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Volume 69 
Part 1 
Page o27  
January 2013  

Received 14 May 2012
Accepted 8 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.158
Data-to-parameter ratio = 14.2
Details
Open access

1-{(Z)-1-(2,4-Dichlorophenyl)-1-[2-(4-methylphenoxy)ethoxy]prop-1-en-2-yl}-1H-imidazol-3-ium nitrate

aJiangsu Engineering Technology Research Center of Polypeptide Pharmaceutical, College of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and bCollege of Pharmaceutical Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: chemywg@126.com

In the title salt, C21H21Cl2N2O2+·NO3-, the imidazole ring makes dihedral angles of 43.39 (14) and 10.9 (2)° with the 4-methylphenyl and 2,4-dichlorophenyl rings, respectively. The molecule adopts a Z conformation about the C=C double bond, which links the imidazole ring to the 4-methylphenoxy unit via an ethoxy chain. In the crystal, cations and anions are linked into chains by N-H...O and C-H...O hydrogen bonds.

Related literature

For background to azole derivatives and synthetic details, see: Jeu et al. (2003[Jeu, L., Piacenti, F. J., Lyakhovetskiy, A. G. & Fung, H. B. (2003). Clin. Ther. 25, 1321-1381.]); Fromtling & Castaner (1996[Fromtling, R. & Castaner, J. (1996). Drugs Fut. 21, 160-166.]); Ludwig & Kurt (1985[Ludwig, Z. & Kurt, T. (1985). US Patent Appl. US4554356.]). For a related structure, see: Kurt et al. (1987[Kurt, T., Ludwig, Z., Max, H. P., Martin, E. & Max, D. (1987). Helv. Chim. Acta, 70, 441-444.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21Cl2N2O2+·NO3-

  • Mr = 466.31

  • Triclinic, [P \overline 1]

  • a = 9.5300 (19) Å

  • b = 9.924 (2) Å

  • c = 12.449 (3) Å

  • [alpha] = 69.05 (3)°

  • [beta] = 80.59 (3)°

  • [gamma] = 88.75 (3)°

  • V = 1083.9 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.905, Tmax = 0.967

  • 4247 measured reflections

  • 3988 independent reflections

  • 2974 reflections with I > 2[sigma](I)

  • Rint = 0.020

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.158

  • S = 1.01

  • 3988 reflections

  • 281 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O4 0.86 2.55 3.218 (5) 135
N2-H2A...O5i 0.86 1.85 2.703 (5) 170
C13-H13A...O5ii 0.93 2.37 3.188 (5) 147
C21-H21A...O3ii 0.93 2.46 3.337 (5) 157
Symmetry codes: (i) -x, -y+3, -z; (ii) x, y-1, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: 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: PV2548 ).


Acknowledgements

This research work was supported by the Program of Six Talent Tops Foundation of Jiangsu Province (2009 NO 2009118) and the Natural Science Basic Research Program of Higher Education in Jiangsu Province (08KJA530002).

References

Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Fromtling, R. & Castaner, J. (1996). Drugs Fut. 21, 160-166.  [ChemPort]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Jeu, L., Piacenti, F. J., Lyakhovetskiy, A. G. & Fung, H. B. (2003). Clin. Ther. 25, 1321-1381.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kurt, T., Ludwig, Z., Max, H. P., Martin, E. & Max, D. (1987). Helv. Chim. Acta, 70, 441-444.
Ludwig, Z. & Kurt, T. (1985). US Patent Appl. US4554356.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o27  [ doi:10.1107/S1600536812046181 ]

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