2,6-Dichloro­aniline–4-(2,6-dichloro­anilino)­pent-3-en-2-one (1/2)

Venter, G.J.S.; Steyl, G.; Roodt, A.

doi:10.1107/S1600536812049227

Volume 69
Part 1
Pages o34-o35
January 2013

Received 27 September 2012
Accepted 30 November 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.077
Data-to-parameter ratio = 20.3
Details

2,6-Dichloroaniline-4-(2,6-dichloroanilino)pent-3-en-2-one (1/2)

Gertruida J. S. Venter,^a ^* Gideon Steyl ^a and Andreas Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa
Correspondence e-mail: ventergjs@ufs.ac.za

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 [pi] - [pi] interactions present, involving the benzene rings of inversion-related enamino-ketone molecules [centroid-centroid distance = 3.724 (4) Å].

Related literature

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).

Experimental

Crystal data

C₆H₅Cl₂N·2C₁₁H₁₁Cl₂NO
M_r = 650.23
Monoclinic, C 2/c
a = 15.7140 (1) Å
b = 8.7210 (2) Å
c = 22.9950 (4) Å
= 104.794 (1)°
V = 3046.81 (9) Å³
Z = 4
Mo K radiation
= 0.60 mm^-1
T = 100 K
0.31 × 0.25 × 0.19 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.837, T_max = 0.895
34421 measured reflections
3785 independent reflections
3305 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.077
S = 1.04
3785 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N21-H21Cl22	0.850 (17)	2.578 (17)	2.9710 (7)	109.4 (13)
N11-H11O12	0.825 (16)	1.932 (16)	2.6223 (13)	140.7 (14)
N21-H21O12	0.850 (17)	2.167 (17)	2.9732 (13)	158.4 (16)

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 ).

Acknowledgements

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.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brink, A., Visser, H. G., Steyl, G. & Roodt, A. (2010). Dalton Trans. 39, 5572-5578.
Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Damoense, L. J., Purcell, W., Roodt, A. & Leipoldt, J. G. (1994). Rhodium Express, 5, 10-13.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond, p. 61. New York: Oxford University Press.
Pyzuk, W., Krówczynsk, A. & Górecka, E. (1993). Mol. Cryst. Liq. Cryst. 237, 75-84.
Roodt, A. & Steyn, G. J. J. (2000). Recent Research Developments in Inorganic Chemistry, Vol. 2, pp. 1-23. Trivandrum: Transworld Research Network.
Shaheen, F., Marchio, L., Badshah, A. & Khosa, M. K. (2006). Acta Cryst. E62, o873-o874.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tan, H. Y., Loke, W. K., Tan, Y. T. & Nguyen, N.-T. (2008). Lab Chip, 8, 885-891.
Venter, G. J. S., Brink, A., Steyl, G. & Roodt, A. (2012). Acta Cryst. E68, o3101-o3102.
Venter, G. J. S., Steyl, G. & Roodt, A. (2010). Acta Cryst. E66, o1593-o1594.
Venter, G. J. S., Steyl, G. & Roodt, A. (2012). Acta Cryst. E68, m666-m667.
Xia, M., Wu, B. & Xiang, G. (2008). J. Fluorine Chem. 129, 402-408.

organic compounds