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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 [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.077
Data-to-parameter ratio = 20.3
Details
Open access

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

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-H...Cl contacts. In the enamino-ketone molecule, there is an N-H...O 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-H...O 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[Pyzuk, W., Krówczynsk, A. & Górecka, E. (1993). Mol. Cryst. Liq. Cryst. 237, 75-84.]). For fluorescence studies of enamino-ketones, see: Xia et al. (2008[Xia, M., Wu, B. & Xiang, G. (2008). J. Fluorine Chem. 129, 402-408.]). For the use of enamino-ketones in medicine, see: Tan et al. (2008[Tan, H. Y., Loke, W. K., Tan, Y. T. & Nguyen, N.-T. (2008). Lab Chip, 8, 885-891.]); and in catalysis, see: Roodt & Steyn (2000[Roodt, A. & Steyn, G. J. J. (2000). Recent Research Developments in Inorganic Chemistry, Vol. 2, pp. 1-23. Trivandrum: Transworld Research Network.]); Brink et al. (2010[Brink, A., Visser, H. G., Steyl, G. & Roodt, A. (2010). Dalton Trans. 39, 5572-5578.]). For background to the ligand preparation, see: Shaheen et al. (2006[Shaheen, F., Marchio, L., Badshah, A. & Khosa, M. K. (2006). Acta Cryst. E62, o873-o874.]); Venter et al. (2010[Venter, G. J. S., Steyl, G. & Roodt, A. (2010). Acta Cryst. E66, o1593-o1594.]); Venter, Brink et al. (2012[Venter, G. J. S., Brink, A., Steyl, G. & Roodt, A. (2012). Acta Cryst. E68, o3101-o3102.]). For applications of rhodium compounds containing bidentate ligand systems, see: Pyzuk et al. (1993[Pyzuk, W., Krówczynsk, A. & Górecka, E. (1993). Mol. Cryst. Liq. Cryst. 237, 75-84.]); Tan et al. (2008[Tan, H. Y., Loke, W. K., Tan, Y. T. & Nguyen, N.-T. (2008). Lab Chip, 8, 885-891.]); Xia et al. (2008[Xia, M., Wu, B. & Xiang, G. (2008). J. Fluorine Chem. 129, 402-408.]). For related rhodium enamino-ketonato complexes, see: Brink et al. (2010[Brink, A., Visser, H. G., Steyl, G. & Roodt, A. (2010). Dalton Trans. 39, 5572-5578.]); Damoense et al. (1994[Damoense, L. J., Purcell, W., Roodt, A. & Leipoldt, J. G. (1994). Rhodium Express, 5, 10-13.]); Roodt & Steyn (2000[Roodt, A. & Steyn, G. J. J. (2000). Recent Research Developments in Inorganic Chemistry, Vol. 2, pp. 1-23. Trivandrum: Transworld Research Network.]); Venter, Steyl et al. (2012[Venter, G. J. S., Steyl, G. & Roodt, A. (2012). Acta Cryst. E68, m666-m667.]). For classification of hydrogen bonds, see: Gilli & Gilli (2009[Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond, p. 61. New York: Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data
  • C6H5Cl2N·2C11H11Cl2NO

  • Mr = 650.23

  • Monoclinic, C 2/c

  • a = 15.7140 (1) Å

  • b = 8.7210 (2) Å

  • c = 22.9950 (4) Å

  • [beta] = 104.794 (1)°

  • V = 3046.81 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.837, Tmax = 0.895

  • 34421 measured reflections

  • 3785 independent reflections

  • 3305 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N21-H21...Cl22 0.850 (17) 2.578 (17) 2.9710 (7) 109.4 (13)
N11-H11...O12 0.825 (16) 1.932 (16) 2.6223 (13) 140.7 (14)
N21-H21...O12 0.850 (17) 2.167 (17) 2.9732 (13) 158.4 (16)

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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.  [CSD] [CrossRef] [ChemPort] [PubMed]
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.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tan, H. Y., Loke, W. K., Tan, Y. T. & Nguyen, N.-T. (2008). Lab Chip, 8, 885-891.  [CrossRef] [PubMed] [ChemPort]
Venter, G. J. S., Brink, A., Steyl, G. & Roodt, A. (2012). Acta Cryst. E68, o3101-o3102.  [CSD] [CrossRef] [details]
Venter, G. J. S., Steyl, G. & Roodt, A. (2010). Acta Cryst. E66, o1593-o1594.  [CSD] [CrossRef] [details]
Venter, G. J. S., Steyl, G. & Roodt, A. (2012). Acta Cryst. E68, m666-m667.  [CSD] [CrossRef] [details]
Xia, M., Wu, B. & Xiang, G. (2008). J. Fluorine Chem. 129, 402-408.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o34-o35   [ doi:10.1107/S1600536812049227 ]

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