Acta Cryst. (2003). E59, o99±o101 DOI: 10.1107/S1600536802023188 R. Sankaranarayanan et al. C 42 H 30 N 2 O 4 S 4 o99 organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 1,2-Bis[1-phenylsulfonyl-3-(phenylthio)- indol-2-yl]ethene R. Sankaranarayanan, a M. Yogavel, b D. Velmurugan, b * K. Sekar, c P. C. Srinivasan, d S. Shanmuga Sundara Raj e and Hoong-Kun Fun e a Molecular Biophysics Unit, Indian Institute of Science, Bangalore 560 012, India, b Department of Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, c Bioinformatics Centre, Supercomputer Education and Research Centre, Indian Institute of Science, Bangalore 560 012, India, d Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and e X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia Correspondence e-mail: d_velu@yahoo.com Key indicators Single-crystal X-ray study T = 293 K Mean (C±C) = 0.003 A Ê R factor = 0.040 wR factor = 0.120 Data-to-parameter ratio = 17.6 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. # 2003 International Union of Crystallography Printed in Great Britain ± all rights reserved The title compound, C 42 H 30 N 2 O 4 S 4 , crystallizes in the space group P 1 with half a molecule in the asymmetric unit and the other half generated by an inversion centre. The indole moiety is planar within 0.043 (1) A Ê . The dihedral angle between the indole system and the thiophenyl ring is 83.4 (1) . The S atom of the sulfonyl substituent has a distorted tetrahedral geometry. The molecular structure is stabilized by CÐHO and CÐHS interactions and the packing of the molecules in the solid state is stabilized by CÐHO, CÐH and ± intermolecular interactions. Comment The indole ring system is present in a number of natural products, many of which are found to possess antibacterial (Okabe & Adachi, 1998), antitumour (Schollmeyer et al., 1995), antidepressant (Grinev et al. , 1984), antimicrobial (El- Sayed et al., 1986; Gadaginamath & Patil, 1999) and anti- in¯ammatory (Rodriguez et al., 1985) activities. Phenyl- sulfones show fungicidal activity comparable to or better than commercial fungicides (Wolf, 1999). The interaction of phenylsulfonyl indole with the calf-thymus DNA has also been studied by spectroscopic methods (Sivaraman et al., 1996). Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). The structure determination of the title compound, (I), was undertaken as part of our studies on indole derivatives. The asymmetric unit of (I) contains one-half molecule with the other half generated by a centre of inversion; the centre of inversion lies at the midpoint of the C21ÐC21 i bond [symmetry code: (i) 1 x,1 y, z]. The bond distance C21ÐC21 i of 1.344 (3) A Ê con®rms its double-bond character. The dihedral angle between the fused benzene and pyrrole rings is 3.9 (1) , and atoms S1, S2 and C21 deviate by 0.702 (1), 0.009 (1) and 0.223 (2) A Ê , respectively, from the mean plane of the indole moiety. The sulfonyl phenyl ring (A) and thiophenyl ring (B) make dihedral angles of 70.1 (1) and 83.4 (1) , respectively, with the indole moiety; rings A and B are inclined at an angle of 80.1 (1) . The torsion angle O2Ð S1ÐN1ÐC1 of 169.6 (1) and O2ÐS1ÐC9ÐC10 of Received 9 December 2002 Accepted 17 December 2002 Online 24 December 2002