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Volume 68 
Part 12 
Page o3357  
December 2012  

Received 15 October 2012
Accepted 9 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 111 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.101
Data-to-parameter ratio = 19.6
Details
Open access

5-Chloro-1-(4-methylphenylsulfonyl)-1H-indole

aDepartment of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland 7602, South Africa
Correspondence e-mail: hassam@sun.ac.za

In the title compound, C15H12ClNO2S, the indole ring is essentially planar (r.m.s. deviation = 0.0107 Å) and makes a dihedral angle of 85.01 (6)° with the benzene ring. In the crystal, three C-H...O hydrogen bonds result in a hydrogen-bonded spiral running parallel to the c axis.

Related literature

For background to the use of indoles as scaffolds in the synthesis of HIV-agents, see: Hassam et al. (2012[Hassam, M., Basson, A. E., Liotta, D. C., Morris, L., Otterlo, W. A. L. & Pelly, S. C. (2012). ACS Med. Chem. Lett. 3, 470-475.]). For the crystal structure of a closely related compound, see: Beddoes et al. (1986[Beddoes, R. L., Dalton, L., Joule, J. 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
  • C15H12ClNO2S

  • Mr = 305.77

  • Tetragonal, I 41 /a

  • a = 26.991 (7) Å

  • c = 7.8345 (19) Å

  • V = 5708 (2) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.41 mm-1

  • T = 111 K

  • 0.1 × 0.1 × 0.01 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.968

  • 17940 measured reflections

  • 3565 independent reflections

  • 2760 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.101

  • S = 1.06

  • 3565 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 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
C2-H2...O2i 0.95 2.54 3.327 (2) 140
C4-H4...O1ii 0.95 2.49 3.192 (2) 131
C14-H14...O1iii 0.95 2.59 3.333 (2) 135
Symmetry codes: (i) [y-{\script{1\over 4}}, -x+{\script{3\over 4}}, z+{\script{3\over 4}}]; (ii) x, y, z+1; (iii) [-y+{\script{3\over 4}}, x+{\script{1\over 4}}, z+{\script{1\over 4}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]; Atwood & Barbour, 2003[Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth Des. 3, 3-8.]); software used to prepare material for publication: X-SEED.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2597 ).


Acknowledgements

MH thanks Professor Willem A. L. van Otterlo and Dr S. C. Pelly for their valuable input and research oversight. Stellenbosch University's Science Faculty is also acknowledged for providing laboratory space and financial research support (Subcommittee B). The South African National Research Foundation (NRF), Pretoria, is also acknowledged for providing some research funds.

References

Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth Des. 3, 3-8.  [CrossRef] [ChemPort]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Beddoes, R. L., Dalton, L., Joule, J. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans 2, pp. 787-797.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hassam, M., Basson, A. E., Liotta, D. C., Morris, L., Otterlo, W. A. L. & Pelly, S. C. (2012). ACS Med. Chem. Lett. 3, 470-475.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3357  [ doi:10.1107/S1600536812046466 ]

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