Received 25 April 2013
aInstitute of Chemistry, Vietnam Academy of Science & Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam,bDepartment of Chemistry, Vietnam National University, 144 Xuan Thuy, Cau Giay, Hanoi, Vietnam,cOrganic Chemistry Department, Russian Peoples Friendship University, Miklukho-Maklai St, 6, Moscow 117198, Russian Federation, and dX-Ray Structural Centre, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St 28, B-334, Moscow 119991, Russian Federation
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The title salt, C13H11N2O2+·C6H2N3O7-, is the unexpected product of a domino reaction of 3-cyanomethyl-1-methylimidazolium chloride with salicylic aldehyde in the presence of picric acid. In the cation, the 1H-imidazole ring is twisted by 63.2 (1)° from the 2H-chromen plane. In the crystal, cations and anions are alternately stacked along the a axis through - stacking interactions between the almost parallel aromatic rings [centroid-centroid distances = 3.458 (2) and 3.678 (2) Å]. The stacks are further linked by C-HO hydrogen bonds into a two-tier layer parallel to (001).
For a recent review on coumarin-based drug patents, see: Kontogiorgis et al. (2012). For analogous domino reactions, see: Voskressensky et al. (2012a,b). For related compounds, see: Yu et al. (2006); Morris et al. (2011).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5268 ).
The authors are grateful to the Russian Foundation for Basic Research (project No. 12-03-93000-Viet-a) and the Vietnam Academy of Science and Technology (grant VAST·HTQT·NGA. 06/2012-2013) for the financial support of this work.
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