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

Naicker, T.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536811052767

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 (C-C) = 0.012 Å
Disorder in main residue
R = 0.077
wR = 0.219
Data-to-parameter ratio = 6.3
Details

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

Tricia Naicker,^a Thavendran Govender,^a Hendrick. G. Kruger ^b and Glenn E. M. Maguire ^b ^*

^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-HO and C-HO 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) and for related structures, see: Clegg & Elsegood (2003); Zalán et al. (2006)

Experimental

Crystal data

C₁₉H₂₁NO₅
M_r = 343.37
Monoclinic, C 2
a = 20.331 (9) Å
b = 5.070 (3) Å
c = 17.580 (9) Å
= 108.489 (8)°
V = 1718.5 (15) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.077

Refinement

R[F² > 2(F²)] = 0.077
wR(F²) = 0.219
S = 0.99
1645 reflections
263 parameters
13 restraints
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O5ⁱ	0.88	2.07	2.924 (9)	163
C2-H2O5ⁱ	0.95	2.55	3.412 (11)	151
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); 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.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Naicker, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2011). Eur. J. Org. Chem. 34, 6923-6932.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zalán, Z., Martinek, T. A., Lázár, L., Sillanpää, R. & Fülöp, F. (2006). Tetrahedron, 62, 2883-2891.

organic compounds