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

Wu, D.-L.; Xiao, Z.-J.

doi:10.1107/S160053681105286X

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 (C-C) = 0.002 Å
R = 0.040
wR = 0.111
Data-to-parameter ratio = 14.5
Details

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

Dong-Liang Wu ^a and Zi-Jing Xiao ^a ^*

^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-HO and C-HO 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); Smith et al. (2000); Jebas et al. (2006); Rademeyer (2007); Hemamalini & Fun (2010a,b,c); Perpétuo & Janczak (2010). For comparable structures, see: Jebas et al. (2006); Perpétuo & Janczak (2010); Hemamalini & Fun (2010a). For the synthesis of 3,5-dinitromethyl salicylate, see: Bartlett & Trachten (1958).

Experimental

Crystal data

C₅H₇N₂⁺·C₈H₅N₂O₇^-
M_r = 336.27
Monoclinic, P 2₁ /n
a = 7.4088 (3) Å
b = 19.1779 (6) Å
c = 9.9784 (4) Å
= 98.2825 (15)°
V = 1403.00 (9) Å³
Z = 4
Mo K radiation
= 0.13 mm^-1
T = 293 K
0.35 × 0.35 × 0.26 mm

Data collection

Rigaku R-AXIS SPIDER IP diffractometer
Absorption correction: scan (TEXRAY; Molecular Structure Corporation, 1999) T_min = 0.951, T_max = 0.969
21789 measured reflections
3200 independent reflections
2760 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.111
S = 1.09
3200 reflections
221 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H01AO3	0.90	1.88	2.6864 (13)	148
N1-H01AO2	0.90	2.23	2.8783 (14)	130
N2-H02AO3	0.88	2.01	2.7592 (14)	142
N2-H02AO4	0.88	2.45	3.2082 (15)	144
N2-H02BO6ⁱ	0.87	2.24	3.0537 (14)	155
C4-H4AO7ⁱⁱ	0.93	2.57	3.2052 (16)	126
C5-H5AO5ⁱⁱⁱ	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); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); 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.
Gellert, R. W. & Hsu, I.-N. (1988). Acta Cryst. C44, 311-313.
Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o691-o692.
Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o1418-o1419.
Hemamalini, M. & Fun, H.-K. (2010c). Acta Cryst. E66, o2323-o2324.
Jebas, S. R., Balasubramanian, T., Peschar, R. & Fraanje, J. (2006). Acta Cryst. E62, o2606-o2607.
McArdle, P. (1995). J. Appl. Cryst. 28, 65.
Molecular Structure Corporation (1999). TEXRAY. MSC, The Woodlands, Texas, USA.
Perpétuo, G. J. & Janczak, J. (2010). Acta Cryst. C66, o225-o228.
Rademeyer, M. (2007). Acta Cryst. E63, o545-o546.
Rigaku (2008). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Bott, R. C. & Wermuth, U. D. (2000). Acta Cryst. C56, 1505-1506.

organic compounds