Ethyl 2-[(4-chloro­phen­yl)hydrazono]-3-oxobutanoate

Fun, H.-K.; Chantrapromma, S.; Padaki, M.; Radhika; Isloor, A.M.

doi:10.1107/S1600536809012951

Volume 65
Part 5
Page o1029
May 2009

Received 3 April 2009
Accepted 6 April 2009
Online 10 April 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.037
wR = 0.108
Data-to-parameter ratio = 28.6
Details

Ethyl 2-[(4-chlorophenyl)hydrazono]-3-oxobutanoate

Hoong-Kun Fun,^a ^*⁺ Suchada Chantrapromma,^b ⁺⁺ Mahesh Padaki,^c Radhika ^c and Arun M. Isloor ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
Correspondence e-mail: hkfun@usm.my

The molecule of the title oxobutanoate derivative, C₁₂H₁₃ClN₂O₃, is nearly planar; the interplanar angle between the benzene ring and the mean plane through the hydrazono-3-oxobutanoate unit is 2.69 (3)°. An intramolecular N-HO hydrogen bond generates an S(6) ring motif. In the crystal packing, C-HO(3-oxo) interactions link molecules into dimers. The dimers thus formed are linked through C-HO(carboxylate C=O) interactions, leading to the formation of ribbons along the [01 $[\overline 1]$ ] direction, which are stabilized via ClCl [3.2916 (3) Å] contacts. The ribbons are stacked via CO contacts [3.2367 (12)-3.3948 (12) Å].

Related literature

For hydrogen-bond motifs, see Bernstein et al. (1995). For background to the bioactivity and applications of oxobutanoate derivatives, see: Alpaslan et al. (2005); Billington et al. (1979); Stancho et al. (2008). For the synthesis, see Amir & Agarwal (1997). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Experimental

Crystal data

C₁₂H₁₃ClN₂O₃
M_r = 268.69
Monoclinic, P 2₁ /c
a = 4.0259 (1) Å
b = 17.0892 (4) Å
c = 18.4934 (5) Å
= 96.802 (1)°
V = 1263.38 (6) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 100 K
0.77 × 0.13 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.799, T_max = 0.982
38796 measured reflections
4723 independent reflections
3972 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.108
S = 1.06
4723 reflections
165 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.91	1.87	2.5721 (12)	132
C2-H2AO2ⁱ	0.93	2.45	3.3536 (13)	164
C5-H5AO1ⁱⁱ	0.93	2.53	3.4293 (12)	163
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+3, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2415 ).

Acknowledgements

AMI is grateful to the Head of the Department of Chemistry and the Director, NITK, Surathkal, India, for providing research facilities. The authors thank the Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Alpaslan, G., Özdamar, O., Odabasoglu, M., Ersanli, C. C., Erdönmez, A. & Ocak Ískeleli, N. (2005). Acta Cryst. E61, o3442-o3444.
Amir, M. & Agarwal, R. (1997). J. Indian Chem. Soc. 74, 154-155.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Billington, D. C., Golding, B. T. & Primrose, S. B. (1979). Biochem. J. 182, 827-836.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stancho, S., Georgi, M., Frank, J. & Ilia, M. (2008). Eur. J. Med. Chem. 43, 694-706.

organic compounds