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Volume 66 
Part 11 
Pages o3011-o3012  
November 2010  

Received 22 October 2010
Accepted 26 October 2010
Online 31 October 2010

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.099
Data-to-parameter ratio = 16.8
Details
Open access

4-[(4-Methylphenyl)amino]pent-3-en-2-one

Gertruida J. S. Venter,a* Gideon Steyla and Andreas Roodta

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
Correspondence e-mail: truidie@hotmail.com

The title enaminoketone, C12H15NO, is a derivative of 4-(phenylamino)pent-3-en-2-one with an approximately planar pentenone backbone, the greatest displacement from the plane being 0.042 (1) Å; the asymmetry in C-C distances in the group suggests the presence of unsaturated bonds. The dihedral angle between the benzene ring and the pentenone plane is 29.90 (4)°. In the crystal, an intramolecular N-H...O interaction and an intermolecular C-H...O hydrogen bond are observed.

Related literature

For synthetic background, 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.]). For applications of enaminoketones, see: Brink et al. (2010[Brink, A., Visser, H. G., Steyl, G. & Roodt, A. (2010). Dalton Trans. pp. 5572-5578.]); Chen & Rhodes (1996[Chen, H. & Rhodes, J. (1996). J. Mol. Med. 74, 497-504.]); 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. Fluorine Chem. 129, 402-408.]). For structures of related ligand systems, see: Venter et al. (2009a[Venter, G. J. S., Steyl, G. & Roodt, A. (2009a). Acta Cryst. E65, m1321-m1322.],b[Venter, G. J. S., Steyl, G. & Roodt, A. (2009b). Acta Cryst. E65, m1606-m1607.]).

[Scheme 1]

Experimental

Crystal data

  • C12H15NO

  • Mr = 189.25

  • Monoclinic, P 21 /c

  • a = 10.0736 (2) Å

  • b = 10.8800 (2) Å

  • c = 10.0723 (2) Å

  • [beta] = 110.291 (1)°

  • V = 1035.43 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.34 × 0.31 × 0.2 mm
Data collection

  • Bruker X8 APEXII 4K Kappa CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.985

  • 17880 measured reflections

  • 2257 independent reflections

  • 2011 reflections with I > 2[sigma](I)

  • Rint = 0.024
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.099

  • S = 1.05

  • 2257 reflections

  • 134 parameters

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C116-H116...O12i 0.95 2.55 3.462 (1) 160
N11-H11...O12 0.916 (16) 1.859 (16) 2.6463 (13) 142.7 (15)
Symmetry code: (i) -x+1, -y+1, -z.

Table 2
Comparative geometric parameters (Å, °) for free and coordinated N,O-bidendate (N,O-bid) compounds

Parameter I II III IV
N11-C111 1.417 (2) 1.422 (2) 1.521 (4)/1.463 (3) 1.440 (4)
N11-C2 1.348 (1) 1.345 (2) 1.320 (4) 1.319 (4)
O12-C4 1.253 (1) 1.257 (2) 1.290 (3) 1.291 (4)
C2-C3 1.384 (2) 1.383 (3) 1.410 (4) 1.423 (4)
C3-C4 1.424 (2) 1.420 (2) 1.365 (3) 1.382 (3)
N11...O12 2.646 (1) 2.635 (2) 2.885 (3) 2.886 (3)
N11-C2-C4-O12 1.70 (9) -0.5 (1) 4.1 (2) -2.6 (2)
Dihedral angle 29.90 (3) 49.53 (5) 87.47 (4)/89.36 (8) 85.58 (8)
(I) This work. (II) Uncoordinated 4-(2-methylphenylamino)pent-3-en-2-one (Venter et al., 2010[Venter, G. J. S., Steyl, G. & Roodt, A. (2010). Acta Cryst. E66, o1593-o1594.]). (III) N,O-bid = 4-(2,3-dimethylphenylamino)pent-3-en-2-onato (Venter et al., 2009a[Venter, G. J. S., Steyl, G. & Roodt, A. (2009a). Acta Cryst. E65, m1321-m1322.]). (IV) N,O-bid = 4-(2,6-dimethylphenylamino)pent-3-en-2-onato (Venter et al., 2009b[Venter, G. J. S., Steyl, G. & Roodt, A. (2009b). Acta Cryst. E65, m1606-m1607.]). The dihedral angle is defined as the torsion angle between the N-C-C-C-O plane and the phenyl ring.

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: IS2620 ).

Acknowledgements

Financial assistance from the University of the Free State is gratefully acknowledged. The authors also express their gratitude to SASOL and the South African National Research Foundation (SA-NRF/THRIP) 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. pp. 5572-5578.  [CSD] [CrossRef]
Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H. & Rhodes, J. (1996). J. Mol. Med. 74, 497-504.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [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. (2009a). Acta Cryst. E65, m1321-m1322.  [CSD] [CrossRef] [details]
Venter, G. J. S., Steyl, G. & Roodt, A. (2009b). Acta Cryst. E65, m1606-m1607.  [CSD] [CrossRef] [details]
Venter, G. J. S., Steyl, G. & Roodt, A. (2010). Acta Cryst. E66, o1593-o1594.  [CrossRef] [details]
Xia, M., Wu, B. & Xiang, G. (2008). J. Fluorine Chem. 129, 402-408.  [ISI] [CSD] [CrossRef] [ChemPort]

Acta Cryst (2010). E66, o3011-o3012   [ doi:10.1107/S1600536810043680 ]

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