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Volume 69 
Part 12 
Page o1780  
December 2013  

Received 10 November 2013
Accepted 11 November 2013
Online 16 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.176
Data-to-parameter ratio = 26.6
Details
Open access

(E)-1-[2-(4-Fluoro-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, C25H19FN2O5S, the substituted phenyl ring makes a dihedral angle of 12.26 (9)° with the indole ring system. The nitro group is twisted at an angle of 26.92 (8)° out of the plane of the ring to which it is attached. The mol­ecular structure is stabilized by weak C-H...O hydrogen bonds. In the crystal, weak C-H...O, C-H...F and [pi]-[pi] [centroid-centroid distance = 3.6645 (11) Å] inter­actions link the mol­ecules, forming a three-dimensional network.

Related literature

For the biological activity of indole derivatives, see: Pomarnacka & Kozlarska-Kedra (2003[Pomarnacka, E. & Kozlarska-Kedra, I. (2003). Il Farmaco, 58, 423-429.]); 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.]). For details of the configuration at the S atom, see: Bassindale (1984[Bassindale, A. (1984). In The Third Dimension in Organic Chemistry. New York: John Wiley and Sons.]). For details of N-atom hybridization, see: Beddoes et al. (1986[Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.]).

[Scheme 1]

Experimental

Crystal data
  • C25H19FN2O5S

  • Mr = 478.48

  • Triclinic, [P \overline 1]

  • a = 8.2615 (3) Å

  • b = 10.7624 (5) Å

  • c = 13.2432 (6) Å

  • [alpha] = 68.606 (2)°

  • [beta] = 80.554 (3)°

  • [gamma] = 81.012 (2)°

  • V = 1075.53 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 295 K

  • 0.30 × 0.24 × 0.20 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.942, Tmax = 0.961

  • 27388 measured reflections

  • 8185 independent reflections

  • 5506 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.176

  • S = 1.03

  • 8185 reflections

  • 308 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.96 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O1 0.93 2.33 2.913 (3) 120
C11-H11...O3 0.93 2.40 2.905 (3) 114
C16-H16A...F1i 0.97 2.54 3.192 (2) 124
C22-H22...O4ii 0.93 2.52 3.438 (2) 170
Symmetry codes: (i) -x+1, -y-1, -z+2; (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: BT6945 ).


Acknowledgements

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

References

Bassindale, A. (1984). In The Third Dimension in Organic Chemistry. New York: John Wiley and Sons.
Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.
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]
Pomarnacka, E. & Kozlarska-Kedra, I. (2003). Il Farmaco, 58, 423-429.  [CrossRef] [PubMed] [ChemPort]
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, o1780  [ doi:10.1107/S1600536813030961 ]

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