4-(3-Chlorophenyl)-1-(3-chloropropyl)piperazin-1-ium chloride redetermined at 100 K

Abstract

The crystal structure of the title salt, C13H19Cl2N2+·Cl−, has been reported previously [Homrighausen & Krause Bauer (2002). Acta Cryst. E58, o1395–o1396] based on room-temperature data, where it was found to contain a disordered chloropropyl group. We now present the structure at 100 K in which the chloropropyl group is ordered. The piperazine ring adopts a chair conformation with the exocyclic N—C bonds in equatorial orientations. The dihedral angle between the piperazine ring (all atoms) and the benzene ring is 28.47 (5)°. The chloropropyl group has an extended conformation [N—C—C—C = −177.25 (8) ° and C—C—C—Cl = 174.23 (7)°]. In the crystal, charge-assisted N—H...Cl hydrogen bonds link the cation and anion into ion pairs. Numerous weak C—H...Cl interactions link the ion pairs into a three-dimensional network. Short Cl...Cl contacts [3.2419 (4) Å] are also observed.

Keywords

• crystal structure
• 5-HT1 serotonin receptor ligands
• piperazinium salts
• disorder