Diethyl 2-{[3-(2,4,6-trimethyl­benz­yl)-1-phenyl­sulfonyl-1H-indol-2-yl]methyl­idene}propane­dioate

Saravanan, B.; Dhayalan, V.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536810019690

Volume 66
Part 6
Page o1509
June 2010

Received 15 May 2010
Accepted 25 May 2010
Online 29 May 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.062
wR = 0.211
Data-to-parameter ratio = 19.9
Details

Diethyl 2-{[3-(2,4,6-trimethylbenzyl)-1-phenylsulfonyl-1H-indol-2-yl]methylidene}propanedioate

B. Saravanan,^a V. Dhayalan,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^aDepartment of Physics, J. J. College of Arts and Science, Pudukkottai 622 422, Tamil Nadu, India,^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India,^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: manivan1948@yahoo.com

In the title compound, C₃₂H₃₃NO₆S, the indole ring system makes dihedral angles of 62.78 (10) and 80.53 (8)°, respectively, with the phenyl and benzene rings. In the crystal, the molecules are linked through intermolecular C-HO hydrogen bonds, forming a chain along the a axis. Between the chains, a weak aromatic [pi] - [pi] stacking interaction [centroid-centroid distance = 3.831 (2) Å] is observed.

Related literature

For the biological activity of indole derivatives, see: Ma et al. (2001); Zhao et al. (2002); Zhou et al. (2006). For related structures, see: Chakkaravarthi et al. (2007, 2008).

Experimental

Crystal data

C₃₂H₃₃NO₆S
M_r = 559.65
Triclinic, $[P \overline 1]$
a = 8.5103 (4) Å
b = 8.9540 (4) Å
c = 19.6546 (10) Å
= 78.456 (3)°
= 87.236 (4)°
= 86.736 (3)°
V = 1463.99 (12) Å³
Z = 2
Mo K radiation
= 0.16 mm^-1
T = 295 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.967, T_max = 0.976
26660 measured reflections
7349 independent reflections
4328 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.211
S = 1.03
7349 reflections
370 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.42 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10O4ⁱ	0.93	2.43	3.179 (4)	138
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2550 ).

Acknowledgements

The authors wish to acknowledge DV University of Madras for the data collection.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.
Ma, C., Liu, X., Li, X., Flippen-Anderson, J., Yu, S. & Cook, J. M. (2001). J. Org. Chem. 66, 4525-4542.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhao, S., Liao, X. & Cook, J. M. (2002). Org. Lett. 4, 687-690.
Zhou, H., Liao, X., Yin, W., Ma, J. & Cook, J. M. (2006). J. Org. Chem. 71, 251-259.

organic compounds