[Journal logo]

Volume 69 
Part 12 
Page o1784  
December 2013  

Received 8 November 2013
Accepted 12 November 2013
Online 16 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.150
Data-to-parameter ratio = 20.6
Details
Open access

(E)-1-[2-(4-Chloro-2-nitro­styr­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]propan-1-one

aResearch Scholar (Chemistry), Bharathiyar University, Coimbatore 641 046, Tamilnadu, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India,cDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com

In the title compound, C25H19ClN2O5S, the phenyl ring forms dihedral angles of 79.62 (12) and 80.02 (13)° with the indole ring system and the benzene ring, respectively. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring. In the crystal, mol­ecules assemble into double layers in the ab plane via C-H...O inter­actions.

Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998[Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.]); Srivastava et al. (2011[Srivastava, Anupam & Pandeya, S. N. (2011). JCPR, 1, 1-17.]). For related structures, see: Chakkaravarthi et al. (2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o749.], 2010[Chakkaravarthi, G., Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2010). Acta Cryst. E66, o2957.]).

[Scheme 1]

Experimental

Crystal data
  • C25H19ClN2O5S

  • Mr = 494.93

  • Triclinic, [P \overline 1]

  • a = 8.4658 (3) Å

  • b = 8.6643 (3) Å

  • c = 16.1126 (6) Å

  • [alpha] = 84.196 (2)°

  • [beta] = 87.768 (3)°

  • [gamma] = 79.541 (2)°

  • V = 1156.01 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 295 K

  • 0.28 × 0.24 × 0.20 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.922, Tmax = 0.943

  • 25531 measured reflections

  • 6333 independent reflections

  • 4536 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.150

  • S = 1.03

  • 6333 reflections

  • 308 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10...O1i 0.93 2.60 3.327 (3) 136
C16-H16B...O5ii 0.97 2.37 3.260 (3) 152
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5271 ).


Acknowledgements

The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o749.  [CSD] [CrossRef] [IUCr Journals]
Chakkaravarthi, G., Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2010). Acta Cryst. E66, o2957.  [CSD] [CrossRef] [IUCr Journals]
Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Srivastava, Anupam & Pandeya, S. N. (2011). JCPR, 1, 1-17.


Acta Cryst (2013). E69, o1784  [ doi:10.1107/S1600536813031073 ]

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.