Crystal structure of [1,3-bis-(2,4,6-tri-methyl-phen-yl)imidazolidin-2-yl-idene]di-chlorido-(2-{[(2-methoxyeth-yl)(meth-yl)amino]-meth-yl}benzyl-idene)ruth-en-ium.

The title compound, [RuCl2(C33H43N3O)], is an example of a new generation of N,N-dialkyl ruthenium catalysts with an N-Ru coordination bond as part of a six-membered chelate ring. The Ru atom has an Addison τ parameter of 0.244, which indicates a geometry inter-mediate between square-based pyramidal and trigonal-bipyramidal. The complex shows the usual trans arrangement of the two chlorides, with Ru-Cl bond lengths of 2.3515 (8) and 2.379 (7) Å, and a Cl-Ru-Cl angle of 158.02 (3)°. One of the chlorine atoms and the atoms of the 2-meth-oxy-N-methyl-N-[(2-methyl-phen-yl)meth-yl]ethane-1-amine group of the title complex display disorder over two positions in a 0.889 (2): 0.111 (2) ratio.

Synthesis, crystal structure and Hirshfeld surface analysis of 5-[2-(di-cyano-methyl-idene)hydrazin-1-yl]-2,4,6-tri-iodo-isophthalic acid ethanol monosolvate.

The title compound, C11H3I3N4O4·C2H6O, crystallizes in the triclinic P space group with one independent mol-ecule and one ethanol solvent mol-ecule in the asymmetric unit. The benzene ring and the methyl-carbonohydrazonoyl dicyanide group of the main mol-ecule makes a dihedral angle of 57.91 (16)°. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link pairs of mol-ecules, forming dimers with R 2 2(14) motifs. These dimers are connected by O-H⋯O hydrogen bonds into chains along the a-axis direction, forming R 2 2(16) ring motifs. Further O-H⋯O inter-actions involving the ethanol solvent mol-ecule connect the chains into a three-dimensional network. In addition, C-I⋯π inter-actions are observed. The inter-molecular inter-actions in the crystal structure were qu-anti-fied and analysed using Hirshfeld surface analysis.

Crystal structure and Hirshfeld surface analysis of 4-cyano-N-[(4-cyano-phen-yl)sulfon-yl]-N-[2-(5-methyl-furan-2-yl)phen-yl]benzene-sulfonamide.

In the title compound, C25H17N3O5S2, intra-molecular π-π inter-actions [centroid-to-centroid distance = 3.5640 (9) Å] are observed between the furan and benzene rings of the 4-cyano-phenyl group. In the crystal, mol-ecules are connected via C-H⋯O and C-H⋯N hydrogen bonds, forming layers parallel to the (100) plane. These layers are inter-connected by C-H⋯π inter-actions and weak van der Waals inter-actions. Hirshfeld surface analysis indicates that H⋯H (30.2%), N⋯H/H⋯N (22.3%), C⋯H/H⋯C (17.9%) and O⋯H/H⋯O (15.4%) inter-actions make the most significant contributions to the crystal packing.

Crystal structures and Hirshfeld surface analyses of N,N-di-methyl-acetamide-1-(dimethyl-λ4-aza-nyl-idene)ethan-1-ol tribromide (1/1), N,N-di-methyl-acetamide-1-(dimethyl-λ4-aza-nyl-idene)ethan-1-ol di-bromido-iodate (1/1) and N,N-di-methyl-acetamide-1-(dimethyl-λ4-aza-nyl-idene)ethan-1-ol di-chlorido-iodate (1/1).

In the title compounds, N,N-di-methyl-acetamide-1-(dimethyl-λ4-aza-nyl-idene)ethan-1-ol tribromide (1/1), C4H9NO·C4H10NO+·Br3 - or [(C4H9NO)·(C4H10NO)](Br3), (I), N,N-di-methyl-acetamide-1-(dimethyl-λ4-aza-nyl-idene)ethan-1-ol di-bromido-iodate (1/1), C4H9NO·C4H10NO+·Br2I- or [(C4H9NO)·(C4H10NO)](Br2I), (II), and N,N-di-methyl-acetamide-1-(dimethyl-λ4-aza-nyl-idene)ethan-1-ol di-chlorido-iodate (1/1), C4H9NO·C4H10NO+·Cl2I- or [(C4H9NO)·(C4H10NO)]·(Cl2I), (III), all the anions are almost linear in geometry and all the cations, except for the methyl H atoms, are essentially planar. In the crystal structure of (I), the cations are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. These dimers also exhibit O-H⋯O hydrogen bonding. Dimerized cation pairs and anions are arranged in columns along the a axis. In the crystal of (II), the cations are linked by pairs of O-H⋯O and C-H⋯O hydrogen bonds, forming an R 4 4(14) ring motif. These groups of cations and the anions form individual columns along the a axis and jointly reside in planes roughly parallel to (011). In the crystal of (III), cations and anions also form columns parallel to the a axis, resulting in layers parallel to the (020) plane. Furthermore, the crystal structures of (I), (II) and (III) are consolidated by strong halogen (Br and/or I and/or Cl)⋯H and weak van der Waals inter-actions. In addition to the structural evaluation, a Hirshfeld surface analysis was carried out.

Crystal structure and Hirshfeld surface analysis of bis-{(Z)-N'-[(E)-(furan-2-yl)methyl-idene]carbamo-hydrazono-thio-ato}nickel(II) methanol disolvate.

In the title complex, [Ni(C6H6N3OS)2]·2CH3OH, the NiII atom is coordinated by the S and N atoms of two N'-[(Z)-(furan-2-yl)methyl-idene]carbamohydrazono-thioic acid ligands in a distorted square-planar geometry. The two mutual ligands bound to NiII are also connected by C-H⋯S inter-actions, while the H atoms of the NH2 group of the ligands form R 4 4(8) motifs with the O atoms of the solvent ethyl alcohol mol-ecules. At the same time, the OH groups of the solvent ethyl alcohol mol-ecules form parallel layers to the (011) plane by the O-H⋯N inter-actions with the ligand N atom that is not bonded to the NiII atom.. The layers are connected by van der Waals inter-actions. A Hirshfeld surface analysis indicates that the most important contacts are H⋯H (37.7%), C⋯H/H⋯C (14.6%), O⋯H/H⋯O (11.5%) and S⋯H/H⋯S (10.6%).

Crystal structure and Hirshfeld surface analysis of N-[2-(5-methyl-furan-2-yl)phen-yl]-3-nitro-N-[(3-nitro-phen-yl)sulfon-yl]benzene-sulfonamide.

In the title compound, C23H17N3O9S2, C-H⋯O hydrogen bonds link adjacent mol-ecules in a three-dimensional network, while π-π stacking inter-actions, with centroid-centroid distances of 3.8745 (9) Å, between the furan and an arene ring of one of the two (3-nitro-phen-yl)sulfonyl groups, result in chains parallel to the a axis. The Hirshfeld surface analysis indicates that O⋯H/H⋯O (40.1%), H⋯H (27.5%) and C⋯H/H⋯C (12.4%) inter-actions are the most significant contributors to the crystal packing.

Crystal structure and Hirshfeld surface analysis of 10-hy-droxy-2-(4-meth-oxy-phen-yl)-3-oxo-2,3,3a,4,10,10a-hexa-hydro-1H-9-thia-2-aza-cyclo-penta-[b]fluorene-4-carb-oxy-lic acid dimethyl sulfoxide-d6 monosolvate.

In the title compound, C22H19NO5S·C2D6OS, the central six-membered ring has a slightly distorted boat conformation, while the fused pyrrolidine ring adopts an envelope conformation. These conformations are stabilized by O-H⋯O hydrogen bonds between the main compound and solvent mol-ecules. In addition, intra-molecular C-H⋯O hydrogen bonds in the main mol-ecule form two S(6) rings. Mol-ecules are connected by pairs of inter-molecular C-H⋯O hydrogen bonds, forming dimers with a R 2 2(8) motif. These dimers form a three-dimensional network through O-H⋯O, O-H⋯S and C-H⋯O hydrogen bonds with each other directly and through solvent mol-ecules. In addition, weak π-π stacking inter-actions [centroid-to-centroid distances = 3.9937 (10) and 3.9936 (10) Å, slippages of 2.034 and 1.681 Å] are observed. The inter-molecular contacts were qu-anti-fied using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing the relative contributions of the contacts to the crystal packing to be H⋯H 41.7%, O⋯H/H⋯O 27.7%, C⋯H/H⋯C 17.0%, and S⋯H/H⋯S 7.5%.

Crystal structure and Hirshfeld surface analysis of (3aSR,6RS,6aSR,7RS,11bSR,11cRS)-2,2-dibenzyl-2,3,6a,11c-tetra-hydro-1H,6H,7H-3a,6:7,11b-di-epoxy-dibenzo[de,h]isoquinolin-2-ium tri-fluoro-methane-sulfonate.

In the cation of the title salt, C30H28NO2 +·CF3O3S-, the four tetra-hydro-furan rings adopt envelope conformations. In the crystal, pairs of cations are linked by dimeric C-H⋯O hydrogen bonds, forming two R 2 2(6) ring motifs parallel to the (001) plane. The cations and anions are connected by further C-H⋯O hydrogen bonds, forming a three-dimensional network structure. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (47.6%), C⋯H/H⋯C (20.6%), O⋯H/H⋯O (18.0%) and F⋯H/H⋯F (9.9%) inter-actions.

Crystal structure and Hirshfeld surface analysis of 2,2,2-tri-chloro-N,N-bis-{[(1RS,4SR)-1,4-di-hydro-1,4-ep-oxy-naphthalen-1-yl]meth-yl}acetamide.

In the title compound, C24H18Cl3NO3, the tetra-hydro-furan rings adopt envelope conformations. In the crystal, C-H⋯O hydrogen bonds connect mol-ecules, generating layers parallel to the (001) plane. These layers are connected along the c-axis direction by C-H⋯π inter-actions. The packing is further stabilized by inter-layer van der Waals and inter-halogen inter-actions. The most important contributions to the surface contacts are from H⋯H (36.8%), Cl⋯H/H⋯Cl (26.6%), C⋯H/H⋯C (18.8%) and O⋯H/H⋯O (11.3%) inter-actions, as concluded from a Hirshfeld surface analysis.

Crystal structure and Hirshfeld surface analysis of dimethyl 5-[2-(2,4,6-trioxo-1,3-diazinan-5-yl-idene)hydrazin-1-yl]benzene-1,3-di-carboxyl-ate 0.224-hydrate.

In the crystal, the whole mol-ecule of the title compound, C14H12N4O7·0.224H2O, is nearly planar with a maximum deviation from the least-squares plane of 0.352 (1) Å. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal, mol-ecules are linked by centrosymmetric pairs of N-H⋯O hydrogen bonds, forming ribbons along the c-axis direction. These ribbons connected by van der Waals contacts, forming sheets parallel to the ac plane. There are also inter-molecular van der Waals contacts and and C-H⋯π inter-actions between the sheets. A Hirshfeld surface analysis indicates that the most prevalent inter-actions are O⋯H/H⋯O (41.2%), H⋯H (19.2%), C⋯H/H⋯C (12.2%) and C⋯O/ O⋯C (8.4%).

Crystal structure and Hirshfeld surface analysis of 5,7-diphenyl-1,2,3,5,6,7-hexa-hydro-imidazo[1,2-a]pyridine-6,6,8-tricarbo-nitrile methanol mono-solvate.

In the title compound, C22H17N5·CH4O, the imidazolidine ring of the 1,2,3,5,6,7-hexa-hydro-imidazo[1,2-a]pyridine ring system is a twisted envelope, while the 1,2,3,4-tetra-hydro-pyridine ring adopts a twisted boat conformation. In the crystal, pairs of mol-ecules are linked by O-H⋯N and N-H⋯O hydrogen bonds via two methanol mol-ecules, forming a centrosymmetric R 4 4(16) ring motif. These motifs are connected to each other by C-H⋯N hydrogen bonds and form columns along the a axis. The columns form a stable mol-ecular packing, being connected to each other by van der Waals inter-actions. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H⋯H (43.8%), N⋯H/H⋯N (31.7%) and C⋯H/H⋯C (18.4%) contacts.

Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-methyl-benzyl-idene)amino]-5-phenylthiazolidin-2-iminium bromide N,N-di-methyl-formamide monosolvate.

In the cation of the title salt, C17H18N3S+·Br-·C3H7NO, the central thia-zolidine ring adopts an envelope conformation with puckering parameters Q(2) = 0.310 (3) Šand φ(2) = 42.2 (6)°. In the crystal, each cation is connected to two anions by N-H⋯ Br hydrogen bonds, forming an R 4 2(8) motif parallel to the (10) plane. van der Waals inter-actions between the cations, anions and N,N-di-methyl-formamide mol-ecules further stabilize the crystal structure in three dimensions. The most important contributions to the surface contacts are from H⋯H (55.6%), C⋯H/H⋯C (17.9%) and Br⋯H/H⋯Br (7.0%) inter-actions, as concluded from a Hirshfeld analysis.

Crystal structure and Hirshfeld surface analysis of (E)-1-(2,6-di-chloro-phen-yl)-2-(2-nitro-benzyl-idene)hydrazine.

In the title compound, C13H9Cl2N3O2, the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 21.16 (14)°. In the crystal, face-to-face π-π stacking inter-actions occur along the a-axis direction between the centroids of the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring. Furthermore, these mol-ecules show intra-molecular N-H⋯Cl and C-H⋯O contacts and are linked by inter-molecular N-H⋯O and C-H⋯Cl hydrogen bonds, forming pairs of hydrogen-bonded mol-ecular layers parallel to (20). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (23.0%), O⋯H/H⋯O (20.1%), Cl⋯H/H⋯Cl (19.0%), C⋯C (11.2%) and H⋯C/C⋯H (8.0%) inter-actions.

Crystal structure and Hirshfeld surface analysis of (E)-4-{2,2-di-chloro-1-[(3,5-di-methyl-phen-yl)diazen-yl]ethen-yl}-N,N-di-methyl-aniline.

In the title compound, C18H19Cl2N3, the planes of the benzene rings subtend a dihedral angle of 77.07 (10)°. In the crystal, mol-ecules are associated into inversion dimers via short Cl⋯Cl contacts [3.3763 (9) Å]. A Hirshfeld surface analysis indicates that the most important contact percentages for the different types of inter-actions are H⋯H (43.9%), Cl⋯H/H⋯Cl (22.9%), C⋯H/H⋯C (20.8%) and N⋯H/H⋯N (8.0%).

(E)-1-(2,6-Di-chloro-phen-yl)-2-(3-nitro-benzyl-idene)hydrazine: crystal structure and Hirshfeld surface analysis.

The stabilized conformation of the title compound, C13H9Cl2N3O2, is similar to that of the isomeric compound (E)-1-(2,6-di-chloro-phen-yl)-2-(2-nitro-benzyl-idene)hydrazine. The 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 26.25 (16)°. In the crystal, face-to-face π-π stacking inter-actions along the a-axis direction occur between the centroids of the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring. The mol-ecules are further linked by C-H⋯O contacts and N-H⋯O and C-H⋯Cl hydrogen bonds, forming pairs of hydrogen-bonded mol-ecular layers parallel to (100). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (22.1%), Cl⋯H/H⋯Cl (20.5%), O⋯H/H⋯O (19.7%), C⋯C (11.1%) and C⋯H/H⋯C (8.3%) inter-actions.

Crystal structure and Hirshfeld surface analysis of phen-yl(5,7,8a-triphenyl-1,2,3,7,8,8a-hexa-hydro-imidazo[1,2-a]pyridin-6-yl)methanone with an unknown solvent.

In the title compound, C32H28N2O, the imidazolidine and pyridine rings of the central hexa-hydro-imidazo[1,2-a]pyridine ring system adopt envelope and screw-boat conformations, respectively. The mol-ecule exhibits two weak intra-molecular π-π inter-actions between phenyl rings. In the crystal, mol-ecules are linked via pairs of C-H⋯ O hydrogen bonds, forming inversion dimers. The dimers are further linked by pairs of C-H⋯π inter-actions, forming infinite chains along the c-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (73.4%), C⋯H/H⋯C (18.8%) and O⋯H/H⋯O (5.7%) contacts. The contribution of some disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9-18] in PLATON. The solvent contribution was not included in the reported mol-ecular weight and density.

Crystal structure and Hirshfeld surface analysis of 4-{2,2-di-chloro-1-[(E)-2-(4-methyl-phen-yl)diazen-1-yl]ethen-yl}-N,N-di-methyl-aniline.

In the tile compound, C17H17Cl2N3, the dihedral angle between the benzene rings is 62.73 (9)°. In the crystal, there are no classical hydrogen bonds. Mol-ecules are linked by a pair of C-Cl⋯π inter-actions, forming an inversion dimer. A short inter-molecular HL⋯HL contact [Cl⋯Cl = 3.2555 (9) Å] links the dimers, forming a ribbon along the c-axis direction. The Hirshfeld surface analysis and two-dimensional fingerprint plots reveal that the most important contributions for the crystal packing are from H⋯H (45.4%), Cl⋯H/H⋯Cl (21.0%) and C⋯H/H⋯C (19.0%) contacts.

Crystal structure and Hirshfeld surface analysis of (E)-3-(benzyl-idene-amino)-5-phenyl-thia-zolidin-2-iminium bromide.

The central thia-zolidine ring of the title salt, C16H16N3S+·Br-, adopts an envelope conformation, with the C atom bearing the phenyl ring as the flap atom. In the crystal, the cations and anions are linked by N-H⋯Br hydrogen bonds, forming chains parallel to the b-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (46.4%), C⋯H/H⋯C (18.6%) and H⋯Br/Br⋯H (17.5%) inter-actions.

Crystal structure and Hirshfeld surface analysis of 3-amino-5-phenyl-thia-zolidin-2-iminium bromide.

In the cation of the title salt, C9H12N3S+·Br-, the thia-zolidine ring adopts an envelope conformation with the C atom adjacent to the phenyl ring as the flap. In the crystal, N-H⋯Br hydrogen bonds link the components into a three-dimensional network. Weak π-π stacking inter-actions between the phenyl rings of adjacent cations also contribute to the mol-ecular packing. A Hirshfeld surface analysis was conducted to qu-antify the contributions of the different inter-molecular inter-actions and contacts.

Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-chloro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide.

The title salt, C16H15ClN3S+·Br-, is isotypic with (E)-3-[(4-fluoro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide [Khalilov et al. (2019 ▸). Acta Cryst. E75, 662-666]. In the cation of the title salt, the atoms of the phenyl ring attached to the central thia-zolidine ring and the atom joining the thia-zolidine ring to the benzene ring are disordered over two sets of sites with occupancies of 0.570 (3) and 0.430 (3). The major and minor components of the disordered thia-zolidine ring adopt slightly distorted envelope conformations, with the C atom bearing the phenyl ring as the flap atom. In the crystal, centrosymmetrically related cations and anions are linked into dimeric units via N-H⋯Br hydrogen bonds, which are further connected by weak C-H⋯Br contacts into chains parallel to the a axis. Furthermore, not existing in the earlier report of (E)-3-[(4-fluoro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide, C-H⋯π inter-actions and π-π stacking inter-actions [centroid-to-centroid distance = 3.897 (2) Å] between the major components of the disordered phenyl ring contribute to the stabilization of the mol-ecular packing. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions for the crystal packing are from H⋯H (30.5%), Br⋯H/H⋯Br (21.2%), C⋯H/H⋯C (19.2%), Cl⋯H/H⋯Cl (13.0%) and S⋯H/H⋯S (5.0%) inter-actions.