Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phen-oxy]phthalo-nitrile dimethyl sulfoxide monosolvate.

This work presents the synthesis and structural characterization of [4-(1H-benzo[d]imidazol-2-yl)phen-oxy]phthalo-nitrile, a phthalo-nitrile derivative carrying a benzimidazole moiety. The compound crystallizes as its dimethyl sulfoxide monosolvate, C21H12N4O·(CH3)2SO. The dihedral angle between the two fused rings in the heterocyclic ring system is 2.11 (1)°, while the phenyl ring attached to the imidazole moiety is inclined by 20.7 (1)° to the latter. In the crystal structure, adjacent mol-ecules are connected by pairs of weak inter-molecular C-H⋯N hydrogen bonds into inversion dimers. N-H⋯O and C-H⋯O hydrogen bonds with R 2 1(7) graph-set motifs are also formed between the organic mol-ecule and the disordered dimethyl sulfoxide solvent [occupancy ratio of 0.623 (5):0.377 (5) for the two sites of the sulfur atom]. Hirshfeld surface analysis and fingerprint plots were used to investigate the inter-molecular inter-actions in the crystalline state.

(Z)-3-({[3-Meth-oxy-5-(tri-fluoro-meth-yl)phen-yl]imino}meth-yl)benzene-1,2-diol.

The title compound, C15H12F3NO3, crystallizes with one mol-ecule in the asymmetric unit. The mean planes of the two phenyl rings of the Schiff base moiety, bearing the OH groups and the imine group, respectively, are inclined to each other by 4.91 (1)°. In the crystal, mol-ecules are linked via pairs of bifurcated O-H⋯O hydrogen bonds between the phenol OH groups, forming inversion dimers with an R 1 2(5) ring motif. The structure exhibits also intra-molecular O-H⋯N and C-H⋯F hydrogen-bonding inter-actions. Hirshfeld surfaces analysis and two-dimensional fingerprint plots were applied to qu-antify the inter-molecular inter-actions. The three F atoms of the tri-fluoro-methyl group are disordered over two sets of sites, with occupancy factors of 0.578 (8) and 0.422 (8). The crystal studied was refined as an inversion twin.

Crystal structure and Hirshfeld surfaces analysis of the nickel(II) complex of the Shiff base ligand 6,6'-{(1E,1'E)-[ethane-1,2-diylbis(aza-nylyl-idene)]bis-(methanylyl-idene)}bis-[2-(tri-fluoro-meth-oxy)phenol].

In the title complex, (6,6'-{(1E,1'E)-[ethane-1,2-diylbis(aza-nylyl-idene)]bis(methanylyl-idene)}bis-[2-(tri-fluoro-meth-oxy)phenol]-κ4 O,N,N',O')nickel(II), [Ni(C18H12F6N2O4)], the nickel(II) ion has a square-planar coordination sphere, being ligated by two N and two O atoms of the Schiff base ligand 6,6'-{(1E,1'E)-[ethane-1,2-diylbis(aza-nylyl-idene)]bis-(methanylyl-idene)}bis-[2-(tri-fluoro-meth-oxy)phenol] (L). Inversion-related mol-ecules are linked by a short Ni⋯Ni inter-action of 3.2945 (6) Šforming a dimer. In the crystal, the dimers stack up the a axis, with a closest Ni⋯Ni separation of ca 3.791 Å. There are no other significant inter-molecular inter-actions present. However, the Hirshfeld surface analysis and the two-dimensional fingerprint plots indicate that the packing is dominated by H⋯F/F⋯H, H⋯H, O⋯H/H⋯O and C⋯H/H⋯C contacts.

Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-meth-oxy-anilino)methyl-idene]-2-hy-droxy-cyclo-hexa-2,4-dien-1-one.

The title compound, C14H12ClNO3, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the mol-ecule is stabilized by a strong intra-molecular N-H⋯O hydrogen bond. In the crystal, pairs of centrosymmetrically related mol-ecules are linked by O-H⋯O hydrogen bonds, forming R 2 2(10) rings. Besides this, the mol-ecules form stacks along the [001] direction with C-H⋯π and C-H⋯Cl contacts between the stacks. The inter-molecular inter-actions in the crystal were analysed using Hirshfeld surfaces. The most significant contribution to the crystal packing is from H⋯H contacts (30.8%).