Two NdIII ions are bridged by four carboxylate groups in bi- and tridentate modes, forming a centrosymmetric dinuclear unit, with an Nd⋯Nd distance of 4.0021 (5) Å, and intramolecular π–π interactions between the pyridine rings [centroid–centroid distance = 3.960 (2) Å]. Intermolecular π–π interactions [centroid–centroid distances = 3.820 (2) and 3.804 (2) Å] and O—H⋯N and O—H⋯O hydrogen bonds connect the dinuclear molecules into a three-dimensional supramolecular network.In the title compound, [Nd DOI: 10.1107/S1600536811023798/hy2440Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The axial Cu—O distances are significantly longer [2.512 (2) Å], than the Cu—N [2.022 (2) Å] and Cu—Cl [2.3232 (4) Å] distances as a result of Jahn–Teller distortion. Aqua ligands are involved in intra- and intermolecular hydrogen bonding, and N—H⋯O intermolecular hydrogen bonds are formed between the organic ligands. In addition, weak π–π interactions are observed between the benzene rings of the ligand [centroid–centroid distance = 3.678 (1) Å].In the title complex, [CuCl H)-one was reported by Vaillancourt et al. (1998H)-one, see: Turgunov & Englert 2(H2O)2] = 0.032                           wR(F                           2) = 0.089                           S = 1.10                           1725 reflections137 parameters3 restraintsH atoms treated by a mixture of independent and constrained refinementmax = 0.37 e Å−3                        Δρmin = −0.46 e Å−3                        Δρ                                 CrysAlis PRO  used to solve structure: SHELXS97 (Sheldrick, 2008SHELXL97 (Sheldrick, 2008XP (Bruker, 1998publCIF (Westrip, 2010Data collection: 10.1107/S1600536810048890/nk2075sup1.cif            Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048890/nk2075Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The Hf—O bond lengths vary from 2.073 (2) to 2.244 (2) Å and the O—Hf—O bite angles vary from 73.49 (9) to 75.60 (9)°. Weak O—H⋯O hydrogen-bonding interactions are observed between the bridging hydroxy groups and the dimethylformamide solvent molecules. The unit cell contains solvent-accessible voids of 131 Å3, but the residual electron density in the difference Fourier map suggests no solvent molecule occupies this void.The binuclear molecule of the title compound, [Hf O,O′-and N,O-bidentate ligands with hafnium(IV) and zirconium(IV) to exploit possible separation techniques and for the crystal structures of hafnium(IV) and zirconium(IV) complexes, see: Viljoen et al. 6(OH)2]·2C3H7NO = 0.030                           wR(F                           2) = 0.072                           S = 1.03                           8726 reflections475 parameters1 restraintH atoms treated by a mixture of independent and constrained refinementmax = 1.33 e Å−3                        Δρmin = −0.97 e Å−3                        Δρ                                 APEX2  used to solve structure: SIR92  I, global. DOI: 10.1107/S1600536811049543/pv2484Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


As a result of this difference in the coordination modes, the C—S bond lengths are different, viz. 1.687 (2) and 1.692 (2) Å in the bidentate ligand and 1.723 (2) Å in the monodentate ligand, whereas the non-coordinating S atom has a C—S distance of 1.649 (2) Å. The crystal packing is stabilized by C—H⋯O interactions.The title compound, [Pd(C DOI: 10.1107/S1600536811040487/bt5655Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In the crystal, the 2-trifluoromethyl-1H-benzimidazolium cations link to the [HgCl4]2− complex anions and lattice water molecules via N—H⋯Cl and N—H⋯O hydrogen bonds, and the lattice water molecules further link to the Hg complex anion and the organic cations via O—H⋯Cl and O—H⋯F hydrogen bonding. One of the trifluoromethyl groups is disordered over two orientations in a 0.59 (4):0.41 (4) ratio.In the title compound, (C DOI: 10.1107/S1600536812018855/xu5519Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The NiII atom is coordinated by four PzMe3 molecules and two thiocyanate anions to define a trans N4S2 distorted octahedral geometry. A number of intramolecular N—H⋯N, N—H⋯S and C—H⋯N interactions contribute to the stability of the complex. The crystal structure is stabilized by intermolecular N—H⋯S interactions, which link neighbouring molecules into chains along the a axis.In the title compound, [Ni(NCS) DOI: 10.1107/S1600536811041419/tk2796Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The dpa ligand coordinates the PdII atom in a boat conformation of the resulting chelate ring; the dihedral angle between the pyridine rings is 39.3 (2)°. The two acetate anions coordinate the PdII atom as monodentate ligands and are located on the same sides of the PdN2O2 unit plane. The carboxylate groups of the anionic ligands appear to be delocalized on the basis of the C—O bond lengths. Two complex molecules are assembled through intermolecular N—H⋯O hydrogen bonds, forming a dimer-type species. Intermolecular C—H⋯O hydrogen bonds further stabilize the crystal structure.In the title complex, [Pd(CH II complexes [PdX2(dpa)] (X = Cl or Br), see: Rauterkus et al. 2(C10H9N3)] = 0.049wR(F2) = 0.116S = 0.922925 reflections205 parametersH atoms treated by a mixture of independent and constrained refinementmax = 0.99 e Å−3Δρmin = −0.81 e Å−3ΔρSMART  used to solve structure: SHELXS97  global. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


Intramolecular N—H⋯O and C—H⋯O hydrogen-bonding interactions stabilize the molecular conformation. The dihedral angles formed by the central benzene ring with the outer benzene rings of the terphenyl groups are 47.92 (8), 59.38 (8), 48.24 (8) and 52.37 (8)°. The dichloromethane solvent molecule interacts with the complex molecule via a C—H⋯O hydrogen bond. In the crystal, centrosymmetrically related complex molecules are linked into dimers through pairs of C—H⋯O hydrogen bonds.In the title compound, [Fe(C DOI: 10.1107/S1600536812015553/rz2736Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thiophene ring takes part in weak π–π stacking interactions with the pyridine ring [centroid-to-centroid separation = 3.7553 (19) Å and interplanar angle = 5.48 (12)°] and the benzene ring [3.7927 (19) Å and 4.58 (12)°]. Together, these lead to [100] stacks of molecules in an alternating head-to-tail arrangement, with two π–π stacking contacts between each adjacent pair.In the title compound, C DOI: 10.1107/S1600536812005673/kp2384Isup2.hklStructure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005673/kp2384Isup3.cmlSupplementary material file. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


II atom in the title compound, [Cu(C16H10ClN2O)2], is located on an inversion center and is tetracoordinated by two N and two O atoms from two bidentate 1-[(E)-(2-chlorophenyl)diazenyl]naphthalen-2-olate ligands, forming a square-planar complex. In the crystal, molecules are linked via weak C—H⋯O and C—H⋯Cl hydrogen bonds, forming chains propagating along [010]. There are also π–π interactions present involving adjacent naphthalene rings [centroid–centroid distance = 3.661 (13) Å].The Cu DOI: 10.1107/S1600536813016681/su2613Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


An intramolecular O—H⋯O hydrogen bond occurs. Intermolecular O—H⋯O hydrogen bonds link pairs of molecules into centrosymmetric dimers. Weak intermolecular C—H⋯O and C—H⋯F hydrogen bonds and π–π interactions between the aromatic rings [shortest centroid–centroid distance = 3.4962 (2) Å] further stabilize the crystal packing.In the title compound, [Co(C DOI: 10.1107/S1600536811051804/cv5209Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The 1,10-phenanthroline ligand is slightly folded for one complex, the dihedral angle between the pyridine planes being 5.3 (1)°. In contrast it is nearly planar [0.5 (1)°] as it complexes with the other HgII atom. The thiocyanate ligands are virtually linear and the S atom is bonded to HgII with N⋯S—Hg angles ranging from 99.3 (1) to 103.5 (1)°. Despite the presence of six aromatic rings in the asymmetric unit, there are no significant intermolecular π–π contacts between phenanthroline ligands as the centroid–centroid distance of the closest contact between six-membered rings is 4.11 (1) A°.The asymmetric unit of the title compound, [Hg(SCN) DOI: 10.1107/S1600536812038160/vn2049Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


In the crystal, the anions and cations are linked by N—H⋯O interactions along the b axis and a short N—O⋯π contact [3.2899 (5) Å] also occurs.In the title compound, C DOI: 10.1107/S1600536810032629/bx2300Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The crystal packing is stabilized by intermolecular N—H⋯O, O—H⋯O and weak C—H⋯O hydrogen bonds. There are also π–π interactions between the pyridine rings of the pydc ligands and between the pydc ligands and the benzene-1,3-diammonium cations, with centroid–centroid distances of 3.4575 (15) and 3.7521 (15) Å.In the title compound, (C DOI: 10.1107/S1600536811009858/hy2407Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The carboxylate groups of the PEB ions are twisted away from the attached benzene rings by 4.0 (6) and 13.3 (5)°. The two benzene rings of the PEB ions bonded to the same metal ion are oriented at a dihedral angle of 87.4 (3)°. In the polymeric chain, the NA ligand is linked to one of the carboxylate groups via N—H⋯O hydrogen bonding. In the crystal, adjacent polymeric chains interact via N—H⋯O and weak C—H⋯O hydrogen bonds; and the lattice water molecule links with the polymeric chains via N—H⋯O and O—H⋯O hydrogen bonding. π–π stacking between the benzene and the pyridine rings [centroid–centroid distance = 3.805 (5) Å] and weak C—H⋯π interactions are also observed in the crystal structure.In the crystal structure of the polymeric title compound, {[Pb(C N,N-diethylnicotinamide, see: Bigoli et al. 2(C6H6N2O)]·H2O = 0.043                           wR(F                           2) = 0.099                           S = 1.06                           5076 reflections314 parameters5 restraintsH atoms treated by a mixture of independent and constrained refinementmax = 1.11 e Å−3                        Δρmin = −0.96 e Å−3                        Δρ                                 CrystalClear  used to solve structure: SHELXS97  I, global. DOI: 10.1107/S1600536811026535/xu5254Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The two Bi atoms and two of the C atoms directly bonded to bismuth are quasi-planar  with the carbonate group. The remaining two ligands are in a trans arrangement relative to the quasi-planar (CBi)2CO3 system. The metal atom is strongly coordinated by the N atom of one pendant arm [Bi—N = 2.739 (6) Å], almost trans to the O atom, while the N atom of the other pendant arm exhibits a weaker intramolecular interaction [Bi⋯N = 3.659 (7) Å] almost trans to a C atom. If both these intramolecular N→Bi interactions per metal atom are considered, the overall coordination geometry at bismuth becomes distorted square-pyramidal [2BiO cores] and the compound can be described as a hypervalent 12-Bi-5 species. Additional quite short intramolecular Bi⋯O interactions are also present [3.796 (8)–4.020 (9) Å]. Intermolecular associations through weak η6⋯Bi interactions [Bi⋯centroid of benzene ring = 3.659 (1) Å] lead to a ribbon-like supramolecular association.The molecular structure of the title compound, [Bi DOI: 10.1107/S160053681005453X/rk2252Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In the complex cation, the FeII atom is coordinated by six N atoms from three chelating dimephen ligands at an average Fe—N distance of 1.963 (4) Å giving a distorted octahedral geometry. The crystal structure is stabilized by weak C—H⋯N hydrogen bonds and C N⋯π interactions between planar [maximum deviations of 0.024 (3) and 0.015 (3) Å] tcm anions and pyridine rings of dimephen .The title compound, [Fe(C DOI: Click here for additional data file.10.1107/S1600536812046880/bx2428Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The deprotonated ligand intramolecularly hydrogen bonds to the thiazole ring N atom, while the deprotonated ligand forms an intermolecular hydrogen bond to the thiolate S atom. The deprotonation of the tridentate ligand and its coordination to Hg via the S atom strikingly affects the C—S bond lengths. In the free ligand, the C—S bond distance is 1.685 (7) Å, whereas it is 1.749 (7) Å in the deprotonated ligand. Similarly, the Hg—S bond distance is slightly longer to the neutral ligand [2.6682 (18) Å] than to the deprotonated ligand [2.5202 (19) Å]. The Hg—I distance is 2.7505 (8) Å.In the title compound, [Hg(C I(C12H12N4S2)] = 0.042                           wR(F                           2) = 0.085                           S = 1.02                           5837 reflections346 parametersH-atom parameters constrainedmax = 1.36 e Å−3                        Δρmin = −1.27 e Å−3                        Δρ                                 COLLECT  used to solve structure: SIR97 (Altomare et al., 1999SHELXL97 (Sheldrick, 2008ORTEP-3 for Windows (Farrugia, 1997SHELXL97.Data collection: 10.1107/S160053681101974X/vm2089sup1.cif            Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101974X/vm2089Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The isobutyl group is disordered over two sets of sites in a 0.899 (9):0.101 (9) ratio. In the crystal, weak aromatic π–π stacking interactions involving the imidazole and thiadiazole rings with a centroid–centroid distance of 3.8067 (7) Å occur.In the title compound, C DOI: 10.1107/S1600536810053201/hb5776Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The four O atoms in the equatorial plane around the ZnII cation form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two N atoms of the NA ligands in the axial positions. The dihedral angle between the carboxylate group and the adjacent benzene ring is 24.13 (8)°, while the pyridine ring and the benzene ring are oriented at a dihedral angle of 88.52 (4)°. The coordinating water molecule links with the carboxylate group via an O—H⋯O hydrogen bond. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds, and a weak C—H⋯π interaction link the molecules into a two-dimensional network parallel to (010). These networks are linked via C—H⋯O and π–π interactions between inversion-related benzene rings [centroid–centroid distance = 3.8483 (7) Å], forming a three-dimensional supramolecular structure.In the title complex, [Zn(C N,N-diethylnicotinamide, see: Bigoli et al. 2(C6H6N2O)2(H2O)2] = 0.022wR(F2) = 0.060S = 1.063475 reflections216 parametersH atoms treated by a mixture of independent and constrained refinementmax = 0.43 e Å−3Δρmin = −0.31 e Å−3ΔρAPEX2  used to solve structure: SHELXS97  I, global. DOI: 10.1107/S160053681203320X/su2483Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The two phen ligands exhibit nearly perfect coplanarity (r.m.s. deviations = 0.027 and 0.031 Å), making a dihedral angle of 85.7 (1)°. The mean interplanar distances of 3.36 (2) and 3.41 (3) Å between adjacent phen ligands indicate π–π stacking interactions. The uncoordinated water molecules are partly occupied. One carboxylate O atom and two Br atoms are each disordered over two sites, with occupancy factors of 0.60 and 0.40. In the crystal structure, O—H⋯O and C—H⋯O hydrogen bonds and π–π stacking interactions link the complex cations, uncoordinated 4-bromobenzoate anions and water molecules into a three-dimensional supramolecular network. An intramolecular O—H⋯·O hydrogen bond is observed in the cation.In the title compound, [Zn(C DOI: 10.1107/S160053681003864X/hy2357Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The N atoms occupy one axial and one equatorial site and the terminal chloride ion occupies an equatorial site. The dihedral angle between the pyridine and pyrazole rings is 12.8 (2)°. In the crystal, aromatic π–π stacking [centroid–centroid separations = 3.812 (3) and 3.848 (3) Å] and C—H⋯Cl and C—H⋯π interactions help to establish the packing.In the centrosymmetric binuclear title compound, [Zn DOI: 10.1107/S1600536810026127/hb5500Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


Adjacent chains are linked by Owater—H⋯O hydrogen-bonding interactions. The Cu(OH2)3O4 cluster displays a pentagonal bipyrimadal geometry with two weak coordinations [Cu—Ofuran = 2.790 (2) Å) and Cu—Ocarboxylate = 2.684 (2) Å] and two water molecules located in axial positions. In the title compound, [Cu(C DOI: 10.1107/S1600536812010161/zj2064Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The Ca—O bond lengths are in the range 2.354 (3)–2.453 (2) Å, while the Ca—N bond lengths are in the range 2.523 (2)–2.548 (2) Å. An intramolecular O—H⋯O hydrogen bond between the carboxy and carboxylate groups stabilizes the molecular configuration. A three-dimensional network of N—H⋯O and O—H⋯O hydrogen bonds help to stabilize the crystal packing.In the title compound, [Ca(C DOI: 10.1107/S1600536812035544/ff2078Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


One of the nearly planar quinoline ligands [maximum deviations = 0.042 (6) and 0.018 (7) Å] is almost perpendicular to the PtCl2N2 unit [maximum deviation = 0.024 (3) Å], making a dihedral angle of 89.6 (1)°, whereas the other is slightly inclined to the central plane with a dihedral angle of 74.1 (1)°. The dihedral angle between the quinoline ligands is 88.3 (2)°. In the crystal, each solvent molecule is linked to the metal complex by weak intermolecular C—H⋯O hydrogen bonds.In the title compound, [PtCl DOI: 10.1107/S1600536812012469/xu5489Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The geometry around the CuII ion is highly distorted with the range of Cl—Cu—Cl angles being 94.94 (1)–141.03 (1)°. The crystal structure is stabilized by N—H⋯Cl and C—H⋯Cl hydrogen bonds. In the three-dimensional network, cations and anions pack in the lattice so as to generate chains of [CuCl4]2− anions separated by two orientations of cation layers, which are interlocked through π–π stacking contacts between pairs of pyridine rings, with centroid–centroid distances of 3.7874 (7) Å.The asymmetric unit of the title salt, (C DOI: 10.1107/S1600536813028006/bq2389Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The crystal structure is stabilized by intermolecular N—H⋯O, C—H⋯O and C—H⋯π interactions.In the title complex, [Ag(C DOI: 10.1107/S1600536811017776/jh2288Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The negatively charged N atom of the group binds to the terminal SnIV atom at a shorter distance [Sn—N = 2.236 (2) Å] compared with the neutral N atom that binds to the central SnIV atom [Sn← N = 2.805 (2) Å]. The terminal SnIV atom is five-coordinate in a cis-C2SnNO2 trigonal–bipyramidal geometry [C—Sn—C = 136.4 (1)°], whereas the central SnIV atom is six-coordinate in a C2SnNO3 skew-trazepoidal bipyramidal geometry [C—Sn—C = 145.4 (1)°]. The C atoms of the isopropoxy group are disordered over two positions in a 0.591 (7):0.409 (7) ratio.The tetranuclear title compound, [Sn DOI: Click here for additional data file.10.1107/S160053681204771X/bt6864Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The supramolecular structure is based on interactions involving the methoxy groups , π–π stacking of the electron-rich methoxy-substituted rings [centroid–centroid distances of 3.6454 (9)–3.738 (1) Å] and C—H⋯π contacts .The title compound, C DOI: 10.1107/S1600536811012888/vm2079Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


II–LuIII salen-type complex, [CuLu(C22H24N2O4)(NO3)3], with the ligand 6,6′-dimethoxy-2,2′-diphenolate, the irregular nine-coordinate LuIII coordination sphere comprises four O atoms from the ligand and five O atoms from three nitrate groups, two bidentate and one monodentate [Lu—O = 2.230 (3)–2.621 (4) Å]. The slightly distorted square-planar four-coordinate CuII atom comprises two imine N atoms [Cu—N = 1.903 (4) and 1.912 (4) Å] and two phenolate O atoms from the ligand molecule [Cu—O = 1.897 (3) and 1.906 (3) Å]. All atoms of the cyclohexane ring of the ligand molecule are disordered over two sets of sites with equal occupancy.In the title dinuclear Cu DOI: 10.1107/S1600536810048245/zs2074Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


This disorder is correlated with the disorder of one of the H atoms of the water molecule. The carboxyl group is twisted relative to the attached benzene ring by 75.1 (4)°. The intramolecular I⋯O distance is 2.112 (6) Å. Molecules are linked via O—H⋯O hydrogen bonding, C—I⋯O halogen bonding, with I⋯O distances in the range 3.156 (5)–3.274 (6) Å, and dipolar C=O⋯C=O interactions between the carboxyl and carboxylate groups, with an O⋯C distance of 2.944 (10) Å.In the title compound, C DOI: 10.1107/S1600536812005351/gk2447Isup2.hklStructure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005351/gk2447Isup3.cmlSupplementary material file. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The oxide O atoms adopt a cis conformation: one is trans to the methanol O atom and the other is trans to the ligand N atom. The dihedral angle between the two benzene rings in the hydrazone ligand is 4.0 (3)°. In the crystal, molecules are linked by O—H⋯N and O—H⋯O hydrogen bonds.In the title dioxidomolybdenum(VI) complex, [Mo(C O2(CH4O)] = 0.044wR(F2) = 0.093S = 1.034300 reflections269 parameters1 restraintH atoms treated by a mixture of independent and constrained refinementmax = 0.62 e Å−3Δρmin = −0.69 e Å−3ΔρSMART  used to solve structure: SHELXS97  global, I. DOI: 10.1107/S1600536812008549/hb6656Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The dihedral angle between the pyridine rings is 1.92 (11)°. In the crystal, π–π stacking between parallel pyridine rings of adjacent complex molecules is observed, the centroid–centroid distance being 3.6788 (19) Å. Weak C—H⋯O hydrogen bonds further link the molecules into a three-dimensional supramolecular architecture.In the title complex, [Cu(NO DOI: 10.1107/S1600536813028201/xu5745Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The Li+ ion is N,N′-chelated by the N-silylated amido ligand, with Li—N = 2.015 (5) and 2.074 (5) Å. The two amido ligands are arranged cis to each other. The molecule exhibits a twofold rotational symmetry operation along the Li–Na axis. The Na+ ion is coordinated by two N atoms from the tetramethylethylenediamine ligand [Na—N = 2.553 (4) Å] and shares two amido N atoms from the N-silylated amido ligands with the Li+ ion. Although the crystal structure contains voids with an approximate volume of 50 Å3 there is no inclusion of solvent molecules.In the heterometallic title bulky amido complex, [LiNa(C N-silylated quinolyl amido ligands, see: Engelhardt et al. 2(C6H16N2)] = 0.062wR(F2) = 0.195S = 0.974001 reflections209 parameters1 restraintH-atom parameters constrainedmax = 0.32 e Å−3Δρmin = −0.26 e Å−3ΔρSMART  used to solve structure: SHELXS97  I, global. DOI: Click here for additional data file.10.1107/S160053681204576X/rk2385Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The complex molecules are connected via water O—H⋯O and O—H⋯N hydrogen bonds and weak π–π stacking interactions between the benzene rings [minimum ring centroid separation = 3.750 (6) Å] into a three-dimensional polymeric structure. The imidazolyl group of the ligand is partially disordered over two sets of sites with refined occupancies of 0.531 (7):0.469 (7).In the title compound, [Mn(C DOI: 10.1107/S1600536812010446/zs2182Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


Intermolecular C—H⋯Cl hydrogen bonds and π–π stacking interactions between the pyridyl rings [centroid–centroid distance = 3.7337 (18) Å] are present in the crystal structure.In the title compound, [CdCl DOI: 10.1107/S1600536810029399/hy2335Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The metal atom is further chelated by a carboxylate group and is covalently bonded to a monodentate carboxylate group and to a monodentate sulfonate group in a distorted square-antiprismatic geometry. The coordinating and the solvent water molecules are hydrogen bonded to the network. In the crystal, one solvent water molecule is disordered over two positions [major component = 59 (3)%].The 4-sulfophthalate trianion in the polymeric title complex, {[Dy(C III complex, see: Zhang et al. (C12H8N2)(H2O)2]·2H2O = 0.037wR(F2) = 0.093S = 1.204022 reflections353 parameters33 restraintsH atoms treated by a mixture of independent and constrained refinementmax = 0.97 e Å−3Δρmin = −1.85 e Å−3ΔρAPEX2  used to solve structure: SHELXS97  global, I. DOI: 10.1107/S1600536812003613/xu5457Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The benzene rings of the anions are involved in π–π stacking. The centroid–centroid distance between parallel benzene rings of adjacent molecules is 3.9017 (17) Å, and the centroid–centroid distance between benzene and pyridine rings of adjacent molecules is 3.584 (2) Å. Intramolecular O—H⋯O hydrogen bonding is present.In the title compound, [Zn(C DOI: 10.1107/S1600536811020435/ng5174Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


II ion in the title centrosymmetric dinuclear complex, [Hg2Cl4(C13H12N2)2]·[HgCl2], adopts a distorted square-pyramidal geometry, being coordinated by the bis-chelating N-heterocyclic ligand, two bridging Cl atoms and one terminal Cl atom. One of the bridging Hg—Cl bonds [2.8428 (11) Å] is significantly longer than the other [2.5327 (10) Å]. In the crystal, there are weak π–π interactions [centroid–centroid distance = 3.630 (3) Å] between the aromatic rings of the discrete units. The HgCl2 adduct molecule is located on an inversion centre and has an Hg—Cl bond length of 2.2875 (11) Å.The Hg DOI: 10.1107/S1600536810050725/jh2236Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In the crystal, molecules are linked into sheets parallel to the bc plane by C—H⋯Cl and C—H⋯O hydrogen bonds and weak π–π interactions [centroid–centroid distance = 3.669 (1) Å].In the title compound, [ZnCl DOI: 10.1107/S160053681004119X/ci5172Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In the crystal, molecules are connected by C—H⋯Br and C—H⋯O hydrogen bonds, and π–π interactions between the oxazole and benzene rings [centroid–centroid distance = 3.7344 (19) Å], resulting in a three-dimensional supramolecular structure.In the title compound, [PdBr(C DOI: Click here for additional data file.10.1107/S1600536812049197/hy2606Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


Four water O atoms in the equatorial plane around the CoII ion [Co—O = 2.0593 (16) and 2.1118 (16) Å] form a slightly distorted square-planar arrangement, and the distorted octahedral geometry is completed by the two N atoms [Co—N = 2.1306 (18) Å] from two isonicotinamide ligands. In the anion, the carboxylate group is twisted from the attached benzene ring at 8.84 (17)°. In the crystal, a three-dimensional hydrogen-bonding network, formed by classical O—H⋯O and N—H⋯O hydrogen bonds, consolidates the crystal packing, which exhibits π–π interactions between the benzene and pyridine rings, with centroid–centroid distances of 3.458 (1) and 3.606 (1) Å, respectively.The asymmetric unit of the title compound, [Co(C DOI: 10.1107/S1600536812003911/cv5239Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The dihedral angle between the aromatic ring and the pyridyl ring is 71.7 (1)°. In the crystal, the molecules are stacked in columns along the c axis and several intermolecular π–π interactions are present between the six-membered rings, with a shortest centroid–centroid distance of 3.707 (2) Å.The title compound, C DOI: 10.1107/S1600536811003011/ng5109Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In the crystal structure, adjacent molecules are connected by π–π contacts between the thiazole rings [centroid–centroid distance = 3.591 (3) Å].In the title compound, [HgI DOI: 10.1107/S1600536810029302/hy2334Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In the crystal, the components are linked by O—H⋯O, C—H⋯O and aromatic π–π stacking [shortest centroid–centroid separation = 3.659 (5) Å] interactions.In the title compound, [Co(C DOI: 10.1107/S1600536810022750/hb5497Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The 5-hydroxynicotinate ligand is protonated at the N atom and deprotonated at the hydroxy group. The HoIII atoms are bridged by the carboxylate and phenolate O atoms, forming a three-dimensional framework. N—H⋯O and O—H⋯O hydrogen bonds, as well as π–π interactions between the pyridine rings [centroid–centroid distance = 3.794 (2) Å], are observed.In the title compound, {[Ho DOI: 10.1107/S1600536812032916/hy2567Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


One of the Cp ligands is additionally substituted by a dimethylaminomethyl group causing the chirality of the molecule. Surprisingly, although the synthetic procedure yielded the title compound as a racemic mixture, the reported crystal is enantiomerically pure with the R absolute configuration. The dimethylamino group is exo with respect to the Cp ring. Both diphenylthiophosphine groups are trans with respect to the centroid–Fe–centroid direction. Weak intramolecular C—H⋯S and C—H⋯π interactions between symmetry-related molecules are observed. The contribution of the disordered solvent was removed from the refinement using SQUEEZE in PLATON . In the title compound, [Fe(CSpek 2009. Acta Cr For the al. 2010; Debono  al. 2010; Diab et al. 2008; Le Roux al. 2007; Malaceal. 2006a,b ▶; Ro20H21NPS)(C17H14PS)]·CH2Cl2 = 0.042wR(F2) = 0.102S = 1.097854 reflections393 parametersH-atom parameters constrainedmax = 0.63 e Å−3Δρmin = −0.36 e Å−3ΔρAbsolute structure: Flack 1983, 3441 FrFlack parameter: 0.043 (16)APEX2  used to solve structure: SIR97  I, global. DOI: 10.1107/S1600536812022301/im2377Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The resulting N2O3 donor set defines a distorted square-pyramidal geometry with the coordinated water molecule in the apical position. In the crystal, the presence of O—Hw⋯Oc (w = water and c = carbonyl) hydrogen bonding leads to the formation of a supramolecular chain propagating along the c axis, which associates into a double chain via C—H⋯ O and π–π contacts between pyridyl rings [centroid–centroid distance = 3.527 (3) Å]. The solvent molecules, which are disordered over two orientations in a 0.678 (11):0.322 (11) ratio, occupy voids defined by the complex molecules and are held in place via C—H⋯O interactions.The title complex, [Cu(C DOI: 10.1107/S1600536810030436/hb5590Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


IV atom in the title compound, [Sn(C6H5)2Cl2(C13H12OS)], displays a distorted C2Cl2O trigonal–bipyramidal coordination environment, with a mean Sn—C distance of 2.121 (9) Å and with Sn—O = 2.331 (2) Å. The SnIV atom is displaced by 0.169 (2) Å from the equatorial C2Cl plane towards the direction of the second axially bonded Cl atom.The Sn DOI: 10.1107/S1600536811014474/wm2481Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The CuII atom is tetracoordinated, displaying a slightly distorted square-planar geometry. The main deviation from the ideal geometry is seen in the differences in the Cu—O [1.8833 (10) Å] and Cu—N [1.9405 (13) Å] bond lengths, while angular deviations are less than 3°. Intramolecular O—H⋯O and intermolecular C2sp—H⋯O hydrogen bonds form S(5) and R22(8) ring motifs, respectively. The latter interaction results in chains of molecules along [100].In the title compound, [Cu(C DOI: 10.1107/S1600536812032187/lr2071Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


Three RuCp+ (Cp is cyclopentadienyl) groups are bonded to the three aromatic rings of the ligand. Surprisingly, the pyramidalized N atom of the heterocycle (Σ C—N—C = 329.0°) points towards the anthracenyl group, so losing its coordinative ability. There is an intermolecular C—H⋯π interaction involving an acetone molecule and the adjacent benzyl ring of the ligand. In the crystal, molecules are linked via a number of C—H⋯O and C—H⋯F interactions and a C—H⋯π interaction, leading to the formation of a three-dimensional supramolecular structure. One of the Cp groups is disordered over two positions, with refined occupancies of 0.695 (14):0.305 (14). Two of the three hexafluorophospate anions are disordered, with refined occupancies of 0.630 (6):0.370 (6) and 0.771 (8):0.229 (8). One of the two solvent acetone molecules is also disordered, with refined occupancies of 0.82 (2):0.18 (2).In the title compound, [Ru DOI: 10.1107/S1600536812040652/su2499Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The CdII ions are connected by two bridging benzoate anions and each ion is seven-coordinated by five O atoms from three benzoate ligands and by two N atoms from 1,10-phenanthroline. The benzoate ligands adopt two different coordination modes, acting as bidentate and bridging tridentate ligands. The discrete neutral molecules further extend their structure into a three-dimensional supramolecular framework by intermolecular π–π [interplanar distances of 3.392 (4) Å] and C—H⋯π stacking interactions [H–mean plane = 2.567 (4) and 2.781 (4) Å].The dinuclear title compound, [Cd DOI: 10.1107/S1600536811022185/zq2105Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The ZnII ion is coordinated by two N atoms from one molecule of the aromatic base and four O atoms from two bidentate, symmetry-related acetate anions, which coordinate asymmetrically [Zn—O distances of 2.058 (2) and 2.362 (3) Å], while the two Zn—N bond distances are equal as imposed by symmetry [2.079 (2) Å]. The crystal structure is supported by a number of weak C—H⋯O interactions and C—H⋯π contacts, with no π–π interactions present, mainly hindered by the substituent methyl groups and the relative molecular orientation. The result is a three-dimensional structure in which each molecule is linked to eight different neighbors.The molecular structure of the title compound, [Zn(CH DOI: Click here for additional data file.10.1107/S1600536812042699/br2212Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


It should be noted, that a solvent-masking procedure as implemented in OLEX2 [Dolomanov et al. (2009). J. Appl. Cryst.42, 339–341II ion is five-coordinated by two phenanthroline ligands and one chloride ion in a distorted trigonal–bipyramidal geometry. The dihedral angle between the phen ligands is 65.21 (5)°. The MnII ion is six-coordinated by one Cl atom, two N atoms from a phen ligand, as well one N atom and two O atoms from pydc in a distorted octahedral coordination geometry, with cis angles ranging from 72.00 (8) to 122.07 (8)° and trans angles ranging from 143.98 (8) to 163.15 (6)°. In the crystal, C—H⋯O, O—H⋯O and C—H⋯Cl hydrogen bonds, cation–anion π–π interactions between the phen ring systems with centroid–centroid distances in the range 3.881 (34)–4.123 (36) Å, as well as cation–cation, anion–anion π–π interactions between the phen rings with centroid–centroid distances in the range 3.763 (4)–3.99 (5) Å and pydc rings with centroid–centroid distances 3.52 (5) Å link the various components. The title complex, [CuCl(C DOI: 10.1107/S1600536814006369/br2237Isup2.hklStructure factors: contains datablock(s) I. DOI: 993053CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The dihedral angles between the mean planes of the central phenolate rings and the peripheral phenyl rings are 46.62 (10)/87.06 (9), 60.44 (8)/23.13 (8) and 46.49 (6)/65.29 (6)°. The crystal packing is stabilized by weak intermolecular C—H⋯O interactions. Molecules are further linked by two π–π [centroid–centroid distances = 3.8612 (14) and 3.9479 (14) Å] and four C—H⋯π interactions, forming a three-dimensional network.In the title compound, [Co(C DOI: 10.1107/S1600536814001664/hg5379Isup2.hklStructure factors: contains datablock(s) I. DOI: CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The slightly distorted square-planar coordination sphere of the CuII atom comprises two phenolate O atoms and two oxime N atoms from two bidentate–chelate 2-[1-(ethoxyimino)ethyl]-1-naphtholate O-ethyl oxime (L               −) ligands [Cu—O = 1.8919 (17) Å and Cu—N = 1.988 (2) Å]. The two naphthalene ring systems in the molecule are parallel, with a perpendicular interplanar spacing of 1.473 (2) Å, while each complex unit forms links to four other molecules via intermolecular methyl C—H⋯π interactions, giving an infinite cross-linked layered supramolecular structureIn the title complex, [Cu(C DOI: 10.1107/S1600536810047574/zs2078Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The ligands are mutually transoid with respect to the metal atom. Weak intermolecular C—H⋯Cl hydrogen bonds and π–π interactions, with centroid–centroid distances of 3.8452 (14) and 3.9932 (14) Å, are found in the crystal packing.In the title complex, [ZnCl DOI: 10.1107/S1600536811022884/fj2423Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In each molecule, the geometry around the Pd atom is distorted square-planar, with the Pd atom displaced by 0.0549 (12) and 0.0734 (13) Å from the least-squares plane of the I—P—P—C atoms. The PPh3 ligands are in trans positions, with P—Pd—P angles of 173.12 (4) and 170.29 (4)°, while the pyrazinyl ligands and I atoms, also trans to each other, form C—Pd—I angles of 179.38 (12) and 178.44 (12)°. In the crystal, C—H⋯π interactions occur, resulting in a three-dimensional supramolecular architecture.There are two independent molecules with similar configurations in the asymmetric unit of the title complex, [Pd(C I(C18H15P)2] = 0.048wR(F2) = 0.101S = 1.0415924 reflections829 parametersH-atom parameters constrainedmax = 1.35 e Å−3Δρmin = −0.55 e Å−3ΔρSMART  used to solve structure: SHELXS97  I, global. DOI: Click here for additional data file.10.1107/S1600536812043589/bg2480Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The pyrimidinethiolate anion acts both as a bridging and a chelating ligand. The AgI ions are linked via two μ2-S donor atoms, which generate a strictly planar Ag2S2 core with an Ag⋯Ag separation of 2.9569 (4) Å. The AgI ion presents a distorted tetrahedral coordination geometry. In the crystal, weak C—H⋯N and C—H⋯S hydrogen bonds link the complex molecules into a two-dimensional network parallel to (010).The dinuclear title complex, [Ag For rel al. 2000; Lobana  al. 2008; Isab et al. 2010.2(C6H7N2S)2(C18H15P)2] = 0.032wR(F2) = 0.088S = 1.045568 reflections266 parametersH atoms treated by a mixture of independent and constrained refinementmax = 0.54 e Å−3Δρmin = −0.29 e Å−3ΔρSMART  used to solve structure: SHELXS97  I, global. DOI: Click here for additional data file.10.1107/S1600536812048210/bh2464Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


A weak intramolecular C—H⋯O hydrogen bond occurs between the DMBP and DMSO ligands. π–π stacking between pyridine rings [centroid–centroid distances = 3.682 (3) and 3.598 (3) Å] is observed in the crystal.In the title compound, [CdBr DOI: 10.1107/S1600536812028553/xu5571Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The Pd atom is located on an inversion centre, and thus the asymmetric unit contains one half of the complex; the PdN2Cl2 unit is exactly planar. The dihedral angle between the PdN2Cl2 unit and quinoline ligand is 85.63 (8)°. In the crystal, the complex molecules are stacked into columns along the b axis. In the columns, several intermolecular π–π interactions between the six-membered rings are present, the shortest ring centroid–centroid distance being 3.764 (3) Å between pyridine rings.In the title complex, [PdCl II complex cis-[PtCl2(quinoline)2]·0.25DMF, see: Davies et al. 2] = 0.040wR(F2) = 0.095S = 1.051577 reflections106 parametersH-atom parameters constrainedmax = 1.30 e Å−3Δρmin = −0.40 e Å−3ΔρSMART  used to solve structure: SHELXS97  global. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


In the crystal, there are aromatic π–π contacts between the pyridine rings [centroid–centroid distances = 3.9577 (13) Å] and intermolecular O—H⋯O and C—H⋯O hydrogen bonds.In the title compound, [Zn(NO DOI: 10.1107/S1600536811050227/bt5709Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The geometry around the RuII atom is pseudo-octahedral, with two cis-binding PPh3 ligands and one chelating bidentate [Fc(O)PS2]2− ligand via two S atoms. The average Ru—S and Ru—P bond lengths are 2.434 (1) and 2.398 (1) Å, and the Ru—O and Ru—C bond lengths are 2.157 (3) and 1.826 (4) Å, respectively. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent molecules into dimers.The structure of the title complex, [FeRu(C DOI: Click here for additional data file.10.1107/S1600536813014311/ds2231Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The whole repeating molecular unit is generated by inversion symmetry. This leads to the formation of a looped-chain one-dimensional coordination polymer propagating along [110]. The dimethylformamide (DMF) molecules are linked to the chains via O—H⋯O hydrogen bonds. The chains are linked via N—H⋯O hydrogen bonds, forming two-dimensional networks parallel to (001). There are also a number of C—H⋯O interactions present and a parallel slipped π–π interaction. The latter involves inversion-related pyridine rings with a centroid–centroid distance of 3.594 (2) Å [normal distance = 3.3338 (13) and slippage = 1.341 Å]. These interactions lead to the formation of a three-dimensional structure.In the title coordination polymer, {[Cu(SO N,N′-bis-(4-pyridyl)isophthalamide ligand, see: Adarsh et al. (C18H14N4O2)(H2O)]·C3H7NO = 0.052wR(F2) = 0.124S = 1.075581 reflections339 parameters4 restraintsH atoms treated by a mixture of independent and constrained refinementmax = 0.44 e Å−3Δρmin = −0.48 e Å−3ΔρCrystalClear  used to solve structure: SHELXS97  I, global. DOI: Click here for additional data file.10.1107/S1600536813003413/su2555Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


Two symmetry-related azide ligands bridge in μ2-modes giving a Cu⋯Cu distance of 3.533 (2) Å. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the components into a three-dimensional network. In addition, there are weak intermolecular C—H⋯N hydrogen bonds and π–π stacking interactions with centroid–centroid distances ranging from 3.562 (2) to 3.974 (2) Å. In the centrosymmetric dinuclear title complex, [Cu DOI: 10.1107/S1600536811045909/lh5362Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The SnIV atom of the one-dimensional coordination polymer is located on a mirror plane and is coordinated by two chelating oxalate ions with two rather different Sn—O bond lengths of 2.150 (1) and 2.425 (1) Å, and two t-butyl groups with Sn—C bond lengths of 2.186 (2) and 2.190 (2) Å. The coordination polyhedron around the SnIV atom is a distorted tetragonal disphenoid. The centrosymmetric oxalate ion also has an asymmetric coordination geometry, as reflected by the two slightly different C—O bond lengths of 1.242 (2) and 1.269 (2) Å. The chains of the polymer propagate along the b-axis direction. Only van der Waals interactions are observed between the chains.The title compound, [Sn(C For 2(C2O4)] = 0.015wR(F2) = 0.038S = 1.101548 reflections83 parametersH-atom parameters constrainedmax = 0.53 e Å−3Δρmin = −0.37 e Å−3ΔρAPEX2  used to solve structure: SHELXS97  I. DOI: 10.1107/S160053681400539X/cq2010Isup2.hklStructure factors: contains datablock(s) I. DOI: 990826CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


IV ion in the title complex, [PtBr4(C10H9N3)], is six-coordinated in a slightly distorted octahedral environment by two pyridine N atoms from a chelating di-2-pyridylamine (dpa) ligand and four Br− anions. The complex molecule has mirror symmetry, with the PtIV atom, two Br atoms and the central N atom of the dpa ligand lying on the mirror plane. The dpa ligand is not planar, showing a dihedral angle of 34.7 (2)° between the pyridine rings. The complex molecules are connected by intermolecular N—H⋯Br hydrogen bonds, forming chains along [001]. Intermolecular C—H⋯Br hydrogen bonds and π–π interactions between the pyridine rings [centroid–centroid distance = 3.667 (4) Å] are also observed.The Pt DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The geometry around the MoVI atom is distorted octahedral in each complex molecule, supported by two oxide O atoms and the N2O2 donor atoms of the coordinating ligand. The dihedral angle between the benzene rings is 74.96 (11) Å for molecule A and 76.05 (11) Å for molecule B. In the crystal, the B molecules are linked by pairs of C—H⋯Cl hydrogen bonds, forming inversion dimers. The crystal structure is further stabilized by C—H⋯π interactions. An interesting feature of the crystal structure is a Cl⋯Cl contact [3.3748 (18) Å], which is shorter than the sum of the van der Waals radii of Cl atoms (3.50 Å).The asymmetric unit of the title compound, [Mo(C O2] = 0.027wR(F2) = 0.079S = 1.078626 reflections541 parametersH-atom parameters constrainedmax = 0.69 e Å−3Δρmin = −0.71 e Å−3ΔρCrysAlis PRO  used to solve structure: SIR92  global, I. DOI: 10.1107/S160053681203807X/su2496Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


The MnII atom is six-coordinated by 2− anions in a tridentate fashion and is at the centre of a distorted octahedron formed by the MnO4N2 bonding set. In the crystal, various intermolecular interactions between different moieties can be found, such as different kinds of hydrogen bonds, offset or slipped π–π [centroid–centroid distances in the range 3.3704 (12) to 3.8674 (13)Å] and C=O⋯π [3.563 Å] interactions, which lead to the formation of a three-dimensional supramolecular network. The asymmetric unit of the title compound, (C DOI: 10.1107/S1600536811036981/om2447Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


N,N′-(o-phenylene)bis(pyridine-2-carboxamidato)]manganese(II)} ethanol heptasolvate 3.5-hydrate, [Mn(C18H12N4O2)(C7H10N2)(NO)]8·7C2H5OH·3.5H2O, or 8[Mn(bpb)(DMAP)(NO)]·7EtOH·3.5H2O, is an unusual example of a structure with Z′ = 8. The tetradentate bpb ligand, together with the nitrosyl and dimethylaminopyridine ligands, gives rise to a distorted octahedral coordination environment for the Mn(II) ion. The average Mn—N(N=O) bond length is 1.631 (13) Å. The eight molecules in the asymmetric unit differ mainly in the rotation of the DMAP pyridine plane with respect to a reference plane of the Mn and three N atoms, one of which is the N atom of the NO group. The dihedral angles between the normals to these planes range from a minimum of 28.0 (2)° to a maximum of 64.2 (2)°. There are also some differences in O—H⋯O hydrogen bonding interactions. For example, of the sixteen C=O acceptors, there are seven different interactions with EtOH donors and two interactions with H2O donors. The crystal studied was found to be a two-component twin, with a 179.9° rotation about the real axis . Due to the presence of a superlattice and, consequently, the large number of weak reflections, the refinement utilized rigid solvate groups and isotropic displacement parameters for all except the Mn atoms. H atoms were not located for hydrate molecules.The structure of the title compound octakis{[4-(dimethylamino)pyridine](nitrosyl)[ DOI: 10.1107/S1600536811038669/wm2529Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The previous structure report [Spofford & Amma  and 0.001 Å (new)]. The asymmetric unit contains two formula units, with both CuI atoms coordinated by one terminal S atom and two bridging S atoms of thiourea ligands. This connectivity leads to polymeric [100] chains in the crystal. If very long contacts to nearby chloride ions [2.8687 (9) and 3.1394 (12) Å] are considered to be bonding, then very distorted CuS3Cl tetrahedral coordination polyhedra arise. The crystal structure is consolidated by weak intra- and inter-chain N—H⋯S and N—H⋯Cl hydrogen bonds.The structure of the polymeric title compound, [CuCl(CHAmma 1970. Acta Cr For the structure of a related thiourea salt, see: Zouihri 2012. For the4N2S)2] = 0.043wR(F2) = 0.081S = 1.154089 reflections245 parameters16 restraintsAll H-atom parameters refinedmax = 0.58 e Å−3Δρmin = −0.85 e Å−3ΔρAPEX2  used to solve structure: SHELXS97  I, global. DOI: 10.1107/S1600536812004448/hb6598Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


It is built up by association of (2-(diphenylphosphino)ferrocenyl)methyl)dimethylammonium cations and diphenylphosphino dithioate anions. N—H⋯S, C—H⋯S and C—H⋯π interactions link the anions and cations. Each anion–cation pair is linked two by two through C—H⋯π interactions, forming pseudo dimers.2-(Diphenylthiophosphino)dimethylaminomethylferrocene is a key intermediate in the synthesis of various ferrocenyl ligands. During one such synthesis, the title compound, [Fe(C DOI: 10.1107/S1600536812009129/hp2031Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supplementary materials:


VI atom in the title compound, [Mo(C16H14N2O4)O2(C2H6OS)], is distorted octahedral. The phenolate O, imino N, oxide O from the enolized carbonyl group and one of the terminal O atoms form the equatorial plane; the axial positions are occupied by the other terminal O atom of the dioxidomolybdenum group and the donor O atom of DMSO. The O=Mo=O angle is 105.31 (6)°. An intramolecular O—H⋯N hydrogen bond and weak intermolecular C—H⋯O hydrogen bonds are present in the structure.The coordination geometry at the Mo O2(C2H6OS)] = 0.024                           wR(F                           2) = 0.120                           S = 1.15                           4556 reflections266 parametersH-atom parameters constrainedmax = 0.47 e Å−3                        Δρmin = −1.68 e Å−3                        Δρ                                 APEX2  used to solve structure: SHELXS97  I, global. DOI: 10.1107/S1600536811020290/xu5215Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The molecules form an inversion dimer via a pair of weak C—H⋯O hydrogen bonds and a π–π stacking interaction with a centroid–centroid distance of 3.7401 (12) Å. Weak intramolecular C—H⋯Br interactions and an intramolecular π–π stacking interaction with a centroid–centroid distance of 3.8118 (15) Å are also observed.In the title compound, [MoBr DOI: 10.1107/S1600536811015881/is2705Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The benzimidazole ring system forms dihedral angles of 26.68 (9) and 56.16 (9)° with the adjacent benzene ring and the methylphenolate group benzene ring, respectively. In the crystal, molecules are linked by N—H⋯Cl hydrogen bonds into chains along [100]. Furthermore, weak C—H⋯O and C—H⋯π interactions, in addition to π–π interactions with centroid–centroid distances in the range 3.5826 (13)–3.9681 (13) Å, are also observed.In the title mononuclear complex, [Zn(C Cl] = 0.042                           wR(F                           2) = 0.088                           S = 1.03                           5678 reflections249 parametersH atoms treated by a mixture of independent and constrained refinementmax = 0.64 e Å−3                        Δρmin = −0.39 e Å−3                        Δρ                                 APEX2  used to solve structure: SHELXTL  global, I. DOI: 10.1107/S1600536811030170/lh6598Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


The SnIV ion is five-coordinated in a distorted trigonal–bipyramidal geometry by two monodentate carboxylate groups and three phenyl rings. The axial sites are occupied by the O atoms of two symmetry-related carboxylate groups [O—Sn—O = 170.88 (3)°]. The benzene ring of the 5-amino-2-nitrobenzoate ligand forms dihedral angles of 82.92 (6), 81.10 (6) and 83.54 (6)° with respect to the three phenyl rings. In the crystal, the chains are linked by intermolecular N—H⋯O and weak C—H⋯O interactions into a three-dimensional network. The crystal structure is further stabilized by weak intermolecular C—H⋯π interactions.The title compound, [Sn(C For the al. 1987.       6H5)3(C7H5N2O4)] = 0.018                           wR(F                           2) = 0.046                           S = 1.07                           7981 reflections297 parametersH atoms treated by a mixture of independent and constrained refinementmax = 0.51 e Å−3                        Δρmin = −0.54 e Å−3                        Δρ                                 APEX2  used to solve structure: SHELXTL  global, I. DOI: 10.1107/S1600536811033332/lh5316Isup2.hkl            Structure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In the [FeBr4]− anion, the FeIII atom (3 symmetry) is four-coordinated in a distorted tetrahedral geometry. In the crystal, intermolecular C—H⋯Br hydrogen bonds and Br⋯π interactions [Br⋯centroid distances = 3.562 (3) and 3.765 (2) Å] link the cations and anions, stabilizing the structure.In the [Fe DOI: 10.1107/S1600536811004181/hy2404Isup2.hkl            Structure factors: contains datablocks I. DOI:  crystallographic information; 3D view; checkCIF report            Additional supplementary materials:


In the crystal, C—H⋯O and π–π interactions connect the molecules, forming double layers that stack along the  30H28N2O6, the pyran ring adopts a slightly distorted half-chair conformation and the pyrone ring adopts an envelope conformation, with the C atom bearing the carboxylate group as the flap. The pyrazole ring [maximum deviation = 0.002 (2) Å] forms a dihedral angle of 13.2 (1)° with the attached benzene ring. The near-planar atoms of the pyran ring and the pyrazole ring are close to coplanar, the dihedral angles between their mean planes being 6.4 (1)°. The dihedral angle between the pyrone ring and the benzene ring of the chromene unit is 10.7 (1)°. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, C—H⋯O interactions generate supramolecular chains propagating in [100] and these are connected into double layers that stack along the c-axis direction by weak π–π interactions between pyrazole rings [centroid–centroid distance = 3.801 (1) Å].In the title compound, C The pyrazole ring is approximately planar, with a maximum deviation of 0.002 (2) Å for atom C2, and forms a dihedral angle of 13.2 (1)° with the attached benzene ring. The planar atoms of the pyran ring and the pyrazole ring are close to coplanar, the dihedral angles between their mean planes being 6.4 (1)°. Moreover, the planar atoms of the pyrone ring and the benzene ring of the chromene unit are also almost coplanar, the dihedral angle between their mean planes being 10.7 (1)°. The geometric parameters of the title molecule agree well with those reported for similar structures  ring motif. The crystal packing features C17—H17⋯O3 hydrogen bonds, which form a supramolecular chain along the a axis. This chain is connected into double layer that stacks along the c axis (Table 1Cg is the centroid of the pyrazole N1/N2/C3/C1/C2 ring) by π–π interactions, with Cg⋯Cgii = 3.801 (1) Å .The molecular conformation is stabilized by an intramolecular C19—H19⋯O1 hydrogen bond, which generates an et al., 2013a2,7.013,17]heptadeca-2(7),3,5,13 (17),15-pentaene-10-carboxylate, (III) E)-methyl 2-[(2-formyl-6-methoxyphenoxy)methyl]-3-(4-methoxyphenyl)acrylate  and 3-methyl-1-phenyl-1H-pyrazol-5-one  was placed in a round-bottomed flask and melted at 453 K for 1 h. After completion of the reaction as indicated by thin-layer chromatography, the crude product was washed with 5 ml of an ethyl acetate and hexane mixture (1:49 ratio), which successfully provided the title compound as a colourless solid in 93% yield. Colourless blocks were obtained by slow evaporation of an ethyl acetate solution at room temperature.A mixture of (Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. Owing to poor agreement, the reflections 100, 011 and 100 were omitted from the final cycles of refinement.Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S1600536814017929/hb7257sup1.cifCrystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814017929/hb7257Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S1600536814017929/hb7257Isup3.cmlSupporting information file. DOI: 962784CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


Figure legend 1 is incorrect. The correct figure legend is:Figure 1. Effect of maggot secretions on the tPA-induced lysis of plasma clots (representative example). No secretions —; 12.5 µg of secretions/mL — — —; 25 µg of secretions/mL – — – —; 50 µg of secretions/mL – – –.


The title compound crystallized with two independent molecules in the asymmetric unit. In the crystal, they are linked to one another, forming chains enclosing  22H17NO4, crystallizes with two independent molecules (A and B) in the asymmetric unit. Each molecule exists as an E isomer with C—C=C—C torsion angles of −175.69 (17) and −178.41 (17)° in A and B, respectively. In molecule A, the planes of the terminal benzene rings are twisted by an angle of 26.67 (10)°, while the biphenyl unit is non-planar, the dihedral angle between the rings being 30.81 (10)°. The dihedral angle between the nitrophenyl ring and the inner phenyl ring is 6.50 (9)°. The corresponding values in molecule B are 60.61 (9), 31.07 (8) and 31.05 (9)°. In the crystal, molecules are arranged in a head-to-head manner, with the 3-nitrophenyl groups nearly parallel to one another. The A and B molecules are linked to one another via C—H⋯O hydrogen bonds, forming chains lying parallel to (-320) and enclosing R22(10) and R22(12) ring motifs. The methoxy group in both molecules is positionally disordered with a refined occupancy ratio of 0.979 (4):0.021 (4) for molecule A and 0.55 (4):0.45 (4) for molecule B.The title compound, C Each molecule exists as an E isomer with the C17—C16—C15—C14 and C39—C38—C37—C36 torsion angles being −175.69 (17) and −178.41 (17)°, respectively. In molecule A, the terminal benzene rings (C2–C7) and (C17–C22) are twisted by an angle of 26.67 (10)°, while the biphenyl rings (C2–C7 and C8–C13) are non-planar, the dihedral angle being 30.81 (10)°. The dihedral angle between rings (C8–C13) and (C17–C22) is 6.50 (9)°. The corresponding dihedral angles in molecule B are (C24–C29 and C39–C44) 60.61 (9), (C30—C35 and C24–C29) 31.07 (8) and (C30–C35 and C39–C44) 31.05 (9)°.The title compound, Fig. 1A and B lie head-to head almost parallel to one another. They are linked via C—H⋯O hydrogen bonds, forming chains lying parallel to -3-(biphenyl-4-yl)-1-prop-2-en-1-one -1--3-(2-methylphenyl)prop-2-en-1-one -3-(3-nitrophenyl)prop-2-en-1-one  and 6.50 (9)°, respectively.A search of the Cambridge Structural Database  and 3-nitro benzaldehyde  in ethanol (25 ml) in the presence of NaOH (10 ml 30%) was heated in a water bath for 30 min. and then allowed to cool. The solid that separated was filtered and recrystallized from ethanol. The yellow-coloured crystals of the title compound used for the X-ray diffraction study were grown by slow evaporation from acetone .Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms. The refined occupancy ratios for the disordered methoxy groups are 0.979 (4):0.021 (4) for atoms O1A/O1B and C1A/C1B in molecule A and 0.55 (4):0.45 (4) for atoms O5A/O5B and C23A/C23B in molecule B.Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989014025110/su5021sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989014025110/su5021Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989014025110/su5021Isup3.cdxSupporting information file. DOI: Click here for additional data file.10.1107/S2056989014025110/su5021Isup4.cmlSupporting information file. DOI: 1034620CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The amide group is twisted by 31.30 (16)° with respect to the pyridine ring. In the crystal, molecules are linked by O—H⋯O, O—H⋯S and N—H⋯S hydrogen bonds into a three-dimensional supramolecular network. Weak π–π stacking is observed between parallel pyridine rings of adjacent molecules, the centroid–centroid distance being 3.8270 (19) Å.In the title compound, [Co(NCS) DOI: 10.1107/S1600536814011453/xu5790Isup2.hklStructure factors: contains datablock(s) I. DOI: 850080CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In the structure of the naphthoquinone derivative 2-hydroxy-3-(2-methylprop-1-en-1-yl)naphthalene-1,4-dione, the molecules form a centrosymmetric cyclic dimer through intermolecular O—H⋯O hydrogen bonds which, together with intermolecular C—H⋯O hydrogen bonds and weak π–π ring interactions, give rise to an overall two-dimensional structure. 14H12O3, the substituent side chain, in which the H atoms of both methyl groups are disordered over six equivalent sites, lies outside of the plane of the naphthalenedione ring. The ring-to-chain C—C—C—C torsion angles are 50.7 (3), −176.6 (2) and 4.9 (4)°. An intramolecular methyl–hydroxy C—H⋯O hydrogen bond is present. In the crystal, molecules are primarily connected by intermolecular O—H⋯O hydrogen bonds, forming a centrosymmetric cyclic dimer motif [graph set R22(10)]. Also present is a weak intermolecular C—H⋯O hydrogen bond linking the dimers and a weak π–π ring interaction [ring centroid separation = 3.7862 (13) Å], giving layers parallel to (10-3).In the structure of the title compound, C Also present in the structure is a weak intermolecular C7—H⋯O2ii hydrogen bond [3.339 (3) Å], linking the dimers and a weak π–π ring interaction between the benzene and quinone ring moieties of the parent ring system , giving layers parallel to  = 1.2Ueq(C). Rotational disorder was identified in the hydrogen atoms of the methyl carbon atoms C12 and C22 and these were included in the refinement over six equivalent 60° sites with 50% occupation, with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C).Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989015024755/zs2357sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015024755/zs2357Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015024755/zs2357Isup3.cmlSupporting information file. DOI: 1444109CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The ligand selection of bidentate β‐diketonates is shown to be key to isolating a cyclic trimer. Additional reaction of β‐diketonates with diethyl zinc were spectroscopically characterized as compounds of the type [{Zn(Et)(β‐diketonate)}n] (β‐diketonate=OC(Me)CHC(Me)O, 2, OC(OtBu)CHC(Me)O, 3). Further studies have shown that selective oxidation of these species produces cubanes of the general formula [{Zn(OC(R)CHC(Me)O)2Zn(Et)OEt}2] , allowing a high oxygen content whilst remaining structurally suitable for use as precursors. The successful deposition of thin films of zinc oxide through aerosol‐assisted chemical vapor deposition (AACVD), using a novel precursor, is described and fully characterized.A conventional solution‐based route to a cyclic trimeric organozinc compound [{Zn(Et)( Studies involving zinc alkoxides were first reported by Frankland in 18492Zn compounds through the contributions of Lewiński et al. and a handful of other groups.azol)]2[EtZn(azol)]2,  bridged by peroxide groups. Interestingly, this work was the first to ‘suggest the presence of a trimer as the predominate species in solution’ of the precursor aggregate, namely, [EtZn(azol)]n.The widely accepted belief that the oxidation of zinc alkyls is so fast, selectivity is not possible, was first dispelled by the structural characterization of a novel zinc alkylperoxide.It is known that the structure of organozinc compounds can be enormously varied, including multinuclear rings3 ‐2‐(dimethylaminomethyl)‐iso‐propoxide), whilst not crystallographically characterized, has a cyclic, not a roof‐like, trimeric structure (thf)}2] under mild conditions to give [{tBuZnOtBu}3]. This cluster was reported to have two distinct types of organozinc centers: two four‐coordinate zinc centers linked by two μ3‐ and one μ2‐oxygen atoms, and one three‐coordinate zinc center binding to two μ2‐oxygen atoms. It was found to be a metastable product, as solution‐based attempts to form the compound resulted solely in the tetramer. Later in 2012, it was shown that by using a more rigid quinoline ligand, thus moving from a ZnCO3 coordination environment to ZnCNO2, a trimer could be isolated and was structurally characterized as [tBuZn(q)]3 (q=8‐hydroxyquinoline).In 2010, the first crystallographically characterized organozinc ‘dimeric aggregate’ with a Zn3 , in which the use of bidentate β‐diketonate ligands facilitated crystallization. Similar reactions of diethyl zinc with β‐diketonates yielded compounds of the type [{Zn(Et)(β‐diketonate)}n], which were spectroscopically characterized. In addition, selective reaction of these compounds with oxygen yields distorted cubanes of the general formula [{Zn(β‐diketonate)2Zn(Et)OEt}2]. These compounds exhibit a similar central motif to that reported previously.Herein, we report the first instance of a conventional solution‐based synthetic route to a structurally characterized cyclic trimeric organozinc compound with the coordination environment ZnCO3 Figure  a, [{Zn(β‐diketonate [{Zn(Et)(OC(OMe)CHC(Me)O)}3] (1) was isolated and structurally characterized; furthermore, compounds of stoichiometry [{Zn(Et)(OC(R)CHC(Me)O)}n], where R=Me (2) and OtBu (3) (Scheme 1–3 were isolated from the equimolar reaction of Et2Zn with the respective carbonyl in high yield (>90 %) and characterized by using spectroscopic techniques. Although 2 and 3 formed crystalline solids, none were of suitable quality for crystallographic analysis.The trimeric Me)O)}3]  was isol1 crystallizes in the monoclinic space group P21/n with three zinc centers, all exhibiting a distorted tetrahedral coordination –O(O(1):2.0489(9) Å, Zn(2)–O(4):2.0247(9) Å, Zn(3)–O(7):2.0367(9) Å] and the longer bridging Zn−O lengths , which is comparable to similar structures found in the literature.1 results largely from the constraints of the central Zn3O3 ring and the three outer ZnO2C3 rings formed from coordination to the bidentate ligands.Compound tBuZnOtBu}3] –O(7), 3.042 Å, which is considerably larger than the comparable distance in [{tBuZnOtBu}3] (2.164 Å),1.For comparison with the previously reported ‘dimeric aggregate’ [{] Figure  c, the ctBu}3] 2.4 Å,16 prβ‐diketonate ligand facilitates the isolation of a novel type of cyclic trimeric organozinc complex (1) with a coordination environment of ZnCO3, as confirmed by crystallographic characterization. The monodentate tBu groups used by Lewiński resulted in a metastable roof‐like trimer (or aggregated dimer), whereas the flexible amino alcoholates utilized by Molloy and co‐workers yielded oils, not solids, although NMR studies did suggest a cyclic trimeric center.The above data indicate that the use of a rigid bidentate 1–3 were explored.The rationale behind this ligand choice firstly lies in the successful isolation of a novel structural type, but also in increasing the oxygen loading of the compounds (as zinc precursors can lead to oxygen‐deficient thin films).2Zn(Et)OEt}2] (R=OMe (4), Me (5), OtBu (6)) were synthesized through the controlled addition of O2 to solutions of 1–3 (Scheme μ2‐OEt group in accordance with previous reports.4–6 were isolated in high yields (>80 %) and characterized by using spectroscopic techniques. Compounds 5 and 6 both crystallized out of concentrated solutions held at −18 °C as centrosymmetric clusters in the triclinic P̄1 space group with four zinc centers; two of which are unique and two are symmetrically generated about an inversion center . (2 and 3). Through selective oxidation, we have subsequently shown the synthesis of [{Zn(OC(R)CHC(Me)O)2Zn(Et)OEt}2] (4–6). X‐ray crystallography of 5 and 6 revealed these complexes to have a face‐shared, corner‐removed, inversion‐related, bis‐heterocubane central motif. Of additional importance is that these materials can be used as precursors to thin films of zinc oxide; as exemplified in the successful deposition of hexagonal wurtzite zinc oxide thin films. We believe these results provide a new route, through careful ligand selection, to cyclic organozinc trimers, whose rarity was commented on by Power and co‐workers back in 1991.In summary, we have demonstrated the solution‐based synthesis of the first structurally characterized cyclic trimer with a Zn1, 5, and 6 can be found in the Supporting Information.Crystallographic/refinement data for compounds m in hexanes) was obtained from Sigma Aldrich and used as supplied. Acetylacetone, methyl acetoacetate, and tert‐butyl acetoacetate were obtained from Sigma Aldrich, degassed, and stored over activated molecular sieves.All manipulations were performed under a dry dinitrogen atmosphere by using standard Schlenk techniques. Hexane was stored in an alumina column and dried with anhydrous engineering equipment. Diethylzinc solution . Mass spectroscopy was performed on a Thermo Finnigan MAT900 XP operating in electron impact and chemical ionization modes. Single‐crystal X‐ray diffraction datasets were collected on a SuperNova  Atlas diffractometer by using either monochromated Cu Kα radiation (λ=1.54184 Å) or monochromated Mo Kα (λ=0.71073 Å).m solution in hexanes, 9.76 mmol) was added to dry hexane (5 mL) at −78 °C. Dry methyl acetoacetate  was added dropwise to the solution and stirred at RT for 48 h. Hexane was fully removed in vacuo, resulting in an off‐white solid. Off‐white crystals grew from a concentrated solution held at −18 °C. Yield: 1.86 g, 91 %; 1H NMR (600 MHz) δ (C6D6): 0.55 , 1.47 , 1.90 , 3.27 , and 4.95 ppm ; 13C{1H} NMR (600 MHz) δ (C6D6): 1.0 (CH2CH3), 12.5 (CH2CH3), 27.5 (CCH3), 51.1 (OCH3), 89.3 (CCHC), 174.0 (COCH3), and 184.4 ppm (CCH3); anal. calcd. for C21H36O9Zn3: C 40.12, H 5.77; found: C 40.21, H 5.89.Diethylzinc  was added to dry hexane (5 mL) at −78 °C. Dry acetylacetone  was added dropwise to the solution and stirred at RT for 48 h. Hexane was fully removed in vacuo, resulting in an off‐white solid. Yield: 1.71 g, 90 %; 1H NMR (600 MHz) δ (C6D6): 0.57 , 1.48 , 1.79 , and 5.03 ppm ; 13C{1H} NMR (600 MHz) δ (C6D6): 1.0 (CH2CH3), 12.4 (CH2CH3), 28.3 (CCH3), 102.0 (CCHC), and 193.1 ppm (CCH3); anal. calcd. for C21H36O6Zn3: C 43.44, H 6.25; found: C 43.09, H 6.77.Diethylzinc  was added to dry hexane (5 mL) at −78 °C. Dry tert‐butyl acetoacetate  was added dropwise to the solution and stirred at RT for 48 h. Hexane was fully removed in vacuo, resulting in an off‐white solid. Yield: 2.25 g, 91 %; 1H NMR (600 MHz) δ (C6D6): 0.37 , 1.31 3), 1.33 , 1.94 , and 4.90 ppm ; 13C{1H} NMR δ (600 MHz) (C6D6): 3.4 (CH2CH3), 11.7 (CH2CH3), 27.6 (CCH3), 28.4 (C(CH3)3), 80.9 C(CH3)3, 91.0 (CCHC), 173.8 (COC(CH3)3), and 183.2 ppm (CCH3); anal. calcd. for C30H54O9Zn3: C 47.73, H 7.21; found: C 46.93; H 6.97.Diethylzinc  was added to a solution of 1 and stirred for 15 min at −78 °C. The flask was purged with N2 and stirred at room temperature for 24 h. Off‐white crystals formed from a concentrated solution held at −18 °C. Yield: 1.85 g, 87 %; 1H NMR (600 MHz) δ (C6D6): 0.62 , 1.33 , 1.60 , 1.90 , 3.33 , 3.87 , and 4.99 ppm ; 13C{1H} NMR (600 MHz) δ (C6D6): 2.2 (ZnCH2CH3), 12.6 (ZnCH2CH3), 19.7 (OCH2CH3), 27.3 (CCH3), 50.6 (OCH3), 61.3 (OCH2CH3), 87.0 (CCHC), 173.6 (COCH3), and 183.3 ppm (CCH3); anal. calcd. for C28H48O14Zn4: C 38.64, H 5.56; found: C 38.45, H 5.64. MS: m/z [M−Zn2O5C13H27]+⋅: 474.87; [M−Zn3O8C18H34]+⋅: 294.97.O2 (5 mL) was added to a solution of 2 and stirred for 15 min at −78 °C. The flask was purged with N2 and stirred at room temperature for 24 h. Off‐white crystals formed from a concentrated solution held at −18 °C. Yield: 1.66 g, 84 %; 1H NMR (600 MHz) δ (C6D6): 0.69 , 1.42 , 1.61 , 1.79 , 3.80 , and 5.06 ppm ; 13C{1H} NMR (600 MHz) δ (C6D6): 2.7 (ZnCH2CH3), 12.9 (ZnCH2CH3), 20.1 (OCH2CH3), 28.1 (CCH3), 61.1 (OCH2CH3), 100.6 (CCHC), and 193.1 ppm (CCH3); anal. calcd. for C28H48O10Zn4: C 41.71, H 6.00; found: C 42.06, H 5.92. MS: m/z [M+C3H5]+⋅: 847.04; [M−C8H20]+⋅: 691.11; [M−Zn2O4C13H27]+⋅: 426.91; [M−Zn3O6C18H34]+⋅: 263.00.O2 (5 mL) was added to a solution of 3 and stirred for 15 min at −78 °C. The flask was purged with N2 and stirred at room temperature for 24 h. Off‐white crystals formed from a concentrated solution held at −18 °C. Yield: 2.09 g, 83 %; 1H NMR (600 MHz) δ (C6D6): 0.58 (q (br), 4 H, ZnCH2CH3), 1.44 3), 1.51 (t (br), 6 H, OCH2CH3), 1.66 , 1.92 , 4.02 , and 4.96 ppm ; 13C{1H} NMR (600 MHz) δ (C6D6): 1.8 (ZnCH2CH3), 13.1 (ZnCH2CH3), 19.8 (OCH2CH3), 27.4 (CCH3), 28.7 (C(CH3)3), 61.4 (OCH2CH3), 79.7 (C(CH3)3), 88.7 (CCHC), 173.4 (COC(CH3)3), and 182.1 ppm (CCH3); anal. calcd. for C40H72O14Zn4: C 46.26, H 6.99; found: C 46.43, H 7.27. MS: m/z [M−Zn2O5C16H33]+⋅: 601.05; [M−Zn3O8C24H46]+⋅: 379.04.O2. [(Zn(OC(Me)CHC(Me)O)2Zn(Et)O(Et))2] (5)  was dissolved in dry toluene (30 mL) under N2 and stirred for 10 min. Thin films were deposited by using optimal conditions of a N2 flow rate of 1.2 L min−1, a substrate temperature of 450 °C, and annealing in air for 5 h at 600 °C. XRD was performed using a Bruker D8 Discover X‐ray diffractometer by using monochromatic Cu Kα1 and Cu Kα2 radiation of wavelengths 1.54056 and 1.54439 Å, respectively, emitted in an intensity ratio of 2:1 with a voltage of 40 kV and a current of 40 mA. SEM was performed by using a Philips XL30 FEG operating in plan and cross‐section mode with an electron beam accelerating energy of 30 kV. XPS surface and depth profiling was performed by using a Thermo Scientific K‐Alpha XPS system with monochromatic Al Kα radiation at 1486.6 eV as the X‐ray source. Etching was achieved by using an Ar‐ion etch beam at 1 KeV with a current of 1.51 μA. CasaXPS software was used to analyze the data with binding energies referenced to an adventitious C 1s peak at 284.8 eV. UV/Vis/NIR transmission spectra were recorded by using a PerkinElmer Lambda 950 spectrometer in the range of 300–1400 nm with an air background.Films were deposited onto float‐glass substrates with a 25 nm barrier layer of crystalline SiOAs a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.SupplementaryClick here for additional data file.


E,E)-2′,4′-dihydroxyacetophenone azine molecule is located on an inversion centre and linked with dimethylformamide solvent molecules via O—H⋯O hydrogen bonds.The approximately planar -2′,4′-dihydroxyacetophenone azine molecule is centrosymmetric, the mid-point of the N—N bond being located on an inversion centre. All the non-H atoms of the azine molecule are approximately coplanar, the maximum deviation being 0.017 (2) Å. An intramolecular O—H⋯N hydrogen bond occurs between the azine N atom and the hydroxy group. In the crystal, azine and dimethylformamide solvent molecules are linked by O—H⋯O hydrogen bonds.In the title compound {systematic name: 4,4′-bis}, C Fluorescence properties of hydrazones have been reported -2′,4′-dihydroxyacetophenone azine dimethylformamide disolvate, (I)Although 2′,4′-dihydroxyacetophenone azine has been prepared and studied as a fluorescent probe, its structure has not been reported. As a part of our studies on synthesis and structural peculiarities of Schiff base ligands derived from 2′,4′-dihydroxyacetophenone and hydrazine, we determined the structure of the title compound, -2′,4′-dihydroxyacetophenone azine and one dimethylformamide (DMF) molecule. The complete azine molecule is centrosymmetric and exists in an E,E configuration with respect to the two C=N bonds. The N1—C2 bond length of 1.301 (3) Å shows double-bond character. The C—O bond lengths [1.349 (3) and 1.358 (3) Å] are comparable with similar bonds in related structures  are essentially planar, with a mean deviation of 0.0024 Å. Each hydroxy group is nearly coplanar with its attached benzene ring; the r.m.s. deviation is 0.0045 Å for the seven non-H atoms. Intramolecular O—H⋯N hydrogen bonds exist in the azine molecule , intermolecular O—H⋯O hydrogen bonds exist between azine molecules and DMF molecules Table 1.E,E)-2,2′-diphenol -4,4′-dichloro-2,2′-diphenol -3,3′-diethoxy-2,2′-diphenol -4,4′-dimethoxy-2,2′-diphenol : δ 13.59 , 10.14 , 7.58–7.61 , 6.37–6.41 , 6.30–6.31 , 3.34 .A mixture of 2′,4′-dihydroxyacetophenone , hydrazine sulfate  and triethylamine  in ethanol (40 ml) was heated under reflux for 24 h. After cooling, the precipitate was filtrated and washed with water to afford a yellow solid. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in DMF at room temperature for 5 d . Uiso(H) = 1.2Ueq(C) for aromatic H atoms or 1.5Ueq for methyl and hydroxy groups.Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989016003686/xu5885sup1.cifCrystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016003686/xu5885Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989016003686/xu5885Isup3.cmlSupporting information file. DOI: 1457201CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The Pd—N bond distances are 2.022 (2) and 2.027 (2) Å, the Pd—Cl bond distances are 2.2880 (7) and 2.2833 (7) Å, and the ligand bite angle is 80.07 (9)°. The dimethyl sulfoxide and water molecules form linear chains along [100] by O—H⋯O and O—H⋯S hydrogen bonds, generating eight- and 12-membered rings. C—H⋯Cl interactions link the chains, forming a three-dimensional arrangement. In addition, the 4,4-di-tert-butyl-2,2′-bipyridine ligand exhibits π–π stacking interactions [centroid–centroid distances = 3.8741 (15) and 3.8353 (15) Å]. The DMSO solvent is disordered and was refined with an occupancy ratio of 0.866 (3):0.134 (3).The title compound, [PdCl DOI: 10.1107/S1600536814009453/pj2010Isup2.hklStructure factors: contains datablock(s) I. DOI:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains propagating along the  23H20BrNO3S, the –(CH2)4– atoms are positionally disordered [occupancy ratio = 0.753 (6):0.247 (6)]. The ring has a half-chair conformation for both the major and minor components. The dihedral angles between the mean plane of the thiophene ring and those of the benzene and phenyl rings are 35.2 (4) and 57.7 (3)°, respectively. The planes of the two aryl rings are twisted with respect to each other by 86.4 (6)°. In the molecule, there is an O—H⋯N hydrogen bond forming an S(6) ring motif. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming chains parallel to [100].In the cyclohexene ring of the title compound, C Reviews on the synthesis and properties of these compounds have been reported (Sabnis A/C4–C7/C7A) and (C3A/C44–C47/C7A) adopt a half-chair conformation. The mean plane of the major component (C3A/C4–C7/C7A) is slightly twisted from the mean plane of the thiophene ring (S1/C2/C3/C3A/C7A) by 5.18 (14)°. The dihedral angles between the mean plane of the thiophene ring and the benzene (C21–C26) and phenyl (C31–C36) rings are 35.2 (4) and 57.7 (3)°, respectively. The two aryl rings are normal to each other, making a dihedral angle of 86.4 (6)°. In the molecule there is an O—H⋯N hydrogen bond forming an S(6) ring motif methanone derivatives gave eight hits, which include five structures closely related to the title compound. These include [2-[(2-hydroxybenzylidene)amino](phenyl)methanone (I)et al., 2014aet al., 2014bb]thiophen-3yl](phenyl)methanone (III) -4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl](phenyl)methanone (IV) thiophene-3-yl](phenyl)methanone (V) thiophen-3-yl)-phenylmethanone  in 10 ml of methanol an equimolar amount of 5-bromo-2-hydroxy-3-methoxybenzaldehyde  was added with constant stirring. The mixture was refluxed for 6 h. A yellowish brown precipitate was obtained. Completion of the reaction was confirmed by thin layer chromatography. The precipitate obtained was filtered and dried at room temperature overnight. The solid was then recrystallized using a 1:1 solution of acetonitrile and dichloromethane, giving colourless block-like crystals.To a solution of  = 1.5Ueq for the hydroxyl and methyl H atoms, and = 1.2Ueq(C) for other H atoms. A single weak outlier reflection  I. DOI: 10.1107/S2056989015000195/su5055Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015000195/su5055Isup3.cmlSupporting information file. DOI: 1042320CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


These interactions exhibit a parallel displaced π–π stacking mode. Additional weak C—H⋯π-ring and C—H⋯N and C—H⋯F interactions are found, leading to a three-dimensional architecture. The RuII atom is coordinated in a distorted octahedral geometry. The counter-charge is provided by two hexafluoridophosphate anions and the asymmetric unit is completed by three acetonitrile solvent molecules of crystallization. Four F atoms of one PF6− anion are disordered over three sets of sites with occupancies of 0.517 (3):0.244 (3):0.239 (3). Two acetonitrile solvent molecules are highly disordered and their estimated scattering contribution was subtracted from the observed diffraction data using the SQUEEZE option in PLATON .In the title compound, Spek 2009. Acta Cr II complexes with tape and bpy-type ligands, see: Brietzke et al. 2(C16H8N4)](PF6)2·3C2H3N = 0.047wR(F2) = 0.124S = 0.948918 reflections743 parameters363 restraintsH-atom parameters constrainedmax = 0.51 e Å−3Δρmin = −0.54 e Å−3ΔρX-AREA  global, I. DOI: 10.1107/S1600536814011969/tk5315Isup2.hklStructure factors: contains datablock(s) I. DOI: 1004679CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


In the crystal, molecules are linked  25H25N3O, comprises a 2-aminopyridine ring fused with a cycloheptane ring, which adopts a chair conformation. The central pyridine ring (r.m.s. deviation = 0.013 Å) carries three substituents, viz. a benzylamino group, a methoxyphenyl ring and a carbonitrile group. The N atom of the carbonitrile group is significantly displaced [by 0.2247 (1) Å] from the plane of the pyridine ring, probably due to steric crowding involving the adjacent substituents. The phenyl and benzene rings are inclined to one another by 58.91 (7)° and to the pyridine ring by 76.68 (7) and 49.80 (6)°, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯Nnitrile hydrogen bonds generate R22(14) loops. The dimers are linked by C—H⋯π and slipped parallel π–π interactions [centroid–centroid distance = 3.6532 (3) Å] into a three-dimensional structure.The title compound, C The cycloheptane ring adopts a chair conformation with puckering parameters Q2 = 0.4634 (15) Å, ϕ2 = 304.24 (18)° and Q3 = 0.6481 (16) Å and ϕ3 = 284.37 (12)°. The phenyl (C22–C27) and benzene (C31–C36) rings are inclined to one another by 58.91 (7)° and to the pyridine (N3/C2–C6) ring by 76.68 (7) and 49.80 (6)°, respectively. The N atom of the carbonitrile group, N1, is significantly displaced by 0.2247 (1) Å from the plane of the pyridine ring, perhaps due to steric crowding. The shortening of the C—N distance [C5—N3 = 1.3390 (14) Å] and the opening of the N3—C5—C4 angle to 124.47 (10)° may be attributed to the size of the substituent at C1, and correlates well with the values observed in a similar structure  Å is shorter than the average conjugated C—N single bond, 1.370 (1) Å, found in the Cambridge Structural Database  Å is significantly shorter than the O1—C37 distance of 1.410 (2) Å. An enlargement of bond angle [C33—C34—O1 = 124.34 (13)°] on one side and a narrowing of bond angle [C35—C34—O1 = 116.29 (12)°] on the other side of the benzene ring may be due to the steric repulsion between the aromatic rings and the methyl group, as found in a similar structure , normal distance = 3.5920 (5), slippage = 0.667 Å; Cg1 is the centroid of the N3/C2–C6 ring; symmetry code: (i) −x + 1, −y + 1, −z + 1], as shown in Fig. 2In the crystal, molecules are linked r Table 1. They arH-cyclohepta[b]pyridine -4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5p-TSA (1.0 mmol) was added. The reaction mixture was heated under reflux for 2–3 h. On completion of the reaction, checked by thin-layer chromatography (TLC), the mixture was poured into crushed ice and extracted with ethyl acetate. The excess solvent was removed under vacuum and the residue was subjected to column chromatography using petroleum ether/ethyl acetate mixture (97:3 v/v) as eluent to afford pure product. The product was recrystallized from ethyl acetate, affording colourless crystals of the title compound. .A mixture of cycloheptanone (1 mmol), 4-methoxy aldehyde (1 mmol) and malononitrile (1 mmol) and benzylamine (1mmol) was taken in ethanol (10 ml) to which Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq for other H atoms. The DELU restraint was applied.Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S1600536814024878/su5014sup1.cifCrystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814024878/su5014Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S1600536814024878/su5014Isup3.cmlSupporting information file. DOI: 1033842CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information:


The naphthyl moieties are close to perpendicular [dihedral angle = 72.08 (5)°]. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, generating layers which surround channels occupied by disordered guest molecules.In the solid-state, bis- 44H44N2O8, iminiumyl]methyl}-3,3′-dimethyl-2,2′-binaphthalene-7,7′-diolate) has been obtained by the addition of p-anizidine to gossypol dissolved in dichloromethane. In the solid state, the title compound exists in the enamine or quinoid form. The two naphthyl moieties are inclined to one another by 72.08 (5)°. The pendant phenyl rings are inclined at 22.26 (14) and 23.86 (13)° to the corresponding naphthyl rings. In the crystal, molecules are incorporated into layers through inversion-related pairs of O—H⋯O interactions [graph sets R22(20) and R22(10)] and translation-related O—H⋯O interactions [graph set C(15)]. The packing of these layers in the crystal structure gives rise to channels in the [011] direction, with hydrophobic interactions occurring between adjacent layers. The channels are 5–7 Å wide, and the void volume of each cell is 655 Å3, corresponding to 26.6% of the cell volume. Disordered guest molecules, probably solvent and water molecules, occupy these voids of the crystal; their contribution to the scattering was removed with the SQUEEZE routine  of PLATON .The title compound, CSpek 2015. Acta CrSpek 2009. Acta Cr However, bis-p-anizidinegossypol crystallizes in a triclinic  and 1.476 (4) Å. In addition, the N1—C22 [1.332 (4) Å] and N2—C27 [1.319 (4) Å] bonds are shorter than N1—C31 [1.433 (4) Å] and N2—C38 [1.441 (4) Å], respectively. Contrarily, C7=O3 [1.289 (3) Å] and C17=O7 [1.275 (3) Å] bonds are longer than typical standard values.The molecule consists of four ring systems, two of which are naphthalene ring systems, and the other two are phenyl rings. The C1–C10 naphthyl unit is more planar then C11–C20 naphthyl one in which atoms C12, C16, C17, C18 and C19 deviate by 0.051 (3), 0.070 (3), 0.059 (3), 0.082 (3) and 0.054 (3) Å, respectively, from the mean plane. The two naphthyl moieties are inclined to one another by 72.08 (5)°. The phenyl rings are inclined at 22.26 (14) and 23.86 (13)° to the corresponding naphthyl rings. The bond lengths and angles are mostly in good agreement with those observed in the analogous fragments of the gossypol and dianilinegossypol molecules (Gdaniec A⋯O3 (and N2—H2⋯O7) bond closes a six-membered ring C7—C8—C22—N1—H1A⋯O3 (and C17—C18—C27—N2—H3⋯O7), while the other type of hydrogen bond O4—H4⋯O3 (and O8—H8⋯O7) forms a five-membered ring C6—C7—O3⋯H4—O4 (and C16—C17—O7⋯H8—O8) (Table 1There are two intramolecular hydrogen bonds in the molecule. The N1—H1) Table 1.p-anizidinegossypol molecules are incorporated into centrosymmetric dimers typical for gossypol and dianilinogossypol crystal structures by means of a pair of inversion-related hydrogen bonds O5—H5⋯O3  and a very weak aromatic π–π stacking interaction with a Cg⋯Cg distance of 4.182 (2) Å where Cg is the centroid of the C31–C36 ring. The packing of these layers in the crystal structure gives rise to wide ragged channels in the [011] direction. The stabilization of the crystal structure is supported by hydrophobic interactions between adjacent layers. The channels in the structure are 5-7 Å wide and the void volume of each cell is 655 Å3, corresponding to 26.6% of the cell volume. Disordered solvated molecules, probably solvent and water molecules, occupy these voids of the crystal; their contribution to the scattering was removed with the SQUEEZE routine . C-bound H atoms were positioned geometrically and refined using a riding model, with d(C—H) = 0.93 Å and Uiso = 1.2Ueq(C) for aromatic, d(C—H) = 0.98 Å and Uiso = 1.2Ueq (C) for methine, d(C—H) = 0.96 Å and Uiso = 1.5Ueq (C) for methyl H atoms.Crystal data, data collection and structure refinement details are summarized in Table 210.1107/S2056989015020393/hb7516sup1.cifCrystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020393/hb7516Isup2.hklStructure factors: contains datablock(s) I. DOI: Click here for additional data file.10.1107/S2056989015020393/hb7516Isup3.cmlSupporting information file. DOI: 1433643CCDC reference:  crystallographic information; 3D view; checkCIF reportAdditional supporting information: