A near-perfect octahedral zinc(II) complex coordinated to two coumarin fluorophores. 14H14NO4)2(H2O)2]·2C2H6OS, shows that the ZnII cation adopts an octahedral geometry and lies on an inversion center. Two organic ligands occupy the equatorial positions of the coordination sphere, forming a chelate ring motif via the O atom on the formyl group and another O atom of the carbonyl group (a pseudo-β-diketone motif). Two water molecules occupy the remaining coordination sites of the ZnII cation in the axial positions. The water molecules are each hydrogen bonded to a single dimethyl sulfoxide molecule that has been entrapped in the crystal lattice. The structure of the title coordination complex, [Zn(C This is indicated by the short C=O bond of the dione (O3—C4) and the C=O bond length of the formyl moiety (O4—C9), with values of 1.2686 (10) and 1.2603 (10) Å, respectively. The Zn—O bonds complete the stable six-membered chelating motif, which is favorable for smaller metal ions  distance is 2.09 Å  to 93.18 (3)°. A single DMSO solvent molecule completes the asymmetric unit.The molecular structure of (1) is shown in Fig. 1II ion S1—O6⋯H52—O5 [1.983 (9) Å]. Interestingly, there are also two C—H⋯O hydrogen-bonding interactions from the methyl moiety of DMSO; one with the O atom on the formyl functional group in the equatorial position (H13A⋯O4 = 2.52 Å) and an additional hydrogen-bonding interaction from the carbonyldione group occupying another equatorial position (H12B⋯O3 = 2.62 Å). Together these two interactions form three C⋯O6 (2.29 Å), forming an infinite chain.The crystal structure of the title compound shows an extensive array of hydrogen-bonding interactions Table 1 forming et al., 2013A) and the electron-rich region of the second coumarin ring system (C4A–C8A) of an adjacent compound, whereby the centroids are 3.734 Å apart  and 5(b); however, these did not yield any results. Therefore a modification of the search by specifically searching structures that have a bidentate chelating β-diketone motif coordinated to the zinc(II) in the equatorial position, with two water molecules in the axial position, as shown in Fig. 5c) was carried out. This refined search yielded two similar structures with ZnII octahedrally coordinated, the first by Solans et al., whereby two 1,3-bis(2-hydroxyphenyl)propane-1,3-dionate ligands coordinate to the ZnII ion, with the remaining two coordination sites occupied by two ethanol molecules  was then added to the solution. After stirring for 20 min, a yellow solid formed, which was collected by filtration and dried. A small amount of the solid (20 mg) was redissolved in a 1:1 mixture of MeOH and DMSO to form a saturated solution (1 mL) which was was allowed to stand for several weeks to form the title compound as colorless needles suitable for X-ray analysis. 1H NMR : δ 9.68 , 7.91 , 6.53 , 6.33 , 3.41 , 1.23 ; 13C NMR  δ 192.2, 169.1, 165.8, 159.5, 157.7, 153.3, 128.3, 108.4, 108.0, 102.8, 96.9, 44.9, 40.6, 29.7, 12.5; LRMS–ESI (negative mode), NaCl was added as a charging agent [M − 2H2O + Cl]− = 619 m/z, [M − H2O − C14H15NO4 + 2Cl]− = 396 m/z, CID 396 yields [C14H15NO4]− = 261 m/z; IR (ATR solid); 3364  νOH, 2972, 2926 (m) νCH, 1722 (m) νCO (δ-lactone), 1689 νCO (ketone), 1590 νCO (formyl), 564 νCO (Zn—O) cm−1.7-(Diethylamino)-4-hydroxycoumarin  was dissolved in 2-propanol (20 mL), triethyl orthoformate  and 2-aminopyriimidine  were added and the solution was heated to reflux for 4 h. Upon cooling, the solid was collected and used without further purification. This compound  was then dissolved in methanol (10 mL), to which Zn(OAc)sp2, 0.99 Å for CH2, and 0.98 Å for methyl groups. Those on O atoms were assigned from difference maps, and their positions refined, with O—H distances restrained to 0.86 (1) Å. Uiso values for H atoms were assigned as 1.2 times Ueq of the attached atoms (1.5 for methyl and water groups).Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989016009853/zl2668sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989016009853/zl2668Isup2.hklStructure factors: contains datablock(s) I. DOI: 1486125CCDC reference: crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In the crystal of the title purine derivative, molecules are linked by O—H⋯N, N—H⋯O and N—H⋯N hydrogen bonds, forming a three-dimensional framework. 7H7N5O3, is an adduct of guanine with glyoxal. In the molecule, the dihydroimidazole ring adopts a twisted conformation on the C—C bond, and the two hydroxyl groups lie on opposite sides of the mean plane of the ring. In the crystal, the molecules are linked by N—H⋯O, O—H⋯N and N—H⋯N hydrogen bonds forming a three-dimensional framework. The crystal packing is reinforced by C—H⋯O hydrogen bonds and by offset π–π stacking of the purine ring systems of inversion related molecules [intercentroid distance = 3.4839 (12) Å].The title purine derivative, C Purine derivatives have been developed as inhibitors of cyclin-dependent kinase  Å, interplanar distance = 3.311 (1) Å, slippage = 1.112 Å; Cg2 and Cg3 are the centroids of the N3/C4/C3/N4/C5 and N1/C1/C4/C3/N2/C2 rings, respectively; symmetry code: (i) −x, −y, −z + 2].In the crystal, molecules are also linked e Table 1. The laye Table 1. Within e Table 1, and invet al., 2016H-6-one as substructure, gave 61 hits. Many of these compounds concern guanine and guaninium and some metal complexes, but none involve a fused third ring. The structure of the title compound has not been reported previously.A search of the Cambridge Structural Database  medium.The title compound was synthesized according to a literature method  = 1.2Ueq(C) and 1.5Ueq.Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989016009087/xu5887sup1.cifCrystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016009087/xu5887Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989016009087/xu5887Isup3.cmlSupporting information file. DOI: 1469976CCDC reference: crystallographic information; 3D view; checkCIF reportAdditional supporting information:


III compounds with 4-aminobenzoic acid and 4-chloro-3-nitrobenzoic acid, discrete centrosymmetric bridged dinuclear complex units are present giving an overall three-dimensional hydrogen-bonded structure in the first complex and a one-dimensional coordination polymer in the second.In the structures of two Er 2-4-aminobenzoato-κ2O:O′)bis[bisdiaquaerbium(III)] dihydrate, [Er2(C7H6NO2)6(H2O)4]·2H2O, (I), and 4-chloro-3-nitrobenzoic acid (CLNBAH), namely poly[hexakis(μ2-4-chloro-3-nitrobenzoato-κ2O:O′)bis(dimethyl sulfoxide-κO)dierbium(III)], [Er2(C7H3ClNO4)6(C2H6OS)2]n, (II), have been determined. In the structure of solvatomorphic compound (I), the symmetry-related irregular ErO8 coordination polyhedra in the discrete centrosymmetric dinuclear complex comprise two monodentate water molecules and six carboxylate O-atom donors, four from two bidentate carboxylate O,O′-chelate groups and two from the bis-monodentate O:O′-bridging group of the third 4-ABA anion. The Er—O bond-length range is 2.232 (3)–2.478 (3) Å and the Er⋯Er separation in the dinuclear complex unit is 4.7527 (4) Å. One of the coordinating water molecules is involved in an intra-unit O—H⋯O hydrogen-bonding association with an inversion-related carboxylate O-atom acceptor. In contrast, the anhydrous compound (II) is polymeric, based on centrosymmetric dinuclear repeat units comprising ErO7 coordination polyhedra which involve four O-atom donors from two bidentate O:O′-bridging carboxylate groups, one O-atom donor from the monodentate dimethyl sulfoxide ligand and two O-atom donors from the third bridging CLNBA anion. The latter provides the inter-unit link in the one-dimensional coordination polymer extending along [100]. The Er—O bond-length range in (II) is 2.239 (6)–2.348 (6) Å and the Er⋯Er separation within the dinuclear unit is 4.4620 (6) Å. In the crystal of (I), extensive inter-dimer O—H⋯O and N—H⋯O hydrogen-bonding interactions involving both the coordinating water molecules and the solvent water molecules, as well as the amine groups of the 4-ABA anions, give an overall three-dimensional network structure. Within this structure are also weak π–π ring interactions between two of the coordinating ligands [ring-centroid separations = 3.676 (3) and 3.711 (2) Å]. With (II), only weak intra-polymer C—H⋯O, C—H⋯Cl and C—H⋯S interactions are present.The crystal structures of two erbium(III) complexes with 4-aminobenzoic acid (4-ABAH), namely bis(μ RE) metals has been investigated extensively and the structures of a large number of complexes with various ligand types are known  series of complexes  (La–Tb as well as Dy and Er), in which the structures are two-dimensional, the second triclinic (P2(4-ABA)6(H2O)2]; triclinic [[Tb2(4-ABA)6(H2O)2]·2H2O]} is of interest and its occurrence was indicated as being dependent on pH control in the preparation.The coordination chemistry of the rare earth (RE series (predominantly triclinic) might also show the same effect so this was tested with Er in a reaction of erbium(III) acetate with 4-ABA in aqueous ethanol under mild reaction conditions, with no additional pH control. The title triclinic complex [Er2(C7H6NO2)6(H2O)4]·2H2O, (I)3+ complex with 4-ABA , b = 11.0117 (1), c = 12.7430 (2) Å, α = 89.372 (5), β = 72.0360 (6), γ = 75.0730 (7)°, V = 1169.97 (2) Å3, confirming that the two are isotypic.It was considered that some of the other later members of the 2(C7H3ClNO4)6(C2H6OS)2]n, was obtained in a similar reaction to (I)Complex (II)8 complex units  , four O-atom donors from two slightly asymmetric bidentate O,O’ chelate carboxylate groups (the A and B 4-ABA ligands) and two bridging O-atom donors from two symmetry-related ligands (C). The Er⋯Eri separation in the dinuclear unit is 4.7527 (4) Å. Unlike the polymeric solvatomorphic ErIII complex [Er2(4-ABA)6(H2O)2]n·nH2O carboxylate hydrogen bond is present between one of the the coordinating water molecules (O1W) and an inversion-related carboxylate O-atom (O11Ai) ] Table 1, compris) Table 2. This stO,O′-chelate ligands (A) and the bridging ligand (C), the groups are essentially coplanar with the benzene ring , while in the second bidentate chelate ligand (B) the group is rotated out of the plane [corresponding torsion angle = 155.9 (4)°]. Such a ’planar’ conformation is also found in the structure of the parent acid III atoms , a monodentate DMSO O-atom and O-donors (O12Ci) and O11Ci from the C ligand which extends the dinuclear unit into a one-dimensional coordination polymer lying along [100]  Å. Also present within the repeat unit are a C2B—H⋯O11 hydrogen bond [3.298 (13) Å] and a C2A—H⋯S1 interaction [3.743 (10) Å] ms Fig. 2 being se0] Fig. 3. The Er—0] Fig. 3 and the ] Table 4.A/B/C—C1A/B/C—C11A/B/C—O11A/B/C = 158.7 (9), 177.2 (9) and 160.3 (8)°, respectively. The torsion angles of the nitro groups C2A/B/C—C3A/B/C—N3A/B/C—O32A/B/C are −150.4 (12), 174.1 (16) and 120.3 (13)°, respectively. In the structure of the parent CLNBAH acid water and Ocarboxyl hydrogen bonds give a three-dimensional network structure  Å] and C ligands [C⋯Cviii = 3.676 (3) Å] 6(H2O)4]2·6H2O e Figs. 4 and 5 ▸.With (II)The title compounds were synthesized by warming together for 10 min, a solution obtained by mixing 5 ml of ethanolic 4-aminobenzoic acid (1 mmol: 135 mg) [for (I)] or 4-chloro-3-nitrobenzoic acid (1 mmol: 200 mg) [for (II)], with 10 ml of aqueous erbium(III) acetate hexahydrate (0.3 mmol: 216 mg). Partial room-temperature evaporation of these solutions provided pale-pink block-like single crystals of (I)Uiso(H) = 1.5Ueq(O) or 1.2Ueq(N). Other H atoms were included in the refinement at calculated positions , using a riding-model approximation. In the refinement of (II)−3) located within 1.0 Å of the Er1 site were present. These are possibly due to poor crystal quality coupled to effects of an insufficient absorption correction.Crystal data, data collection and structure refinements for (I)10.1107/S2056989015020319/wm5228sup1.cifCrystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989015020319/wm5228Isup2.hklStructure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020319/wm5228IIsup3.hklStructure factors: contains datablock(s) II. DOI: 1433543, 1433542CCDC references:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


N-[3-(dimethylamino)propyl]-N′-(2-hydroxyphenyl)oxamide trianion bridges two CuII cations to form the binuclear complex, in which the CuII cations have distorted square-planar and square-pyramidal coordination geometries.The  2(C13H16N3O3)(C12H6N2O2)(H2O)]ClO4·0.5H2O, consists of a cis-oxamide-bridged binuclear CuII complex cation, a perchlorate anion and half a solvent water molecule. One CuII cation is N,N′,N",O-chelated by an N-[3-(dimethylamino)propyl]-N′-(2-hydroxyphenyl)oxamide trianion in a distorted square-planar geometry, whereas the other CuII cation is O,O′-chelated by the oxamide moiety of the anion and N,N′-chelated by a 1,10-phenanthroline-5,6-dione molecule, and a water molecule further coordinates the second CuII cation, completing a distorted square-pyramidal coordination geometry. In the crystal, classical O—H⋯O hydrogen bonds, weak C—H⋯O hydrogen-bonding interactions and π–π stacking interactions link the complex cations, anions and solvent water molecules into a three-dimensional supramolecular architecture. In the crystal, the dimethylaminopropyl unit of the oxamide anion is disordered over two positions with an occupancy ratio of 0.561 (11):0.439 (11); the solvent water molecule is also disordered over two positions, the occupancy ratio being 0.207 (10):0.293 (10).The title compound, [Cu Its crystal structure and supramolecular structure are reported here. 1,10-Phenanthroline-5,6-dione (Phdo) is a multifaceted ligand since the structure and electronic properties thereof incorporate the features of the diimine and quinone functionalities  Å, which is consistent with structures reported previously  Å for N4], and a water molecule (O4) occupies the apical position, completing a distorted square-pyramidal coordination geometry with a τ value of 0.06  cations with three planar five-membered chelate rings and one six-membered ring, the latter being disordered over two positions. The puckering parameters of the first component (containing atoms C10A and C11A) are Q = 0.554 (8) Å, θ = 47.6 (6)° and ϕ = 206.0 (7)°, and those of the other are Q = 0.565 (11) Å, θ = 123.4 (8)° and ϕ = 38.8 (9)°; both suggest an approximate half-chair conformation.The hexadentate oxamide anion, Dmapoxx, 1 − y, −z [symmetry code (iv)], and vice versa , 3.211 (4) (C3iv) and 3.252 (4) Å (C19iv).Besides classical O—H⋯O hydrogen bonds, weak C—H⋯O hydrogen bonds and aromatic stacking interactions are important to the supramolecular structure. As illustrated in Fig. 2sa Fig. 3. The sepII complexes of 1,10-phenanthroline-5,6-dione have been reported previously, for example, Chetana et al. propyl]-N′-2-(oxidophenyl)oxamide 2·6H2O  in methanol (5 ml) was added dropwise to a solution of H3Dmapox  and piperidine  in methanol (5 ml). The solution was stirred continuously for 0.5 h. Then a solution of Phdo  in methanol (5 ml) was added dropwise, and the mixture was stirred continuously at 313 K for 6 h and then filtered. Dark-blue crystals of the title compound suitable for X-ray analysis were obtained from the filtrate by slow evaporation at room temperature for 7 d. Yield: 0.026 g (71.62%). Analysis calculated for Cu2C25H25ClN5O10.5: C 41.44, H 3.48, N 9.67%; found: C 42.57, H 3.15, N 9.19%.A–C13A, with occupancies of 0.561 (11); C10B–C13B, 0.439 (11)], three oxygen atoms of the perchlorate ion  and the solvent water molecule ; O7B, 0.293 (10)]. The occupancies were refined freely except for the sum of atoms O7A and O7B which was fixed at 0.5. Some restraints on distances (DFIX) and anisotropic displacement parameters (SIMU) were applied to the disordered atoms to avoid unreasonable geometries. The hydrogen atoms of the water molecules were found in a difference Fourier map and then refined as riding. Other H atoms were placed in calculated positions, with C—H = 0.96 (methyl), 0.97 (methylene) and 0.93 Å (aromatic), and refined using a riding model, with Uiso(H) = 1.2 Ueq(C) or 1.5 for methyl groups.Crystal data, data collection, and refinement details are summarized in Table 310.1107/S2056989015009391/xu5850sup1.cifCrystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015009391/xu5850Isup2.hklStructure factors: contains datablock(s) I. DOI: 1401557CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The latter is coordinated by two Cl atoms and two N,N′-dimethylthiourea (Dmtu) ligands through their S atoms, defining a distorted tetrahedral coordination sphere with bond angles in the range 102.47 (4)–118.32 (4)°. Intra- and intermolecular hydrogen bonds of the type N—H⋯Cl with S(6) and R22(12) ring motifs are present. The intermolecular contacts make up polymeric chains extending parallel to [101].The molecular structure of the title compound, [HgCl L) or derivatives thereof have shown that in combination with a halide or pseudohalide X, some of the complexes exist as mononuclear species [HgX2L2] 2 complexes with methylthiourea as an auxiliary ligand  complexes with thiourea ligands (2 with dimethylthiourea (Dmtu) as an additional ligand, [HgCl2(C3H8N2S)2], (I)In this article, we report on synthesis and crystal structure of HgCl2L2] complexes et al., 1995S(6) loop motifs 2] 2] 2] 2Cl2] and [Hg(tetramethylthiourea)2Cl2] 2] and [CdBr2(Dmtu)2], the coordination spheres around Cd deviate only slightly from ideal tetrahedral values. On the other hand in [Hg(Dmtu)2(CN)2], the HgII atom exhibits a severely distorted tetrahedral coordination sphere with bond angles in the range 94.31 (2) to 148.83 (13)°  HgClUiso(H) = 1.5Ueq(C) and Uiso(H) = 1.2Ueq(N).Crystal data, data collection and structure refinement details are summarized in Table 310.1107/S2056989015015406/wm5202sup1.cifCrystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015015406/wm5202Isup2.hklStructure factors: contains datablock(s) I. DOI: 1419298CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In both dimers, the platinum(II) complexes are arranged antiparallel to each other. Each complex exhibits a slightly distorted square-planar coordination environment around the central Pt(II) atom. The dihedral angles between two chelate rings including the PtII atom in these complexes are 0.08 (12) and 1.54 (9)°.The title cyclometalated platinum(II) complex with 2-(4-bromophenyl)pyridinato and acetylacetonato ligands, [Pt(C Although these complexes afford luminescence in the solid state, their crystal structures have not been sufficiently explored. We report herein the crystal structure of the cyclometalated platinum(II) complex with 2-(4-bromophenyl)pyridinato  and acetylacetonato  ligands, [Pt(Brppy)(acac)].Square-planar cyclometalated platinum(II) complexes with luminescent properties have recently attracted attention because of their potential applications  are slightly distorted from an ideal square-planar configuration, with angles around Pt1 in the range 81.89 (18)–93.04 (17)° and around Pt2 in the range 81.73 (18)–93.57 (16)°. The Pt—C bond lengths [Pt1—C11 = 1.970 (5) and Pt2—C27 = 1.969 (5) Å] are slightly shorter than the Pt—N bond lengths [Pt1—N1 = 1.995 (4) and Pt2—N2 = 1.999 (4) Å] due to the stronger electron-donating ability of a C atom compared to that of an N atom. Pt—O bond lengths are compiled in Table 1The asymmetric unit of the title compound contains two complex molecules with very similar configurations (r.m.s. deviation of fit of two molecules = 0.07 Å). The structure of one of the complex molecules of the title compound is shown in Fig. 1II complex (Pt1) is directed to the b axis, on the other hand, that of the other complex (Pt2) is directed to the a axis. The shortest intermolecular contacts are C4⋯C15i = 3.406 (7) and C22⋯O3ii = 3.402 (6) Å . Weak C—H⋯O and C—H⋯Br interactions might also help to consolidate the crystal packing  and Pt2⋯Pt2ii = 3.723 (1) Å] are longer than the van der Waals diameter of the Pt atom (μ-Cl)]2 ([Pt(Cμ2:-Cl)] A mixture of 2-(4-bromophenyl)pyridine  and K2PtCl4  in a 2-ethoxyethanol–water mixture (45 ml/15 ml) was stirred for 6 h at 333 K under an Ar atmosphere. After cooling to room temperature, the yellow–green precipitate was filtered off, washed with dichloromethane, and dried in vacuo. Yield: 0.535 g, (48.2%).11H7BrN)(C5H7O2)]:: 262 (29800), 280 (27500), 317 , 330 , 363 (6400), 389 (4200). 1H NMR ; 8.97 , 7.81 , 7.71 , 7.57 , 7.31-7.45 , 7.14 , 5.48 , 2.03 , 2.01 .Analysis found  = 1.2Ueq(C) for Csp2–H, and Uiso(H) = 1.5Ueq(C) for methyl H atoms.Crystal data, data collection and structure refinement details are summarized in Table 310.1107/S2056989015017478/wm5214sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015017478/wm5214Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015017478/wm5214Isup3.tifSupporting information file. DOI: 1425736CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


N-(11-hydroxyundecyl)isoxazole-3-carboxamide hemihydrate, a derivative of antiviral ‘WIN compounds’, are reported.The crystal structure and supramolecular features of 5-{3-propyl}- 29H42N4O5·0.5H2O, comprises four structural units. A flexible propyloxy unit in a gauche conformation, with a –C(H2)—C(H2)—C(H2)—O– torsion angle of −64.32 (18)°, connects an isoxazole ring and an approximately planar phenyloxadiazole ring system [with a maxixmum devation of 0.061 (2) Å], which are oriented almost parallel to one another with a dihedral angle of 10.75 (7)°. Furthermore, a C11-alkyl chain with a terminal hydroxy group links to the 3-position of the isoxazole ring via an amide bond. In the crystal, a half-occupancy solvent water molecule connects to a neighbouring molecule via an intermolecular O—H⋯O(water) hydrogen bond to the C11-alkyl chain hydroxy group.The title compound, C The three heterocyclic rings are approximately coplanar to one another, having dihedral angles between the rings of 11.57 (8) (C19–C21/N22/O23 and C7–C12), 10.68 (9) (C19–C21/N22/O23 and C2/O3/N4/C5/N6) and 4.81 (9)° (C7–C12 and C2/O3/N4/C5/N6), maintaining the WIN framework in a linear conformation. The dihedral angle between the isoxazole ring (C19–C21/N22/O23) and the approximately planar phenyloxadiazole ring system  is 10.75 (7)°. The isoxazole and phenyloxadiazole ring systems are connected by a propyloxy unit (O15–C18), which is in a gauche conformation, with a C18—C17—C16—O15 torsion angle of −64.32 (18)°. The amide group (N26–C24) at the 3-position of the isoxazole ring which joins the C11-alkyl chain (C27–O38) and the WIN framework is likewise almost coplanar with the isoxazole ring, with a dihedral angle of 10.92 (9)° between the amide (H26/N26/C24/O25) and isoxazole planes. The amide hydrogen (H26) and the acidic isoxazole hydrogen (H20) are on opposite sides, with a torsion angle (N26—C24—C21—C20) of 172.31 (15)°. The C11-alkyl chain (C27–C37) is in an all-anti conformation, with an average torsion angle of 178.80°. The WIN framework and the C11-linker arm structural units are aligned roughly in a 160° angle and the total length of the title molecule measures up to 3.4 nm.The molecular structure of the title compound is shown in Fig. 111-alkyl chain hydroxy [O—H⋯O = 1.90 (1) Å], solvent water [O—H⋯O = 1.87 (1) Å], amide carbonyl and isoxazole hydrogen (C—H⋯O = 2.56 Å) groups of two parallel neighbouring molecules  and The title compound packs in the crystal lattice in layers, in which the molecules are held together by solvent-mediated O—H⋯O and C—H⋯O hydrogen bonds (motif 1), as well as C—H⋯N and C—H⋯O intermolecular interactions between the heterocyclic isoxazole and phenyloxadiazole units of neighbouring molecules (motif 2) Table 1. In the es Fig. 2. In a sips Fig. 2.et al., 2014et al., 2014et al., 2014et al., 2004et al., 2014et al., 2004et al., 2014et al., 2014ca 60.8°. In all of the structures, the propyloxy unit is in a gauche conformation, with torsion angles in the range 62.4–69.2°.A search of the Cambridge Structural Database propyl]-N-ethylcarbodiimide (0.19 mmol) and a catalytic amount of 1-hydroxybenzotriazole at 273 K gave the title compound in 68% yield after subsequent chromatographic purification in silica with a dichloromethane–methanol mixture (95:5 v/v). Needle-like crystals of the title compound were obtained from an ethanol solution by vapor diffusion with water.An amide coupling reaction of 5-{3-propyl}isoxazole-3-carboxylic acid  = 1.5Ueq(C) for methyl and 1.2Ueq(C) for other H atoms, and N—H = 0.88 Å and Uiso(H) = 1.2Ueq(N). The positions of the O-bound H atoms were located in a difference Fourier map and refined as riding atoms with Uiso(H) = 1.5Ueq(O). The O—H distance of the half-occupied water molecule was restrained to 0.84 (1) Å.Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989015007367/lh5758sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015007367/lh5758Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015007367/lh5758Isup3.cmlSupporting information file. DOI: 1059505CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information: interactive version of Fig. 3Enhanced figure:


The basal plane consists of two N atoms [Cu—N = 2.008 (3) and 2.032 (3) Å] from the phenanthroline ligand, and of two carboxylate O atoms [Cu—O = 1.942 (3) and 1.948 (3) Å] from two 2,3,4,5-tetrafluorobenzoate anions. Another 2,3,4,5-tetrafluorobenzoate anion provides the apical carboxylate O atom [Cu—O = 2.262 (3) Å] and bridges two CuII ions into a binuclear centrosymmetric dimer. Intramolecular π–π interactions between one of the tetrafluorobenzene rings and the middle of the phenenanthroline rings [3.617 (3) Å] stabilize the molecular configuration. O—H⋯O hydrogen bonds between the lattice water molecules and the unbound carboxylate O atoms of the metal complexes leads to the formation of a chain structure parallel to [100].In the title compound, [Cu DOI: 10.1107/S1600536814022065/wm5062Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S1600536814022065/wm5062fig1.tifx y z . DOI: x + 1, –y + 1, –z + 2.The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level for non-H atoms. The non-labelled atoms are generated by symmetry code –Click here for additional data file.10.1107/S1600536814022065/wm5062fig2.tif. DOI: The packing of the molecular entities of the title compound. O—H⋯O hydrogen-bonding interactions are indicated by dashed lines.1027857CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


II ion atom is octahedrally coordinated in diaquatris(1-ethyl-1H-imidazole)sulfatonickel(II). There are three organic ligands, two water and the sulfate anion coordinated around the NiII centre. Two complex molecules form an inversion dimer via two pairs of O—H⋯O hydrogen bonds between the coordinating sulfate anion and a water molecule in the unit cell.The Ni 4)(C5H8N2)3(H2O)2], the NiII ion is coordinated by three facial 1-ethyl-1H-imidazole ligands, one monodentate sulfate ligand and two water molecules in a slightly distorted octahedral coordination environment. In the crystal, two pairs of O—H⋯O hydrogen bonds link complex molecules, forming inversion dimers incorporating R24(8), R22(8) and R22(12) rings. The dimeric unit also contains two symmetry-unique intramolecular O—H⋯O hydrogen bonds. In addition, weak C—H⋯O hydrogen bonds, weak C—H⋯π interactions and π–π interactions with a centroid–centroid distance of 3.560 (2) Å combine to form a three-dimensional network. One of the ethyl groups is disordered over two sets of sites with occupancies in the ratio 0.586 (7):0.414 (7).In the title complex, [Ni(SO H-imidazole molecules as ligands. The title compound was prepared by the reaction of NiSO4·6H2O and 1-ethyl-1H-imidazole. The crystal structure of the title compound is presented herein.In spite of efforts in the past decades to synthesize structurally highly varying metal-organic complexes, no structures up to this point have been reported which contain the combination of a hydrophilic sulfate anion, water molecules and hydrophobic 1-ethyl-1II ion is coordinated in a slightly distorted octahedral geometry by three facially arranged 1-ethyl-1H-imidazole ligands, one monodentate sulfate ligand and two water molecules. The Ni—N bond lengths are in the range 2.0630 (16)–2.0817 (17)Å and the Ni—O bond lengths are in the range 2.1195 (15)–2.1502 (14). The Niii ion is displaced by 0.1038 (3) Å from the O1/O2/N11/N13 plane. The distances of two water O atoms O1 and O2 from the S1/O3/Ni1/N12 plane are the same within experimental error, with values of 1.520 (2) and −1.504 (2) Å, respectively. The sulfate atom O6 is displaced by only 0.144 (2) Å from the S1/O3/Ni1/N12 plane, while atoms O4 and O5 are displaced by 1.114 (2) and −1.298 (2) Å, respectively, from this plane .In the crystal, two pairs of O—H⋯O hydrogen bonds Table 1 link comds Fig. 3. In addiet al., 2004et al., 2003et al., 2009et al., 2006et al., 1995et al., 2011et al., 2002et al., 2000A search of the Cambridge Structural Database  I. DOI: 10.1107/S2056989016002863/lh5802Isup2.hklStructure factors: contains datablock(s) I. DOI: 1454040CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In the complex cation, two MnII atoms are bridged by two O atoms of two different 2-benzoylbenzoate ligands, each MnII atom being further coordinated by two 2,2′-bipyridine (bipy) ligands in a distorted octahedral environment. Within the binuclear molecule, the Mn⋯Mn separation is 4.513 (7) Å. Intermolecular C—H⋯O and C—H⋯ π interactions link the molecules into a three-dimensional network. The title compound, [Mn DOI: 10.1107/S2056989015023671/bg2577Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015023671/bg2577fig1.tifx y z . DOI: x + 1, −y, −z + 2.The molecular structure of the title compound, (displacement ellipsoids are shown at 50% probability levels). Symmetry code: (i) −Click here for additional data file.10.1107/S2056989015023671/bg2577fig2.tifc . DOI: c axis, showing O—H⋯O, C—H⋯C hydrogen bonds and C—H⋯ π, and π–π stacking interactions drawn as dotted lines.Packing view drawn along the 1014518CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In the crystal, weak C—H⋯O hydrogen bonds and weak C—H⋯π interactions connect molecules forming a three-dimensional network.In the title molecule, C 21H20ClF2NO2, the piperidine ring adopts a slightly distorted boat conformation. The two benzene rings form a dihedral angle of 87.43 (1)°. A weak intramolecular C—H⋯π interaction is observed. In the crystal, weak C—H⋯O hydrogen bonds and weak C—H⋯π interactions connect the molecules, forming a three-dimensional network.In the title molecule, C The N1—C14 [1.356 (2) Å] and C14—O1 [1.221 (2) Å] bond distances indicate the presence electron delocalization in this part of the molecule. The six-membered piperidine ring adopts a slightly distorted boat conformation. The benzene rings form a dihedral angle of 87.43 (1)°. The equatorial and axial orientation of the methyl substituents bonded to atom C2 are described by the N1—C1—C2—C6 and N1—C1—C2—C7 torsion angles of −117.45 (16)° and −57.2 (2)°, respectively. A weak intramolecular C—H⋯π interaction is observed, which involves the C8–C13 benzene ring -t-3,t-5-dimethylpiperidin-4-one [50.4 (1)°] -c-3,t-3-dimethylpiperidin-4-one [77.23 (7)°] -t-3-isopropyl-1-nitrosopiperidin-4-one [21.56°] -t-3-isopropylpiperidin-4-one [52.4 (1)°]  piperidin-4-one , and triethylamine  in benzene (20 ml), dichloroacetylchloride  in benzene (20 ml) was added dropwise for about half an hour. Stirring was continued with mild heating using a magnetic stirrer for 7 h. The progress of the reaction was monitored by TLC. After the completion of reaction, it was poured into water and extracted with ether. The collected ether extracts were then washed well with 3% sodium bicarbonate solution and dried over anhydrous Na2SO4. The pasty mass obtained was purified by crystallization from a benzene–petroleum ether solution (333–353 K) in the ratio of 95:5. X-ray quality crystals were grown by slow evaporation of an ethanol solution of the title compound at ambient temperature.The synthesis followed the procedure of Aridoss  al. 2007. To a stUiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S1600536814021278/lh5727sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814021278/lh5727Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S1600536814021278/lh5727Isup3.tifSupporting information file. DOI: Click here for additional data file.10.1107/S1600536814021278/lh5727Isup4.cmlSupporting information file. DOI: 1026047CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The ligand adopts an E conformation and the gold(I) atom displays the expected linear geometry with a Cl atom also bonded to the metal ion [Cl—Au—S = 174.23 (5)°]. One of the pyridyl rings is protonated, giving the gold complex an overall positive charge. Two solvent water molecules, one of which is located on a twofold rotation axis, and a non-coordinating chloride ion complete the structural assembly. The molecular structure is stabilized by intramolecular and intermolecular N—H⋯Cl, N—H⋯N, O—H⋯Cl and O—H⋯O hydrogen bonding.The title complex, [AuCl(C They are compounds that can coordinate to transition metals and exhibit keto–enol tautomerism  of the starting material [HPy][AuClsp hybridization of the metal.The gold(I) atom displays the expected linear geometry, with a Cl—Au—S coordination angle of 174.23 (5)°, close to the ideal angle of 180° expected for et al., 2006The C12—S1 bond length reported for di-2-pyridyl ketone phenylthiosemicarbazone is 1.676 (2) Å and it is lengthened to 1.713 (4) Å on coordination to gold; this is typical of the ketone form with a concomitant shortening of the N3—N4 bond  in 5 ml of CH3CN. A clear yellow solution was formed after heating the mixture to reflux for three h. Orange crystals deposited upon slow cooling of the solvent. Yield: 69%, m.p. 491 K. Elemental analysis, found: C, 33.71; H, 3.15; N, 10.04%; calculated for C36H38Au2Cl4N10O3S2: C, 33.87; H, 3.16; N, 10.97%. IR (νmax cm−1): 3421 (O—H), 3281 (N—H), 2927 (N—H+), 1694 (C=N), 1150 (N—N), 765 (C=S).Di-2-pyridyl ketone phenylthiosemicarbazone (1 mmol) was dissolved in about 5 ml of CHUiso = 1.5Ueq(O). Other H atoms were included in the refinement at calculated positions and treated as riding with Uiso(H) = 1.2Ueq(C).Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989015015480/zl2637sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015015480/zl2637Isup3.hklStructure factors: contains datablock(s) I. DOI: 1419509CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The asymmetric unit contains a [1-NaMePy]+ cation and one half of an Ni(imnt)22− anion. The NiII ion lies on an inversion centre and adopts a square-planar configuration with Ni—S bond lengths of 2.200 (1) and 2.216 (1) Å. In the [1-NaMePy]+ cation, the naphthyl ringsystem and the pyridinium ring make a dihedral angle of 90.0 (2)°. In the crystal, C—H⋯N and C—H⋯Ni hydrogen bonds, as well as π–π interactions between the chelate ring and the pyridinium ring [centroid–centroid distance = 3.675 (2) Å] link the ions into a three-dimensional network.A new ion-pair complex, (C Transition metal complexes with dithiolate ligands such as 2,2-dicyanoethene-1,1-dithiolate (imnt) or 1,2-dicyanoethene-1,2-dithiolate (mnt) are important molecular materials with interesting electrical conductivity, superconductivity, optical and magnetic properties 22− anion located about an inversion center. The NiS4 core exhibits a square-planar configuration, with Ni—S bond lengths of 2.200 (1) and 2.216 (1) Å. The S1—Ni1—S2 bond angle within the four-membered ring (Ni1/S1/C1/S2) is 78.91 (3)°. The N1 and N2 atoms of the C N groups deviate from the Ni1/S1/C1/S2 plane by 0.078 (3) and 0.169 (3) Å, respectively. The [1-NaMePy]+ cation adopts a conformation in which both the naphthyl ring system and the pyridinium ring are twisted with respect to the N3/C11/C10 reference plane, making dihedral angles of 10.5 (2)° and 87.3 (3)°, respectively. The naphthyl ring system and the pyridinium ring make a dihedral angle of 90.0 (2)°.The asymmetric unit of the title compound consists of one [1-NaMePy]22− anion and [1-NaMePy]+ cation. The first is a π–π contact between the chelate ring  of the anion and the pyridinium ring of the cation on Fig. 2 with a don Fig. 2. The comon Fig. 2.22− anion have been reported, typical examples being [TBA]2[Ni(imnt)2] and [4NO2BzPy]2[Ni(imnt)2]  2] [4FBzPy is 1-(4-fluorobenzyl)pyridinium] 2] (Bz2NH2Py is 1-benzyl-2-aminopyridinium) 2] [BzDMAP is 1-benzyl-4-(dimethylamino)pyridinium] 2] and [2-NaMe-4-MePy]2[Ni(imnt)2]  2] and [Bz-4-MeQl]2[Ni(imnt)2]  al., 2009. For a d al. 2013.2·6H2O, K2imnt and 1-(4-naphthylmethylene)pyridinium bromide in water  = 0.93 Å, Uiso(H) = 1.2Ueq(C) for aromatic and d(C—H) = 0.97 Å, Uiso(H) = 1.2Ueq(C) for CH2 atoms. Crystal data, data collection and structure refinement details are summarized in Table 2All H-atoms were positioned geometrically and refined using a riding model with 10.1107/S1600536814017012/kp2472sup1.cifCrystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814017012/kp2472Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S1600536814017012/kp2472Isup3.cmlSupporting information file. DOI: 1015644CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In both cases, the Pd2+ cations are coordinated by the Se and N atoms of the chelating bidentate 2-[(dimethylamino)methyl]benzeneselenolate ligand. The chloride ligand lies trans to selenium and the triphenylphosphane ligand is trans to nitrogen. The Pd—Se bond lengths in the two independent coordination environments of Pd are 2.3801 (4) and 2.3852 (4) Å, the Pd—P bond lengths are 2.2562 (8) and 2.2471 (8) Å, the Pd—N bond lengths are 2.172 (2) and 2.158 (2) Å, and the Pd—Cl bond lengths are 2.3816 (8) and 2.3801 (8) Å. The square-planar coordination around one Pd2+ cation is less distorted than that around the other.The asymmetric unit of the title compound, [PdCl(C DOI: 10.1107/S1600536814010678/nk2221Isup2.hklStructure factors: contains datablock(s) I. DOI: 1002116CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The backbone torsion angles  for β3,3-Ac6c-OH are restricted to gauche conformations in all the derivatives, with a chair conformation of the cyclohexane ring. In the crystal structure of (I), the packing of molecules shows both carboxylic acid R22(8) O—H⋯O and centrosymmetric R22(14) N—H⋯O hydrogen-bonding interactions, giving rise to chains along the c-axis direction. In (II), centrosymmetric carboxylic acid R22(8) O—H⋯O dimers are extended through N—H⋯O hydrogen bonds and together with inter-ring π–π interactions between Fmoc groups [ring centroid distance = 3.786 (2) Å], generate a layered structure lying parallel to (010). In the case of compound (III), carboxylic acid O—H⋯Npyrazine hydrogen bonds give rise to zigzag ribbon structures extending along the c-axis direction.N-Protected derivatives of 1-aminocyclohexaneacetic acid (β Valeroyl-β3,3-Ac6c-OH (I)3,3-Ac6c-OH (II)3,3-Ac6c-OH (III)In order to investigate the effect of protecting groups and disubstitution on the conformation of β-amino acids, N-protected derivatives of 1-aminocyclohexaneacetic acid 3,3-Ac6c-OH (II)3,3-Ac6c-OH (III)B —C1A and N1—C1B—C1A—C1′) adopt a gauche conformation in all three compounds . In a 3,3-disubstituted β-amino acid residue, β3,3-Ac6c-OH, the cyclohexane ring imposes a restriction on the torsion angles ϕ and θ. The protecting groups at the N-terminus of (I)trans geometry [ω0 (C4—C0′—N1—C1B) = 177.4 (2) for (I)0 (O—C0′—N1—C1B) = −175.64 (19) for (II)0 (C6—C0—N1— C1A) = −170.04 (17)° for (III)]. In the case of the N-protected tert-butyloxycarbonyl (Boc) group, the protecting group adopts a cis geometry with ω0 = 14.50° 3,3-Ac6c-OH residue and N3 of the pyrazine ring as shown in Fig. 3c. There are no intramolecular hydrogen bonding interactions observed in the crystal structures of derivatives (I)The molecular conformations of Valeroyl-βii bond pairs . In (II)c). Also present in the structure are π–π interactions between the Fmoc groups with an intercentroid distance of 3.786 (2) Å. Fig. 4c shows the aromatic rings of Fmoc groups stacked in a face-to-face and edge-to-face manner, together with inter-plane distances that are within the range for stabilizing π–π interactions s Table 1 give a cif Fig. 4a. In 3,3Ac6c-OH  was dissolved in 5 ml of a 2M NaOH solution and a solution of 5 mmol of valeric anhydride (931 mg) dissolved in 1,4-dioxane was added, after which the mixture was stirred for 4 h at room temperature. On completion of the reaction, the 1,4-dioxane was evaporated and the product was extracted with diethyl ether (3 × 5 ml). The aqueous layer was acidified with 2M HCl and extracted with ethyl acetate (3 × 10ml) and the combined organic layer was washed with brine solution. The organic layer was passed over anhydrous Na2SO4 and evaporated to give Valeroyl-β3Ac6c-OH . Single crystals were grown by slow evaporation from a solution in methanol/water.Preparation of Valeroyl-β3,3Ac6c-OH (II)3,3Ac6c-OH  was dissolved in 1M Na2CO3 solution and Fmoc-OSu  dissolved in CH3CN was added. The reaction mixture was stirred at room temperature for 6 h. After completion of the reaction, the CH3CN was evaporated and the residue was extracted with diethyl ether (3 × 10 ml). The aqueous layer was acidified with 2M HCl and extracted with ethyl acetate (3 × 15 ml). The combined organic layer was washed with brine solution. The ethyl acetate layer was passed over anhydrous Na2SO4 and evaporated. The residue was purified by crystallization in ethyl acetate/n-hexane, affording Fmoc-β3,3Ac6c-OH . Single crystals were obtained by slow evaporation from an ethyl acetate/n-hexane solution.Preparation of Fmoc-β3,3Ac6c-OH (III)2Cl2 and then 200 µl of N-methylmorpholine was added, followed by β3,3Ac6c-OMe. HCl  and EDCI. HCl  at 273 K. The reaction mixture was stirred at room temperature for 12 h. After completion of the reaction, water was added and the reaction mixture was extracted with CH2Cl2 (3 × 5ml). The combined organic layer was washed with 2M HCl (2 × 5ml), Na2CO3 (2 × 5ml) and brine solution (2 × 5ml). The organic layer was passed over anhydrous Na2SO4 and evaporated to give Pyr-β3,3Ac6c-OMe . Pyr-β3,3Ac6c-OMe  was dissolved in 2 ml of methanol and 1 ml of 2M NaOH, and the reaction mixture was stirred at room temperature for 4 h. Methanol was evaporated and the residue was extracted with diethyl ether (2 × 5ml). The aqueous layer was acidified with 2M HCl and extracted with ethyl acetate (3 × 5ml). The combined organic layer was washed with brine solution (1 × 5ml). The ethyl acetate layer was passed over anhydrous Na2SO4 and evaporated to give Pyr-β3,3Ac6c-OH . Single crystals were grown from an ethanol/water solution.Preparation of Pyr-βUiso values were refined. The remaining H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.96–0.98 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). For derivatives (II)Uiso values were refined. In (II)Pca21, the structure was inverted in the final cycles of refinement as the Flack parameter was 0.8 (14). The inverted structure gave a value of 0.2 (14) for 1585 Friedel pairs.Crystal data, data collection and structure refinement details are summarized in Table 410.1107/S1600536814020777/zs2313sup1.cifCrystal structure: contains datablock(s) I, II, III, New_Global_Publ_Block. DOI: 10.1107/S1600536814020777/zs2313Isup2.hklStructure factors: contains datablock(s) I. DOI: 10.1107/S1600536814020777/zs2313IIsup3.hklStructure factors: contains datablock(s) II. DOI: 10.1107/S1600536814020777/zs2313IIIsup4.hklStructure factors: contains datablock(s) III. DOI: Click here for additional data file.10.1107/S1600536814020777/zs2313Isup5.cmlSupporting information file. DOI: Click here for additional data file.10.1107/S1600536814020777/zs2313IIsup6.cmlSupporting information file. DOI: Click here for additional data file.10.1107/S1600536814020777/zs2313IIIsup7.cmlSupporting information file. DOI: 1024488, 1024489, 1024490CCDC references:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


By contrast to this almost  17H14PS)2], is a second monoclinic polymorph  of the previously reported monoclinic  form [Fang et al. °. By contrast to this almost syn disposition, in the C2/c polymorph, the Fe atom lies on a centre of inversion so that the S atoms are strictly anti, with a pseudo-S—P⋯P—S torsion angle of 180°. The significant difference in molecular conformation between the two forms does not result in major perturbations in the P=S bond lengths nor in the distorted tetrahedral geometries about the P atoms. The crystal packing of the new monoclinic polymorph features weak Cp—C—H⋯π(phenyl) interactions consolidating linear supramolecular chains along the a axis. These pack with no directional interactions between them.The title compound, [Fe(C al. 1995. Polyhed R3PAu(S2CNR′2), attract on-going interest owing to impressive biological activities against both cancer ferrocene (dppf), were isolated as orange needles, being a side-product of a reaction, see Synthesis and crystallization for details. Crystallography shows the title compound to be a new monoclinic polymorph of a previously described C2/c form  dithiocarbamates, 2 is shown in Fig. 12P=S units linked via the P atoms through a C5H4FeC5H4 link. The S atoms lie to the same side of the molecule and might be described as having a syn conformation. When viewed down the P⋯P axis, the S atoms are gauche with the pseudo S—P⋯P—S torsion angle being −53.09 (3)°. This represents the major difference between dppfS2 and its C2/c–dppfS2 polymorph  and Cg(C6–C10) are 1.6487 (8) and 1.6451 (8) Å, respectively, and the Cg(C1–C5)⋯Fe⋯Cg(C6–C10) angle is 178.92 (5)°. The comparable parameters for the C2/c–dppfS2 polymorph are 1.650 (3) Å and 180°, and the Cp rings are strictly staggered when viewed down the Cg(C1–C5)⋯Fe⋯Cg(C1–C5)i axis. In dppfS2, the P=S bond lengths are experimentally distinct, i.e. P1=S1 of 1.9449 (6) Å is shorter than P2=S2 of 1.9530 (6) Å, with the former being equivalent to P1=S1 of 1.9384 (18) Å in C2/c–dppfS2. Finally, the P1 and P2 atoms have distorted tetrahedral environments with the range of angles subtended at P1 of 103.94 (7)–113.78 (6)° being comparable to those subtended at P2, i.e. 105.55 (7)–114.92 (5)°; the equivalent range of angles in C2/c–dppfS2 is 104.8 (2)–114.28 (15)°. In each case, the angles involving the S atom are wider than those involving C atoms only, and the narrowest angle always involves the two ipso-C atoms.The conformational differences in the polymorphs are highlighted in the overlay diagram shown in Fig. 2a axis. Based on the distance criteria employed in PLATON C5H4FeC5H4P(=Y)Ph2, Y = 0, O, S and Se, have been described in the crystallographic literature. The parent compound, i.e. with Y = lone pair, has the Fe atom situated on a centre of inversion C5H4FeC5H4P(=Y)Ph2, Y = 0, O, S and Se, compounds suggesting a low energy barrier for the interchange from one conformation to another. The structural data for Ph2P(=Y)C5H4FeC5H4P(=Y)Ph2 are summarized in Table 2The structures of several oxidation products of dppf, Ph2 molecule can function as a ligand in metal complexes, often forming zero-dimensional mononuclear species  and CS2 (84.6 µl) were added. Chloroform (150 ml) was then added and the reaction mixture was stirred for 2 h. A second solution containing bis[chloridogold(I)] (1.4 mmol) was prepared by dissolving potassium tetrachloridoaurate(III) (1.06 g) in a solvent mixture of acetone and water . Drop-wise addition of sodium sulfite (0.71 g) in water (10 ml) followed. Upon discolouration, bis(diphenylphosphane)ferrocene  in chloroform (25 ml) was added. After stirring for 15 mins, the resulting gold precursor was extracted with chloroform (150 ml). Acetonitrile (50 ml) was added to this to form solvent mixture of chloroform and acetonitrile (3:1). The solution containing the dithiocarbamate was added to that containing the gold precursor. The resulting mixture was stirred for 3 h. and then filtered. After three weeks, orange needles appeared, along with the precipitate, and these were subjected to the crystallographic study. Yield: 0.0890 g, 10.3% (based on dppf). M.p.: 519.5–519.9 K. IR: ν(P=S) 628 (m).Two solutions were prepared. Firstly, a solution sodium salt of piperazine dithiocarbamate (0.7 mmol) was prepared by dissolving piperazine (0.0582 g) in acetonitrile (50 ml). NaOH (112 µl of 50% Uiso(H) set to 1.2Uequiv(C).Crystal data, data collection and structure refinement details are summarized in Table 310.1107/S2056989015012682/hg5450sup1.cifCrystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015012682/hg5450Isup2.hklStructure factors: contains datablock(s) I. DOI: 1409866CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In the crystal, the canagliflozin molecules and lattice water molecules are connected  A and B) and one water molecule in the asymmetric unit of the title compound, C24H25FO5S·0.5H2O [systematic name: -2-(3-{[5-(4-fluorophenyl)thiophen-2-yl]methyl}-4-methylphenyl)-6-(hydroxymethyl)-3,4,5,6-tetrahydro-2H-pyran-3,4,5-triol hemihydrate]. The dihedral angles between the methylbenzene and thiophene rings are 115.7 (4) and 111.7 (4)°, while the dihedral angles between the fluorobenzene and thiophene rings are 24.2 (6) and 20.5 (9)° in molecules A and B, respectively. The hydropyran ring exhibits a chair conformation in both canagliflozin molecules. In the crystal, the canagliflozin molecules and lattice water molecules are connected via O—H⋯O hydrogen bonds into a three-dimensional supramolecular architecture.There are two canagliflozin molecules ( The conformational difference is also shown by the angle C10—C11—C12, which is 115.7 (4)° in molecule A and 111.7 (4)° in molecule B. The terminal aromatic rings (C1–C6) are inclined to the thiophene rings, forming dihedral angles of 24.2 (6) and 20.5 (9)° in molecules A and B, respectively. The tetrahydropyran rings exhibit a distorted chair conformation in both molecules A and B.The conformations of the two canagliflozin molecules are somewhat different with regard to the orientation of the central benzene ring (C12–C17) with respect to the thiophene ring, as indicated by torsion angles C9B—H3B1⋯O4Bi, O2B–H2B1⋯O4Aiii, and O5B—H5B1⋯O3Biv  link canagliflozin molecules, generating a ring of graph-set motif B—H4B⋯O6, O6—H61⋯O2A and O4A—H4A⋯O5Bii  hydrogen bonds propagating along the a axis; the chains are stacked along the c axis by further hydrogen-bonding interactions, O3A—H3A1⋯O2Bi and O2A–-H2A1⋯O2Bi  = 1.2Ueq or 1.5Ueq(carrier atom).Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989016006769/xu5886sup1.cifCrystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016006769/xu5886Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989016006769/xu5886Isup3.cmlSupporting information file. DOI: 1475516CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The title complex is composed of saddle-shaped molecules which closely interact in a pairwise fashion through π–π and C—H⋯π contacts to form ‘dimers’. These ‘dimers’ further interact through C—H⋯S and C—H⋯π contacts to construct a complex three-dimensional extended structure. 20H12S4, (I), also known as exTTF, is reported. The molecular structure of (I) consists of a dihydroanthracene moiety with two 1,3-dithiol-2-ylidene substituents. This is a saddle-shaped molecule, which interacts with a close neighbor through various π–π and C—H⋯π contacts to form a ‘dimer’. These ‘dimers’ interact through a series of C—H⋯S and C—H⋯π contacts to construct a complex three-dimensional extended structure.The crystal structure of the well-studied 9,10-bis-9,10-dihydroanthracene molecule, C The molecule is saddle shaped in that the 1,3-dithiol-2-ylidene groups bend significantly up out of the plane of the central ring and the two benzene rings of dihydroanthracene moiety bend down out of the plane, Fig. 1b. The central six-membered ring (C4–C5–C10–C11–C12–C17) is in a boat conformation in which the 1,3-dithiol-2-ylidene-substituted carbon atoms [C4 and C11] are bent out of the plane defined by C5, C10, C12, and C17. The torsion angles C10—C12—C17—C4 = 17.97 (12)° and C17—C5—C10—C11 = 17.22 (16)° for these two carbon atoms are quite similar.The molecular structure of (I)The benzene rings bend out of the C5–C10–C12–C17 plane; the dihedral angle between this plane and the plane of the C5–C6–C7–C8–C9–C10 ring is 17.72 (15)° while the dihedral angle for the C12–C13–C14–C15–C16–C17 ring is 20.14 (13)°. The 1,3-dithiol-2-ylidene groups are bent more sharply out of the C5-C10-C12-C17 plane as evidenced by the torsion angles C3—C4—C5—C10 τ = 138.06 (15)° and C18—C11—C12—C17 τ = 139.23 (15)°. The five-membered rings both adopt an envelope conformation with the carbon atom bonded to the dihydroanthracene [C3 and C18] being the one puckered out of the plane. The torsion angles C3—S1—C1—C2 τ = −8.09 (14)° and C18—S4—C20—C19 τ = −6.65 (15)° show that the bend in each ring is fairly similar.The average C—C bond length within the benzene rings  is 1.391 Å as is typical of phenyl rings. The length of the edges shared with the central ring are slightly longer C5—C10 = 1.419 (2) Å and C12—C17 = 1.412 (2) Å. The remaining C—C distances making up the central ring are longer still with an average of 1.477 Å. Since the distances within the central ring are in between those of typical C—C single and double bonds; this supports the idea of a highly delocalized bonding motif throughout the dihydroanthracene ring system. The bond distances between the dihydroanthracene and the 1,3-dithiol-2-ylidene groups are on the order of typical C=C bonds, C3=C4 = 1.360 (2) Å and C11=C18 = 1.361 (2) Å.i–C2i–S2i–C3i–S1i ring  and is rather long at 4.068 (15) Å. There are five C—H⋯π interactions between the two molecules in which atoms H1 and H2 of one molecule interact with various π systems of the neighbor. The shortest contact is between H1 and the C11i=C18i double bond at 2.606 (12) Å . There is another short contact between H1 and the central ring of the dihydroanthracene, H1⋯centroid (C4i–C5i–C10i–C11i–C12i–C17i) 2.852 (11) Å. Two other C—H⋯π interactions involve H1; H1⋯centroid (C18i–S3i–C19i–C20i–S4i) 3.167 (11) Å, and H1⋯centroid (C5i–C6i–C7i–C8i–C9i–C10i) 3.553 (15) Å. The fifth interaction between the ‘dimer’ molecules is H2⋯centroid (C5i–C6i–C7i–C8i–C9i–C10i) 3.222 (12) Å.Through a series of C—H⋯π and π–π interactions, each molecule of (I)ii 2.922 (12) Å and one C—H⋯π contact H14⋯centroid (C5ii–C6ii–C7ii–C8ii–C9ii–C10ii) 3.779 (17) Å . H15 also interacts with two groups on a neighboring molecule through two C—H⋯π contacts; H15⋯centroid (C12iii–C13iii–C14iii–C15iii–C16iii–C17iii) 3.385 (17) Å and H15⋯centroid (C4iii–C5iii–C10iii–C11iii–C12iii–C17iii) 3.543 (14) Å . It should be noted that the molecules generated by symmetry operations (ii) and (iii) form a ‘dimer’. The final interaction involving a CH group on the dihydroanthracene is H6⋯centroid (S1iv–C1iv–C2iv–S2iv–C3iv) 2.865 (11) Å . Taking these interactions into account, a two-dimensional layered structure is formed ed Fig. 3 in whichv–C6v–C7v–C8v–C9v–C10v) 2.829 (18) Å, H19⋯centroid (C4v–C5v–C10v–C11v–C12v–C17v) 3.301 (11) Å, and H20⋯centroid (C12v–C13v–C14v–C15v–C16v–C17v) 2.767 (11) Å . These hydrogen atoms also interact with another molecule via C—H⋯S contacts; H19⋯S4vi 3.367 (12) Å and H20⋯S3vi 3.288 (14) Å [symmetry operation: (vi) −x, y + 0.5, −z + a axis to form a three-dimensional extended structure, Fig. 4There are also five C—H⋯S and C—H⋯π interactions in which the CH group involved resides on the 1,3-dithiol-2-ylidene portion of (I)et al., 1990P21/c) and has a similar saddle shape. It also appears to form similar ‘dimers’ in which there are both C—H⋯π and π–π interactions between the two molecules.Many derivatives of (I)−1 less stable than the predicted favorite. The study details π–π stacking between two of the dithiol rings, C—H⋯π contacts between the dithiol H atoms and the anthracene rings, π–π stacking between anthracene units, as well as an interaction between the partial positive charge of the S atoms and the anthracene rings for the preferred computational ‘dimer’. The study briefly describes the C—H⋯π and π–π interactions found in (I)A recent computational study focused on predicting the most energetically favored ‘dimers’ of (I)et al., 1989The title complex, 9,10-bis-9,10-dihydroanthracene (I)Uiso(H) = 1.2Ueq(C).Crystal data, data collection and structure refinement details are summarized in Table 110.1107/S2056989015020800/bg2573sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020800/bg2573Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015020800/bg2573Isup3.cdxSupporting information file. DOI: Click here for additional data file.10.1107/S2056989015020800/bg2573Isup4.cmlSupporting information file. DOI: 1434765CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The components of the 2:1 co-crystal are linked by hydroxy-O—H⋯N(pyridyl) hydrogen bonds into a three-molecule aggregate having the shape of the letter Z. These are connected into a supramolecular ladder by tight amide-N—H⋯O(nitro) hydrogen bonds. 7H5NO4·C14H14N4O2, in which the complete diamide molecule is generated by crystallographic inversion symmetry, features a three-molecule aggregate sustained by hydroxyl-O—H⋯N(pyridyl) hydrogen bonds. The p-nitrobenzoic acid molecule is non-planar, exhibiting twists of both the carboxylic acid and nitro groups, which form dihedral angles of 10.16 (9) and 4.24 (4)°, respectively, with the benzene ring. The diamide molecule has a conformation approximating to a Z shape, with the pyridyl rings lying to either side of the central, almost planar diamide residue (r.m.s. deviation of the eight atoms being 0.025 Å), and forming dihedral angles of 77.22 (6)° with it. In the crystal, three-molecule aggregates are linked into a linear supramolecular ladder sustained by amide-N—H⋯O(nitro) hydrogen bonds and orientated along [10-4]. The ladders are connected into a double layer via pyridyl- and benzene-C—H⋯O(amide) interactions, which, in turn, are connected into a three-dimensional architecture via π–π stacking interactions between pyridyl and benzene rings [inter-centroid distance = 3.6947 (8) Å]. An evaluation of the Hirshfeld surfaces confirm the importance of intermolecular interactions involving oxygen atoms as well as the π–π interactions.The title 2:1 co-crystal, 2C The results of this investigation are reported herein.Arguably, the most prominent motivation for the study of co-crystals relates to their potential applications in the pharmaceutical industry whereby co-crystals of active pharmaceutical ingredients (APIs) formed with generally regarded as safe (GRAS) co-crystal coformers might provide drugs with enhanced useful properties, p-nitrobenzoic acid molecule  in a general position, and a N,N′-bis(pyridin-3-ylmethyl)ethanediamide molecule  situated about a centre of inversion. This results in the 2:1 co-crystal stoichiometry.The title co-crystal, Fig. 1A2/a: Tonogaki et al., 1993P21/m: Bolte, 2009Twists are noted in the acid molecule so that the dihedral angle between the benzene ring and the non-hydrogen atoms of the carboxylic acid group is 10.16 (9)°. The comparable angle involving the nitro group is 4.24 (4)°, consistent with a smaller twist. The substituents have a conrotatory disposition forming a dihedral angle of 13.50 (8)°. The crystal structure of the free acid was first reported almost fifty years ago  Å in the title co-crystal.The diamide features an essentially flat central residue with the r.m.s. deviation for the eight non-hydrogen atoms  being 0.025 Å. This planar arrangement allows for the formation of intramolecular amide-N—H⋯O(amide) hydrogen bonds Table 2. The pyret al., 20085NO⋯HNC2NC3N}2 supramolecular rings, Fig. 2i.e. Cg(pyridyl)⋯Cg(benzene)i = 3.7214 (8) Å, with an angle of 4.69 (7)° between the rings; symmetry operation: (i) 2 − x, 1 − y, 1 − z. The connections between the layers to consolidate the three-dimensional architecture, Fig. 4i.e. Cg(pyridyl)⋯Cg(benzene)ii = 3.6947 (8) Å with an angle of inclination = 4.69 (7)°; symmetry operation: (ii) 2 − x, 2 − y, 1 − z.In the packing, the anticipated  interaction and the similar long spike at the same ed + id distance in the lower right region indicates the contribution of the amide-N—H⋯O(nitro) interaction. The donor–acceptor contributions of these co-crystal constituents are highlighted with the label ‘d′ in the fingerprint plot, Fig. 7i.e. 32.3%, to the Hirshfeld surface of the acid, a smaller contribution, i.e. 8.3%, is provided by the diamide; the reverse is true for for the O⋯H contacts, i.e. 8.5 and 30.4%, respectively. The overall fingerprint plot for the co-crystal when delineated into O⋯H/H⋯O contacts leads to the pair of spikes corresponding to donors and acceptors with a 37.1% contribution to surface  and amide-N—H⋯O(nitro) interactions between the pair of acid molecules and a diamide molecule can be observed through their corresponding Hirshfeld surfaces mapped over the electrostatic potential, Fig. 5i.e. the enrichment ratio, ER  hydrogen bonding was observed  hydrogen bonding is seen along with hydroxy-O—H⋯N(pyridyl) hydrogen bonding 2C6H3CO2− anion , prepared in accord with the literature procedure (Schauer Uiso(H) set to 1.2Uequiv(C). The oxygen- and nitrogen-bound H-atoms were located in a difference Fourier map but were refined with distance restraints of O—H = 0.84±0.01 Å and N—H = 0.88±0.01 Å, and with Uiso(H) set to 1.5Ueq(O) and 1.2Ueq(N).Crystal data, data collection and structure refinement details are summarized in Table 610.1107/S2056989015024068/hb7557sup1.cifCrystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015024068/hb7557Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015024068/hb7557Isup3.cmlSupporting information file. DOI: 1442547CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In the title chalcone derivative, molecules are linked into a three-dimensional network by C—H⋯O hydrogen bonds and aromatic π–π stacking interactions are also observed. The intermolecular interactions in the crystal structure were quantified and analysed using Hirshfeld surface analysis. 16H11ClF2O2, the enone group adopts an E conformation. The dihedral angle between the benzene rings is 0.47 (9)° and an intramolecular C—H⋯F hydrogen bond closes an S(6) ring. In the crystal, molecules are linked into a three-dimensional network by C—H⋯O hydrogen bonds and aromatic π–π stacking interactions are also observed [centroid–centroid separation = 3.5629 (18) Å]. The intermolecular interactions in the crystal structure were quantified and analysed using Hirshfeld surface analysis.In the title chalcone derivative, C The molecule is slightly twisted at the C9—-C10 bond with a C8—C9—C10—C15 torsion angle of −2.2 (4)° and a maximum deviation of 0.193 (16) Å for atom O1. The dihedral angle between the terminal benzene rings (C1–C6 and C10–C15) is 0.47 (9)°. The least-squares plane through the enone moiety (O1/C7–C9) makes dihedral angles of 2.87 (14) and 3.33 (14)° with the C1–C6 and C10–C15 benzene rings, respectively. An intramolecular C8—H8A⋯F1 hydrogen bond (Table 1S(6) ring motif. The bond lengths and angles are comparable with the equivalent data for previously reported structures; d Table 1 is observia C2—H2A⋯O1 , centroid-to-centroid distance = 3.5629 (18) Å, where Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively].In the crystal, molecules are linked into a three-dimensional network s Table 1, as showCrystal Explorer 3.1 with neighbouring molecules connected by C2—H2A⋯O1 and C3—H3A⋯O2 hydrogen bonds. This finding is corroborated by Hirshfeld surfaces mapped over the electrostatic potential  showing the negative potential around the oxygen atoms as light-red clouds and the positive potential around hydrogen atoms as light-blue clouds.The strong C—H⋯O interactions are visualized as bright-red spots between the respective donor and acceptor atoms on the Hirshfeld surfaces mapped over rm Fig. 3a with nal Fig. 3b showined = id ∼1.4 Å  with overall Hirshfeld surfaces of 27.5%. The contribution from the O⋯H/H⋯O contacts, corresponding to C—H⋯O interactions, is represented by a pair of sharp spikes characteristic of a strong hydrogen-bond interaction having almost the same ed + id ∼2.3 Å .Significant intermolecular interactions are plotted in Fig. 4 Å Fig. 4a with o Å Fig. 4b.ed = id ∼1.8 Å . The presence of the π–π stacking interactions is also indicated by the appearance of red and blue triangles on the shape-indexed surfaces, identified with black arrows in Fig. 5The C⋯C contacts, which refer to π–·π stacking interactions, contribute 13.7% of the Hirshfeld surfaces. This appears as a distinct triangle at around  Å Fig. 4c. The pA mixture of 3-fluoro-4-methoxyacetophenone  and 2-chloro-6-fluorobenzaldehyde  was dissolved in methanol (20 ml). A catalytic amount of NaOH  was added to the solution dropwise with vigorous stirring. The reaction mixture was stirred for about 5–6 h at room temperature. After stirring, the contents of the flask were poured into ice-cold water (50 ml) and the resulting crude solid was collected by filtration. Brownish blocks of (I)Uiso(H) = 1.2Ueq(C). In the final refinement, the most disagreeable reflection (020) was omitted.Crystal data collection and structure refinement details are summarized in Table 210.1107/S2056989016006526/hb7578sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989016006526/hb7578Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989016006526/hb7578Isup3.cmlSupporting information file. DOI: 1474605CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In [Cu(Hspar)2](bdc)·2H2O,the Cu2+ ion lies on a crystallographic inversion centre and a CuO4 square-planar geometry arises from its coordination by two O,O′-bidentate Hspar molecules. The bdc dianion acts as a counter-ion to the cationic complex and does not bond to the metal ion.The Mn 2O,O′)bismanganese(II) dihydrate, [Mn(C8H4O4)(C19H22F2N4O3)2(H2O)0.25]·2H2O or [Mn(bdc)(Hspar)2(H2O)0.25]·2H2O, (I), and biscopper(II) benzene-1,4-dicarboxylate dihydrate, [Cu(C19H22F2N4O3)2](C8H4O4)·2H2O or [Cu(Hspar)2](bdc)·2H2O, (II), are reported . The Mn2+ ion in (I) is coordinated by two O,O′-bidentate Hspar neutral molecules (which exist as zwitterions) and an O,O′-bidentate bdc dianion to generate a distorted MnO6 trigonal prism. A very long bond [2.580 (12) Å] from the Mn2+ ion to a 0.25-occupied water molecule projects through a square face of the prism. In (II), the Cu2+ ion lies on a crystallographic inversion centre and a CuO4 square-planar geometry arises from its coordination by two O,O′-bidentate Hspar molecules. The bdc dianion acts as a counter-ion to the cationic complex and does not bond to the metal ion. The Hspar ligands in both (I) and (II) feature intramolecular N—H⋯O hydrogen bonds, which close S(6) rings. In the crystals of both (I) and (II), the components are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, generating three-dimensional networks.The syntheses and crystal structures of 0.25-aqua(benzene-1,4-dicarboxylato-κ As well as their biological significance, this class of compounds is of interest in coordination chemistry due to their potential to act as multi-dentate and bridging ligands in the construction of mononuclear and dinuclear complexes  complexes with nickel  with BF4− 0.25]·2H2O (I)2](bdc)·2H2O (II)8H4O42−).As a continuation of these studies, we now describe the syntheses and crystal structures of the title mixed-ligand complexes  Mn—O bond to the partly occupied O13 water molecule. Together, these lead to a distorted MnO6+1 trigonal–prismatic polyhedron n Table 1 with theds Fig. 2. The meads Fig. 2 for the 2 groups mutually syn.The conformation of the –O2–C1–C2–C3–O3–Mn1– chelate ring approximates to a shallow envelope with the metal atom as the flap, displaced by −0.222 (4) Å from the mean plane of the ligand atoms (r.m.s. deviation = 0.022 Å). The –O5–C20–C21–C22–O6–Mn1– ring can be described in the same way, with Mn1 displaced by 0.128 (4) Å from the other atoms (r.m.s. deviation = 0.019 Å). The dihedral angle between the near-planar segments of the chelate rings is 29.74 (13)°. Both Hspar molecules are orientated in the same sense with respect to the metal ion, with the NH6+1 grouping is unusual and calls for some further comment: the dihedral angle between the top (O3/O6/O8) and bottom (O2/O5/O7) triangular faces of the prism is 14.40 (11)°, which is largely due to the O7⋯O8 edge of the prism (the two O atoms of the bdc dianion) being much shorter [2.174 (3) Å] than the O2⋯O3 [2.799 (3) Å] and O5⋯O6 [2.802 (3) Å] edges, which correspond to the C1- and C-20 Hspar molecules, respectively. The metal atom is displaced from the top and bottom faces of the prism by −1.2513 (14) and 1.3670 (12) Å, respectively. The degree of twist of the prism may be estimated from the pseudo torsion angles involving the centroids of the triangular faces (denoted X1 for the O3/O6/O8 face and X2 for the O2/O5/O7 face) and the pairs of atoms forming the edges of the prism: values of X1⋯O7⋯O8⋯X2 (–14.6), X1⋯O5⋯O6⋯X2 (–11.2) and X1⋯O2⋯O3⋯X2 (–8.5°) arise. These angles would be zero for a perfect triangular prism.The capped trigonal–prismatic geometry of the MnOsp2 hybridization for this atom. The dihedral angle between the N2 ring and the C5 ring (r.m.s. deviation = 0.028 Å), which are fused at the C4—C9 bond, is 7.9 (2)°, indicating a substantial puckering to the quinolone system. The piperazinium ring adopts a typical chair conformation with the exocyclic N—Cq (q = quinolone) bond in an equatorial orientation. The dihedral angle between the four C atoms that form the ‘seat’ of the chair and the C5 ring is 60.3 (2)°. There was some suggestion that atoms C14 and C17 of this ring are positionally disordered, but refinements that attempted to model this effect were inconclusive.The most important geometrical features of the first Hspar molecule (containing C1) are as follows: the C1—O1 and C1—O2 bond lengths of 1.251 (4) and 1.256 (4) Å, respectively, are typical for a delocalized carboxylate group and the dihedral angle between C1/O1/O2 and the adjacent N2-containing ring (r.m.s. deviation = 0.045 Å) is 8.6 (8)°. The dihedral angle between the cyclopropane ring and the N2 ring is 67.5 (3)°. The N2 bond-angle sum of 359.8° is consistent with a bonding model of S(6) ring. The C45/O7/O8 and C46/O9/O10 carboxylate groups of the bdc dianion are rotated by 3.90 (7) and 25.28 (14)°, respectively with respect to the central ring plane. The O7—Mn1—O8 bite angle is 56.58 (8)°.The second Hspar molecule (containing C20) has a broadly similar geometry: the C20—O4 and C20—O5 bond lengths are 1.254 (4) and 1.257 (4) Å, respectively, and the dihedral angle between C20/O4/O5 and the N6 ring (r.m.s. deviation = 0.050 Å) is 8.8 (7)°. The dihedral angle between the N6 (bond-angle sum = 359.7°) ring and the pendent three-membered ring is 69.8 (2)°. The N6 and C24 rings (r.m.s. deviation for the latter = 0.020 Å), fused at the C23—C28 bond, are tilted by 8.1 (2)°. The piperazine ring adopts a chair conformation and the dihedral angle between the chair seat and the C24 ring is 58.71 (9)°. Each Hspar molecule features an intramolecular N—H⋯O hydrogen bond Table 2, which c2+ cation lying on a crystallographic inversion centre, a neutral, zwitterionic, Hspar molecule, half a bdc dianion and a water molecule of crystallization on Fig. 3.O,O-bidentate Hspar molecules in the usual bonding mode of quinoline O atom + syn-carboxylate O atom  with a bite angle of 93.24 (8)°, which generates a six-membered chelate ring. The result is a CuO4 square-planar coordination polyhedron (Table 3The copper ion in (II)n Table 3 with a mIn the Hspar molecule, the C1—O1 and C1—O2 bond lengths are distinctly different at 1.226 (4) Å and 1.283 (4) Å, respectively, unlike the situation in (I)In the bdc dianion, the C23/O4/O5 carboxylate group is rotated by 2.7 (6)° with respect to the aromatic ring plane. The C23—O4 and C23—O5 bond lengths of 1.244 (4) and 1.253 (4) Å, respectively, are consistent with the approximately equal delocalization of the negative charge over both C—O bonds.In the crystal of (I)In (II)2+ ions and Hspar molecules. The O,O-chelating mode of the Hspar molecules is normal for other divalent transition metals ] : as these authors note, the high-spin d5 electronic configuration of Mn2+ is the ‘least unexpected’ to show a trigonal–prismatic geometry because it has no crystal-field stabilization energy, which normally favours octahedral over trigonal–prismatic geometry ] have almost the same energy and the trigonal–prismatic geometry is adopted in the crystal because of favourable packing interactions 2]2+ cations seen here. In [Cu(H2spar)(H2O)(phen)]BF4·3H2O  and the N,N-bidentate phen ligand in a square-planar arrangement; the water molecule completes the square-based pyramidal coordination polyhedron in the apical site. Finally, in the novel bimetallic complex [Cu2(spar)4]·4H2O  Å] arising from the –NH2 group of an adjacent spar− anion generating a centrosymmetric, bimetallic assembly. It is thus notable that sparfloxacin can bind to Cu2+ ions in its anionic, neutral and cationic forms and we are continuing our explorations of these systems.Compound (II)3CO2)2·4H2O (0.25 mmol), sparfloxacin (0.5 mmol), 1,4-benzenedicarboxylic acid (0.25 mmol), sodium hydroxide (1 mmol) and water (15 ml) was stirred for 30 minutes in air. The mixture was placed in a sealed 25 ml Teflon-lined hydrothermal reactor and heated to 423 K for 72 h under autogenous pressure. Upon cooling, colourless prisms of (I)46H52.5MnF4N8O12.25: C 52.90 (52.63), H 5.07 (4.91), N 10.73 (10.58). IR : br3420, br3300, s1633 (C=O pyridone), s1562 (CO2asym), s1443, s1375 (CO2symm), s1292, w1184, m819, m756, m686, m517 [IR assignments following Llinàs et al. (2008To prepare (I) al. 2008].3CO2)2]·H2O (0.25 mmol) used in place of the manganese acetate tetrahydrate and the vessel heated to 413 K for 72 h. Upon cooling, green blocks of (II)46H50CuF4N8O12: C 52.80 (52.70), H 4.82 (4.72), N 10.71 (10.64). IR : br3427, br3304, s1633 (C=O pyridone), s1556 (CO2asym), s1435, s1358 (CO2symm), s1294, w1182, w1012, w928, w814, m748, m527.Compound (II)Both (I)Uiso(H) = 1.2–1.5Ueq(C) applied. The N- and O-bound H atoms were located in difference maps and refined as riding atoms in their as-found relative positions.Crystal data, data collection and structure refinement details for (I)10.1107/S205698901502424X/sj5492sup1.cifCrystal structure: contains datablock(s) I, II, global. DOI: 10.1107/S205698901502424X/sj5492Isup2.hklStructure factors: contains datablock(s) I. DOI: 10.1107/S205698901502424X/sj5492IIsup3.hklStructure factors: contains datablock(s) II. DOI: 932077, 932078CCDC references:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The central cyclohexane ring has a chair conformation. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions, forming layers parallel to (100). 28H22O5S3, the central cyclohexane ring adopts a chair conformation. The atoms of the furan ring attached to the 6-position of the central cyclohexane ring are disordered over two sets of sites with occupancies of 0.832 (5) and 0.168 (5). The hydroxy group is disordered over two positions (at the 4- and 6-positions of the cyclohexane ring) in the ratio 0.832 (5):0.168 (5). In the crystal, molecules are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions, forming layers parallel to (100).In the title compound, C The resulting product is a racemate crystallizing in a centrosymmetric space group.Domino or cascade reactions have many applications in organic chemistry (Tietze QT = 0.586 (3) Å, θ = 0.0 (3)° and φ = 169 (17)°]. The mean plane of this ring makes dihedral angles of 80.42 (14), 59.57 (17), 85.65 (17), 66.82 (19), 84.88 (18) and 83.1 (8)°, respectively, with the five associated five-membered rings .In the title compound, Fig. 1a- and b-axis directions, Figs. and 3. Short S3⋯S3ii contacts  at 3.5210 (12) Å may also contribute to the crystal packing  method -2,6-bis(furan-2-yl)-4-hydroxy-4-(thiophen-2-yl)cyclohexane-1,3-diyl]bis(thiophen-2-ylmethanone) was synthesized according to a literature method  were found from a difference Fourier map and their positions were constrained to the expected geometries [C—H = 0.95±0.02 Å] with a fixed U value of 0.05 Å2. All other H atoms were placed in calculated positions  and refined using a riding model with Uiso(H) = 1.2Ueq(carrier).Crystal data, data collection and structure refinement details are summarized in Table 310.1107/S2056989016009452/sj5500sup1.cifCrystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989016009452/sj5500Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989016009452/sj5500Isup3.cmlSupporting information file. DOI: 1484675CCDC reference: crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In this article we report a synthetic procedure and structure of the novel dinuclear copper(II) complex, with a bridging oxalodihydroxamate ligand and terminal 2,2′-bipyridine and DMSO ligands completing the square pyramidal coordination spheres of the Cu(II) centres.. 2(C2H2N2O4)(C10H8N2)2(C2H6OS)2](ClO4)2, contains two copper(II) ions, connected through an N-deprotonated oxalodihydroxamic acid dianion, two terminal 2,2′-bipyridine ligands, and two apically coordinating dimethylsulfoxide molecules. Two non-coordinating perchlorate anions assure electrical neutrality. The copper(II) ions in the complex dication [Cu2(C10H8N2)2(μ-C2H2N2O4)(C2H6SO)2]2+ are in an O2N3 square-pyramidal donor environment, the Cu–Cu separation being 5.2949 (4) Å. Two hydroxamate groups in the deprotonated oxalodihydroxamic acid are located trans to one each other. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the complex cations to the perchlorate anions. Further C—H⋯O hydrogen bonds combine with π–π contacts with a centroid-to-centroid separation of 3.6371 (12) Å to stack the molecules along the a-axis direction.The centrosymmetric binuclear complex, [Cu The twoet al., 2000et al., 2003et al., 2004et al., 2000et al., 1999The C—N and C—C bond lengths in the 2,2′-bipyridine ligands are also normal for 2-substituted pyridine derivatives  Å to stack the cations along the a-axis direction, Fig. 2In the crystal structure, O5—H5trans-form. The bond lengths in oxalodihydroxamic acid itself and in its ammonium and thallium salts do not differ significantly [C—C bonds are in the range 1.51 (2)–1.528 (3) Å, C=O 1.231 (3)–1.248 (3) Å, C—N 1.310 (4)–1.33 (2) Å while the N—O bond lengths vary from 1.36 (2) to 1.388 (1) Å; Lowe-Ma & Decker, 1986et al., 1987et al., 1991II complexes with ligands derived from doubly or triply deprotonated oxalodihydroxamic acid. In one of these complexes 2·6H2O in 10 ml of DMSO the solution of 2,2′-bipyridine  in 10 ml of methanol was added upon stirring. The resulted solution was stirred for 1 h and then left for slow evaporation.To the warm mixture containing 0.060 g (0.5 mmol) of oxalodihydroxamic acid and 0.370 g (1 mmol) of Cu of the title compound.Uiso = 1.2–1.5 Ueq(parent atom). The highest peak is located 0.99 Å from atom Cu1 and the deepest hole is located 0.82 Å from atom Cu1.Crystal data, data collection and structure refinement details are summarized in Table 310.1107/S2056989016000050/sj5487sup1.cifCrystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989016000050/sj5487Isup2.hklStructure factors: contains datablock(s) I. DOI: 1445115CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


III ion in the title compound is coordinated by six N atoms of three chelating 1,2-cyclohexanediamine (chxn) ligands, displaying a distorted octahedral environment. The crystal packing is stabilized by extensive hydrogen-bonding interactions between the N—H groups of the chxn ligands, O—H groups or O atoms of the water molecules, chloride ions and Cl atoms of the disordered [ZnCl4]2− anions.The Cr rac-chxn)3][ZnCl4]Cl·3H2O , has been determined from synchrotron data. The CrIII ion is coordinated by six N atoms of three chelating chxn ligands, displaying a slightly distorted octahedral coordination environment. The distorted tetrahedral [ZnCl4]2− anion, the isolated Cl− anion and three lattice water molecules remain outside the coordination sphere. The Cr—N(chxn) bond lengths are in a narrow range between 2.0737 (12) and 2.0928 (12) Å; the mean N—Cr—N bite angle is 82.1 (4)°. The crystal packing is stabilized by hydrogen-bonding interactions between the amino groups of the chxn ligands and the water molecules as donor groups, and O atoms of the water molecules, chloride anions and Cl atoms of the [ZnCl4]2− anions as acceptor groups, leading to the formation of a three-dimensional network. The [ZnCl4]2− anion is disordered over two sets of sites with an occupancy ratio of 0.94:0.06.The structure of the title double salt, [Cr( The synthetic procedures, crystal structures and detailed spectroscopic properties of such [Cr(chxn)3]3+ complexes with chloride or nitrate anions have been reported previously 6][ZnCl4]Cl 2(cyclam)][ZnCl4]Cl·H2O 3][ZnCl4]Cl·3H2O, (I)3]Cl3·2H2O with 98 K synchrotron data to determine the exact composition and coordination geometry of the CrIII ion. The complex crystallizes in the space group Id with eight formula units in a cell of dimensions a = 18.893 (3) and c = 14.069 (3) Å. The Cr—N(chxn) bond lengths are in the range 2.0723 (19) to 2.0937 (19) Å, and the N—Cr—N bite angles are in the range 82.53 (7) to 82.69 (10)°. In comparison with the bond lengths and angles of the structure of this complex determined with 223 K data rac-chxn)3]3+, three lattice water molecules, together with one tetrahedral [ZnCl4]2− and one isolated Cl− counter-ion. The nitrogen atoms of the three 1,2-cyclohexanediamine ligands define a distorted octahedral coordination environment around the Cr(III) ion with a mean N—Cr—N bite angle of 82.1 (4)°. The resulting five-membered chelate rings of chxn ligands have the expected stable gauche conformation. The Cr—N(chxn) bond lengths are in the range 2.0737 (12) to 2.0928 (12) Å, in good agreement with those determined in [Cr(RR-chxn)3](NO3)3·3H2O 3]Cl3·2H2O 3](NO3)3·3H2O 3]Cl3·2H2O 3][Co(SS-chxn)3]Cl6·4H2O 3]Cl3·2H2O was prepared according to the literature  chloride salt suitable for X-ray structural analysis.Commercially available (Aldrich) Uiso(H) values of 1.2 or 1.5Ueq of the parent atoms. The hydrogen atoms of water molecules were restrained using DFIX and DANG commands during the least-squares refinement  I. DOI: 10.1107/S2056989016005788/wm5284Isup2.hklStructure factors: contains datablock(s) I. DOI: 1472901CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


All complexes adopt the expected square-planar coordination geometry, and the benzothiazole is engaged in bonding to the metal atom through the imine N atom (Pt—N).Four new platinum(II) complexes, [PtBr3(C8H7NS)] (1), tetraethylammonium tribromidoplatinate(II), [NEt4][PtBr3(C9H9NOS)] (2), tetraethylammonium tribromidoplatinate(II), [NEt4][PtBr3(C10H11NS)] (3), and tetraethylammonium tribromidoplatinate(II), [NEt4][PtBr3(C8H6N2O2S)] (4), have been synthesized and structurally characterized by single-crystal X-ray diffraction techniques. These species are precursors of compounds with potential application in cancer chemotherapy. All four platinum(II) complexes adopt the expected square-planar coordination geometry, and the benzothiazole ligand is engaged in bonding to the metal atom through the imine N atom (Pt—N). The Pt—N bond lengths are normal: 2.035 (5), 2.025 (4), 2.027 (5) and 2.041 (4) Å for complexes 1, 2, 3 and 4, respectively. The benzothiazole ligands are positioned out of the square plane, with dihedral angles ranging from 76.4 (4) to 88.1 (4)°. The NEt4 cation in 3 is disordered with 0.57/0.43 occupancies.Four new platinum(II) complexes, namely tetraethylammonium tribromido(2-methyl-1,3-benzothiazole-κ All complexes showed the benzothiazoles to coordinate the PtII atom through the imino nitrogen atom. Also, the benzothiazole is positioned out of the square plane with dihedral angles between 76.4 (4) and 88.1 (4)°, as previously reported in other platinum–benzothiazole complexes. Given that benzothiazoles have anticancer properties, these platinum complexes may have enhanced properties as a result of potential synergism between the ligand and PtII. This deserves further studies as suggested by Noolvi et al.  complexes with benzothiazole ligands of general formula  (1) crystallizes in an orthorhombic unit cell with eight formula units. It is a square-planar complex with Pt—N and average Pt—Br bond lengths of 2.035 (5) and 2.433 (6) Å, respectively, which are within the expected range for PtII complexes. There is no trans-influence observed in the Pt—Br bond trans to the Pt—N bond. The benzothiazole ligand is planar and the methyl group resides in the ligand plane. The dihedral angle between the PtBr3N unit and the benzothiazole ring is 88.1 (4)°, similar to those observed in other PtII–benzothiazole complexes, as a result of reducing the steric strain between PtBr3 and the benzothiazole ligand ] (2), [NEt4][PtBr3] (3) and [NEt4][PtBr3(5-NO2-2-Me-benzothiazole)] (4) crystallize in the same type of unit cell and space group, monoclinic P21/n, containing four formula units. The Pt—N and average Pt—Br bond lengths for 2, 3, and 4 are 2.025 (4)/2.430 (6) Å, 2.027 (5)/2.425 (6) Å and 2.041 (4)/2.431 (8) Å, respectively, which are within the expected range. The dihedral angle between PtBr3N and the benzothiazole in 2 is 86.7 (3)° and the torsion angle between the aromatic ring and the OCH3 group is 11.9 (7)°. The C—O (OCH3) bond length is 1.427 (7) Å, and the C—O—CH3 angle is 116.3 (5)°. In contrast to 1 and 2, [NEt4][PtBr3] and [NEt4][PtBr3(5-NO2-2-Me-benzothiazole)] have lower dihedral angles between the PtBr3N unit and the benzothiazole ring, 78.6 (4) and 76.(4)°, respectively. The methyl groups on 3 and 4 are almost co-planar with the benzothiazole plane with deviations ≤ 1.60° but in 4, the NO2 group is out of the benzothiazole plane with a torsion angle of 7.5 (7)°. The C—NO2 bond length is 1.476 (7) Å, and the O—N—O angle is 117.4 (5)°. The C—NO2 bond length and O—N—O angle in 4 are smaller than those observed in nitrobenzene [C—NO2 = 1.486 (2) Å and O—N—O = 123.9 (5)°], which suggests higher electron delocalization between the nitro group and the aromatic ring in 4 ]− anions. The [NEt4][PtBr3(2-Me-benzothiazole)] and [NEt4][PtBr3(6-OMe-2-Me-benzothiazole)] complexes showed partial π-stacking between the phenyl and the thiazole rings  and the corresponding amount of ligand was added with stirring. For 2-methyl-1,3-benzothiazole (99%) 18 μL  were added; for 2-methyl-5-nitro-1,3-benzothiazole (98%)  were added, and for 2-methyl-6-methoxy-1,3-benzothiazole (97%)  were added. The reaction mixtures were stirred without heating until the volume reduced considerably; then the samples were placed in desiccators containing CaCl2 at room temperature to evaporate slowly, leading to the formation of X-ray quality single crystals. For the synthesis with 2,5,6-trimethyl-1,3-benzothiazole (99%), the ligand  was added to 20 mL of an acetone solution  of [NEt4]2[Pt2Br6] with stirring, and a portion of the reaction mixture was slowly evaporated at 277 K in a small beaker in a secondary container which also contained CaCl2 to form X-ray quality single crystals.Acetone solutions of [NEtd(C—H) = 0.95 Å, Uiso(H) = 1.2Ueq(C); d(C—H2) = 0.99 Å, Uiso(H) = 1.2Ueq(C); d(C—H3) = 0.98 Å, Uiso(H) = 1.5Ueq(C). The NEt4 cation in 3 presented disorder with 0.57/0.43 occupancies.Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989016002826/bg2580sup1.cifCrystal structure: contains datablock(s) 1, 2, 3, 4. DOI: 10.1107/S2056989016002826/bg25801sup2.hklStructure factors: contains datablock(s) 1. DOI: 10.1107/S2056989016002826/bg25802sup3.hklStructure factors: contains datablock(s) 2. DOI: 10.1107/S2056989016002826/bg25803sup4.hklStructure factors: contains datablock(s) 3. DOI: 10.1107/S2056989016002826/bg25804sup5.hklStructure factors: contains datablock(s) 4. DOI: 1441324, 1441327, 1441326, 1441325CCDC references:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


I complex, the AgI atom is coordinated by two S atoms of thiourea and two P atoms of triphenylphosphane in a distorted tetrahedral geometry. In the crystal, the component ions are linked by C—H⋯O, C—H⋯S, N—H⋯O and N—H⋯S hydrogen bonds, generating (10-1) sheets.In the nitrate salt of this Ag 4N2S)2(PPh3)2]NO3, the AgI atom is coordinated by two thiourea S atoms and two triphenylphosphane P atoms in a distorted tetrahedral geometry, with bond angles in the range 102.90 (4)–123.29 (4)°. The Ag—S=C bond angles are 101.75 (19) and 111.29 (18)°. In the crystal, the component ions are linked by C—H⋯O, C—H⋯S, N—H⋯O and N—H⋯S hydrogen bonds, generating (10-1) sheets.In the title salt, [Ag(CH In the cationic complex, [Ag(PPh3)2(tu)2]+, the silver(I) atom is bound to two P atoms of PPh3 and two sulfur atoms of thiourea, assuming a slightly distorted tetrahedral geometry , B (C7–C12), C (C13–C18), D (C19–C24), E (C25–C30) and F (C31–C36) are as follows: A/B, A/C, B/C, D/E, D/F and E/F = 82.67 (15), 62.77 (17), 86.59 (14), 73.72 (14), 85.01 (16) and 84.06 (17)°, respectively. The thiourea units G (S1/C37/N1/N2) and H (S2/C38/N3/N4) are almost planar with r.m.s. deviations of 0.0031 and 0.0007 Å, respectively, and are oriented at a dihedral angle of 76.82 (11)° to each other.In (I)S(6) and In the asymmetric unit, strong N—H⋯S, N—H⋯O hydrogen bonds complete distorted s Table 2 and lead3 and PPh3 in a methanol–acetonitrile medium . Mixing resulted in the formation of a white precipitate. After stirring for half an hour, the mixture was filtered and the filtrate was left for crystallization. Colorless crystals of (I)et al., 2010The title complex was prepared by adding one equivalent of thiourea dissolved in 10 ml methanol to a 1:1 mixture of AgNOUiso(H) = 1.2Ueq.Crystal data, data collection and structure refinement details are summarized in Table 310.1107/S2056989015001395/hb7352sup1.cifCrystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015001395/hb7352Isup2.hklStructure factors: contains datablock(s) I. DOI: 1044766CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


S(9) ring motif. In the crystal, molecules are linked via C—H⋯O hydrogen bonds forming inversion dimers with an R44(10) ring motif. The dimers are linked by C—H⋯N hydrogen bonds, forming ribbons along [01-1].In the title compound, there is an intramolecular O—H⋯N hydrogen bond forming an  22H19ClN4O, the quinolinol moiety is almost planar [r.m.s. deviation = 0.012 Å]. There is an intramolecular O—H⋯N hydrogen bond involving the hydroxy group and a pyridine N atom forming an S(9) ring motif. The dihedral angles between the planes of the quinolinol moiety and the pyridine rings are 44.15 (9) and 36.85 (9)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds forming inversion dimers with an R44(10) ring motif. The dimers are linked by C—H⋯N hydrogen bonds, forming ribbons along [01-1]. The ribbons are linked by C—H⋯π and π–π interactions [inter-centroid distance = 3.7109 (11) Å], forming layers parallel to (01-1).In the title compound, C Analysis calculated for C22H19ClN4O: C 67.60, H 4.90, N 14.33%; found: C 67.50, H 5.01, N 14.37%.A suspension of paraformaldehyde  and bis(2-pyridylmethyl)amine  in 100 ml of MeOH was stirred for 18 h at room temperature. The solvent was removed under vacuum. To the product obtained was added 100 ml of toluene and 5-chloro-8-quinolinol , and the mixture was heated for 24 h at 353 K. The solvent was removed under vacuum to give an oily product, which was crystallized from hexane–dichloromethane. The crude solid was recrystallized from acetonitrile to obtain yellow crystals of the title compound . HRMS (Uiso(H) = 1.2Ueq(C).Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989015022410/su5241sup1.cifCrystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015022410/su5241Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015022410/su5241Isup3.cmlSupporting information file. DOI: 1438483CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information: