[5-(2-Furyl)-6-nitro-1,2,3,5,6,7-hexa- hydroimidazo[1,2-a]pyridin-8-yl]- (phenyl)methanone Muhammad Yaqub,* Zahid Shafiq, Ashfaq M. Qureshi and Muhammad Najam-ul-Haq Department of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan Correspondence e-mail: mayaqub2@yahoo.com Received 27 July 2009; accepted 24 August 2009 Key indicators: single-crystal X-ray study; T = 173 K; mean (C–C) = 0.003 A ˚ ; R factor = 0.055; wR factor = 0.128; data-to-parameter ratio = 12.4. In the title compound, C 18 H 17 N 3 O 4 , the furyl and phenyl rings are inclined at almost right angles [85.77 (7) and 63.25 (7) , respectively] to the central imidazo[1,2-a]pyridinyl unit. The structure displays both inter- and intramolecular N—HO hydrogen bonding. Related literature For cyclic 1,1-enediamines as intermediates for the construc- tion of heterocyclic compounds, see: Yu et al. (2006); Yaqub et al. (2008); Wang et al. (1999). For related structures, see: Yu et al. (2007); Yaqub et al. (2009). Experimental Crystal data C 18 H 17 N 3 O 4 M r = 339.35 Monoclinic, C2=c a = 11.980 (2) A ˚ b = 15.047 (3) A ˚ c = 17.932 (4) A ˚ = 101.94 (3) V = 3162.7 (11) A ˚ 3 Z =8 Mo K radiation = 0.10 mm 1 T = 173 K 0.45 0.33 0.32 mm Data collection Rigaku R-AXIS RAPID IP area- detector diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T min = 0.955, T max = 0.968 5401 measured reflections 2801 independent reflections 2426 reflections with I >2(I) R int = 0.031 Refinement R[F 2 >2(F 2 )] = 0.055 wR(F 2 ) = 0.128 S = 1.14 2801 reflections 226 parameters H-atom parameters constrained Á max = 0.37 e A ˚ 3 Á min = 0.36 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—HA D—H HA DA D—HA N1—H1AO4 0.88 2.17 2.714 (2) 119 N1—H1AO4 i 0.88 2.40 3.025 (3) 128 Symmetry code: (i) x; y; z þ 3 2 . Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97. We thank the Institute of Chemistry Chinese Academy of Science, Beijing, China for providing X-ray single-crystal facilities and the Higher Education Commission, Islamabad, Pakistan for providing financial support. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2191). References Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Wang, M.-X., Miao, W.-S., Cheng, Y. & Huang, Z.-T. (1999). Tetrahedron, 55, 14611–14622. Yaqub, M., Shafiq, Z., Qureshi, A. M. & Najam-ul-Haq, M. (2009). Acta Cryst. E65, o1869. Yaqub, M., Yu, C.-Y., Jia, Y.-M. & Huang, Z.-T. (2008). Synlett, pp. 1357–1360. Yu, C.-Y., Yang, P.-H., Zhao, M.-X. & Huang, Z.-T. (2006). Synlett, pp. 1835– 1840. Yu, C.-Y., Yuan, X.-N. & Huang, Z.-T. (2007). Acta Cryst. E63, o3186. organic compounds Acta Cryst. (2009). E65, o2283 doi:10.1107/S1600536809033716 Yaqub et al. o2283 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368