N-(4-Methoxyphenyl)-N 0 -(4-methyl- benzoyl)thiourea S. Aminah A. Razis, a M. Sukeri M. Yusof a * and Bohari M. Yamin b a Department of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and b School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia Correspondence e-mail: mohdsukeri@umt.edu.my Received 26 September 2007; accepted 27 September 2007 Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.004 A ˚ ; R factor = 0.050; wR factor = 0.123; data-to-parameter ratio = 14.7. In the title compound, C 16 H 16 N 2 O 2 S, one of the C—N bonds adopts a transoid configuration, whereas the other C—N bond is cisoid configured. The molecular conformation is stabilized by an intramolecular N—HO hydrogen bond, and the crystal packing is stabilized by intermolecular N—HS and C—HO hydrogen bonds, forming chains parallel to the a axis. Related literature For related crystal structures of the title compound, see: Saeed & Flo ¨ rke (2007); Yusof et al. (2006). For related literature, see: Allen et al. (1987). Experimental Crystal data C 16 H 16 N 2 O 2 S M r = 300.37 Monoclinic, P2 1 =c a = 13.102 (3) A ˚ b = 6.4224 (17) A ˚ c = 18.292 (5) A ˚  = 102.340 (4)  V = 1503.6 (7) A ˚ 3 Z =4 Mo K radiation  = 0.22 mm 1 T = 298 (2) K 0.28  0.23  0.12 mm Data collection Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000) T min = 0.941, T max = 0.974 7756 measured reflections 2794 independent reflections 2040 reflections with I >2(I) R int = 0.027 Refinement R[F 2 >2(F 2 )] = 0.050 wR(F 2 ) = 0.123 S = 1.03 2794 reflections 190 parameters H-atom parameters constrained Á max = 0.24 e A ˚ 3 Á min = 0.17 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ ,  ). D—HA D—H HA DA D—HA N2—H2AO1 0.86 1.95 2.644 (3) 138 N1—H1AS1 i 0.86 2.64 3.463 (2) 160 C11—H11AO1 ii 0.93 2.53 3.405 (3) 157 Symmetry codes: (i) x þ 2; y þ 1; z þ 2; (ii) x þ 1; y þ 1; z þ 2. Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003). The authors thank the Malaysian government, Universiti Kebangsaan Malaysia and Universiti Malaysia Terengganu for research grant IRPA No. 09-02-02-993, and the Ministry of Higher Education, Malaysia, for FRGS grant No. 59001. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2523). References Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. Bruker (2000). SADABS (Version 2.01), SMART (Version 5.630) and SAINT (Version 6.36a). Bruker AXS Inc., Madison, Wisconsin, USA. Nardelli, M. (1995). J. Appl. Cryst. 28, 659. Saeed, A. & Flo ¨rke, U. (2007). Acta Cryst. E63, o3695. Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Go ¨ttingen, Germany. Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Yusof, M. S. M., Hamid, M. A., Ramli, R. N. H. R. & Yamin, B. M. (2006). Acta Cryst. E62, o2131–o2132. organic compounds Acta Cryst. (2007). E63, o4225 doi:10.1107/S1600536807047551 # 2007 International Union of Crystallography o4225 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368