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

Wang, C.-P.; Yu, J.-L.; Zhang, Z.-Q.; Yan, J.-B.

doi:10.1107/S1600536811052135

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 (C-C) = 0.002 Å
R = 0.037
wR = 0.110
Data-to-parameter ratio = 16.5
Details

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

Cui-Ping Wang,^a Jiang-Long Yu,^a Zhi-Qiang Zhang ^a ^* and Jing-Bo Yan ^a

^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-HO interactions.

Related literature

For background to the catalysed arylation of indoles, see: Zhang et al. (2007). For reference bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₇H₁₅NO₃
M_r = 281.30
Monoclinic, P 2₁ /c
a = 15.023 (8) Å
b = 5.871 (3) Å
c = 16.867 (9) Å
= 113.721 (6)°
V = 1361.9 (12) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.981, T_max = 0.987
13161 measured reflections
3241 independent reflections
2460 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(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
_max = 0.24 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
N1-H1Cg2ⁱ	0.90 (1)	2.54 (2)	3.295 (2)	142 (1)
C6-H6O1ⁱⁱ	0.95	2.43	3.369 (2)	172
C17-H17BO2ⁱⁱⁱ	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); cell refinement: CrystalClear; data reduction: CrystalClear; 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: 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.
Zhang, Z., Hu, Z., Yu, Z., Lei, P., Chi, H., Wang, Y. & He, R. (2007). Tetrahedron Lett. 48, 2415-2419.

organic compounds