Received 25 April 2009
The asymmetric unit of the title compound, C21H23ClN4S, contains nine crystallographically independent molecules, labelled A to I. The orientation of the 2-[4-(2-methylpropyl)phenyl]ethyl unit with respect to the rest of the molecule is significantly different in molecules E, F, H and I compared to the other independent molecules. The isobutyl group of molecule B is disordered over two orientations, with occupancies of 0.764 (7) and 0.236 (7). The benzene rings of the chlorophenyl and methylpropylphenyl units form dihedral angles of 21.90 (11) and 71.47 (11)°, respectively, with the triazole ring in molecule A [9.15 (11) and 80.37 (11)° in B, 7.14 (11) and 84.06 (11)° in C, 25.76 (11) and 76.59 (11)° in D, 13.68 (11) and 76.82 (10)° in E, 8.38 (11) and 69.77 (10)° in F, 30.34 (11) and 78.12 (11)° in G, 21.20 (11) and 71.58 (10)° in H, and 27.65 (11) and 65.23 (11)° in I]. In each independent molecule, a C-HS hydrogen bond is observed. The crystal packing is stabilized by N-HS and C-HS hydrogen bonds, and by C-H interactions involving the methylpropylphenyl ring.
For the activity of ibuprofen, see: Amir & Kumar (2007). For the activity of 1,2,4-triazol-5-one compounds, see: Demirbas et al. (2002, 2004). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2008a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2794 ).
HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a postdoctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.
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