the π–π* transitions in the coordinated triazole ligand are modified by minor changes of the ligand geometry associated with coordination to the metal centres.

In the title compound, C16H12F2N4OS, the whole molecule is essentially planar (r.m.s deviation = 0.003 Å), with only the H atoms of the methyl group lying out of the molecular plane. A planar indole fused-ring system (r.m.s deviation = 0.004 Å) is linked through a hydrazine–carbothioamide bridge to a fluorobenzene ring, with the indole ring system and inclined to the fluorobenzene ring by 4.26 (14)°. The planarity of the molecule is strengthened by three intramolecular N—H...N, N—H...O and C—H...S hydrogen bonds that generateS(5),S(6) andS(6) ring motifs, respectively. In the crystal, π–π stacking interactions combine with C—H...·F hydrogen bonds to link the molecules into layers parallel to the (10-1) plane.

The title molecule, C17H15FN4OS2, obtained from 5-fluoro-1-methyl-1H-indol-2,3-dione, and 3-[4-(methylsulfanyl)phenyl]thiosemicarbazide, has an essentially planar conformation (r.m.s deviation for all non-H atoms = 0.116 Å). Intramolecular N—H...N and N—H...O hydrogen bonds generateS(5) andS(6) ring motifs, respectively. In the crystal, C—H...S hydrogen bonds occur between layers of molecules parallel to the (10-1) plane. Face-to-face π–π stacking interactions are also observed.

In the title compound, C10H7Br2NO, the methoxy C atom deviates from the quinoline ring system (r.m.s deviation = 0.003 Å) by 1.204 (4) Å. In the crystal, C—H...O hydrogen bonds link the molecules into infinite chains along theb-axis direction. Aromatic π–π stacking interactions [centroid-to-centroid distance = 3.7659 (19) Å] are also observed.

The title compound, C14H11ClN2O4, is a Schiff base. Its molecule is approximatelly planar, with a maximum deviation of 0.096 (4) Å from planarity for the methyl C atom of the methoxy group. The dihedral angle between the 5-chloro-2-methoxyphenyl ring and the phenol ring is 2.40 (10)°. In the crystal structure, intermolecular C—H...O hydrogen bonds and π–π stacking interactions consolidate the crystal packing.

In the title compound, C5H3BrN4, the almost planar triazolopyrimidine ring system (r.m.s. deviation = 0.014 Å) carries a bromo substituent at the 5-position. In the crystal, C—H...N hydrogen bonds form inversion dimers enclosingR22(8) rings and also link molecules intoC(5) chains along thec-axis direction. Br...N halogen bonds [3.185 (4) Å], π–π stacking interactions, centroid-to-centroid separation [3.663 (3) Å] and C—Br...π contacts [Br...Cg= 3.7881 (17) Å] are also found and combine with the C—H...N hydrogen bonds to stack the molecules along thea-axis direction.

The title compound, bis­[4′-(1,4,7,10-tetra­oxa-13-aza­cyclo­penta­decan-13-yl)-2,2′:6′,2"-terpyridine]­cobalt(III) tris­(perchlorate) methanol monosolvate monohydrate, is a novel complex in which the metal centre is hexa­coordinated., In the title compound, [Co(C25H30N4O4)2](ClO4)3·CH3OH·H2O, the metal atom is coordinated by two tridentate crown ether terpyridine ligands, forming a distorted CoN6 octa­hedron. The three pyridine rings in each crown–terpyridine ligand are approximately coplanar [maximum deviations = 0.088 (12) and 0.102 (15) Å] and the mean planes through the three pyridine rings are perpendicular to each other, making a dihedral angle of 89.95 (17)°. An intra­molecular C—H⋯π inter­action is observed between the two terpyridine ligands. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds, a π–π stacking inter­action [centroid–centroid distance = 3.923 (7) Å] and a C—H⋯π inter­action connect the complex cation, the perchlorate anions and the two types of solvent molecules, forming a three-dimensional network.

In the solid state, the title compound, adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intra­molecular N—H⋯O hydrogen bond with an S(6) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds to generate C(16) chains propagating in the [301] direction., In the solid state, the title compound, C20H19N3O2, adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intra­molecular N—H⋯O hydrogen bond with an S(6) ring motif. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, generating C(16) chains propagating in [301]. Weak aromatic π–π stacking inter­actions [centroid–centroid distances = 3.6123 (10) and 3.6665 (10) Å] link the chains into a three-dimensional network.

In the title molecule, C16H19NO2, all the non-hydrogen atoms except two of the C atoms of thetert-butyl group lie on a crystallographic mirror plane. No classical hydrogen bonds are observed. The crystal packing is influenced by weak π–π and C—H...π interactions.

The mol­ecule of the title compound is approximately planar with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. In the crystal, mol­ecules are linked by bifurcated O—H⋯(O,N) hydrogen bonds, forming inversion dimers, which are in turn linked via C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (502)., The mol­ecule of the title compound, C14H13N5O2, is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å), with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. The oxime group is syn to the amide group, probably due to the formation of an intra­molecular N—H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, mol­ecules are linked by pairs of bifurcated O—H⋯(O,N) hydrogen bonds, forming inversion dimers. The latter are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (502). The sheets are linked via π–π stacking inter­actions [inter-centroid distance = 3.7588 (9) Å], involving the pyridine rings of inversion-related mol­ecules, forming a three-dimensional structure.

The template effect of 1,5-Bis[2-(2-triisopropyloxyethoxy)ethoxy]naphthalene (5) on the ring closure reaction of 2-(4-Bromomethylbenzyl)-7-[4-(2,7-diazapyrenyl)-methylbenzyl]-2,7-diazapyrenium (3), to give the corresponding [2]rotaxane (7), has been quantitatively evaluated. The results are compared to those relative to the self-assembly of [2]rotaxane (8), and [2]pseudorotaxanes (9) and (10).

In C6H6N2O2·H2O, the N-hy­droxy­picolinamide mol­ecule adopts a strongly flattened conformation. O—H⋯O inter­actions and π–π stacking inter­actions between the pyridine rings organize the crystal components into columns extending along the b axis while N—H⋯N hydrogen bonds link these columns into a two-dimensional framework parallel to (100)., The crystal structure of the title compound, C6H6N2O2·H2O, consists of N-hy­droxy­picolinamide and water mol­ecules connected through O—H⋯O and N—H⋯N hydrogen bonds. The O—H⋯O inter­actions and π–π stacking inter­actions between the pyridine rings [centroid–centroid distance = 3.427 (1) Å] organize the components into columns extending along the b axis and the N—H⋯N hydrogen bonds link these columns into a two-dimensional framework parallel to (100). The N-hy­droxy­picolinamide mol­ecule adopts a strongly flattened conformation and only the O—H group H atom deviates significantly from the mol­ecule best plane. The dihedral angle between the hydroxamic group and the pyridine ring is 5.6 (2)°. The conformation about the hydroxamic group C—N bond is Z and that about the C—C bond between the pyridine and hydroxamic groups is E.

The structure of the title salt, (C8H10NO)2[CoCl4], is isotypic with the analogous cuprate(II) structure. The asymmetric unit contains one 4-acetylanilinium cation and one half of a tetrachloridocobaltate(II) anion for which the CoIIatom and two Cl−ligands lie on a mirror plane. The Co—Cl distances in the distorted tetrahedral anion range from 2.2519 (6) to 2.2954 (9) Å and the Cl—Co—Cl angles range from 106.53 (2) to 110.81 (4)°. In the crystal, cations are self-assembled by intermolecular N—H...O hydrogen-bonding interactions, leading to aC(8) chain motif with the chains running parallel to thebaxis. π–π stacking interactions between benzene rings, with a centroid-to-centroid distance of 3.709 Å, are also observed along this direction. The CoCl42−anions are sandwiched between the cationic chains and interact with each other through intermolecular N—H...Cl hydrogen-bonding interactions, forming a three-dimensional network structure.

The title compound, C10H8BrNO2, is almost planar (r.m.s. deviation for the non-H atoms = 0.031 Å) and the conformation across the C=N bond istrans. Further, the O atom of the benzofuran ring issynto the N atom of the oxime group. In the crystal, inversion dimers linked by pairs of O—H...N hydrogen bonds generateR22(6) loops. Very weak aromatic π–π stacking interactions [centroid–centroid separations = 3.9100 (12) and 3.9447 (12) Å] are also observed.

In the crystal, pairs of centrosymmetrically related mol­ecules are linked into dimers via N—H⋯O hydrogen bonds, forming (8) ring motifs. The dimers are connected via C—H⋯O and C—H⋯Cl hydrogen bonds, forming a three-dimensional network·Semi-empirical mol­ecular orbital calculations were carried out using the AM1 method., In the title compound, C14H14ClN3O2, the morpholine ring adopts a chair conformation, with the exocyclic N—C bond in an equatorial orientation. The 1,6-di­hydro­pyridazine ring is essentially planar, with a maximum deviation of 0.014 (1) Å, and forms a dihedral angle of 40.16 (7)° with the plane of the benzene ring. In the crystal, pairs of centrosymmetrically related mol­ecules are linked into dimers via N—H⋯O hydrogen bonds, forming R 2 2(8) ring motifs. The dimers are connected via C—H⋯O and C—H⋯Cl hydrogen bonds, forming a three-dimensional network. Aromatic π–π stacking inter­actions [centroid–centroid distance = 3.6665 (9) Å] are also observed. Semi-empirical mol­ecular orbital calculations were carried out using the AM1 method. The calculated dihedral angles between the pyridizine and benzene rings and between the pyridizine and morpholine (all atoms) rings are 34.49 and 76.96°, respectively·The corresponding values obtained from the X-ray structure determination are 40.16 (7) and 12.97 (9)°, respectively. The morpholine ring of the title compound in the calculated gas-phase seems to have a quite different orientation compared to that indicated by the X-ray structure determination.

The title compound, C18H20N2OS, displays whole-molecule disorder over two adjacent sets of sites with an occupancy ratio of 0.630 (11):0.370 (11). In each disorder component, the cyclohexyl ring shows a chair conformation with the exocyclic C—C bond in an equatorial orientation. The dihedral angles between the cyclohexyl ring (all atoms) and the naphthyl ring system are 36.9 (6) for the major component and 20.7 (12)° for the minor component. Each component features an intramolecular N—H...O hydrogen bond, which closes anS(5) ring. In the crystal, inversion dimers linked by pairs of N—H...S hydrogen bonds generateR22(8) loops for both components. Aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.593 (9) Å] and a C—H...π interaction are also observed.

In the crystal of the title salt, the 2,6-di­amino-4-oxo-1,3-di­hydro­pyrimidin-1-ium cations and the p-toluene­sulfonate anions are linked by a series of N—H⋯O hydrogen bonds, forming tunnel-like polymer chains propagating along [010]., In the title salt, C4H7N4O+·C7H7O3S−, the 2,6-di­amino-4-oxo-1,3-di­hydro­pyrimidin-1-ium cation inter­acts with the sulfonate group of the p-toluene­sulfonate anion via a pair of N—H⋯O hydrogen bonds, forming a hetero-synthon R 2 2(8) that mimics the role of a carboxyl­ate. The self-assembled cations form a homo-synthon R 2 1(6) motif which is further linked with the sulfonate anion via N—H⋯O hydrogen bonds to generate an R 3 2(10) ring motif. The three motifs are fused together and extended as supra­molecular ribbons along the b-axis direction. Adjacent ribbons are further linked via N—H⋯O hydrogen bonds to form an annulus, with an R 4 4(20) ring motif, resulting in a tunnel-like arrangement propagating along [010]. There are slipped parallel π–π stacking inter­actions [inter-centroid distance = 3.6539 (7) Å], between the tunnel-like polymer chains, forming slabs parallel to (100).

In the title compound, C14H17N3O3, the dihedral angle between the benzene ring and the five-membered dihydropyrazole ring is 52.26 (9)°. The ethyl ester group is approximately planar (r.m.s. deviation 0.0568 Å) and subtends an angle 67.73 (8)° to the pyrazole ring. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with anR22(10) ring motif. Weaker C—H...O contacts link these dimers into a three-dimensional network of molecules stacked along thea-axis direction. Offset π–π stacking interactions between the benzene rings [centroid-to-centroid distance = 3.8832 (12) Å] further stabilize the crystal packing.

In the anion of the title hydrated molecular salt, C9H8N+·C8H4NO6−·H2O, the protonated carboxyl and nitro groups makes dihedral angles of 27.56 (5) and 6.86 (8)°, respectively, with the attached benzene ring, whereas the deprotonated carboxy group is almost orthogonal to it with a dihedral angle of 80.21 (1)°. In the crystal, the components are linked by O—H...O and N—H...O hydrogen bonds, generating [001] chains. The packing is consolidated by weak C—H...N and C—H...O interactions as well as aromatic π–π stacking [centroid-to-centroid distances: 3.7023 (8) & 3.6590 (9)Å] interactions, resulting in a three-dimensional network.

WOS: 000369971500046 PubMed: 25878858 The asymmetric unit of the title compound, C13H10N2O3, contains four independent molecules (I, II, III and IV). Molecule IV shows whole-molecule disorder over two sets of adjacent sites in a 0.669 (10):0.331 (10) ratio. The dihedral angles between the aromatic rings are 32.30 (13)degrees in molecule I, 2.24 (14)degrees in II, 41.61 (13)degrees in III, 5.0 (5)degrees in IV (major component) and 10.2 (3)degrees in IV (minor component). In the crystal, molecules are linked into layers lying parallel to (024) by C-H center dot center dot center dot O and O-H center dot center dot center dot O interactions. The layers interact by C-H center dot center dot center dot pi and weak aromatic pi-pi stacking interactions [centroid-centroid distances = 3.8476 (16), 3.725 (3) and 3.733 (5) angstrom]. Faculty of Arts and Sciences, Ondokuz Mayis University, TurkeyOndokuz Mayis University [F.279]; Shiraz University Research Council The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). AJ and EE thank the Shiraz University Research Council for financial support.

The salt 3-amino-2H,4H-1,2,4-triazolium pyrazine-2-carboxyl­ate was isolated by reacting 5-amino-1H-1,2,4-triazole-3-carb­oxy­lic acid and pyrazine-2,3-di­carb­oxy­lic acid in the presence of silver nitrate and 1-butyl-3-methyl­imidazolium bromide in ionothermal conditions., Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxyl­ate anion in the title salt, C2H5N4 +·C5H3N2O2 −, were formed by an unexpected deca­rboxylation reaction, from 5-amino-1H-1,2,4-triazole-3-carb­oxy­lic acid and pyrazine-2,3-di­carb­oxy­lic acid, respectively. The dihedral angle between the pyrazine ring (r.m.s. deviation = 0.008 Å) and the carboxyl­ate group in the anion is 3.7 (3)°. The extended structure of the salt contains a supra­molecular zigzag tape in which cations and anions are engaged in strong and highly directional N—H⋯N,O hydrogen bonds, forming R 2 2(8) and R 2 2(9) graph-set motifs. The packing between the tapes is mediated by π–π stacking inter­actions between the triazole and pyrazine rings.

WOS: 000369973400038, PubMed ID: 25844239, The central beta-lactam ring of the title compound, C36H24N2O4, is almost planar (r.m.s. deviation = 0.003 angstrom) and makes dihedral angles of 17.17 (19), 89.76 (17) and 78.44 (17)degrees with the benzene ring, the anthracene ring (r.m.s. deviation = 0.003 angstrom) and the 1H-benzo[de] isoquinoline-1,3(2H)-dione moiety, which is nearly planar [maximum deviation = 0.098 (2) angstrom], respectively. The molecular structure is stabilized by an intramolecular C-H center dot center dot center dot N hydrogen bond. In the crystal, molecules are linked via C-H center dot center dot center dot pi and pi-pi stacking interactions [centroid-centroid distances = 3.5270 (19) and 3.779 (2) angstrom], forming a three-dimensional structure. A region of disordered electron density, probably disordered solvent molecules, was treated with the SQUEEZE procedure in PLATON [Spek (2015). Acta Cryst. C71, 9-18], which indicated a solvent cavity of 322 angstrom(3) containing approximately 91 electrons. Their formula mass and unit-cell characteristics were not taken into account during the refinement.

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].

In the title compound, C22H19NO2S, the cyclohexene ring adopts a half-chair conformation. The dihedral angles between the plane of the thiophene ring and those of its amide- and carbonyl-bonded benzene rings are 7.1 (1) and 59.0 (2)°, respectively. An intramolecular N—H...O hydrogen bond generates anS(6) ring. In the crystal, very weak aromatic π–π stacking interactions [centroid–centroid separation = 3.9009 (10) Å] are observed.

In the title molecule, C13H13N3O2, the planes of the benzene and imidazole rings form a dihedral angle of 7.72 (5)°. In the crystal, molecules are linked by weak C—H...N and C—H...O hydrogen bonds, forming layers parallel to (100). A weak C—H...π interaction connects these layers into a three-dimensional network. A π–π stacking interaction, with a centroid–centroid distance of 3.5373 (9) Å, is also observed.

In the title salt, C6H10N3O2+·C5H3O2S−, the 2-amino-4,6-dimethoxypyrimidinium cation interacts with the carboxylate group of the thiophene-2-carboxylate anion through a pair of N—H...O hydrogen bonds, forming anR22(8) ring motif. These motifs are centrosymmetrically pairedviaN—H...O hydrogen bonds, forming a complementaryDDAAarray. The separateDDAAarrays are linked by π–π stacking interactions between the pyrimidine rings, as well as by a number of weak C—H...O and N—H...O interactions. In the anion, the dihedral angle between the ring plane and the CO2group is 11.60 (3)°. In the cation, the C atoms of methoxy groups deviate from the ring plane by 0.433 (10) Å.

The title molecular salt, C15H21N2O+·ClO4−, crystallizes with four cations (A,B,CandD) and four anions in the chiral unit cell (space groupP21). The alkaloid was isolated from the aerial parts ofGenista Hispanicacollected in the Samarkand region of Uzbekistan. Each cation is protonated at the N atom that bridges the alkaloid ringsCandD. In each cation, ringAis almost planar and ringBadops a sofa conformation with the methylene group bridging to theCring as the flap. RingsCandDadopt chair conformations with acisring junction in all four cations. In the crystal,A+BandC+Ddimeric pairs linked by pairs of N—H...O hydrogen bonds are observed, which generateR22(16) loops in each case. The dimers are consolidated by weak aromatic π–π stacking interactions between theArings [centroid–centroid distances = 3.913 (3) and 3.915 (3) Å].

The title compound, C13H14ClNO3, crystallizes withZ′ = 2 in the space groupPca21, but a search for possible additional crystallographic symmetry found none. However, the crystal structure exhibits pseudosymmetry as the two independent molecules are related by an approximate but non-crystallographic inversion located close to (0.38, 0.26, 1/2) in the selected asymmetric unit, and the structure exhibits partial inversion twinning. The approximate inversion relationship between the two molecules in the selected asymmetric unit is clearly shown by comparison of the relevant torsion angle in the two molecules; the corresponding torsion angles have similar, although not identical magnitudes but with opposite signs. The mean planes of the quinoline rings in the two independent molecules are almost parallel, with a dihedral angle of only 0.16 (3)° between them, and the mutual orientation of these rings permits significant π–π stacking interactions between them [centroid–centroid distances = 3.7579 (15) and 3.7923 (15) Å]. In addition, the bimolecular aggregates which are related by translation along [010] are linked by a further π–π stacking interaction [centroid–centroid distance = 3.7898 (15) Å], so forming a π-stacked chain running parallel to [010]. However, there are no C—H...N hydrogen bonds in the structure nor, despite the number of independent aromatic rings, are there any C—H...π hydrogen bonds; hence there are no direction-specific interactions between adjacent π-stacked chains.