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

Hassam, M.; Smith, V.J.

doi:10.1107/S1600536812046466

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 (C-C) = 0.003 Å
R = 0.039
wR = 0.101
Data-to-parameter ratio = 19.6
Details

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

Mohammad Hassam ^a ^* and Vincent J. Smith ^a

^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-HO 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). For the crystal structure of a closely related compound, see: Beddoes et al. (1986).

Experimental

Crystal data

C₁₅H₁₂ClNO₂S
M_r = 305.77
Tetragonal, I 4₁ /a
a = 26.991 (7) Å
c = 7.8345 (19) Å
V = 5708 (2) Å³
Z = 16
Mo K radiation
= 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) T_min = 0.950, T_max = 0.968
17940 measured reflections
3565 independent reflections
2760 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.101
S = 1.06
3565 reflections
182 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O2ⁱ	0.95	2.54	3.327 (2)	140
C4-H4O1ⁱⁱ	0.95	2.49	3.192 (2)	131
C14-H14O1ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); 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.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds