4-(2-Methoxyphenyl)-3-(3,4,5-tri- methoxyphenethyl)-2H-1,2,4-triazole- 5(4H)-thione Ghulam Qadeer, a Nasim Hasan Rama, a * Javeed Akhtar, b Mohammad Azad Malik b and Madeleine Helliwell b a Department of Chemistry, Quaid-i-Azam Univeristy, Islamabad 45320, Pakistan, and b School of Chemistry and Materials Science Centre, University of Manchester, Oxford Road, Manchester M13 9PL, England Correspondence e-mail: [email protected] Received 10 December 2007; accepted 11 December 2007 Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 A ˚ ; R factor = 0.036; wR factor = 0.099; data-to-parameter ratio = 15.9. The title compound, C 20 H 23 N 3 O 4 S, is an important biologically act ive het erocyclic compound. The five -me mbe red ring is oriented with respect to the six-membered rings at dihedral ang les of 78.60 (3) (tr ime thox ypheny l ring) and 71.57 (3) (methoxyphenyl ring). In the crystal structure, intermolecular N—HO hydrogen bonds link the molecules into infinite chains along the c axis. Related literature For general background, see: Holla et al . (1998); Turan-Zitouni et al. (1999); Demirbas et al. (2002); Paulvannan et al. (2000); Kritsanida et al. (2002); Omar et al. (1986). For related struc- tures, see: O ¨ ztu ¨ rk et al. (2004a,b); Zhang et al. (2004). For bond-le ngth data, see: Allen et al. (1987). Experimental Crystal data C 20 H 23 N 3 O 4 S M r = 401.47 Triclinic, P1 a = 8.6368 (6) A ˚ b = 10.5422 (7) A ˚ c = 11.6944 (8) A ˚ = 91.733 (1) = 92.955 (1) = 104.075 (1) V = 1030.44 (12) A ˚ 3 Z = 2 Mo K radiation = 0.19 mm 1 T = 100 (2) K 0.55 0.35 0.30 mm Data collection Bruker SMART CCD area-detect or diffractometer Absorption correction: integration (SADABS; Sheldrick, 1996) T min = 0.926, T max = 0.946 8266 measured reflections 4149 independent reflections 3689 reflections with I > 2 ( I ) R int = 0.061 Refinement R[F 2 > 2 (F 2 )] = 0.036 wR(F 2 ) = 0.099 S = 1.07 4149 reflections 261 parameters H atoms treated by a mixture of independent and constrained refinement max = 0.31 e A ˚ 3 min = 0.25 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—H A D—H H A D A D—H A N2—H2NO2 i 0.878 (1 7) 1.890 ( 18) 2.7558 (15) 168.4 (15) Symmetry code: (i) x; y; z þ 1. Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker , 1999); data reduct ion: SAINT ; program(s) used to solve structure: SIR2004 (Burla et al ., 200 5); program(s) used to refine structure: SHELXL97 (Sheldric k, 199 7); mol ecular grap hics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL. The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan. Supp leme ntar y data and figur es for this pape r are available from the IUCr electronic archives (Reference: HK2411). 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 (1998). SMART . Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999 ). SAINT and SHELXTL. Bru ker AXS Inc., Mad is on, Wisconsi n, USA. Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Demirbas , N., Ugurluoglu, R. & Demirbas, A. (2002). Bioorg. Med. Chem. 10, 3717–3723. Holla, B. S., Gonsalves, R. & Shenoy, S. (1998). Il Farmaco, 53, 574–578. Kritsanida , M., Mouroutsou, A., Marakos, P. , Pouli, N., Papakonstantino u- Garoufalias, S., Pannecouque, C., Witvrouw, M. & Clercq, E. D. (2002). Il Farmaco, 57, 253–257. Omar, A., Mohsen, M. E. & Waf a, O. A. (1986). J. Heterocycl. Chem. 23, 1339– 1341. O ¨ ztu ¨ rk, S., Akkurt, M., Cansız, A., Koparır, M., S ¸ ekerci, M. & Heinemann, F. W. (2004a). Acta Cryst. E60, o425–o427. O ¨ ztu ¨ rk, S., Akkurt, M., Cansız, A., Koparır, M., S ¸ ekerci, M. & Heinemann, F. W. (2004b). Acta Cryst. E60, o642–o644. Paulvannan, K., Chen, T. & Hale, R. (2000). Tetrahedron, 56, 8071–8076. Sheldrick, G. M. (1996). SADABS. University of Go ¨ ttingen, Germany. She ldr ick , G. M. (19 97) . SHELXS97 and SHELXL97 . Uni ver sit y of Go ¨ ttingen, Germany. Turan-Zitouni, G., Kaplancikli, Z. A., Erol, K. & Kilic, F. S. (1999). Il Farmaco, 54, 218–223. Zhang, L.-X., Zhang, A.-J., Lei, X.-X., Zou, K.-H. & Ng, S. W. (2004). Acta Cryst. E60, o613–o615. organi c compou nds o284 # 2008 International Union of Cr ys tallography doi:10.1107/ S1600536807066433 Acta Cryst. (2008). E64, o284 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368