S,S′-(Pyridazine-3,6-diyl)dithiouronium dichloride methanol monosolvate

In the title compound, C6H10N6S2 2+·2Cl−·CH3OH, the pyridazine ring is almost planar, the greatest deviation from the mean plane being 0.025 (2) Å for one of the ring N atoms. The two thiouronium substituents are tilted out of this plane by 60.87 (6) and 57.94 (7)°. The thiouronium cations and the chloride anions are linked by strong N—H⋯Cl hydrogen bonds. The methanol solvent molecule interacts with both the chloride ion (through an O—H⋯Cl hydrogen bond) and the cation (through an N—H⋯O hydrogen bond), resulting in a three-dimensional supramolecular arrangement.

In the title compound, C 6 H 10 N 6 S 2 2+ Á2Cl À ÁCH 3 OH, the pyridazine ring is almost planar, the greatest deviation from the mean plane being 0.025 (2) Å for one of the ring N atoms. The two thiouronium substituents are tilted out of this plane by 60.87 (6) and 57.94 (7) . The thiouronium cations and the chloride anions are linked by strong N-HÁ Á ÁCl hydrogen bonds. The methanol solvent molecule interacts with both the chloride ion (through an O-HÁ Á ÁCl hydrogen bond) and the cation (through an N-HÁ Á ÁO hydrogen bond), resulting in a three-dimensional supramolecular arrangement.
Data collection: X-AREA (Stoe &Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXTL (Sheldrick, 2008). This work was performed within the Cluster of Excellence "Structure Design of Novel High-Performance Materials via Atomic Design and Defect Engineering (ADDE)" that is financially supported by the European Union (European Regional Development fund) and by the Ministry of Science and Art of Saxony (SMWK). LI is grateful to the DFG for a travel grant.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2416).

Comment
Pyridazine derivatives are important compounds for pharmacological applications, among them 3,6-dithiopyridazine being a secondary substance of the title compound (Cignarella & Barlocco, 2002).

Experimental
The title compound has been obtained as an intermediate substance of the synthesis of 3,6-dithiopyridazine involving the reaction of 3,6-dichloropyridazine with thiourea in methanol solution and was isolated before alkaline treatment (Steck & Brundage, 1959); (Kumagai, 1960). The colourless plate-type single crystals are stable in the air.