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Volume 69 
Part 12 
Page o1781  
December 2013  

Received 6 November 2013
Accepted 8 November 2013
Online 16 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.118
Data-to-parameter ratio = 22.4
Details
Open access

(Z)-3-(1-Chloro­prop-1-en­yl)-2-methyl-1-phenyl­sulfonyl-1H-indole

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, C18H16ClNO2S, the indole ring system forms a dihedral angle of 75.07 (8)° with the phenyl ring. The mol­ecular structure is stabilized by a weak intra­molecular C-H...O hydrogen bond. In the crystal, mol­ecules are linked by weak C-H...O hydrogen bonds, forming a chain along [10-1]. C-H...[pi] inter­actions are also observed, leading to a three-dimensional network.

Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998[Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.]); Schollmeyer et al. (1995[Schollmeyer, D., Fischer, G. & Pindur, U. (1995). Acta Cryst. C51, 2572-2575.]). For related structures, see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.], 2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16ClNO2S

  • Mr = 345.83

  • Monoclinic, P 21 /n

  • a = 12.5204 (10) Å

  • b = 10.4962 (7) Å

  • c = 12.983 (1) Å

  • [beta] = 98.892 (2)°

  • V = 1685.7 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 295 K

  • 0.28 × 0.24 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.906, Tmax = 0.938

  • 20036 measured reflections

  • 4705 independent reflections

  • 3357 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.118

  • S = 1.03

  • 4705 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/C12-C14 ring.

D-H...A D-H H...A D...A D-H...A
C8-H8...O1 0.93 2.39 2.973 (2) 120
C10-H10...O2i 0.93 2.49 3.364 (2) 157
C5-H5...Cg1ii 0.93 2.82 3.477 (2) 128
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}].

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: IS5320 ).


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. (2007). Acta Cryst. E63, o3698.  [CSD] [CrossRef] [IUCr Journals]
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.  [CSD] [CrossRef] [IUCr Journals]
Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.  [CSD] [CrossRef] [IUCr Journals]
Schollmeyer, D., Fischer, G. & Pindur, U. (1995). Acta Cryst. C51, 2572-2575.  [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]


Acta Cryst (2013). E69, o1781  [ doi:10.1107/S1600536813030730 ]

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