Received 19 May 2008
The title compound, C12H9N2+·C7H4ClO3-·C12H8N2·C7H5ClO3, contains one phenanthrolinium (Hphen) cation, one phenanthroline (phen) molecule, one 4-chloro-2-hydroxybenzoate anion (hcba) and one 4-chloro-2-hydroxybenzoic acid (Hhcba) molecule in the asymmetric unit. The phen molecule is approximately parallel to Hphen, making a dihedral angle of 1.98 (6)°. The centroid-centroid distance between pyridine rings of adjacent phen and Hphen species is 3.7718 (15) Å, and that between the benzene and pyridine rings of adjacent phen and Hphen species is 3.7922 (16) Å, indicative of - stacking interactions. The crystal structure contains an extensive network of classical (O-HO, N-HN and O-HCl) and weak (C-HO and C-HN) hydrogen bonds. Finally, C-H interactions are seen between Hphen and hcba and between phen and Hhcba in the crystal structure. The hydroxy group of the anion is disordered over the two sites ortho to the carboxylate group in a 0.75:0.25 ratio.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2735 ).
The work was supported by the ZIJIN project of Zhejiang University, China.
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