Synthesis and coordination to the coinage metals of a trimethylpyrazolyl substituted 3-arylacetylacetone

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Steven van Terwingen ◽  
Noah Nachtigall ◽  
Ulli Englert
Keyword(s):  
Coordination Compound ◽  
Coordination Polymers ◽  
Dihedral Angles ◽  
Rotational Degree ◽  
Two Dimensional ◽  
Π Interactions ◽  
Square Planar ◽  
Coinage Metals ◽  
Close Proximity ◽  
Linear Coordination

Abstract The ligand 3-(4-(1,3,5-trimethyl-1H-pyrazol-4-yl)phenyl)acetylacetone (1) combines a Pearson hard O,O′ chelating acetylacetone donor with a softer pyrazole N donor bridged by a phenylene spacer. Deprotonation and coordination to CuII leads to a square planar bis-acetylacetonato complex; interpreting the close proximity of an adjacent complex’s pyrazole moiety as an η 2 ${{\eta}}^{2}$ coordination to the axial CuII position leads to a two dimensional extended structure. The N donor capabilities are proven by coordination to AgPF6 and AuCl; for AgI a cationic linear bis-pyrazole complex as a toluene solvate is obtained with toluene-pyrazole π-interactions and an essentially uncoordinated PF 6 - ${{\mathrm{PF}}_{6}}^{-}$ anion. In the case of AuCl a neutral linear coordination compound with one chlorido and one pyrazole ligand 1 is obtained. Comparing the dihedral angles with a closely related but shorter ligand reveals a larger rotational degree of freedom in 1, allowing for richer architectures in emerging coordination polymers.

scholarly journals Crystal structures oftrans-dichloridotetrakis[1-(2,6-diisopropylphenyl)-1H-imidazole-κN3]iron(II),trans-dibromidotetrakis[1-(2,6-diisopropylphenyl)-1H-imidazole-κN3]iron(II) andtrans-dibromidotetrakis[1-(2,6-diisopropylphenyl)-1H-imidazole-κN3]iron(II) diethyl ether disolvate

2014 ◽  
Vol 70 (8) ◽  
pp. 72-76
Author(s):  
Roger Mafua ◽  
Titus Jenny ◽  
Gael Labat ◽  
Antonia Neels ◽  
Helen Stoeckli-Evans
Keyword(s):  
Hydrogen Bonds ◽  
Diethyl Ether ◽  
Solvent Molecule ◽  
Dihedral Angles ◽  
Halide Ions ◽  
Π Interactions ◽  
Close Proximity ◽  
Coordination Spheres ◽  
Solvent Molecules ◽  
Compound Ii

The title compounds, [FeCl2(C15H20N2)4], (I), [FeBr2(C15H20N2)4], (II), and [FeBr2(C15H20N2)4]·2C4H10O, (IIb), respectively, all have triclinic symmetry, with (I) and (II) being isotypic. The FeIIatoms in each of the structures are located on an inversion center. They have octahedral FeX2N4(X= Cl and Br, respectively) coordination spheres with the FeIIatom coordinated by two halide ions in atransarrangement and by the tertiary N atom of four arylimidazole ligands [1-(2,6-diisopropylphenyl)-1H-imidazole] in the equatorial plane. In the two independent ligands, the benzene and imidazole rings are almost normal to one another, with dihedral angles of 88.19 (15) and 79.26 (14)° in (I), 87.0 (3) and 79.2 (3)° in (II), and 84.71 (11) and 80.58 (13)° in (IIb). The imidazole rings of the two independent ligand molecules are inclined to one another by 70.04 (15), 69.3 (3) and 61.55 (12)° in (I), (II) and (IIb), respectively, while the benzene rings are inclined to one another by 82.83 (13), 83.0 (2) and 88.16 (12)°, respectively. The various dihedral angles involving (IIb) differ slightly from those in (I) and (II), probably due to the close proximity of the diethyl ether solvent molecule. There are a number of C—H...halide hydrogen bonds in each molecule involving the CH groups of the imidazole units. In the structures of compounds (I) and (II), molecules are linkedviapairs of C—H...halogen hydrogen bonds, forming chains along theaaxis that encloseR22(12) ring motifs. The chains are linked by C—H...π interactions, forming sheets parallel to (001). In the structure of compound (IIb), molecules are linkedviapairs of C—H...halogen hydrogen bonds, forming chains along thebaxis, and the diethyl ether solvent molecules are attached to the chainsviaC—H...O hydrogen bonds. The chains are linked by C—H...π interactions, forming sheets parallel to (001). In (I) and (II), the methyl groups of an isopropyl group are disordered over two positions [occupancy ratio = 0.727 (13):0.273 (13) and 0.5:0.5, respectively]. In (IIb), one of the ethyl groups of the diethyl ether solvent molecule is disordered over two positions (occupancy ratio = 0.5:0.5).

(E)-N′-(4-Chlorobenzylidene)-, (E)-N′-(4-bromobenzylidene)- and (E)-N′-[4-(diethylamino)benzylidene]- derivatives of 4-hydroxybenzohydrazide

2012 ◽  
Vol 68 (10) ◽  
pp. o408-o412 ◽  
Author(s):  
Ashokkumar Subashini ◽  
Kandasamy Ramamurthi ◽  
Helen Stoeckli-Evans
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angles ◽  
Two Dimensional ◽  
Aromatic Rings ◽  
Space Group ◽  
Π Interactions ◽  
Centroid Distance ◽  
Benzene Rings ◽  
Derivatives Of

The 4-chloro- [C14H11ClN2O2, (I)], 4-bromo- [C14H10BrN2O2, (II)] and 4-diethylamino- [C18H21N3O2, (III)] derivatives of benzylidene-4-hydroxybenzohydrazide, all crystallize in the same space group (P21/c), (I) and (II) also being isomorphous. In all three compounds, the conformation about the C=N bond isE. The molecules of (I) and (II) are relatively planar, with dihedral angles between the two benzene rings of 5.75 (12) and 9.81 (17)°, respectively. In (III), however, the same angle is 77.27 (9)°. In the crystal structures of (I) and (II), two-dimensional slab-like networks extending in theaandcdirections are formedviaN—H...O and O—H...O hydrogen bonds. The molecules stack head-to-tailviaπ–π interactions involving the aromatic rings [centroid–centroid distance = 3.7622 (14) Å in (I) and 3.8021 (19) Å in (II)]. In (III), undulating two-dimensional networks extending in thebandcdirections are formedviaN—H...O and O—H...O hydrogen bonds. The molecules stack head-to-headviaπ–π interactions involving inversion-related benzene rings [centroid–centroid distances = 3.6977 (12) and 3.8368 (11) Å].

Syntheses and structures of two new coordination polymers generated from a 4-aminotriazole-bridged organic ligand and CoII salts

2017 ◽  
Vol 73 (3) ◽  
pp. 247-253 ◽  
Author(s):  
Xue-Ru Wang ◽  
Jian-Ping Ma ◽  
Yu-Bin Dong
Keyword(s):  
Coordination Polymers ◽  
Weak Interactions ◽  
Organic Ligand ◽  
Organic Ligands ◽  
Two Dimensional ◽  
Structural Variations ◽  
X Ray ◽  
Π Interactions ◽  
Coordination Spheres ◽  
Solvothermal Conditions

Organic ligands and counter-anions influence the coordination spheres of metal cations and hence the construction of coordination polymers (CPs). The specific bent geometries of five-membered heterocyclic triazole bridging organic ligands are capable of generating CPs with novel patterns not easily obtained using rigid linear ligands. A multidentate 4-aminotriazole-bridged organic ligand, namely 4-amino-3,5-bis(4,3′-bipyridyl-5′-yl)-4H-1,2,4-triazole (L) has been prepared and used to synthesize two CoII coordination polymers, namely poly[[[μ2-4-amino-3,5-bis(4,3′-bipyridyl-5′-yl)-4H-1,2,4-triazole-κ2 N:N′]bis(methanol-κO)cobalt(II)] bis(perchlorate)], {[Co(C22H16N8)2(CH3OH)2](ClO4)2} n , (I), and poly[[μ3-4-amino-3,5-bis(4,3′-bipyridyl-5′-yl)-4H-1,2,4-triazole-κ3 N:N′:N′′]dichloridocobalt(II)], [CoCl2(C22H16N8)] n , (II), using CoX 2 salts [X = ClO4 for (I) and Cl for (II)] under solvothermal conditions. Single-crystal X-ray structure analysis revealed that they both feature two-dimensional networks. Cobalt is located on an inversion centre in (I) and in a general position in (II). In (I), L functions as a bidentate cis-conformation ligand linking CoII ions, while it functions as a tridentate trans-conformation linker binding CoII ions in (II). In addition, O—H...N and N—H...O hydrogen bonds and C—H...π interactions exist in (I), while N—H...Cl and π–π interactions exist in (II), and these weak interactions play an important role in aligning the two-dimensional nets of (I) and (II) in the solid state. As the compounds were synthesized under the same conditions, the significant structural variations between (I) and (II) are believed to be determined by the different sizes and coordination abilities of the counter-anions. IR spectroscopy and diffuse reflectance UV–Vis spectra were also used to investigate the title compounds.

catena-Poly[[[(pyrazino[2,3-f][1,10]phenanthroline)copper(II)]-μ-4,4′-oxydibenzoato] monohydrate]

2007 ◽  
Vol 63 (11) ◽  
pp. m2823-m2823
Author(s):  
Chun-Bo Liu ◽  
Yang Liu ◽  
Lu Lu ◽  
Jun Sun
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Supramolecular Structure ◽  
Helical Chain ◽  
Coordination Geometry ◽  
Two Dimensional ◽  
Π Interactions ◽  
Centroid Distance ◽  
Square Planar ◽  
Phenanthroline Ligands

In the title compound, {[Cu(C14H8O5)(C14H8N4)]·H2O} n , the CuII atom adopts a distorted cis-CuN2O2 square-planar coordination geometry. 4,4′-Oxydibenzoate (L) ligands link the CuII atoms, generating a helical chain. Neighbouring chains are linked through π–π interactions between pyrazino[2,3-f][1,10]phenanthroline ligands with a centroid–centroid distance of ca 3.44 Å, resulting in a two-dimensional supramolecular structure. The structure is completed by O—H...O hydrogen bonds.

Three isomorphous two-dimensional coordination polymers generated from a benzimidazole bridging ligand and ZnX2(X= Cl, Br and I)

2013 ◽  
Vol 69 (4) ◽  
pp. 367-371
Author(s):  
Yue-Feng Zhang ◽  
Jian-Ping Ma ◽  
Qi-Kui Liu ◽  
Yu-Bin Dong
Keyword(s):  
Solid State ◽  
Benzoic Acid ◽  
Coordination Polymers ◽  
Room Temperature ◽  
Three Dimensional ◽  
Luminescent Properties ◽  
Red Shift ◽  
Two Dimensional ◽  
Π Interactions ◽  
Bridging Ligand

A novel bridging asymmetric benzimidazole ligand, 4-{2-[3-(pyridin-4-yl)phenyl]-1H-benzimidazol-1-ylmethyl}benzoic acid, was used to construct three isomorphous two-dimensional coordination polymers, namelycatena-poly[chlorido(μ3-4-{2-[3-(pyridin-4-yl)phenyl]-1H-benzimidazol-1-ylmethyl}benzoato)zinc(II)], [Zn(C26H18N3O2)Cl]n, (I), and the bromide, (II), and iodide, (III), analogues. Neighbouring two-dimensional networks are stacked into three-dimensional frameworksviainterlayer π–π interactions. The luminescent properties of (I)–(III) were investigated and they display an obvious red-shift in the solid state at room temperature.

Two dimensional cyano-bridged hetero-metallic coordination polymers containing metal⋅⋅⋅π interactions

2014 ◽  
Vol 121 ◽  
pp. 196-204 ◽  
Author(s):  
Dursun Karaağaç ◽  
Güneş Süheyla Kürkçüoğlu ◽  
Okan Zafer Yeşilel ◽  
Tuncer Hökelek
Keyword(s):  
Coordination Polymers ◽  
Two Dimensional ◽  
Π Interactions

scholarly journals Crystal structure and Hirshfeld analysis of diethyl (2E,2′E)-3,3′-[1-(8-phenylisoquinolin-1-yl)-1H-indole-2,7-diyl]diacrylate

2021 ◽  
Vol 77 (9) ◽  
Author(s):  
Xue-Jun Zhang
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Ethyl Acrylate ◽  
Hirshfeld Surface ◽  
Dihedral Angles ◽  
Two Dimensional ◽  
Π Interactions ◽  
Compound C ◽  
Hirshfeld Analysis

The molecule of title compound, C33H28N2O4, comprises an indole unit (A), an isoquinoline moiety (B) and a benzene ring (C). The dihedral angles between these groups are A/B = 57.47 (1), A/C = 18.48 (1) and B/C = 57.97 (1) °. The ethyl acrylate group at the 2-position is nearly co-planar with the indole unit [3.81 (2)°], while that at the 7-position is distinctly non-coplanar [52.64 (1)°]. Intramolecular π–π interactions between the indole unit and benzene ring help to establish the clip-shaped conformation of the molecule. In the crystal, the molecules are assembled into two-dimensional layers via C—H...O hydrogen bonds, π–π and C—H...π interactions. Hirshfeld surface analysis illustrates that the greatest contributions are from H...H (63.2%), C...H/H...C (15.4%) and O...H/H...O (14.8%) contacts. The terminal C2H5 group of one of the ethyl acrylate side chains is disordered over two positions of equal occupancy.

scholarly journals 4-[(E)-({4-[(4-Aminophenyl)sulfonyl]phenyl}imino)methyl]phenol ethanol monosolvate

2012 ◽  
Vol 68 (6) ◽  
pp. o1789-o1789
Author(s):  
Sadaf Afzal ◽  
Zareen Akhter ◽  
M. Nawaz Tahir
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Dihedral Angles ◽  
Two Dimensional ◽  
Sulfonyl Group ◽  
Π Interactions ◽  
Polymeric Network ◽  
Compound C

In the title compound, C19H16N2O3S·C2H6O, the 4-hydroxybenzylidene group is oriented at dihedral angles of 73.17 (7) and 77.06 (7)° with respect to the aniline groups. The sulfonyl group make dihedral angles of 44.89 (13) and 59.16 (12)° with the adjacent aniline groups. In the crystal, a two-dimensional polymeric network parallel to (010) is formed by N—H...O, O—H...N and O—H...O hydrogen bonds. There also exist π–π interactions with a distance of 3.5976 (18) Å between the centroids of hydroxyphenyl rings.

scholarly journals Crystal structure of [5-bromo-2-(pyridin-2-yl-κN)phenyl-κC1](pentane-2,4-dionato-κ2O,O′)platinum(II)

2015 ◽  
Vol 71 (10) ◽  
pp. 1259-1261
Author(s):  
Keito Fukuda ◽  
Tomoaki Sugaya ◽  
Koji Ishihara
Keyword(s):  
Crystal Structure ◽  
Dihedral Angles ◽  
Coordination Environment ◽  
Π Interactions ◽  
Square Planar ◽  
Chelate Rings

The title cyclometalated platinum(II) complex with 2-(4-bromophenyl)pyridinato and acetylacetonato ligands, [Pt(C11H7BrN)(C5H7O2)], consists of two crystallographically non-equivalent dimers, each stacked by π–π interactions with distances of ≃ 3.4 Å. In both dimers, the platinum(II) complexes are arranged antiparallel to each other. Each complex exhibits a slightly distorted square-planar coordination environment around the central Pt(II) atom. The dihedral angles between two chelate rings including the PtIIatom in these complexes are 0.08 (12) and 1.54 (9)°.

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