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

Karthikeyan, S.; Sethusankar, K.; Rajeswaran, G.G.; Mohanakrishnan, A.K.

doi:10.1107/S1600536811051026

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 (C-C) = 0.005 Å
R = 0.058
wR = 0.186
Data-to-parameter ratio = 18.4
Details

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

S. Karthikeyan,^a K. Sethusankar,^a ^* Ganesan Gobi Rajeswaran ^b and Arasambattu K. Mohanakrishnan ^b

^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-HO hydrogen bonds with an R₂²(24) graph-set motif. The crystal structure is stabilized by further C-HO interactions. Short intramolecular C-HO contacts result in several S(6) rings.

Related literature

For the biological activity of sulfonamides and their substituted derivatives, see: Brown (1971). For related structures, see: Seetharaman & Rajan (1995); Varghese et al. (1986). For graph-set motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₃₀H₂₂N₂O₇S₂
M_r = 586.62
Monoclinic, P 2₁ /n
a = 7.9905 (2) Å
b = 22.2076 (6) Å
c = 15.7378 (4) Å
= 102.913 (2)°
V = 2722.04 (12) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.186
S = 1.03
6823 reflections
370 parameters
H-atom parameters constrained
_max = 1.01 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C27-H27O2ⁱ	0.93	2.56	3.221 (3)	128
C13-H13O1ⁱⁱ	0.93	2.58	3.275 (5)	132
C19-H19O4ⁱⁱⁱ	0.93	2.58	3.222 (4)	126
C2-H2O4	0.93	2.37	2.946 (4)	120
C9-H9AO3	0.97	2.21	2.846 (3)	122
C9-H9BO5	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); 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: 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.
Brown, G. M. (1971). Adv. Biochem. 35, 35-40.
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.
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.
Seetharaman, J. & Rajan, S. S. (1995). Acta Cryst. C51, 78-80.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Varghese, B., Srinivasan, S., Ramadas, S. R. & Padmanabhan, P. V. (1986). Acta Cryst. C42, 1542-1544.

organic compounds