Ethyl 2-acetyl-3-(4-bromo­anilino)butanoate

Reddy, D.R.K.; V.Vijayakumar; Suresh, J.; Narasimhamurthy, T.; Lakshman, P.L.N.

doi:10.1107/S1600536809055378

Volume 66
Part 2
Page o296
February 2010

Received 22 December 2009
Accepted 24 December 2009
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.032
wR = 0.084
Data-to-parameter ratio = 17.5
Details

Ethyl 2-acetyl-3-(4-bromoanilino)butanoate

D. Ravi Kishore Reddy,^a V.Vijayakumar,^a J. Suresh,^b T. Narasimhamurthy ^c and P. L. Nilantha Lakshman ^d ^*

^aOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India,^bDepartment of Physics, The Madura College, Madurai 625 011, India,^cMaterials Research Centre, Indian Institute of Science, Bangalore 560 012, India, and ^dDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

The title compound, C₁₄H₁₈BrNO₃, adopts an extended conformation, with all of the main-chain torsion angles associated with the ester and amino groups close to trans. In the crystal, inversion dimers linked by pairs of N-HO hydrogen bonds are observed.

Related literature

For related structures see: Rajesh et al. (2009); Priya et al. (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₈BrNO₃
M_r = 328.20
Triclinic, $[P \overline 1]$
a = 6.9107 (3) Å
b = 10.1549 (4) Å
c = 11.6457 (5) Å
= 88.104 (2)°
= 81.932 (2)°
= 72.872 (2)°
V = 773.26 (6) Å³
Z = 2
Mo K radiation
= 2.66 mm^-1
T = 293 K
0.17 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.646, T_max = 0.746
11063 measured reflections
3140 independent reflections
2298 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.084
S = 1.06
3140 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.46 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N7-H7O12ⁱ	0.82 (3)	2.22 (3)	3.025 (2)	169 (3)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5002 ).

Acknowledgements

The authors acknowledge the use of the CCD facility at the Indian Institute of Science, Bangalore, set up under the IRHPA-DST programme.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Priya, S., Sinha, S., Vijayakumar, V., Narasimhamurthy, T., Vijay, T. & Rathore, R. S. (2006). Acta Cryst. E62, o5367-o5368.
Rajesh, K., Vijayakumar, V., Narasimhamurthy, T., Suresh, J. & Lakshman, P. L. N. (2009). Acta Cryst. E65, o2125.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds