Received 7 December 2012
In the title compound, C21H20BrNO5S, the thiophene group is located above the mean plane of the indole ring and displays rotational disorder (i.e. rotation through 180°). The site occupancy of the major component is 0.902 (2), while that of the minor component is 0.098 (2). In the crystal, pairs of weak C-HO interactions link the molecules into centrosymmetric dimers.
For background to the use of indoles as scaffolds in the synthesis of HIV-agents, see: Hassam et al. (2012) and for a recent review on stages of non-nucleoside reverse transcriptase inhibitors, see: Reynolds et al. (2012). For the crystal structures of closely related compounds, see: Beddoes et al. (1986), Hassam & Smith (2012).
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: JJ2160 ).
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 research funds.
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