(Z)-4-(2,5-Di-tert-butyl­anilino)pent-3-en-2-one

Pastrán, J.; Ramírez, A.; Agrifoglio, G.; Linden, A.; Dorta, R.

doi:10.1107/S1600536811017296

Volume 67
Part 6
Pages o1405-o1406
June 2011

Received 26 April 2011
Accepted 7 May 2011
Online 14 May 2011

Key indicators
Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.118
Data-to-parameter ratio = 15.5
Details

(Z)-4-(2,5-Di-tert-butylanilino)pent-3-en-2-one

Jesús Pastrán,^a Andrea Ramírez,^a Giuseppe Agrifoglio,^a Anthony Linden ^b ^* and Romano Dorta ^a ^*

^aDepartamento de Química, Universidad Simón Bolívar, Caracas 1080A, Venezuela, and ^bInstitute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
Correspondence e-mail: alinden@oci.uzh.ch, rdorta@usb.ve

In the crystal structure of the title ketoamine, C₁₉H₂₉NO, the bond lengths from the N atom through the alkene group to the ketone O atom show the presence of an extensively delocalized [pi] -system. The dihedral angle between the plane of the phenyl ring and that of the alkene component is 63.45 (7)° due to steric hindrance exerted by the tert-butyl groups. The molecule has a Z-configured alkene function, which is facilitated by an intramolecular N-HO hydrogen bond between the amine and ketone groups. The molecules are linked into extended chains, which run parallel to the [010] direction, by a very weak C-HO interaction between the methyl substituent of the alkene group and the ketone O atom of a neighbouring molecule.

Related literature

For the conformations of [beta] -ketoamines, see: Pastrán et al. (2011); Zharkova et al. (2009). For reactions involving aminoketonate complexes, see: He et al. (2003); Hsu, Chang et al. (2004); Lai et al. (2005); Li et al. (2005); Tang et al. (2005); Hsu, Li et al. (2007); Pan et al. (2008). For the preparation and coordination chemistry of aminoketonate ligands, see: Jones et al. (1998); Shukla et al. (2005); Lesikar et al. (2008); Sedai et al. (2008).

Experimental

Crystal data

C₁₉H₂₉NO
M_r = 287.44
Monoclinic, C 2/c
a = 23.7759 (5) Å
b = 9.0517 (2) Å
c = 19.3760 (4) Å
= 120.6308 (11)°
V = 3588.11 (13) Å³
Z = 8
Mo K radiation
= 0.06 mm^-1
T = 160 K
0.32 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD area-detector diffractometer
24643 measured reflections
3153 independent reflections
2769 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.118
S = 1.04
3152 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N15-H15O18	0.908 (17)	1.848 (17)	2.6376 (15)	144.1 (15)
C20-H201O18ⁱ	0.98	2.52	3.474 (2)	164
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5243 ).

Acknowledgements

This work was financed by FONACIT (project S1-2001000851).

References

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