Methyl 3-[(3,5-dichloro­anilino)carbon­yl]propionate

Saraswathi, B.S.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536810001455

Volume 66
Part 2
Page o387
February 2010

Received 10 January 2010
Accepted 12 January 2010
Online 16 January 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.006 Å
R = 0.061
wR = 0.166
Data-to-parameter ratio = 14.4
Details

Methyl 3-[(3,5-dichloroanilino)carbonyl]propionate

B. S. Saraswathi,^a B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C₁₁H₁₁Cl₂NO₃, the amide O atom and the carbonyl O atom of the ester segment are anti to each other and anti to the H atoms of the adjacent -CH₂ groups. In the crystal structure, molecules are packed into centrosymmetric dimers through intermolecular N-HO hydrogen bonds. The dimers are linked into a layer structure extending parallel to ( $[\overline{1}]$ 02) by C-HO hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2009a,b,c).

Experimental

Crystal data

C₁₁H₁₁Cl₂NO₃
M_r = 276.11
Monoclinic, C 2/c
a = 12.865 (2) Å
b = 14.753 (3) Å
c = 14.114 (2) Å
= 109.59 (2)°
V = 2523.7 (7) Å³
Z = 8
Mo K radiation
= 0.51 mm^-1
T = 299 K
0.50 × 0.16 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.785, T_max = 0.941
4503 measured reflections
2259 independent reflections
1453 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.166
S = 1.09
2259 reflections
157 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.37 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.85 (2)	2.17 (2)	3.017 (4)	172 (4)
C4-H4O1ⁱⁱ	0.93	2.45	3.379 (5)	174
Symmetry codes: (i) $[-x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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: CI5017 ).

Acknowledgements

BSS thanks the University Grants Commission (UGC), New Delhi, for the award of a research fellowship under its faculty improvement program.

References

Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009a). Acta Cryst. E65, o2039.
Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009b). Acta Cryst. E65, o3064.
Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009c). Acta Cryst. E65, o873.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds