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Volume 69 
Part 11 
Page o1686  
November 2013  

Received 2 October 2013
Accepted 9 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.063
wR = 0.183
Data-to-parameter ratio = 15.2
Details
Open access

Propyl 2-(1H-indol-3-yl)acetate

aDepartment of Chemical Engineering, Taizhou Institute of Science and Technology, NJUST, Meilan Dong Road No. 8 Taizhou, Taizhou 225300, People's Republic of China
Correspondence e-mail: tgm333@126.com

In the title compound, C13H15NO2, the acetate group [C-C(=O)-O] makes a dihedral angle of 62.35 (13)° with the mean plane of the indole ring system [maximum deviation = 0.011 (3) Å]. In the crystal, mol­ecules are linked by N-H...O hydrogen bonds, forming helical chains propagating along [010].

Related literature

For the use of the title compound as a starting material for the synthesis of platinum complexes with anti­tumor activity, see: Kim et al. (1994[Kim, D.-K., Kim, G., Gam, J., Cho, Y.-B., Kim, H.-T., Tai, J.-H., Kim, K. H., Hong, W.-S. & Park, J.-G. (1994). J. Med. Chem. 37, 1471-1485.]). For its use as an inter­mediate in organic synthesis, see: Pandey et al. (1997[Pandey, G., Hajra, S., Ghorai, M. K. & Kumar, K. R. (1997). J. Org. Chem. 62, 5966-5973.]). For the synthesis of indole-3-acetic acid, see: Johnson & Donald (1973[Johnson, H. E. & Donald, G. C. (1973). Org. Synth. 5, 654-656.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15NO2

  • Mr = 217.26

  • Monoclinic, P 21 /c

  • a = 7.8230 (16) Å

  • b = 8.1740 (16) Å

  • c = 18.994 (4) Å

  • [beta] = 97.18 (3)°

  • V = 1205.1 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.976, Tmax = 0.992

  • 2387 measured reflections

  • 2210 independent reflections

  • 1463 reflections with I > 2[sigma](I)

  • Rint = 0.083

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.183

  • S = 1.00

  • 2210 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.86 2.13 2.953 (3) 160
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2653 ).


Acknowledgements

The authors thank Liu Bo Nian from Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for measuring the X-ray diffraction data.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Johnson, H. E. & Donald, G. C. (1973). Org. Synth. 5, 654-656.
Kim, D.-K., Kim, G., Gam, J., Cho, Y.-B., Kim, H.-T., Tai, J.-H., Kim, K. H., Hong, W.-S. & Park, J.-G. (1994). J. Med. Chem. 37, 1471-1485.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Pandey, G., Hajra, S., Ghorai, M. K. & Kumar, K. R. (1997). J. Org. Chem. 62, 5966-5973.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1686  [ doi:10.1107/S1600536813027633 ]

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