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

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

doi:10.1107/S1600536812042043

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 (C-C) = 0.002 Å
R = 0.025
wR = 0.068
Data-to-parameter ratio = 17.9
Details

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

Gertruida J.S. Venter,^a ^* Alice Brink,^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

In the title compound, C₁₁H₁₂ClNO, intramolecular N-HO hydrogen bonding is present. The dihedral angle between the benzene ring and the pentenone unit is 46.52 (5)°. In the crystal, C-HO 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); Venter et al. (2010, 2012b). For applications, see: Brink et al. (2010); Pyzuk et al. (1993); Roodt & Steyn (2000); Tan et al. (2008); Xia et al. (2008). For related ligand systems, see: Damoense et al. (1994), Venter et al. (2012a).

Experimental

Crystal data

C₁₁H₁₂ClNO
M_r = 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 radiation
= 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) T_min = 0.825, T_max = 0.933
17399 measured reflections
2259 independent reflections
2211 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(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
_max = 0.21 e Å^-3
_min = -0.24 e Å^-3
Absolute structure: Flack (1983), 932 Friedel pairs
Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N11-H11O12	0.82	1.95	2.6317 (16)	139
C113-H113O12ⁱ	0.95	2.42	3.3536 (18)	166
C115-H115O12ⁱⁱ	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); 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, 1999).

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.
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. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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., Steyl, G. & Roodt, A. (2010). Acta Cryst. E66, o3011-o3012.
Venter, G. J. S., Steyl, G. & Roodt, A. (2012a). Acta Cryst. E68, m666-m667.
Venter, G. J. S., Steyl, G. & Roodt, A. (2012b). Acta Cryst. E68, o2930-o2931.
Xia, M., Wu, B. & Xiang, G. (2008). J. Fluor. Chem. 129, 402-408.

organic compounds