6-Bromo-1,3-dimethyl-1H-imidazo- [4,5-b]pyridin-2(3H)-one Siham Dahmani, a Youssef Kandri Rodi, a Hafid Zouihri, b El Mokhtar Essassi c and Seik Weng Ng d * a Laboratoire de Chimie Organique Applique ´e, Faculte ´ des Sciences et Techniques, Universite ´ Sidi Mohamed Ben Abdallah, Fe `s, Morocco, b CNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, c Laboratoire de Chimie Organique He ´te ´rocyclique, Po ˆ le de Compe ´tences Pharmacochimie, Universite ´ Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and d Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia Correspondence e-mail: seikweng@um.edu.my Received 24 June 2010; accepted 26 June 2010 Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.003 A ˚ ; R factor = 0.031; wR factor = 0.086; data-to-parameter ratio = 21.9. The non-H atoms of the two independent molecules in the asymmetric unit of the title compound, C 8 H 8 BrN 3 O, are planar (r.m.s. deviations = 0.015 and 0.019 A ˚ ). In the crystal, the molecules are linked into a zigzag chain along the c axis by C—HO hydrogen bonds. Related literature For the synthesis of the un-brominated compound, see: Yutilov et al. (1998, 2005). Experimental Crystal data C 8 H 8 BrN 3 O M r = 242.08 Monoclinic, P2 1 =c a = 21.7981 (4) A ˚ b = 3.9929 (1) A ˚ c = 20.6636 (3) A ˚ = 95.398 (1) V = 1790.53 (6) A ˚ 3 Z =8 Mo K radiation = 4.55 mm 1 T = 293 K 0.25 0.20 0.15 mm Data collection Bruker X8 APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.396, T max = 0.548 21586 measured reflections 5229 independent reflections 3539 reflections with I >2(I) R int = 0.036 Refinement R[F 2 >2(F 2 )] = 0.031 wR(F 2 ) = 0.086 S = 1.01 5229 reflections 239 parameters H-atom parameters constrained Á max = 0.28 e A ˚ 3 Á min = 0.29 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—HA D—H HA DA D—HA C8—H8CO2 i 0.96 2.33 3.279 (3) 167 C11—H11O1 0.93 2.49 3.321 (3) 148 Symmetry code: (i) x; y þ 5 2 ; z 1 2 . Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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); software used to prepare material for publication: publCIF (Westrip, 2010). The authors thank Universite ´ Mohammed V-Agdal and the University of Malaya for supporting this study. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5119). References Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.. Sheldrick, G. M. (1996). SADABS. University of Go ¨ttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Yutilov, Yu. M., Lopatinskaya, Kh. Ya., Smolyar, N. N. & Gres’ko, S. V. (2005). Russ. J. Org. Chem. 41, 575–579. Yutilov, Yu. M., Malyutina, V. F., Lopatinskaya, Kh. Ya. & Svertilova, I. A. (1998). Russ. J. Org. Chem. 34, 1363–1364. organic compounds o1904 Dahmani et al. doi:10.1107/S1600536810025134 Acta Cryst. (2010). E66, o1904 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368