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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

December 2018 issue

Highlighted illustration

Cover illustration: An overview of six new complexes based on tris(bipyridyl)iron(II) is given, in which the counter-ion is a 2-substituted 1,1,3,3-tetracyanopropenide anion. Polynitrile anions are very versatile ligands, due to their ability to coordinate and bridge metal ions in many different ways. This allows molecular architectures with different topologies and dimensionalities to be obtained. In the present paper, these anions play a major role not as ligands, but in directing the supramolecular structure of the iron complexes, through the formation of C-H...N and C-H...[pi] interactions. A detailed description of the different motifs present in the crystal structures is presented, taking into account the various forms of anion disorder. See: Addala, Setifi, Morimoto, Artetxe, Matsumoto, Gutiérrez-Zorrilla & Glidewell [Acta Cryst. (2018). E74, 1717-1726].

research communications


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The first benzohydrazide complex of a lanthanide is reported. The SmIII ion is nine-coordinated in a distorted tricapped trigonal–prismatic geometry by three oxygen atoms and three nitro­gen atoms from three benzhydrazide (bzz) ligands, one oxygen atom from the isophthalate (itp2−) ligand, and two oxygen atoms from coordinated water mol­ecules. The crystal structure features extensive hydrogen bonding as well as C—H⋯π and π–π inter­actions.

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The closely related title compounds are comprised of three types of rings: thia­zolidinone, nitrophenyl and cyclo­hexyl. In both structures, the rings are close to mutually perpendicular, with inter­planar dihedral angles greater than 80° in each case.

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One O atom of the succinate anion and three O atoms and two N atoms from a tetra­kis­(2-hy­droxy­eth­yl)ethyl­enedi­amine ligand coordinate to the NiII cation to form the complex which has a distorted octa­hedral geometry.

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The title compounds were prepared via chemo- and regioselective [3 + 2]-cyclo­additions. The thio­phene ring in each crystal structure has an envelope conformation. The largest differences between the two mol­ecular structures is in the bond lengths about the quaternary C atom of the thio­phene ring. In the spiro­cyclic structure, the C—C bonds to the spiro C atom in the cyclo­butane ring are around 1.60 Å and weak inter­molecular C—H⋯X (X = S, O) inter­actions link the mol­ecules into extended ribbons. In the other structure, weak C—H⋯π inter­actions link the mol­ecules into sheets.

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The crystal structures of three N′-(aryl­idene)4-nitro­benzene­sulfono­hydrazides, namely, (E)-4-nitro-N′-(2-chloro­benzyl­idene)benzene­sulfono­hydrazide (I), (E)-4-nitro-N′-(2-methyl­benzyl­idene) benzene­sulfono­hydrazide (II) and (E)-4-nitro-N′-(4-methyl­benzyl­idene)benzene­sulfono­hydrazide (III), have been studied to investigate the effect of the nature and site of substitutions on the structural parameters and the supra­molecular features in these compounds. Hirshfeld surface analysis was also carried out to examine the contributions of the various atom–atom inter­actions in the crystal packing of the three compounds.

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The structures are reported of six racemic tris­(bipyrid­yl)iron salts with a range of 2-substituted-1,1,3,3-tetra­cyano­propenide anions, mostly also containing either perchlorate or tetra­fluorido­borate as co-anions. In three of the compounds the polynitrile anions are fully ordered, and in three others they are disordered, while the co-anion is also ordered in three compounds, but disordered in two others. Supra­molecular assemblies range from no continuous aggregation up to a three-dimensional hydrogen-bonded framework structure.

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The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid with ethyl­eneurea and the 1:2 co-crystal of chloranilic acid with hydantoin have been determined at 180 K. In the crystals of both compounds, the base mol­ecules are in the lactam form and no acid–base inter­action involving H-atom transfer is observed. The acid and base mol­ecules are linked by short O—H⋯O and N—H⋯O hydrogen bonds.

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The title compound crystallizes in monoclinic (space group P21/c) and triclinic (space group Pī) forms from N,N-di­methyl­formamide and isopropyl alcohol solutions, respectively. The planar structures of the mol­ecules in both crystals are essentially the same as each other, with maximum deviations of 0.0969 (11) and 0.209 (4) Å for the monoclinic and triclinic forms, respectively, from the mean planes of all non-H atoms.

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Three ammonium salts of 2-amino-4-nitro­benzoate are described. Based on N—H⋯O and O—H⋯O hydrogen-bonding involving the different constituents, supra­molecular chains, tubes and double-layers are found in their crystals.

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Two polymorphic crystal forms of 6-methyl-N-phenyl-2,3-di­hydro-1,4-oxathiine-5-carboxamide) were isolated from a truncated, (12 solvent), polymorph screen on pure lyophillized material. Crystals of form 1 were obtained from all solvents included in the screen with the exception of methanol. As isolated from aceto­nitrile the crystals are triclinic, space group P\overline{1} with Z′ = 2. Crystals of form 2, which were isolated from methanol only are monoclinic, space group I2/a with Z′ = 1.

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In the title compound, the benzo­diazo­lone moieties are planar to within 0.017 (1) and 0.026 (1) Å, and oriented at a dihedral angle of 57.35 (3)°. In the crystal, two sets of inter­molecular C—H⋯O hydrogen bonds generate layers parallel to the bc plane.

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In the binuclear complex, [Cu2(OH)2(C12H7N2(PO3C2H5))2(H2O)2]·7H2O, the two Cu2+ cations each have a square-pyramidal geometry and are bridged by two hydroxide groups. The phenanthroline ligand in this complex acts as a counter-ion due to a negatively charged mono­ethyl­phosphoryl group. In the crystal, O—H⋯O hydrogen bonds link the cations, P(O)(O)(OEt) group and water mol­ecules of crystallization into a three-dimensional supra­molecular architecture.

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The new compound (BEDT-TTF)4[Cu(NCS)4] based on the organic donor BEDT-TTF [bis­(ethyl­enedi­thio)­tetra­thia­fulvalene] has been obtained during a galvanostatic electrocrystallization process with Cu(NCS). It exhibits a pseudo-κ arrangement, never observed up to now in the BEDT-TTF family with thio­cyanato­cuprate(II) anions.

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The crystal structures of the title compounds have been studied to clarify the characteristics of the NO2 ligand as a C—H⋯O hydrogen-bond acceptor, in relation to the solid-state photochemical linkage isomerization.

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The asymmetric unit of the title co-crystal comprises two twisted mol­ecules of 2,2′-thiodi­benzoic acid and four mol­ecules of tri­phenyl­phosphane oxide. The three-dimensional mol­ecular packing is stabilized by hy­droxy-O—H⋯O(oxide) hydrogen bonds and TPPO-C—H⋯O(oxide, carbon­yl) and TDBA-C—H⋯(oxide, carbon­yl) inter­actions.

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Four binary charge-transfer complexes were made using pyromellitic acid dianhydride (pmda), all of which show alternating donor and acceptor stacks, which have weak C—H⋯O hydrogen bonds connecting the donor and acceptor mol­ecules.

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The crystal structure of a second phase, which results from packing polymorphism, is described for a previously reported MnIII complex.

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1-Phenyl-1H-pyrazole-3,4-di­carb­oxy­lic acid and 1-(4-meth­oxy­phen­yl)-1H-pyrazole-3,4-dicarbohydrazide form complex hydrogen-bonded framework structures each containing multiple hydrogen-bond types, but dimethyl 1-phenyl-1H-pyrazole-3,4-di­carboxyl­ate and dimethyl 1-(4-methyl­phen­yl)-1H-pyrazole-3,4-di­carboxyl­ate form simple cyclic dimers containing only C—H⋯O hydrogen bonds.

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The complex [{La(Ph3CCOO)2(Me3AlOMe)}2] has an La2(μ-OCO)4 core, contains the carboxyl­ate ligands in μ21O1O′ bridging and μ22O,O′:κ1O semi-bridging coordination modes, and displays La—C inter­actions with the π-system of a phenyl ring.

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In the polymeric potassium complex [{iPrN= CHN(iPr)N(NiPr)2K}2(μ-DME)]n, the amidino­guanidinate ligand adopts an unusual mixed σ-/π-coordination mode.

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The title mol­ecule is substanti­ally twisted, with a dihedral angle of 43.70 (2)° between the 2-(methyl­sulfan­yl)thio­phene and 4-meth­oxy­phenyl rings. In the crystal, mol­ecules are linked through C—H⋯O inter­actions, forming a bifurcated layer stacking along the b-axis direction enclosing R_{2}^{2}(10) ring motifs.

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Three compounds consisting of pyridinium or morpholinium hydrogen oxalates each display different hydrogen oxalate hydrogen-bonding motifs, resulting in chains for 4-(di­methyl­amino)­pyridinium hydrogen oxalate 0.22-hydrate, dimers for 4-tert-butyl­pyridinium hydrogen oxalate and chains for morpholinium hydrogen oxalate.

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The crystal structures of (E)-4-chloro-N′-(4-chloro­benzyl­idene)benzene­sulfono­hydrazide and (E)-4-chloro-N′-(4-nitro­benzyl­idene)benzene­sulfono­hydrazide have been studied to investigate the effect of substituents on the structural parameters. The two-dimensional fingerprint plots of these two p-substituted compounds indicate that in the 4-chloro-substituted compound, the largest contribution to the Hirshfeld surface comes from the H⋯H contacts (26.6%), in contrast to the 34.8% contribution of the O⋯H/H⋯O contacts in the 4-nitro-substituted compound.

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The title compound is built up from a planar quinoxalinone ring system linked through a methyl­ene bridge to a 1,2,3-triazole ring, which is inclined by 67.09 (4)° to the quinoxalinone ring plane.

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Straight ⋯I—PtIV—I⋯PtII⋯ chains are observed in the mixed-valent title salt. Extensive hydrogen bonding involving the amino groups, hydrogen sulfate counter-anions and water mol­ecules of crystallization stabilizes the crystal packing.

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New Schiff bases containing piperidine and aryl­sulfono­hydrazide moieties have been synthesized, characterized and their crystal structures determined to study the effect of substituents on the structural parameters. Their crystal structures are stabilized by N—H⋯O, C—H⋯O and O—H⋯O inter­actions. Two-dimensional fingerprint plots show that the largest contributions come from H⋯H inter­actions.

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The nine-membered ring system of the title compound is essentially planar. In the crystal, mol­ecules are linked via C—HTrz⋯NTrz and C—HPyrm⋯NTrz (Trz = triazole and Pyrm = pyrimidine) hydrogen bonds together with weaker C—HPyrm⋯NPyrm hydrogen bonds to form layers parallel to (\overline{1}02). The layers are further connected by π–π-stacking inter­actions between the nine-membered ring system, forming oblique stacks along the a-axis direction.

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The binuclear title mol­ecule exhibits point group symmetry 2, with the PdII atom in a square-planar coordination environment defined by two N atoms from ethyl­enedi­amine and two O atoms from methyl­enedi­phospho­nate ligands.

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In the title compound, the benzo­diazole unit is planar while the benzyl and propynyl substituents are rotated significantly out of this plane.

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In the crystal, the Schiff base mol­ecule exists in the zwitterionic form and an intra­molecular N—H⋯O hydrogen bond stabilizes the mol­ecular structure.

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The mefloquinium cation in the title salt is L-shaped as the piperidin-1-ium group is nearly orthogonal to the quinolinyl residue. Supra­molecular chains arise in the crystal as a result of charge-assisted O—HO and N—H⋯O hydrogen-bonding.

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The asymmetric unit of the title compound consist of two independent mol­ecules. In the crystal, N–H⋯O and C—H⋯O hydrogen bonds form zigzag chains along the b-axis direction. Additional C—H⋯O hydrogen bonds link the chains into layers parallel to (10\overline{1}). These are connected by slipped π-stacking and C—H⋯π(ring) inter­actions.

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In the penta­nuclear title complex, [SmZn2(C22H18N2O4)2(NCS)2(C3H7NO)2][Zn2(C22H18N2O4)(NCS)3]·C3H7NO·0.32H2O, a dinuclear unit and a trinuclear unit co-exist. In the crystal, the trinuclear cationic units and dinuclear anionic units are assembled into infinite layers.

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The compound, prepared by the NaBH4 reduction of 4,8,9,10-tetra­kis­(4-fluoro­phen­yl)-1,3-di­aza­adamantan-6-one in chloro­form and ethanol as solvent, crystallizes in the monoclinic space group P21/n with four mol­ecules in the unit cell.

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The mol­ecule of (1) presents a >C(CH3)2 group that bridges two nearly planar salicyl­aldehyde groups, each comprising a planar phenyl ring bonded with a hydroxyl and an aldehyde group. Similarly, mol­ecule (2) presents the same bridging group, but it connects two nearly planar appendants, each comprising a phenyl ring bonded with a hydroxyl and two aldehyde groups. Compound (2) exhibits a strong visible luminescence when excited with ultraviolet radiation.

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The compound tris­(1,1′-dibutyl-4,4′-bi­pyridine-1,1′-diium) bis­(dimethyl sulfoxide)di-μ3-iodido-tetra-μ2-iodido-octa­iodido­tetra­lead(II) dimethyl sulfoxide tetra­solvate belongs a class of organic–inorganic hybrid materials with novel functionalities. In this compound, C—H⋯O and C—H⋯I hydrogen-bonding inter­actions, π–π inter­actions, other short contacts and Pb octa­hedral chains are present, extending the crystal structure into a three-dimensional supra­molecular network.

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We report herein the synthesis, crystallographic analysis and a study of the non-covalent inter­actions observed in the new 4′-substituted terpyridine-based derivative bis­[4′-(isoquinolin-2-ium-4-yl)-4,2′:6′,4′′-terpyridine-1,1′′-diium] tris-[tetra­chlorido­zincate(II)]. The compound is similar in its formulation to the recently reported 2,2′:6′,2′′ terpyridinium analogue, although rather different and much simpler in its structural features, mainly in the number and type of non-covalent inter­actions present, as well as in the supra­molecular structure they define.

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The mol­ecule has mirror symmetry with the all non-H atoms, except tert-butyl groups, located on the mirror plane. An intra­molecular O—H⋯N hydrogen bond forms an S(6) ring motif. In the crystal, the mol­ecules are connected by C—H⋯π inter­actions

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The title mol­ecular salts are stilbazole, or 4-styryl­pyridine, derivatives in which the cation has a methyl group attached to the pyridine ring N atom and a diethyl amine group attached to the benzene ring. In salt (I), the cadmium atom of the [CdI4]2− dianion is located on a twofold rotation axis and the compound crystallizes with one cation in the asymmetric unit. In salt(II), the anion consists of a 4-meth­oxy­benzene­sulfonate ion, and it crystallizes as a monohydrate.

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In the title bimetallic metal–organic framework, {Fe(Brpz)2[Cu(CN)2]2}n, where Brpz is 2-bromo­pyrazine, the FeII cation is located on an inversion centre and has a slightly elongated octa­hedral FeN6 coordination environment. The CuI center has a fourfold CuC3N coordination environment with an almost perfect trigonal–pyramidal geometry. Copper(I) centers related by a twofold rotation axis are bridged by two carbon atoms from a pair of μ-CN groups, resulting in Cu2(CN)2 units that build up the coordination framework.

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In the crystal structure of the title compound, the MnII cations are octa­hedrally coordinated by two terminally N-bonded thio­cyanate anions and four 4-benzoyl­pyridine coligands into discrete complexes, which are further linked into chains by inter­molecular C—H⋯O hydrogen bonding.

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The dihydrate and hydrate forms of the DNA-binding bis-benzimidazole radioprotector methyl­pro­amine are reported. These are the first single-crystal structures of bis-benzimidazoles related to Hoechst 33342 to be reported.

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The crystal structure of the title compound has been studied to show that the macrocyclic cyclam ligand is very suitable as the co-ligand for the nitro–nitrito photo-isomerization of the CoIII complex.

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In the title imidazo[1,2-a]pyridine derivatives, N-tert-butyl-2-(4-meth­oxy­phen­yl)-5-methyl­imidazo[1,2-a]pyridin-3-amine, (I), and N-tert-butyl-2-[4-(di­methyl­amino)­phen­yl]imidazo[1,2-a]pyridin-3-amine, (II), the 4-meth­oxy­phenyl ring in (I) and the 4-(di­methyl­amino)­phenyl ring in (II) are inclined to the mean planes of the respective imidazole rings by 26.69 (9) and 31.35 (10)°.

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The title heterocyclic 1,3,4-oxa­diazole derivatives differ from each other in the groups attached to the carbon atoms: a meth­oxy­phenyl ring and a benzo­nitrile group in (I) and a chloro­phenyl ring and an acetamide group in (II).

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The paper reports the crystal structure of novel salt of 4-amino­benzoic acid (Vitamin B10) with pyrazinoic acid.

addenda and errata



Research communications

Research communications are designed to help authors bring out the science behind their structure determinations. Authors are encouraged to report more than one structure in the same communication and also to include the results of investigations with other techniques. The Research communications format makes Acta E the natural home for structure determinations with interesting science to report.

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