Methyl 3-[(1-butyl-1H-indol-3-yl)carbonyl­amino]propionate

Huang, G.; Xu, X.Y.; Zeng, X.C.; Tang, G.H.; Li, D.D.

doi:10.1107/S1600536809029973

Volume 65
Part 9
Page o2063
September 2009

Received 22 July 2009
Accepted 28 July 2009
Online 8 August 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.135
Data-to-parameter ratio = 15.4
Details

Methyl 3-[(1-butyl-1H-indol-3-yl)carbonylamino]propionate

Gang Huang,^a Xing Yan Xu,^a Xiang Chao Zeng,^a ^* Gui Hong Tang ^a and Dong Dong Li ^a

^aDepartment of Chemistry, Jinan University, Guangzhou, Guangdong 510632, People's Republic of China
Correspondence e-mail: xczeng@126.com

In the title molecule, C₁₇H₂₂N₂O₃, the mean plane of the terminal (C=O)OMe fragment and the indole plane form a dihedral angle of 78.94 (3)°. Intermolecular N-HO hydrogen bonds link the molecules into chains extended along the c axis. The crystal packing exhibits [pi] - [pi] interactions, indicated by the short distance of 3.472 (2) Å between the centroids of the five-membered heterocycles of neighbouring molecules.

Related literature

For the bioactivity of indole derivatives, see: Fabio et al. (2007); Sharma et al. (2004). For related structures, see: Zeng et al. (2005); Siddiquee et al. (2009).

Experimental

Crystal data

C₁₇H₂₂N₂O₃
M_r = 302.37
Monoclinic, P 2₁ /c
a = 14.144 (3) Å
b = 12.685 (3) Å
c = 9.198 (2) Å
= 107.151 (4)°
V = 1576.8 (6) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 173 K
0.46 × 0.42 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.961, T_max = 0.985
7760 measured reflections
3093 independent reflections
2169 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.135
S = 1.05
3093 reflections
201 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.88	2.07	2.860 (2)	149
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2594 ).

Acknowledgements

We thank the Natural Science Foundation of Guangdong Province, China (grant No. 06300581) for generous support of this study.

References

Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Fabio, R. D., Micheli, F., Alvaro, G., Cavanni, P., Donati, D., Gagliardi, T., Fontana, G., Giovannini, R., Maffeis, M., Mingardi, A., Tranquillini, M. E. & Vitulli, G. (2007). Bioorg. Med. Chem. Lett. 17, 2254-2259.
Sharma, V. & Tepe, J. J. (2004). Bioorg. Med. Chem. Lett. 14, 4319-4321.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siddiquee, T., Islam, S., Bennett, D., Zeller, M. & Hossain, M. (2009). Acta Cryst. E65, o1802-o1803.
Zeng, X. C., Xu, S. H., Li, P. R. & Deng, Q. Y. (2005). Chin. J. Struct. Chem. 24, 299-302.

organic compounds