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Volume 68 
Part 11 
Pages o3101-o3102  
November 2012  

Received 21 September 2012
Accepted 8 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.025
wR = 0.068
Data-to-parameter ratio = 17.9
Details
Open access

4-(2-Chlorophenylamino)-pent-3-en-2-one

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

In the title compound, C11H12ClNO, intramolecular N-H...O hydrogen bonding is present. The dihedral angle between the benzene ring and the pentenone unit is 46.52 (5)°. In the crystal, C-H...O interactions between hydrogen atoms of the aryl moiety and two separate oxygen atoms occur, leading to a three-dimensional network.

Related literature

For synthetic background and similar compounds, 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, o3011-o3012.], 2012b[Venter, G. J. S., Steyl, G. & Roodt, A. (2012b). Acta Cryst. E68, o2930-o2931.]). For applications, see: Brink et al. (2010[Brink, A., Visser, H. G., Steyl, G. & Roodt, A. (2010). Dalton Trans. 39, 5572-5578.]); Pyzuk et al. (1993[Pyzuk, W., Krówczynsk, A. & Górecka, E. (1993). Mol. Cryst. Liq. Cryst. 237, 75-84.]); 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.]); 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. Fluor. Chem. 129, 402-408.]). For related ligand systems, see: Damoense et al. (1994[Damoense, L. J., Purcell, W., Roodt, A. & Leipoldt, J. G. (1994). Rhodium Express, 5, 10-13.]), Venter et al. (2012a[Venter, G. J. S., Steyl, G. & Roodt, A. (2012a). Acta Cryst. E68, m666-m667.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12ClNO

  • Mr = 209.67

  • Orthorhombic, P 21 21 21

  • a = 7.3264 (3) Å

  • b = 8.7103 (4) Å

  • c = 16.1960 (7) Å

  • V = 1033.55 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 100 K

  • 0.6 × 0.42 × 0.21 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.825, Tmax = 0.933

  • 17399 measured reflections

  • 2259 independent reflections

  • 2211 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.068

  • S = 1.06

  • 2259 reflections

  • 126 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 932 Friedel pairs

  • Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N11-H11...O12 0.82 1.95 2.6317 (16) 139
C113-H113...O12i 0.95 2.42 3.3536 (18) 166
C115-H115...O12ii 0.95 2.43 3.3217 (18) 157
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) x, y+1, z.

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, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2444 ).


Acknowledgements

Financial assistance from the University of the Free State is gratefully acknowledged. We also express our gratitude towards SASOL, the South African National Research Foundation (SA-NRF/THRIP) and the Inkaba yeAfrica initiative for financial support of this project. 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. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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., Steyl, G. & Roodt, A. (2010). Acta Cryst. E66, o3011-o3012.  [CrossRef] [details]
Venter, G. J. S., Steyl, G. & Roodt, A. (2012a). Acta Cryst. E68, m666-m667.  [CSD] [CrossRef] [details]
Venter, G. J. S., Steyl, G. & Roodt, A. (2012b). Acta Cryst. E68, o2930-o2931.  [CrossRef] [details]
Xia, M., Wu, B. & Xiang, G. (2008). J. Fluor. Chem. 129, 402-408.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3101-o3102   [ doi:10.1107/S1600536812042043 ]

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