[Journal logo]

Volume 69 
Part 6 
Page o839  
June 2013  

Received 25 April 2013
Accepted 29 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.063
wR = 0.165
Data-to-parameter ratio = 14.8
Details
Open access

1-Methyl-3-(2-oxo-2H-chromen-3-yl)-1H-imidazol-3-ium picrate

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
Correspondence e-mail: ngvtuyen@hotmail.com

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 [pi]-[pi] 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-H...O hydrogen bonds into a two-tier layer parallel to (001).

Related literature

For a recent review on coumarin-based drug patents, see: Kontogiorgis et al. (2012[Kontogiorgis, C., Detsi, A. & Hadjipavlou-Litina, D. (2012). Expert Opin. Ther. Pat. 22, 437-454.]). For analogous domino reactions, see: Voskressensky et al. (2012a[Voskressensky, L. G., Festa, A. A., Sokolova, E. A. & Varlamov, A. V. (2012a). Tetrahedron, 68, 5498-5504.],b[Voskressensky, L. G., Festa, A. A., Sokolova, E. A., Khrustalev, V. N. & Varlamov, A. V. (2012b). Eur. J. Org. Chem. pp. 6124-6126.]). For related compounds, see: Yu et al. (2006[Yu, T.-Z., Zhao, Y.-L. & Fan, D.-W. (2006). J. Mol. Struct. 791, 18-22.]); Morris et al. (2011[Morris, J. C., McMurtrie, J. C., Bottle, S. E. & Fairfull-Smith, K. E. (2011). J. Org. Chem. 76, 4964-4972.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N2O2+·C6H2N3O7-

  • Mr = 455.34

  • Monoclinic, P 21

  • a = 6.8142 (12) Å

  • b = 8.1942 (14) Å

  • c = 16.832 (3) Å

  • [beta] = 100.081 (4)°

  • V = 925.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 100 K

  • 0.30 × 0.21 × 0.03 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.961, Tmax = 0.996

  • 10390 measured reflections

  • 4415 independent reflections

  • 3734 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.165

  • S = 1.00

  • 4415 reflections

  • 299 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O7i 0.95 2.58 3.349 (4) 138
C9-H9...O3 0.95 2.33 3.122 (5) 140
C10-H10...O9ii 0.95 2.51 3.303 (5) 141
C11-H11...O3iii 0.95 2.42 3.196 (5) 139
C11-H11...O5iii 0.95 2.51 3.231 (5) 132
C12-H12A...O2iv 0.98 2.58 3.360 (5) 137
C12-H12B...O2v 0.98 2.48 3.448 (5) 171
C12-H12C...O3iv 0.98 2.39 3.269 (4) 148
C12-H12C...O9iv 0.98 2.42 3.160 (5) 132
C17-H17...O5vi 0.95 2.40 3.345 (5) 172
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+2]; (ii) x+1, y-1, z; (iii) x+1, y, z; (iv) [-x+1, y-{\script{1\over 2}}, -z+1]; (v) x, y-1, z; (vi) x, y+1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5268 ).


Acknowledgements

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.

References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Kontogiorgis, C., Detsi, A. & Hadjipavlou-Litina, D. (2012). Expert Opin. Ther. Pat. 22, 437-454.  [CrossRef] [ChemPort] [PubMed]
Morris, J. C., McMurtrie, J. C., Bottle, S. E. & Fairfull-Smith, K. E. (2011). J. Org. Chem. 76, 4964-4972.  [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Voskressensky, L. G., Festa, A. A., Sokolova, E. A., Khrustalev, V. N. & Varlamov, A. V. (2012b). Eur. J. Org. Chem. pp. 6124-6126.  [CSD] [CrossRef]
Voskressensky, L. G., Festa, A. A., Sokolova, E. A. & Varlamov, A. V. (2012a). Tetrahedron, 68, 5498-5504.  [ISI] [CrossRef] [ChemPort]
Yu, T.-Z., Zhao, Y.-L. & Fan, D.-W. (2006). J. Mol. Struct. 791, 18-22.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o839  [ doi:10.1107/S1600536813011690 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.