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Volume 68 
Part 1 
Pages o124-o125  
January 2012  

Received 18 October 2011
Accepted 8 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.111
Data-to-parameter ratio = 14.5
Details
Open access

2-Aminopyridinium 2-methoxycarbonyl-4,6-dinitrophenolate

aCollege of Materials Science & Engineering, Huaqiao University, Xiamen 361021, People's Republic of China
Correspondence e-mail: xzj@hqu.edu.cn

In the title molecular salt, C5H7N2+·C8H5N2O7-, the 2-aminopyridinium cation is essentially planar, with a maximium deviation of 0.015 (1) Å, while the 2-methoxycarbonyl-4,6-dinitrophenolate anion is slightly twisted away from planarity, with a maximium deviation of 0.187 (1) Å. Deprotonation of the hydroxy O atom was observed. The cation and anion are connected by four bifurcated N-H...(O,O) hydrogen bonds, forming a molecular proton-transfer adduct. The dihedral angle between the pyridinium ring in the cation and the benzene ring in the anion is 3.65 (6)°. Every adduct connects to six neighboring adducts by N-H...O and C-H...O hydrogen bonds, yielding extended layers parallel to the bc plane. There is a weak [pi]-[pi] interaction between the benzene rings of two neighboring anions; the interplanar spacing and the centroid-centroid separation are 3.309 (1) and 3.69 (1) Å, respectively.

Related literature

For the structures of molecular proton-transfer adducts containing substituted pyridinium and an acid anion, see Gellert & Hsu (1988[Gellert, R. W. & Hsu, I.-N. (1988). Acta Cryst. C44, 311-313.]); Smith et al. (2000[Smith, G., Bott, R. C. & Wermuth, U. D. (2000). Acta Cryst. C56, 1505-1506.]); Jebas et al. (2006[Jebas, S. R., Balasubramanian, T., Peschar, R. & Fraanje, J. (2006). Acta Cryst. E62, o2606-o2607.]); Rademeyer (2007[Rademeyer, M. (2007). Acta Cryst. E63, o545-o546.]); Hemamalini & Fun (2010a[Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o691-o692.],b[Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o1418-o1419.],c[Hemamalini, M. & Fun, H.-K. (2010c). Acta Cryst. E66, o2323-o2324.]); Perpétuo & Janczak (2010[Perpétuo, G. J. & Janczak, J. (2010). Acta Cryst. C66, o225-o228.]). For comparable structures, see: Jebas et al. (2006[Jebas, S. R., Balasubramanian, T., Peschar, R. & Fraanje, J. (2006). Acta Cryst. E62, o2606-o2607.]); Perpétuo & Janczak (2010[Perpétuo, G. J. & Janczak, J. (2010). Acta Cryst. C66, o225-o228.]); Hemamalini & Fun (2010a[Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o691-o692.]). For the synthesis of 3,5-dinitromethyl salicylate, see: Bartlett & Trachten (1958[Bartlett, P. D. & Trachten, E. N. (1958). J. Am. Chem. Soc. 80, 5808-5812.]).

[Scheme 1]

Experimental

Crystal data
  • C5H7N2+·C8H5N2O7-

  • Mr = 336.27

  • Monoclinic, P 21 /n

  • a = 7.4088 (3) Å

  • b = 19.1779 (6) Å

  • c = 9.9784 (4) Å

  • [beta] = 98.2825 (15)°

  • V = 1403.00 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.35 × 0.35 × 0.26 mm

Data collection
  • Rigaku R-AXIS SPIDER IP diffractometer

  • Absorption correction: [psi] scan (TEXRAY; Molecular Structure Corporation, 1999)[Molecular Structure Corporation (1999). TEXRAY. MSC, The Woodlands, Texas, USA.] Tmin = 0.951, Tmax = 0.969

  • 21789 measured reflections

  • 3200 independent reflections

  • 2760 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.111

  • S = 1.09

  • 3200 reflections

  • 221 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H01A...O3 0.90 1.88 2.6864 (13) 148
N1-H01A...O2 0.90 2.23 2.8783 (14) 130
N2-H02A...O3 0.88 2.01 2.7592 (14) 142
N2-H02A...O4 0.88 2.45 3.2082 (15) 144
N2-H02B...O6i 0.87 2.24 3.0537 (14) 155
C4-H4A...O7ii 0.93 2.57 3.2052 (16) 126
C5-H5A...O5iii 0.93 2.42 3.2604 (17) 151
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) x, y, z+1.

Data collection: RAPID-AUTO (Rigaku, 2008[Rigaku (2008). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: ORTEX (McArdle, 1995[McArdle, P. (1995). J. Appl. Cryst. 28, 65.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2268 ).


Acknowledgements

This project was supported financially by the Natural Science Foundation of China (No. 50971063) and the Natural Science Foundation of Fujian Province (Nos. E0640006, 2003F006, 2010J01042).

References

Bartlett, P. D. & Trachten, E. N. (1958). J. Am. Chem. Soc. 80, 5808-5812.  [CrossRef] [ChemPort] [ISI]
Gellert, R. W. & Hsu, I.-N. (1988). Acta Cryst. C44, 311-313.  [CrossRef] [details]
Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o691-o692.  [CSD] [CrossRef] [details]
Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o1418-o1419.  [CSD] [CrossRef] [details]
Hemamalini, M. & Fun, H.-K. (2010c). Acta Cryst. E66, o2323-o2324.  [CSD] [CrossRef] [details]
Jebas, S. R., Balasubramanian, T., Peschar, R. & Fraanje, J. (2006). Acta Cryst. E62, o2606-o2607.  [CSD] [CrossRef] [details]
McArdle, P. (1995). J. Appl. Cryst. 28, 65.  [CrossRef] [details]
Molecular Structure Corporation (1999). TEXRAY. MSC, The Woodlands, Texas, USA.
Perpétuo, G. J. & Janczak, J. (2010). Acta Cryst. C66, o225-o228.  [CrossRef] [details]
Rademeyer, M. (2007). Acta Cryst. E63, o545-o546.  [CSD] [CrossRef] [details]
Rigaku (2008). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Bott, R. C. & Wermuth, U. D. (2000). Acta Cryst. C56, 1505-1506.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o124-o125   [ doi:10.1107/S160053681105286X ]

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