2-[(2,4,4,6,6-Penta­chloro-1,3,5,2λ⁵,4λ⁵,6λ⁵-triaza­triphosphinin-2-yl)aza­nid­yl]pyridinium

The title compound, C₅H₅Cl₅N₅P₃, crystallizes as a zwitterion in which the pyridine N atom is protonated. An S(6) ring motif is formed via an intra­molecular C—H...N hydrogen bond. The triaza­triphosphinine ring adopts an envelope conformation, with one N atom displaced by 0.145 (1) Å from the other atoms. In the crystal, N—H...N and C—H...N hydrogen bonds link the mol­ecules into centrosymmetric dimers containing one R₂²(7) ring motif and two R₂²(8) ring motifs.

3,3′-[1,2-Phenyl­enebis(methyl­ene)]bis­(1-propyl­benzimidazolium) dibromide hemihydrate

The asymmetric unit of the title compound, C₂₈H₃₂N₄²⁺·2Br⁻·0.5H₂O, contains one 3,3′-[1,2-phenyl­enebis(methyl­ene)]bis­(1-propyl­benzimidazolium) cation, two bromide anions and one half-mol­ecule of water. In the crystal, the whole 3,3′-[1,2-phen­yl­enebis(methyl­ene)]bis­(1-propyl­benzimidazolium) cation and one of the bromide anions are each disordered over two positions with site-occupancy ratios of 0.751 (6):0.249 (6) and 0.680 (8):0.320 (8). For the major component of the disordered cation, the central benzene ring forms dihedral angles of 83.6 (5) and 88.2 (4)° with its adjacent imidazole rings, while these angles for the minor component are 89.2 (15) and 84.9 (13)°. In the crystal, the cations and anions are linked by C—H...Br hydrogen bonds into dimers and then stacked along the c axis. The crystal packing is further stabilized by C—H...π and π–π inter­actions [shortest centroid–centroid distance = 3.646 (4) Å].

3-(3-Cyano­benz­yl)-1-methyl-1H-imidazol-3-ium hexa­fluoro­phosphate

In the title compound, C₁₂H₁₂N₃⁺·PF₆⁻, the hexa­fluoro­phosphate anion is disordered over two orientations with refined site occupancies of 0.8071 (17) and 0.1929 (17). The dihedral angle between the imidazole and benzene rings in the cation is 71.26 (7)°. In the crystal, the cations and anions are linked by C—H...F and C—H...N hydrogen bonds into a three-dimensional network.

3,3′-[1,2-Phenyl­enebis(methyl­ene)]bis­(1-ethyl­benzimidazolium) dibromide

In the title mol­ecular salt, C₂₆H₂₈N₄²⁺·2Br⁻, the central benzene ring makes dihedral angles of 76.75 (11) and 82.40 (10)° with the pendant benzimidazole rings. The corresponding angle between the benzimidazole rings is 57.03 (9)°. In the crystal, the cations and anions are linked via C—H...Br hydrogen bonds, forming sheets lying parallel to the bc plane. The crystal structure also features weak C—H...π inter­actions.

3,3′-[1,4-Phenyl­enebis(methyl­ene)]­bis­(1-propyl­benzimidazolium) dichloride dihydrate

The asymmetric unit of the title compound, C₂₈H₃₂N₄²⁺·2Cl⁻·2H₂O, contains half of a 3,3′-[1,4-phenyl­enebis(methyl­ene)]bis­(1-propyl­benzimidazolium) cation, one chloride anion and one water mol­ecule. The complete cation is generated by a crystallographic inversion center. The central benzene ring forms a dihedral angle of 66.06 (11)° with its adjacent benzimidazolium ring system. In the crystal, the cations, anions and water mol­ecules are linked by O—H...Cl, C—H...O and C—H...Cl hydrogen bonds into a three-dimensional network. The crystal packing is further stabilized by π–π inter­actions, with centroid–centroid distances of 3.5561 (15) and 3.6708 (15) Å.

3,3′-[1,2-Phenyl­enebis(methyl­ene)]bis­(1-octylbenzimidazolium) dibromide monohydrate

In the title hydrated mol­ecular salt, C₃₈H₅₂N₄²⁺·2Br⁻·H₂O, the central benzene ring of the dication makes dihedral angles of 89.47 (13) and 72.69 (12)° with the pendant benzimidazol-3-ium rings. The conformations of the octyl side chains are completely different. In the crystal, the components are linked by O—H...Br, C—H...Br and C—H...O hydrogen bonds into a two-dimensional network lying parallel to the ac plane. Aromatic π–π stacking inter­actions are also observed [shortest centroid-to-centroid separation = 3.5047 (16) Å].

3,3′-[1,2-Phenyl­enebis(methyl­ene)]bis­(1-ethyl-1H-benzimidazol-1-ium) bis­(hexa­flourophosphate)

In the title compound, C₂₆H₂₈N₄²⁺·2PF₆⁻, the complete cation is generated by a crystallographic twofold axis. The benz­imidazole ring is almost planar (r.m.s. deviation = 0.0207 Å) and makes dihedral angles of 50.12 (2)° with its symmetry-related component and 65.81 (2)° with the central benzene ring. In the crystal, mol­ecules are linked into a three-dimensional network by C—H...F inter­actions. A π–π inter­action with a centroid–centroid distance of 3.530 (1) Å is observed. Four F atoms of the hexa­fluoro­phosphate anion are disordered over two sets of sites in a 0.889 (6):0.111 (6) ratio.

3,3′-Dicyclo­pentyl-1,1′-(1,3-phenyl­enedimethyl­ene)dibenzimidazol-1-ium bis­(hexa­fluoro­phosphate)

In the title compound, C₃₂H₃₆N₄²⁺·2PF₆⁻, the cation and the anions each have crystallographic twofold rotation symmetry. The benzimidazole ring is almost planar [r.m.s. deviation = 0.0161 (1) Å] and makes a dihedral angle of 5.77 (4)° with its symmetry-related component and a dihedral angle of 80.96 (5)° with the central benzene ring. The cyclo­pentyl ring adopts a half-chair conformation. In the crystal, mol­ecules are linked into a three-dimensional network through C—H...F hydrogen bonds. A C—H...π inter­action is also observed.

3,3′-Di-n-propyl-1,1′-(1,3-phenyl­ene­dimethyl­ene)di(1H-imidazol-3-ium) bis­(hexa­fluorophosphate)

In the title compound, C₂₀H₂₈N₄²⁺·2PF₆⁻, the dihedral angles between the benzene ring and the imidazole rings are 70.18 (11) and 69.83 (11)°, while the imidazole rings form a dihedral angle of 40.52 (12)°. In the crystal, weak C—H...F inter­actions link the mol­ecules into a two-dimensional network parallel to (001). A π–π inter­action with a centroid–centroid distance of 3.601 (1) Å is also observed in the crystal structure.

3,3′-Diethyl-1,1′-(1,4-phenyl­ene­dimethyl­ene)diimidazol-3-ium bis­(hexa­fluoro­phosphate)

In the title mol­ecular salt, C₁₈H₂₄N₄²⁺·2PF₆⁻, the complete dication is generated by a crystallographic inversion centre. The central benzene ring makes a dihedral angle of 77.19 (9)° with each of the imidazole rings. In the crystal, C—H...F inter­actions link the cations and anions into layers lying parallel to the bc plane. The hexa­fluoro­phosphate anion is disordered over two sets of sites in a 0.520 (11):0.480 (11) ratio.