[Journal logo]

Volume 68 
Part 1 
Page o9  
January 2012  

Received 18 November 2011
Accepted 28 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.058
wR = 0.186
Data-to-parameter ratio = 18.4
Details
Open access

(E)-3-(2-Nitrophenyl)-1-{1-phenylsulfonyl-2-[(phenylsulfonyl)methyl]-1H-indol-3-yl}prop-2-en-1-one

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C30H22N2O7S2, the configuration about the propene C=C bond is E. The indole unit is essentially planar, with a maximum deviation of 0.031 (3) Å. The dihedral angle between the planes of the phenyl rings of the two phenylsulfonyl groups is 80.95 (19)°. The central prop-2-ene-1-one group is oriented at a dihedral angle of 44.26 (11)° with respect to the nitrophenyl ring and at 39.24 (8)° with respect to the indole unit. The S atoms are in a distorted tetrahedral configuration. In the crystal, molecules are linked into centrosymmetric dimers via pairs of C-H...O hydrogen bonds with an R22(24) graph-set motif. The crystal structure is stabilized by further C-H...O interactions. Short intramolecular C-H...O contacts result in several S(6) rings.

Related literature

For the biological activity of sulfonamides and their substituted derivatives, see: Brown (1971[Brown, G. M. (1971). Adv. Biochem. 35, 35-40.]). For related structures, see: Seetharaman & Rajan (1995[Seetharaman, J. & Rajan, S. S. (1995). Acta Cryst. C51, 78-80.]); Varghese et al. (1986[Varghese, B., Srinivasan, S., Ramadas, S. R. & Padmanabhan, P. V. (1986). Acta Cryst. C42, 1542-1544.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C30H22N2O7S2

  • Mr = 586.62

  • Monoclinic, P 21 /n

  • a = 7.9905 (2) Å

  • b = 22.2076 (6) Å

  • c = 15.7378 (4) Å

  • [beta] = 102.913 (2)°

  • V = 2722.04 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • 32862 measured reflections

  • 6823 independent reflections

  • 4782 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.186

  • S = 1.03

  • 6823 reflections

  • 370 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.01 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C27-H27...O2i 0.93 2.56 3.221 (3) 128
C13-H13...O1ii 0.93 2.58 3.275 (5) 132
C19-H19...O4iii 0.93 2.58 3.222 (4) 126
C2-H2...O4 0.93 2.37 2.946 (4) 120
C9-H9A...O3 0.97 2.21 2.846 (3) 122
C9-H9B...O5 0.97 2.37 3.029 (3) 125
Symmetry codes: (i) -x+1, -y, -z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2489 ).


Acknowledgements

SK and KS thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Department of Physics, RKM Vivekananda College, for providing facilities in the department for carrying out this work.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brown, G. M. (1971). Adv. Biochem. 35, 35-40.  [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Seetharaman, J. & Rajan, S. S. (1995). Acta Cryst. C51, 78-80.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Varghese, B., Srinivasan, S., Ramadas, S. R. & Padmanabhan, P. V. (1986). Acta Cryst. C42, 1542-1544.  [CrossRef] [details]


Acta Cryst (2012). E68, o9  [ doi:10.1107/S1600536811051026 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.