3-(4-Methoxy­benz­yl)-2-methyl-1-phenyl­sulfonyl-1H-indole

Kavitha, T.; Thenmozhi, M.; Dhayalan, V.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S1600536809010046

Volume 65
Part 4
Page o847
April 2009

Received 13 March 2009
Accepted 18 March 2009
Online 25 March 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.140
Data-to-parameter ratio = 20.5
Details

3-(4-Methoxybenzyl)-2-methyl-1-phenylsulfonyl-1H-indole

T. Kavitha,^a M. Thenmozhi,^a V. Dhayalan,^b A. K. Mohanakrishnan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: mnpsy2004@yahoo.com

There are two crystallographically independent molecules in the asymmetric unit of the title compound, C₂₃H₂₁NO₃S. The indole ring system is approximately perpendicular to the sulfonyl phenyl ring in both molecules [dihedral angles = 85.42 (8) and 88.30 (9)°]. C-HO interactions between molecules stabilize the crystal structure.

Related literature

For the Thorpe-Ingold effect, see: Bassindale (1984). For bond-length data, see: Allen et al. (1987). For the biological activity of sulfur-containing compounds, see: De-Benedetti et al, (1985); Krishnaiah et al. (1995).

Experimental

Crystal data

C₂₃H₂₁NO₃S
M_r = 391.47
Triclinic, $[P \overline 1]$
a = 11.4366 (4) Å
b = 13.6021 (5) Å
c = 14.0001 (5) Å
= 74.154 (1)°
= 67.773 (2)°
= 88.848 (2)°
V = 1930.96 (12) Å³
Z = 4
Mo K radiation
= 0.19 mm^-1
T = 293 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.963, T_max = 0.970
45568 measured reflections
10459 independent reflections
7561 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.140
S = 1.07
10459 reflections
509 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11A-H11AO1Bⁱ	0.93	2.52	3.397 (2)	157
C11B-H11BO1Aⁱⁱ	0.93	2.49	3.337 (2)	151
C15A-H15AO3Bⁱⁱⁱ	0.93	2.53	3.398 (2)	155
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x-1, y-1, z+1.

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2902 ).

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT- Madras, Chennai, India, for his help with the data collection.

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.
Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.
Bruker (2004). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
De-Benedetti, P. G., Folli, U., Iarossi, D. & Frassineti, C. (1985). J. Chem. Soc. Perkin Trans. 2, pp. 1527-1532.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Krishnaiah, M., Narayana Raju, K. V., Lu, I.-L., Chen, Y.-S. & Narasinga Rao, S. (1995). Acta Cryst. C51, 2429-2430.
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds