Received 27 September 2012
The asymmetric unit of the title compound, C6H5Cl2N·2C11H11Cl2NO, is composed of one molecule of an enamino-ketone [i.e. -(2,6-dichlorophenylamino)pent-3-en-2-one] and half a molecule of 2,6-dichloroaniline, the whole molecule of the latter component being generated by twofold rotational symmetry. In this latter molecule, there are two intramolecular N-HCl contacts. In the enamino-ketone molecule, there is an N-HO hydrogen bond of moderate strength, and the dihedral angle between the benzene ring and pentanone fragment [C-C(-N)=C-C(=O)-C; planar within 0.005 (1) Å] is 81.85 (7)°. In the crystal, two molecules of the enamino-ketone are bridged by a molecule of 2,6-dichloroaniline via N-HO hydrogen bonds of moderate strength. There are also - interactions present, involving the benzene rings of inversion-related enamino-ketone molecules [centroid-centroid distance = 3.724 (4) Å].
For the properties of enamino-ketones as liquid crystals, see: Pyzuk et al. (1993). For fluorescence studies of enamino-ketones, see: Xia et al. (2008). For the use of enamino-ketones in medicine, see: Tan et al. (2008); and in catalysis, see: Roodt & Steyn (2000); Brink et al. (2010). For background to the ligand preparation, see: Shaheen et al. (2006); Venter et al. (2010); Venter, Brink et al. (2012). For applications of rhodium compounds containing bidentate ligand systems, see: Pyzuk et al. (1993); Tan et al. (2008); Xia et al. (2008). For related rhodium enamino-ketonato complexes, see: Brink et al. (2010); Damoense et al. (1994); Roodt & Steyn (2000); Venter, Steyl et al. (2012). For classification of hydrogen bonds, see: Gilli & Gilli (2009).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2272 ).
Mr Leo Kirsten is thanked for the XRD data collection. Financial assistance from the University of the Free State Strategic Academic Cluster Initiative, SASOL, the South African National Research Foundation (SA-NRF/THRIP) and the Inkaba ye Afrika Research Initiative is gratefully acknowledged. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the SA-NRF.
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