Crystal structure, Hirshfeld surface analysis and DFT study of (5E,5'E,6Z,6'Z)-6,6'-[ethane-1,2-diyl-bis(aza-nylyl-idene)]bis-{5-[2-(4-fluoro-phen-yl)hydra-zono]-3,3-di-methyl-cyclo-hexa-none} 2.5-hydrate.

The title compound, C30H34F2N6O2·2.5H2O, was obtained by condensation of 2-[2-(4-fluoro-phen-yl)hydrazono]-5,5-di-methyl-cyclo-hexan-1,3-dione with ethyl-enedi-amine in ethanol and crystallized as a 1:2.5 hydrate in space group C2/c. The two independent mol-ecules, with approximate crystallographic C 2 symmetries, have different conformations and packing environments, are stabilized by intra-molecular N-H⋯N hydrogen bonds and linked by O-H⋯O hydrogen bonds involving the water mol-ecules. A Hirshfeld surface analysis showed that H⋯H contacts make by far the largest (48-50%) contribution to the crystal packing. From DFT calculations, the LUMO-HOMO energy gap of the mol-ecule is 0.827 eV.

Crystal structure and Hirshfeld surface analysis of [2-(1H-benzimidazol-2-yl-κN 3)aniline-κN]di-chlorido-zinc(II) N,N-di-methyl-formamide monosolvate.

The title compound, [ZnCl2(C13H11N3)]·C3H7NO, crystallized in the monoclinic crystal system in space group P21/n. The asymmetric unit contains one neutral complex mol-ecule, which consists of a zinc ion, a bidentate ligand, and two chlorido ligands with di-methyl-formamide monosolvate. The ligand has two moieties, a benzimidazole and an aniline group. The benzimidazole and aniline planes are not coplanar, subtending a dihedral angle of 18.24 (8)°. The Zn(II) ion shows distorted tetra-hedral geometry, being coordinated by an imidazole N atom, the aniline N atom, and two chlorido ligands. The packing features N-H⋯O, N-H⋯Cl, C-H⋯Cl hydrogen bonding.

Synthesis and structural characterization of hexa-µ2-chlorido-µ4-oxido-tetra-kis-{[4-(phenyl-ethyn-yl)pyridine-κN]copper(II)} di-chloro-methane monosolvate.

In the crystal structure of the title compound, [Cu4Cl6O(C13H9N)4]·CH2Cl2, the core mol-ecular structure consists of a Cu4 tetra-hedron with a central inter-stitial O atom. Each edge of the Cu4 tetra-hedron is bridged by a chlorido ligand. Each copper(II) cation is coordinated to the central O atom, two chlorido ligands and one N atom of the 4-phenyl-ethynyl-pyridine ligand. In the crystal, the mol-ecules are linked by inter-molecular C-H⋯Cl inter-actions. Furthermore, C-H⋯π and π-π inter-actions also connect the mol-ecules, forming a three-dimensional network. Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H⋯H and C⋯H/H⋯C inter-actions.

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(2-methyl-3-nitro-phen-yl)imino]-meth-yl}phenol.

The title compound, C15H14N2O3, was prepared by condensation of 2-hy-droxy-5-methyl-benzaldehyde and 2-methyl-3-nitro-phenyl-amine in ethanol. The configuration of the C=N bond is E. An intra-molecular O-H⋯N hydrogen bond is present, forming an S(6) ring motif and inducing the phenol ring and the Schiff base to be nearly coplanar [C-C-N-C torsion angle of 178.53 (13)°]. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming chains along the b-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (37.2%), C⋯H (30.7%) and O⋯H (24.9%) inter-actions. The gas phase density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared to the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hy-droxy-5-methyl-benzyl-idene)amino]-benzo-nitrile.

The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 2-amino-benzo-nitrile, and crystallizes in the ortho-rhom-bic space group Pbca. The phenol ring is inclined to the benzo-nitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intra-molecular O-H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, C-H⋯O and C-H⋯N inter-actions lead to the formation of sheets perpendicular to the a axis. C-H⋯π inter-actions, forming polymeric chains along the a-axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H⋯H and C⋯H/H⋯C inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure and the HOMO-LUMO energy gap is given.

Synthesis, crystal structure at 219†K and Hirshfeld surface analyses of 1,4,6-tri-methyl-quinoxaline-2,3(1H,4H)-dione monohydrate.

The asymmetric unit of the title compound, C11H12N2O2·H2O, contains a mol-ecule of 1,4,6-trimethyl-1,4-di-hydro-quinoxaline-2,3-dione and a solvent water mol-ecule. Four atoms of the benzene ring are disordered over two sets of sites in a 0.706 (7):0.294 (7) ratio while the N-bound methyl groups are rotationally disordered with occupancy ratios of 0.78 (4):0.22 (4) and 0.76 (5):0.24 (5). In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds into layers lying parallel to (10). The Hirshfeld surface analysis indicates that the most important contributions to the packing arrangement are due to H⋯H (51.3%) and O⋯H/H⋯O (28.6%) inter-actions. The mol-ecular structure calculated by density functional theory is compared with the experimentally determined mol-ecular structure, and the HOMO-LUMO energy gap has been calculated.

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl-phen-yl)imino]-meth-yl}-4-methyl-phenol.

The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 3-chloro-4-methyl-aniline, and crystallizes in the monoclinic space group P21/c. The 3-chloro-benzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intra-molecular O-H⋯N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (43.8%) and C⋯H/H⋯C (26.7%) inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure and the HOMO-LUMO energy gap is provided.

Crystal structure, Hirshfeld surface analysis and DFT studies of 4-methyl-2-({[4-(tri-fluoro-meth-yl)phen-yl]imino}-meth-yl)phenol.

The title compound, C15H12F3NO, crystallizes with one mol-ecule in the asymmetric unit. The configuration of the C=N bond is E and there is an intra-molecular O-H⋯N hydrogen bond present, forming an S(6) ring motif. The dihedral angle between the mean planes of the phenol and the 4-tri-fluoro-methyl-phenyl rings is 44.77 (3)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming polymeric chains extending along the a-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from C⋯H/H⋯C (29.2%), H⋯H (28.6%), F⋯H/H⋯F (25.6%), O⋯H/H⋯O (5.7%) and F⋯F (4.6%) inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The crystal studied was refined as an inversion twin.

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl-phen-yl)imino]-meth-yl}phenol.

In the title compound, C15H15NO, the configuration of the C=N bond of the Schiff base is E, and an intra-molecular O-H⋯N hydrogen bond is observed, forming an intra-molecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, mol-ecules are linked along the b axis by O-H⋯N and C-H⋯O hydrogen bonds, forming polymeric chains. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (56.9%) and H⋯C/C⋯H (31.2%) inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure, and the HOMO-LUMO energy gap is provided. The crystal studied was refined as an inversion twin.

Crystal structure and Hirshfeld surface analysis of 2-{[(4-iodo-phen-yl)imino]-meth-yl}-4-nitro-phenol.

The title compound, C13H9IN2O3, was synthesized by a condensation reaction between 2-hy-droxy-5-nitro-benzaldehyde and 4-iodo-aniline, and crystallizes in the ortho-rhom-bic space group Pna21. The 4-iodo-benzene ring is inclined to the phenol ring by a dihedral angle of 39.1 (2)°. The configuration about the C=N double bond is E. The crystal structure features C-H⋯O hydrogen-bonding inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are O⋯H/H⋯O (26.9%) and H⋯H (22.0%) inter-actions.

1,4-Disubstituted 1H-1,2,3-Triazoles for Renal Diseases: Studies of Viability, Anti-Inflammatory, and Antioxidant Activities.

Inflammation is a hallmark of many metabolic diseases. We previously showed that ferrocene-appended 1H-1,2,3-triazole hybrids inhibit nitric oxide (NO) production in in vitro models of lipopolysaccharide-induced inflammation in the BV-2 cell. In the present study, we explored the viability, anti-inflammatory, and antioxidant potential of ferrocene-1H-1,2,3-triazole hybrids using biochemical assays in rat mesangial cells (RMCs). We found that, among all the ferrocene-1H-1,2,3-triazole hybrids, X2-X4 exhibited an antioxidant effect on mitochondrial free radicals. Among all the studied compounds, X4 demonstrated the best anti-inflammatory effect on RMCs. These results were supplemented by in silico studies including molecular docking with human cytosolic phospholipase A2 (cPLA2) and cyclooxygenase 2 (COX-2) enzymes as well as absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiling. Besides, two new crystal structures of the compounds have also been reported. In addition, combining the results from the inducible nitric oxide synthase (iNOS), cPLA2, COX-2, and matrix metalloproteinase-9 (MMP-9) enzymatic activity analysis and NO production also confirmed this argument. Overall, the results of this study will be a valuable addition to the growing body of work on biological activities of triazole-based compounds.

Crystal structure and Hirshfeld surface analysis of 2-amino-3-hy-droxy-pyridin-1-ium 6-methyl-2,2,4-trioxo-2H,4H-1,2,3-oxa-thia-zin-3-ide.

The asymmetric unit of the title compound, C5H7N2O+·C4H4NO4S-, contains one cation and one anion. The 6-methyl-2,2,4-trioxo-2H,4H-1,2,3-oxa-thia-zin-3-ide anion adopts an envelope conformation with the S atom as the flap. In the crystal, the anions and cations are held together by N-H⋯O, N-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds, thus forming a three-dimensional structure. The Hirshfeld surface analysis and fingerprint plots reveal that the crystal packing is dominated by O⋯H/H⋯O (43.1%) and H⋯H (24.2%) contacts.

Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)meth-yl]amino}-benzoic acid.

In the mol-ecule of the title anthracene derivative, C22H17NO2, the benzene ring is inclined to the mean plane of the anthracene ring system (r.m.s. deviation = 0.024 Å) by 75.21 (9)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming classical carb-oxy-lic acid inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C-H⋯π inter-actions, forming a supra-molecular framework.

Crystal structure and DFT study of (E)-2-chloro-4-{[2-(2,4-di-nitro-phen-yl)hydrazin-1-yl-idene]meth-yl}phenol aceto-nitrile hemisolvate.

The title Schiff base compound, C13H9ClN4O5·0.5CH3CN, crystallizes as an aceto-nitrile hemisolvate; the solvent mol-ecule being located on a twofold rotation axis. The mol-ecule is nearly planar, with a dihedral angle between the two benzene rings of 3.7 (2)°. The configuration about the C=N bond is E, and there is an intra-molecular N-H⋯Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, mol-ecules are linked by O-H⋯O and N-H⋯O hydrogen bonds, forming layers lying parallel to (10). The layers are linked by C-H⋯Cl hydrogen bonds, forming a supra-molecular framework. Within the framework there are offset π-π stacking inter-actions [inter-centroid distance = 3.833 (2) Å] present involving inversion-related mol-ecules. The DFT study shows that the HOMO and LUMO are localized in the plane extending from the phenol ring to the 2,4-di-nitro-benzene ring, and the HOMO-LUMO gap is found to be 0.13061 a.u.

Crystal structure and DFT study of benzyl 1-benzyl-2-oxo-1,2-di-hydro-quinoline-4-carboxyl-ate.

In the title quinoline derivative, C24H19NO3, the two benzyl rings are inclined to the quinoline ring mean plane by 74.09 (8) and 89.43 (7)°, and to each other by 63.97 (10)°. The carboxyl-ate group is twisted from the quinoline ring mean plane by 32.2 (2)°. There is a short intra-molecular C-H⋯O contact forming an S(6) ring motif. In the crystal, mol-ecules are linked by bifurcated C-H,H⋯O hydrogen bonds, forming layers parallel to the ac plane. The layers are linked by C-H⋯π inter-actions, forming a supra-molecular three-dimensional structure.

Crystal structure, DFT and MEP study of (E)-2-[(2-hy-droxy-5-meth-oxy-benzyl-idene)amino]-benzo-nitrile.

The asymmetric unit of the title compound, C15H12N2O2, contains two crystallographically independent mol-ecules in which the dihedral angles between the benzene rings in each are 13.26 (5) and 7.87 (5)°. An intra-molecular O-H⋯N hydrogen bonds results in the formation of an S(6) ring motif. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯N hydrogen bonds, forming layers parallel to (011). In addition, π-π stacking inter-actions with centroid-centroid distances in the range 3.693 (2)-3.931 (2) Šcomplete the three-dimensional network.

Crystal structure and the DFT and MEP study of 4-benzyl-2-[2-(4-fluoro-phen-yl)-2-oxoeth-yl]-6-phenyl-pyridazin-3(2H)-one.

The title pyridazin-3(2H)-one derivative, C25H19FN2O2, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In mol-ecule A, the 4-fluoro-phenyl ring, the benzyl ring and the phenyl ring are inclined to the central pyridazine ring by 86.54 (11), 3.70 (9) and 84.857 (13)°, respectively. In mol-ecule B, the corresponding dihedral angles are 86.80 (9), 10.47 (8) and 82.01 (10)°, respectively. In the crystal, the A mol-ecules are linked by pairs of C-H⋯F hydrogen bonds, forming inversion dimers with an R 2 2(28) ring motif. The dimers are linked by C-H⋯O hydrogen bonds and a C-H⋯π inter-action, forming columns stacking along the a-axis direction. The B mol-ecules are linked to each other in a similar manner and form columns separating the columns of A mol-ecules.

Crystal structure and Hirshfeld surface analysis of (E)-2-[1-hy-droxy-2-(pyridin-2-yl)eth-yl]-4-[2-(4-meth-oxy-phen-yl)diazen-1-yl]phenol.

In the title compound, C20H19N3O3, the configuration about the azo N=N bond is E, and the central benzene ring is inclined to the pyridine ring by 31.43 (8)° and to the 4-meth-oxy-phenyl ring by 4.73 (8)°. In the crystal, mol-ecules are linked by pairs of O-H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(12) ring motif. The dimers are linked by O-H⋯O and C-H⋯O hydrogen bonds, forming layers parallel to the ac plane. There are C-H⋯π inter-actions present within the layers and between the layers, leading to the formation of a supra-molecular framework. The layers are also linked by offset π-π inter-actions, with an inter-planar distance of 3.416 (2) Å.

Crystal structure of 4-(2-hy-droxy-3-meth-oxy-benzyl-amino)-benzoic acid di-methyl-formamide monosolvate monohydrate.

The title compound, C15H15NO4·C3H7NO·H2O, a secondary amine mol-ecule, is accompanied by one equivalent of water and one equivalent of di-methyl-formamide (DMF) as solvents. The mol-ecule is non-planar, with a Car-yl-CH2-NH-Car-yl torsion angle of -66.3 (3)°. In the crystal, O-H⋯O and N-H⋯O hydrogen-bonding inter-actions between the amine mol-ecules and the two types of solvent mol-ecule result in the formation of a layered structure extending parallel to (010).

Crystal structure of 4-[(2-hy-droxy-3-meth-oxy-benz-yl)amino]-benzoic acid hemihydrate.

In the crystal of the title vanilline derivative, 2C15H15NO4·H2O, the secondary amine mol-ecule is accompanied by half equivalent of water. The mol-ecule is non-planar, with torsion angle Car-yl-CH2-NH-Car-yl of -83.9 (2)°. In the crystal, the system of O-H⋯O hydrogen bonds, including bridging water mol-ecules residing on crystallographic twofold axes, results in a two-dimensional layered structure. Within the layers, there are also weak N-H⋯π inter-actions involving the vanilline benzene ring.