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Volume 68 
Part 1 
Page o177  
January 2012  

Received 6 December 2011
Accepted 7 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.012 Å
Disorder in main residue
R = 0.077
wR = 0.219
Data-to-parameter ratio = 6.3
Details
Open access

(S)-Methyl 2-benzamido-3-(3,4-dimethoxyphenyl)propanoate

aSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa, and bSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
Correspondence e-mail: maguireg@ukzn.ac.za

The dimethoxypbenzene ring in the title compound, C19H21NO5, is gauche to the amide group and anti to the ester group. The chirality was confirmed to be S from two-dimensional NMR spectroscopy. In the crystal, N-H...O and C-H...O hydrogen bonds and several short-contact interactions (2.07-3.45 Å) create chains parallel to [110]. The phenyl ring is disordered over two orientations in a 0.54 (2):0.46 (2) ratio.

Related literature

The title compound is a precusor to novel chiral organocatalyts. For the synthesis, see: Naicker et al. (2011[Naicker, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2011). Eur. J. Org. Chem. 34, 6923-6932.]) and for related structures, see: Clegg & Elsegood (2003[Clegg, W. & Elsegood, M. R. J. (2003). Acta Cryst. E59, o1946-o1948.]); Zalán et al. (2006[Zalán, Z., Martinek, T. A., Lázár, L., Sillanpää, R. & Fülöp, F. (2006). Tetrahedron, 62, 2883-2891.])

[Scheme 1]

Experimental

Crystal data
  • C19H21NO5

  • Mr = 343.37

  • Monoclinic, C 2

  • a = 20.331 (9) Å

  • b = 5.070 (3) Å

  • c = 17.580 (9) Å

  • [beta] = 108.489 (8)°

  • V = 1718.5 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 173 K

  • 0.75 × 0.05 × 0.03 mm

Data collection
  • Bruker Kappa DUO APEXII diffractometer

  • 3865 measured reflections

  • 1645 independent reflections

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

  • Rint = 0.077

Refinement
  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.219

  • S = 0.99

  • 1645 reflections

  • 263 parameters

  • 13 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O5i 0.88 2.07 2.924 (9) 163
C2-H2...O5i 0.95 2.55 3.412 (11) 151
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]; data reduction: SAINT; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5150 ).


Acknowledgements

The authors wish to thank Dr Hong Su of the Chemistry Department of the University of Cape Town for her assistance with the crystallographic data collection.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Clegg, W. & Elsegood, M. R. J. (2003). Acta Cryst. E59, o1946-o1948.  [CSD] [CrossRef] [details]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Naicker, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2011). Eur. J. Org. Chem. 34, 6923-6932.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zalán, Z., Martinek, T. A., Lázár, L., Sillanpää, R. & Fülöp, F. (2006). Tetrahedron, 62, 2883-2891.


Acta Cryst (2012). E68, o177  [ doi:10.1107/S1600536811052767 ]

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