Received 12 June 2013
The title molecule, C22H17F3N2OS, adopts a trans-cis conformation with respect to the positions of the carbonyl and trifluoromethylbenzene groups against the thiocarbonyl group across the C-N bonds. The molecular structure is stabilized by an intramolecular N-HO hydrogen bond with an S(6) ring motif. The trifluoromethyl-substituted benzene ring forms dihedral angles of 66.05 (9) and 47.19 (9)° with the terminal phenyl rings and is twisted from the O=C-N-(C=S)-N carbonylthiourea plane [maximum deviation = 0.0535 (12) Å], making a dihedral angle of 63.59 (8)°. In the crystal, N-HO and C-HF hydrogen bonds link the molecules into a layer parallel to the bc plane. A C-H interaction is also observed.
For the biological activity of thiourea derivatives, see: Vankatachalam et al. (2001). For related structures, see: Yusof, Arshad et al. (2012); Yusof, Embong et al. (2012); Yusof, Mutalib et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: IS5283 ).
The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the USM Short Term Grant, No. 304/PFIZIK/6312078, to conduct this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship (ASTS).
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