Methyl 3-(1H-indol-3-yl)propano­ate

Hou, R.-B.; Li, D.-F.

doi:10.1107/S1600536811028595

Volume 67
Part 8
Page o2121
August 2011

Received 13 July 2011
Accepted 16 July 2011
Online 23 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.138
Data-to-parameter ratio = 17.5
Details

Methyl 3-(1H-indol-3-yl)propanoate

Rui-Bin Hou ^a and Dong-Feng Li ^a ^*

^aSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, People's Republic of China
Correspondence e-mail: lidongfeng@mail.ccut.edu.cn

The molecule of the title compound, C₁₂H₁₃NO₂, adopts an essentially planar conformation (r.m.s. deviation = 0.057 Å). In the crystal, the molecules are linked by intermolecular N-HO hydrogen bonds, generating chains along [201].

Related literature

For the biological activity of indole derivatives, see: Zeynep et al. (2005); Seefeld et al. (2003). For details of the synthesis, see: Pedras & Soledade (2006).

Experimental

Crystal data

C₁₂H₁₃NO₂
M_r = 203.23
Monoclinic, P 2₁ /c
a = 6.893 (5) Å
b = 9.146 (8) Å
c = 18.052 (10) Å
= 111.27 (3)°
V = 1060.5 (13) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.46 × 0.19 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.961, T_max = 0.984
10015 measured reflections
2414 independent reflections
1509 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.138
S = 1.04
2414 reflections
138 parameters
1 restraint
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.95	2.08	2.972 (3)	157
Symmetry code: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (MSC & Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2396 ).

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of Jilin Province (grant No. 20101548).

References

Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
MSC & Rigaku (2002). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Pedras, M. & Soledade, C. (2006). Med. Chem. 14, 4958-4979.
Rigaku Corporation (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Seefeld, M. A., Miler, W. H., Newlander, K. A., Burgess, W. J., DeWolf, W. E. Jr, Elkins, P. A., Head, M. S., Jakas, D. R., Janson, C. A., Keller, P. M., Manley, P. J., Moore, T. D., Payne, D. J., Pearson, S., Polizzi, B. J., Qiu, X., Rittenhouse, S. F., Uzinskas, I. N., Wallis, N. G. & Huffman, W. F. (2003). J. Med. Chem. 46, 1627-1635.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zeynep, A. A., Tulay, C. & Sibel, S. (2005). Med. Chem. Res. 14, 169-179.

organic compounds