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Volume 69 
Part 9 
Page o1482  
September 2013  

Received 20 August 2013
Accepted 22 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.082
wR = 0.177
Data-to-parameter ratio = 15.7
Details
Open access

Bis(4-methoxy-3,4-dihydroquinazolin-1-ium) chloranilate

aDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
Correspondence e-mail: ishidah@cc.okayama-u.ac.jp

In the title compound [systematic name: bis(4-methoxy-3,4-dihydroquinazolin-1-ium) 2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-diolate], 2C9H11N2O+·C6Cl2O42-, the chloranilate anion lies about an inversion center. The 4-methoxy-3,4-dihydroquinazolin-1-ium cations are linked on both sides of the anion via bifurcated N-H...(O,O) and weak C-H...O hydrogen bonds, giving a centrosymmetric 2:1 aggregate. The 2:1 aggregates are linked by another N-H...O hydrogen bond into a tape running along [1-10]. The tapes are further linked by a C-H...O hydrogen bond into a layer parallel to the ab plane.

Related literature

For NMR and nuclear quadrupole resonance (NQR) studies on proton-transfer in the short hydrogen-bond of the diazine-chloranilic acid (2:1) system, see: Nihei et al. (2000[Nihei, T., Ishimaru, S., Ishida, H., Ishihara, H. & Ikeda, R. (2000). Chem. Phys. Lett. 329, 7-14.]); Seliger et al. (2009[Seliger, J., Zagar, V., Gotoh, K., Ishida, H., Konnai, A., Amino, D. & Asaji, T. (2009). Phys. Chem. Chem. Phys. 11, 2281-2286.]). For a related structure, see: Gotoh & Ishida (2011[Gotoh, K. & Ishida, H. (2011). Acta Cryst. C67, o500-o504.]). For the double [pi] system of the chloranilate anion, see: Andersen (1967[Andersen, E. K. (1967). Acta Cryst. 22, 196-201.]); Benchekroun & Savariault (1995[Benchekroun, R. & Savariault, J.-M. (1995). Acta Cryst. C51, 186-188.]).

[Scheme 1]

Experimental

Crystal data
  • 2C9H11N2O+·C6Cl2O42-

  • Mr = 533.37

  • Triclinic, [P \overline 1]

  • a = 4.9971 (4) Å

  • b = 8.6363 (4) Å

  • c = 13.5808 (9) Å

  • [alpha] = 97.869 (4)°

  • [beta] = 91.660 (6)°

  • [gamma] = 100.968 (5)°

  • V = 569.06 (7) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 200 K

  • 0.45 × 0.35 × 0.04 mm

Data collection
  • Rigaku R-AXIS RAPID II diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.887, Tmax = 0.987

  • 7422 measured reflections

  • 2692 independent reflections

  • 1913 reflections with I > 2[sigma](I)

  • Rint = 0.199

Refinement
  • R[F2 > 2[sigma](F2)] = 0.082

  • wR(F2) = 0.177

  • S = 0.84

  • 2692 reflections

  • 172 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.89 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.95 (3) 1.79 (3) 2.706 (2) 160 (3)
N1-H1...O2i 0.95 (3) 2.56 (3) 3.229 (3) 127 (2)
N2-H2...O2ii 0.90 (3) 1.87 (3) 2.762 (3) 171 (3)
C4-H4...O1iii 0.95 2.34 3.214 (3) 152
C10-H10...O1 0.95 2.52 3.230 (3) 131
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y+1, z; (iii) -x+1, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004[Rigaku/MSC. (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC. (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5342 ).


References

Andersen, E. K. (1967). Acta Cryst. 22, 196-201.  [CSD] [CrossRef] [details]
Benchekroun, R. & Savariault, J.-M. (1995). Acta Cryst. C51, 186-188.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gotoh, K. & Ishida, H. (2011). Acta Cryst. C67, o500-o504.  [CrossRef] [ChemPort] [details]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Nihei, T., Ishimaru, S., Ishida, H., Ishihara, H. & Ikeda, R. (2000). Chem. Phys. Lett. 329, 7-14.  [ISI] [CrossRef] [ChemPort]
Rigaku/MSC. (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Seliger, J., Zagar, V., Gotoh, K., Ishida, H., Konnai, A., Amino, D. & Asaji, T. (2009). Phys. Chem. Chem. Phys. 11, 2281-2286.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1482  [ doi:10.1107/S1600536813023635 ]

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