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Volume 68 
Part 1 
Page o133  
January 2012  

Received 19 November 2011
Accepted 3 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.110
Data-to-parameter ratio = 16.5
Details
Open access

Methyl 4-(5-methoxy-1H-indol-3-yl)benzoate

aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China
Correspondence e-mail: zhangzhiqiang@ustl.edu.cn

In the title compound, C17H15NO3, the dihedral angle between the benzene ring and the indole ring system is 22.5 (3)°. In the crystal, molecules are linked by N-H...[pi] and C-H...O interactions.

Related literature

For background to the catalysed arylation of indoles, see: Zhang et al. (2007[Zhang, Z., Hu, Z., Yu, Z., Lei, P., Chi, H., Wang, Y. & He, R. (2007). Tetrahedron Lett. 48, 2415-2419.]). For reference 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
  • C17H15NO3

  • Mr = 281.30

  • Monoclinic, P 21 /c

  • a = 15.023 (8) Å

  • b = 5.871 (3) Å

  • c = 16.867 (9) Å

  • [beta] = 113.721 (6)°

  • V = 1361.9 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 113 K

  • 0.20 × 0.16 × 0.14 mm

Data collection
  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corp., Tokyo, Japan.]) Tmin = 0.981, Tmax = 0.987

  • 13161 measured reflections

  • 3241 independent reflections

  • 2460 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.110

  • S = 1.06

  • 3241 reflections

  • 196 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid ofthe C2-C5/C8/C9 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...Cg2i 0.90 (1) 2.54 (2) 3.295 (2) 142 (1)
C6-H6...O1ii 0.95 2.43 3.369 (2) 172
C17-H17B...O2iii 0.98 2.60 3.484 (2) 150
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corp., Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6526 ).


Acknowledgements

This work was supported by the Natural Science Foundation of Liaoning Education Department (No. 2008 T094). We would like to thank Dr George Li, at CombiPhos Catalysts, Inc., Princeton, NJ, for helpful discussions regarding the use of POPd catalysts.

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.
Rigaku (2007). CrystalClear. Rigaku Corp., Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhang, Z., Hu, Z., Yu, Z., Lei, P., Chi, H., Wang, Y. & He, R. (2007). Tetrahedron Lett. 48, 2415-2419.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o133  [ doi:10.1107/S1600536811052135 ]

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